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R2625 Sigma

Retinoic acid

≥98% (HPLC), powder

Synonym: ATRA, Tretinoin, Vitamin A acid, all-trans-Retinoic acid

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Description

Frequently Asked Questions

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Packaging

1, 5 g in ampule

50, 100, 500 mg in ampule

Biochem/physiol Actions

all−trans−Retinoic acid (ATRA) is a ligand for both the retinoic acid receptor (RAR) and the retinoid X receptor (RXR). The bound RAR and RXR act as transcription factors that regulate the growth and differentiation of both normal and malignant cells. Cytochromes P450 (CYPs) catalyze the 4-hydroxylation of ATRA. Retinoic acid primes embryonic stem cells to become neurons.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®,1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

This compound is featured on the Nuclear Receptors (Non-Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. R2625.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

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Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
Hazard Codes (Europe) 
Xn
Risk Statements (Europe) 
22
Safety Statements (Europe) 
61
RIDADR 
UN 3077 9 / PGIII
WGK Germany 
2
RTECS 
VH6475000

Protocols & Articles

Articles

Retinoic Acid and Gene Expression

All-trans retinoic acid (RA, ATRA) is a pleiotropic activation factor that regulates genes associated with normal vertebrate cellular processes such as cell differentiation, cell proliferation, apopt...
BioFiles 2008, 3.9, 12.
Keywords: Apoptosis, Cancer, Cell proliferation, Cellular processes, Chromatin immunoprecipitation, Condensations, Degradations, Diseases, Gene expression, Hormones, Immunoprecipitation, Ligands, Metabolism, Oxidations, Phosphorylations, Polymerase chain reaction, Sequences, Teratogens, Transcription, Type, Ubiquitinations, Usage, Vitamins

Peer-Reviewed Papers

References

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Expression analysis of SOX14 during retinoic acid induced neural differentiation of embryonal carcinoma cells and assessment of the effect of its ectopic expression on SOXB members in HeLa cells. Popovic J, Stanisavljevic D, Schwirtlich M, et al. PLoS ONE 9(3), e91852, (2014)

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A Novel Retinoic Acid, Catechin Hydrate And Mustard Oil-based Emulsion For Enhanced Cytokine And Antibody Responses Against Multiple Strains Of HIV-1 Following Mucosal And Systemic Vaccinations. Yu, M., and Vajdy, M. Vaccine 29, 2429-36, (2011)

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Reintroduction of CEBPA in MN1-overexpressing hematopoietic cells prevents their hyperproliferation and restores myeloid differentiation Kandilci, A., and Grosveld, G.C. Blood 114, 1596-606, (2009)

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Retinoic acid and arsenic trioxide for acute promyelocytic leukemia. Lo-Coco F, Avvisati G, Vignetti M, et al. N. Engl. J. Med. 369(2), 111-21, (2013)

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Nuclear lamin-A scales with tissue stiffness and enhances matrix-directed differentiation. Swift J, Ivanovska IL, Buxboim A, et al. Science 341(6149), 1240104, (2013)

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Retinoic acid signaling is essential for embryonic hematopoietic stem cell development. Chanda B, Ditadi A, Iscove NN, et al. Cell 155(1), 215-27, (2013)

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Chemical genetics reveals a complex functional ground state of neural stem cells Diamandis, P., et. al. Nat. Chem. Biol. 3(5), 268-273, (2007)

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Maternal retinoids control type 3 innate lymphoid cells and set the offspring immunity. van de Pavert SA, Ferreira M, Domingues RG, et al. Nature 508(7494), 123-7, (2014)

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A wide-field suprachoroidal retinal prosthesis is stable and well tolerated following chronic implantation. Villalobos J, Nayagam DA, Allen PJ, et al. Invest. Ophthalmol. Vis. Sci. 54(5), 3751-62, (2013)

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Initiating meiosis: the case for retinoic acid. Griswold MD, Hogarth CA, Bowles J, et al. Biol. Reprod. 86(2), 35, (2012)

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Identifying off-target effects and hidden phenotypes of drugs in human cells. Marnie L MacDonald et al Nat. Chem. Biol. 2, 329-37, (2006)

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Modeling retinal degeneration using patient-specific induced pluripotent stem cells. Jin ZB, Okamoto S, Osakada F, et al. PLoS ONE 6(2), e17084, (2011)

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Recessive and dominant mutations in retinoic acid receptor beta in cases with microphthalmia and diaphragmatic hernia. Srour M, Chitayat D, Caron V, et al. Am. J. Hum. Genet. 93(4), 765-72, (2013)

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Coordinated regulation of transcriptional repression by the RBP2 H3K4 demethylase and Polycomb-Repressive Complex 2. Diego Pasini et al Genes Dev. 22, 1345-55, (2008)

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CYP26B1 promotes male germ cell differentiation by suppressing STRA8-dependent meiotic and STRA8-independent mitotic pathways. Saba R, Wu Q, and Saga Y Dev. Biol. 389(2), 173-81, (2014)

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Cdyl, a new partner of the inactive X chromosome and potential reader of H3K27me3 and H3K9me2. Escamilla-Del-Arenal M, da Rocha ST, Spruijt CG, et al. Mol. Cell. Biol. 33(24), 5005-20, (2013)

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Retinoic acid signalling during development. Rhinn M and Dollé P Development 139(5), 843-58, (2012)

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Modulation of T cell and innate immune responses by retinoic Acid. Raverdeau M and Mills KH J. Immunol. 192(7), 2953-8, (2014)

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Directed differentiation of human pluripotent cells to ureteric bud kidney progenitor-like cells. Xia Y, Nivet E, Sancho-Martinez I, et al. Nat. Cell Biol. 15(12), 1507-15, (2013)

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Design, synthesis, and structure-activity analysis of isoform-selective retinoic acid receptor beta ligands. Birgitte W Lund et al J. Med. Chem. 52, 1540-5, (2009)

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β,β-carotene 15,15'-monooxygenase and its substrate β-carotene modulate migration and invasion in colorectal carcinoma cells. Pham DN, Leclerc D, Lévesque N, et al. Am. J. Clin. Nutr. 98(2), 413-22, (2013)

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Retinoids and breast cancer: from basic studies to the clinic and back again. Garattini E, Bolis M, Garattini SK, et al. Cancer Treat. Rev. 40(6), 739-49, (2014)

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The acute promyelocytic leukaemia success story: curing leukaemia through targeted therapies. Rice KL and de Thé H J. Intern. Med. 276(1), 61-70, (2014)

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Mapping of small RNAs in the human ENCODE regions. Borel C Am. J. Hum. Genet. 82(4), 971-81, (2008)

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Outpatient oral treatment for acute promyelocytic leukemia. Lo-Coco F and Cicconi L N. Engl. J. Med. 372(9), 884-5, (2015)

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Outpatient oral treatment for acute promyelocytic leukemia. Lo-Coco F and Cicconi L N. Engl. J. Med. 372(9), 885, (2015)

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SMAD2 and p38 signaling pathways act in concert to determine XY primordial germ cell fate in mice. Wu Q, Fukuda K, Weinstein M, et al. Development 142(3), 575-86, (2015)

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Alitretinoin and Darier disease: "All that glisters is not gold". Balestri R, Patrizi A, and Bardazzi F J. Am. Acad. Dermatol. 72(2), 363-4, (2015)

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Leukocyte homing, fate, and function are controlled by retinoic acid. Guo Y, Brown C, Ortiz C, et al. Physiol. Rev. 95(1), 125-48, (2015)

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Antagonism between granulocytic maturation and deacetylase inhibitor-induced apoptosis in acute promyelocytic leukaemia cells. Hennig D, Müller S, Wichmann C, et al. Br. J. Cancer 112(2), 329-37, (2015)

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Induction of CYP26A1 by metabolites of retinoic acid: evidence that CYP26A1 is an important enzyme in the elimination of active retinoids. Topletz AR, Tripathy S, Foti RS, et al. Mol. Pharmacol. 87(3), 430-41, (2015)

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Oral arsenic and retinoic acid for non-high-risk acute promyelocytic leukemia. Zhu HH and Huang XJ N. Engl. J. Med. 371(23), 2239-41, (2014)

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Interactions between FGF18 and retinoic acid regulate differentiation of chick embryo limb myoblasts. Mok GF, Cardenas R, Anderton H, et al. Dev. Biol. 396(2), 214-23, (2014)

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Retinoic acid regulates Kit translation during spermatogonial differentiation in the mouse. Busada JT, Chappell VA, Niedenberger BA, et al. Dev. Biol. 397(1), 140-9, (2015)

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BMP and RA signaling cooperate to regulate Apolipoprotein C1 expression during embryonic development. Wang Y, Li WH, Li Z, et al. Gene 554(2), 196-204, (2015)

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Role of retinoic acid and platelet-derived growth factor receptor cross talk in the regulation of neonatal gonocyte and embryonal carcinoma cell differentiation. Manku G, Wang Y, Merkbaoui V, et al. Endocrinology 156(1), 346-59, (2015)

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The gene regulatory networks underlying formation of the auditory hindbrain. Willaredt MA, Schlüter T, and Nothwang HG Cell. Mol. Life Sci. 72(3), 519-35, (2015)

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The effect of RA on the chick Ebf1-3 genes expression in somites and pharyngeal arches. El-Magd MA, Saleh AA, El-Aziz RM, et al. Dev. Genes Evol. 224(4-6), 245-53, (2014)

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Cellular retinoic acid-binding protein 2 inhibits tumor growth by two distinct mechanisms. Vreeland AC, Levi L, Zhang W, et al. J. Biol. Chem. 289(49), 34065-73, (2014)

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Clearance of PML/RARA-bound promoters suffice to initiate APL differentiation. Vitaliano-Prunier A, Halftermeyer J, Ablain J, et al. Blood 124(25), 3772-80, (2014)

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Treatment of severe or progressive Kaposi's sarcoma in HIV-infected adults. Gbabe OF, Okwundu CI, Dedicoat M, et al. Cochrane Database Syst. Rev. 8, CD003256, (2014)

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MicroRNA-302b-inhibited E2F3 transcription factor is related to all trans retinoic acid-induced glioma cell apoptosis. Chen PH, Shih CM, Chang WC, et al. J. Neurochem. 131(6), 731-42, (2014)

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Internal tandem duplication of the FLT3 gene confers poor overall survival in patients with acute promyelocytic leukemia treated with all-trans retinoic acid and anthracycline-based chemotherapy: an International Consortium on Acute Promyelocytic Leukemia study. Lucena-Araujo AR, Kim HT, Jacomo RH, et al. Ann. Hematol. 93(12), 2001-10, (2014)

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A nuclear transport inhibitor that modulates the unfolded protein response and provides in vivo protection against lethal dengue virus infection. Fraser JE, Watanabe S, Wang C, et al. J. Infect. Dis. 210(11), 1780-91, (2014)

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Retinoic acid signaling and mouse embryonic stem cell differentiation: Cross talk between genomic and non-genomic effects of RA. Rochette-Egly C Biochim. Biophys. Acta 1851(1), 66-75, (2015)

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Effects of retinoic acid isomers on proteomic pattern in human breast cancer MCF-7 cell line. Flodrova D, Benkovska D, Macejova D, et al. Endocr. Regul. 47(4), 205-9, (2013)

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[Expression of genes involved in retinoic acid biosynthesis in human gastric cancer]. Kropotova ES, Zinov'eva OL, Zyrianova AF, et al. Mol. Biol. (Mosk.) 47(2), 317-30, (2013)

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Retinoic acid syndrome--cardiac complication. Dhar AK and Barman PK J. Assoc. Physicians India 60, 63-5, (2012)

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[Neurogenic potential of human mesenchymal stem cells isolated from bone marrow, adipose tissue and endometrium: a comparative study]. Zemel'ko VI, Kozhukharova IB, Alekseenko LL, et al. Tsitologiia 55(2), 101-10, (2013)

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[Picture in clinical hematology no. 61]. Rinsho. Ketsueki. 54(3), 261, (2013)

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[Signaling pathway of meiosis induced by retinoic acid during spermatogenesis]. Wang K and Wu YJ Zhonghua Nan Ke Xue 19(2), 173-7, (2013)

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[Thrombosis of the cerebral veins and sinuses in acute promyelocytic leukemia after all-trans retinoic acid treatment: a case report and literature review]. Song LX, Zhou LY, and Li X Zhonghua Xue Ye Xue Za Zhi 33(11), 948-50, (2012)

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[Therapeutic effect of retinoic acid in lupus nephritis]. Kinoshita K and Funauchi M Nihon Rinsho. Meneki. Gakkai Kaishi 35(1), 1-7, (2012)

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Clindamycin-tretinoin (veltin gel) for acne. Med. Lett. Drugs Ther. 52(1353-1354), 102-3, (2010)

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Studies on Multifunctional Effect of All-Trans Retinoic Acid (ATRA) on Matrix Metalloproteinase-2 (MMP-2) and Its Regulatory Molecules in Human Breast Cancer Cells (MCF-7). Dutta A J. Oncol. 2009, 627840, (2009)

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Clinical safety and efficacy studies of a novel formulation combining 1.2% clindamycin phosphate and 0.025% tretinoin for the treatment of acne vulgaris. Schlessinger J, Menter A, Gold M, et al. Journal. of. Drugs in. Dermatology. 6(6), 607-15, (2007)

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Clindamycin/tretinoin: clindamycin phosphate/tretinoin gel. Drugs R. D. 6(4), 231-4, (2005)

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Topical tretinoin or adapalene in acne vulgaris: an overview. Jain S J. Dermatolog. Treat. 15(4), 200-7, (2004)

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Spectrophotometric determination of drugs with iodine. Karuna T, et al. J. Sci. Ind. Res. 65(10), 808, (2006)

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Panaxadiol glycosides that induce neuronal differentiation in neurosphere stem cells. Jia Wei Liu et al J. Nat. Prod. 70, 1329-34, (2007)

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Toll-like receptor 3 (TLR3) activation induces microRNA-dependent reexpression of functional RARβ and tumor regression. Galli R, Paone A, Fabbri M, et al. Proc. Natl. Acad. Sci. U. S. A. 110(24), 9812-7, (2013)

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Synaptic signaling by all-trans retinoic acid in homeostatic synaptic plasticity. Aoto J Neuron 60(2), 308-20, (2008)

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Vitamin A and retinoic acid in T cell-related immunity. Ross AC Am. J. Clin. Nutr. 96(5), 1166S-72S, (2012)

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linc-HOXA1 is a noncoding RNA that represses Hoxa1 transcription in cis. Maamar H, Cabili MN, Rinn J, et al. Genes Dev. 27(11), 1260-71, (2013)

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Dimeric combinations of MafB, cFos and cJun control the apoptosis-survival balance in limb morphogenesis. Suda N, Itoh T, Nakato R, et al. Development 141(14), 2885-94, (2014)

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Oral tetra-arsenic tetra-sulfide formula versus intravenous arsenic trioxide as first-line treatment of acute promyelocytic leukemia: a multicenter randomized controlled trial. Zhu HH, Wu DP, Jin J, et al. J. Clin. Oncol. 31(33), 4215-21, (2013)

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Molecular pathways: current role and future directions of the retinoic acid pathway in cancer prevention and treatment. Connolly RM, Nguyen NK, and Sukumar S Clin. Cancer Res. 19(7), 1651-9, (2013)

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Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species. Denis Fourches et al Chem. Res. Toxicol. 23, 171-83, (2010)

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Vitamin A and immune regulation: role of retinoic acid in gut-associated dendritic cell education, immune protection and tolerance. Cassani B, Villablanca EJ, De Calisto J, et al. Mol. Aspects Med. 33(1), 63-76, (2012)

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Synergy against PML-RARa: targeting transcription, proteolysis, differentiation, and self-renewal in acute promyelocytic leukemia. Dos Santos GA, Kats L, and Pandolfi PP J. Exp. Med. 210(13), 2793-802, (2013)

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Chalcones and other compounds from the exudates of Angelica keiskei and their cancer chemopreventive effects. Toshihiro Akihisa et al J. Nat. Prod. 69, 38-42, (2006)

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Synthesis and biological characterization of the histone deacetylase inhibitor largazole and C7- modified analogues. José A Souto et al J. Med. Chem. 53, 4654-67, (2010)

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A monoclonal antibody TrkB receptor agonist as a potential therapeutic for Huntington's disease. Todd D, Gowers I, Dowler SJ, et al. PLoS ONE 9(2), e87923, (2014)

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Topical tretinoin in acne therapy. Webster GF J. Am. Acad. Dermatol. 39(2 Pt 3), S38-44, (1998)

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How well can the Caco-2/Madin-Darby canine kidney models predict effective human jejunal permeability? Alex Avdeef et al J. Med. Chem. 53, 3566-84, (2010)

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miR-34a regulates mouse neural stem cell differentiation. Márcia M. Aranha et al PLoS ONE 6, e21396, (2011)

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Developing structure-activity relationships for the prediction of hepatotoxicity. Nigel Greene et al Chem. Res. Toxicol. 23, 1215-22, (2010)

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The angiogenic factor midkine is regulated by dexamethasone and retinoic acid during alveolarization and in alveolar epithelial cells. Zhang H Respir. Res. 10, 77, (2009)

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Analysis, occurrence, and function of 9-cis-retinoic acid. Kane MA Biochim. Biophys. Acta 1821(1), 10-20, (2012)

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Prognostic impact of KMT2E transcript levels on outcome of patients with acute promyelocytic leukaemia treated with all-trans retinoic acid and anthracycline-based chemotherapy: an International Consortium on Acute Promyelocytic Leukaemia study. Lucena-Araujo AR, Kim HT, Jacomo RH, et al. Br. J. Haematol. 166(4), 540-9, (2014)

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Alpha-synuclein alters Notch-1 expression and neurogenesis in mouse embryonic stem cells and in the hippocampus of transgenic mice. Crews L J. Neurosci. 28(16), 4250-60, (2008)

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Sex-specific differences in expression of histone demethylases Utx and Uty in mouse brain and neurons. Jun Xu et al J. Neurosci. 28, 4521-7, (2009)

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Retinoid-like activity and teratogenic effects of cyanobacterial exudates. Jonas A, Buranova V, Scholz S, et al. Aquat. Toxicol. 155, 283-90, (2014)

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Arsenic trioxide during consolidation for patients with previously untreated low/intermediate risk acute promyelocytic leukaemia may eliminate the need for maintenance therapy. Coutre SE, Othus M, Powell B, et al. Br. J. Haematol. 165(4), 497-503, (2014)

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Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum. Jing Yuan et al Nat. Chem. Biol. 5, 765-71, (2009)

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Cell differentiation inducers derived from thalidomide. Tomomi Noguchi et al Bioorg. Med. Chem. Lett. 15, 3212-5, (2005)

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Synthesis of new alkylaminooxysterols with potent cell differentiating activities: identification of leads for the treatment of cancer and neurodegenerative diseases. Philippe de Medina et al J. Med. Chem. 52, 7765-77, (2009)

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Photoaging therapy with topical tretinoin: an evidence-based analysis. Kang S and Voorhees JJ J. Am. Acad. Dermatol. 39(2 Pt 3), S55-61, (1998)

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Enzymology of retinoic acid biosynthesis and degradation. Kedishvili NY J. Lipid Res. 54(7), 1744-60, (2013)

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Cancer chemopreventive effects of cycloartane-type and related triterpenoids in in vitro and in vivo models. Takashi Kikuchi et al J. Nat. Prod. 70, 918-22, (2007)

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Tazarotene versus tretinoin or adapalene in the treatment of acne vulgaris. Kakita L J. Am. Acad. Dermatol. 43(2 Pt 3), S51-4, (2000)

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p62/SQSTM1 upregulation constitutes a survival mechanism that occurs during granulocytic differentiation of acute myeloid leukemia cells. Trocoli A, Bensadoun P, Richard E, et al. Cell Death Differ. 21(12), 1852-61, (2014)

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Diverting T helper cell trafficking through increased plasticity attenuates autoimmune encephalomyelitis. Califano D, Sweeney KJ, Le H, et al. J. Clin. Invest. 124(1), 174-87, (2014)

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Mechanisms of action and resistance to all-trans retinoic acid (ATRA) and arsenic trioxide (As2O 3) in acute promyelocytic leukemia. Tomita A, Kiyoi H, and Naoe T Int. J. Hematol. 97(6), 717-25, (2013)

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Adamantyl-substituted retinoid-derived molecules that interact with the orphan nuclear receptor small heterodimer partner: effects of replacing the 1-adamantyl or hydroxyl group on inhibition of cancer cell growth, induction of cancer cell apoptosis, and inhibition of SRC homology 2 domain-containing protein tyrosine phosphatase-2 activity. Marcia I Dawson et al J. Med. Chem. 51, 5650-62, (2008)

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Differential BMP signaling controls formation and differentiation of multipotent preplacodal ectoderm progenitors from human embryonic stem cells. Leung AW, Kent Morest D, and Li JY Dev. Biol. 379(2), 208-20, (2013)

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Long-range regulation by shared retinoic acid response elements modulates dynamic expression of posterior Hoxb genes in CNS development. Ahn Y, Mullan HE, and Krumlauf R Dev. Biol. 388(1), 134-44, (2014)

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Retinoic acid inhibits CD25+ dendritic cell expansion and γδ T-cell activation in experimental autoimmune uveitis. Liang D, Zuo A, Shao H, et al. Invest. Ophthalmol. Vis. Sci. 54(5), 3493-503, (2013)

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Hemogenic endothelial cell specification requires c-Kit, Notch signaling, and p27-mediated cell-cycle control. Marcelo KL, Sills TM, Coskun S, et al. Dev. Cell 27(5), 504-15, (2013)

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Dynamics and precision in retinoic acid morphogen gradients. Schilling TF, Nie Q, and Lander AD Curr. Opin. Genet. Dev. 22(6), 562-9, (2012)

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Biflavonoids isolated from Selaginella tamariscina regulate the expression of matrix metalloproteinase in human skin fibroblasts. Chan-Woo Lee et al Bioorg. Med. Chem. 16, 732-8, (2008)

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Polycomb recruitment attenuates retinoic acid-induced transcription of the bivalent NR2F1 gene. Laursen KB, Mongan NP, Zhuang Y, et al. Nucleic Acids Res. 41(13), 6430-43, (2013)

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Reduced skin irritation with tretinoin containing polyolprepolymer-2, a new topical tretinoin delivery system: a summary of preclinical and clinical investigations. Quigley JW and Bucks DA J. Am. Acad. Dermatol. 38(4), S5-10, (1998)

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Control of T cell fates and immune tolerance by p38α signaling in mucosal CD103+ dendritic cells. Huang G, Wang Y, and Chi H J. Immunol. 191(2), 650-9, (2013)

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Discovery of a potent, orally available, and isoform-selective retinoic acid β2 receptor agonist. Lund, B.W., et al. J. Med. Chem. 48, 7517-7519, (2005)

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Rapid suppression of inhibitory synaptic transmission by retinoic acid. Sarti F, Zhang Z, Schroeder J, et al. J. Neurosci. 33(28), 11440-50, (2013)

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A predictive ligand-based Bayesian model for human drug-induced liver injury. Sean Ekins et al Drug Metab. Dispos. 38, 2302-8, (2010)

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Histone H3K27 trimethylation inhibits H3 binding and function of SET1-like H3K4 methyltransferase complexes. Kim DH, Tang Z, Shimada M, et al. Mol. Cell. Biol. 33(24), 4936-46, (2013)

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Macrophages are more potent immune suppressors ex vivo than immature myeloid-derived suppressor cells induced by metastatic murine mammary carcinomas. Hamilton MJ, Bosiljcic M, Lepard NE, et al. J. Immunol. 192(1), 512-22, (2014)

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Biophysical characteristics reveal neural stem cell differentiation potential. Labeed FH PLoS ONE 6(9), e25458, (2011)

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Small GTPase Rab39A interacts with UACA and regulates the retinoic acid-induced neurite morphology of Neuro2A cells. Mori Y, Matsui T, Omote D, et al. Biochem. Biophys. Res. Commun. 435(1), 113-9, (2013)

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Amiodarone and bepridil inhibit anthrax toxin entry into host cells. Ana M Sanchez et al Antimicrob. Agents Chemother. 51, 2403-11, (2007)

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Design, synthesis, and evaluation of novel mutual prodrugs (hybrid drugs) of all-trans-retinoic acid and histone deacetylase inhibitors with enhanced anticancer activities in breast and prostate cancer cells in vitro. Lalji K Gediya et al J. Med. Chem. 51, 3895-904, (2008)

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Switching axial progenitors from producing trunk to tail tissues in vertebrate embryos. Jurberg AD, Aires R, Varela-Lasheras I, et al. Dev. Cell 25(5), 451-62, (2013)

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Modulation of neuritogenesis by a protein implicated in X-linked mental retardation. Jiao X J. Neurosci. 29(40), 12419-27, (2009)

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Syntheses, antiproliferative activity and theoretical characterization of acitretin-type retinoids with changes in the lipophilic part. Magoulas, G. E.; et al. Eur. J. Med. Chem. 46, 721, (2011)

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Role of UTX in retinoic acid receptor-mediated gene regulation in leukemia. Rocha-Viegas L, Villa R, Gutierrez A, et al. Mol. Cell. Biol. 34(19), 3765-75, (2014)

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Apoptotic cells induce dendritic cell-mediated suppression via interferon-γ-induced IDO. Charlotte A Williams et al Immunology 124, 89-101, (2008)

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Increased production of retinoic acid by intestinal macrophages contributes to their inflammatory phenotype in patients with Crohn's disease. Sanders TJ, McCarthy NE, Giles EM, et al. Gastroenterology 146(5), 1278-88.e1-2, (2014)

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Retinoic acid signaling in cancer: The parable of acute promyelocytic leukemia. Ablain J and de Thé H Int. J. Cancer 135(10), 2262-72, (2014)

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Genome-wide analysis reveals a role for BRCA1 and PALB2 in transcriptional co-activation. Gardini A, Baillat D, Cesaroni M, et al. EMBO J. 33(8), 890-905, (2014)

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Retinoic acid controls body axis extension by directly repressing Fgf8 transcription. Kumar S and Duester G Development 141(15), 2972-7, (2014)

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Spalt-like 4 promotes posterior neural fates via repression of pou5f3 family members in Xenopus. Young JJ, Kjolby RA, Kong NR, et al. Development 141(8), 1683-93, (2014)

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Retinoic acid regulation of male meiosis. Hogarth CA and Griswold MD Curr. Opin. Endocrinol. Diabetes. Obes. 20(3), 217-23, (2013)

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Identification and quantitation of biomarkers for radiation-induced injury via mass spectrometry. Jones JW, Scott AJ, Tudor G, et al. Health Phys. 106(1), 106-19, (2014)

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DLG1 influences distal ureter maturation via a non-epithelial cell autonomous mechanism involving reduced retinoic acid signaling, Ret expression, and apoptosis. Kim ST, Ahn SY, Swat W, et al. Dev. Biol. 390(2), 160-9, (2014)

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Activation of c-jun N-terminal kinase upon influenza A virus (IAV) infection is independent of pathogen-related receptors but dependent on amino acid sequence variations of IAV NS1. Nacken W, Anhlan D, Hrincius ER, et al. J. Virol. 88(16), 8843-52, (2014)

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Prohibitin 2 represents a novel nuclear AKT substrate during all-trans retinoic acid-induced differentiation of acute promyelocytic leukemia cells. Bavelloni A, Piazzi M, Faenza I, et al. FASEB J. 28(5), 2009-19, (2014)

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MicroRNA-432 contributes to dopamine cocktail and retinoic acid induced differentiation of human neuroblastoma cells by targeting NESTIN and RCOR1 genes. Das E and Bhattacharyya NP FEBS Lett., doi:10.1016/j.febslet.2014.03.015, (2014)

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All trans-retinoic acid (ATRA) induces re-differentiation of early transformed breast epithelial cells. Arisi MF, Starker RA, Addya S, et al. Int. J. Oncol. 44(6), 1831-42, (2014)

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The effects of retinoic acid on human corneal stromal keratocytes cultured in vitro under serum-free conditions. Gouveia RM and Connon CJ Invest. Ophthalmol. Vis. Sci. 54(12), 7483-91, (2013)

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Removal characteristics of retinoic acids and 4-oxo-retinoic acids in wastewater by activated sludge treatment. Inoue D, Sawada K, Wada Y, et al. Water Sci. Technol. 67(12), 2868-74, (2013)

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Epidermal growth factor receptor transactivation by intracellular prostaglandin E2-activated prostaglandin E2 receptors. Role in retinoic acid receptor-β up-regulation. Fernández-Martínez AB and Lucio Cazaña FJ Biochim. Biophys. Acta 1833(9), 2029-38, (2013)

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The potential mechanism for the different expressions of gelatinases induced by all-trans retinoic acid in different cells. Zhou TB and Qin YH J. Recept. Signal Transduct. Res. 32(3), 129-33, (2012)

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Short- and long-term histologic effects of topical tretinoin on photodamaged skin. Bhawan J Int. J. Dermatol. 37(4), 286-92, (1998)

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ATRA alters humoral responses associated with amelioration of EAMG symptoms by balancing Tfh/Tfr helper cell profiles. Xie X, Mu L, Yao X, et al. Clin. Immunol. 148(2), 162-76, (2013)

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Retinoic acid signalling in gastrointestinal parasite infections: lessons from mouse models. Hurst RJ and Else KJ Parasite Immunol. 34(7), 351-9, (2012)

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Use of tretinoin in female health practice. Elson ML Int. J. Fertil. Womens. Med. 43(2), 117-21, (1998)

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Germ lineage properties in the urochordate Botryllus schlosseri - from markers to temporal niches. Rosner A, Moiseeva E, Rabinowitz C, et al. Dev. Biol. 384(2), 356-74, (2013)

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Design and synthesis of 4-HPR derivatives for rhabdoid tumors. Bhaskar C Das et al Bioorg. Med. Chem. Lett. 18, 3805-8, (2008)

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Micronutrients and oral clefts: a case-control study. McKinney CM, Chowchuen B, Pitiphat W, et al. J. Dent. Res. 92(12), 1089-94, (2013)

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ERF and ETV3L are retinoic acid-inducible repressors required for primary neurogenesis. Janesick A, Abbey R, Chung C, et al. Development 140(15), 3095-106, (2013)

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How we prevent and treat differentiation syndrome in patients with acute promyelocytic leukemia. Sanz MA and Montesinos P Blood 123(18), 2777-82, (2014)

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Stromal heparan sulfate differentiates neuroblasts to suppress neuroblastoma growth. Knelson EH, Gaviglio AL, Nee JC, et al. J. Clin. Invest. 124(7), 3016-31, (2014)

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Preparation of spermine conjugates with acidic retinoids with potent ribonuclease P inhibitory activity. George Magoulas et al Eur. J. Med. Chem. 44, 2689-95, (2009)

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Mesenchymal TGF-β signaling orchestrates dental epithelial stem cell homeostasis through Wnt signaling. Yang G, Zhou J, Teng Y, et al. Stem Cells 32(11), 2939-48, (2014)

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14-3-3ε and NAV2 interact to regulate neurite outgrowth and axon elongation. Marzinke MA, Mavencamp T, Duratinsky J, et al. Arch. Biochem. Biophys. 540(1-2), 94-100, (2013)

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Photoaging and tretinoin. Kang S Dermatol. Clin. 16(2), 357-64, (1998)

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Reversal of skin aging with topical retinoids. Hubbard BA, Unger JG, and Rohrich RJ Plast. Reconstr. Surg. 133(4), 481e-90e, (2014)

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All-trans retinoic acid regulates hepatic bile acid homeostasis. Yang F, He Y, Liu HX, et al. Biochem. Pharmacol. 91(4), 483-9, (2014)

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Cyp26 enzymes are required to balance the cardiac and vascular lineages within the anterior lateral plate mesoderm. Rydeen AB and Waxman JS Development 141(8), 1638-48, (2014)

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Retinoic acid controls proper head-to-trunk linkage in zebrafish by regulating an anteroposterior somitogenetic rate difference. Retnoaji B, Akiyama R, Matta T, et al. Development 141(1), 158-65, (2014)

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Activation of K(2)P channel-TREK1 mediates the neuroprotection induced by sevoflurane preconditioning. Tong L, Cai M, Huang Y, et al. Br. J. Anaesth. 113(1), 157-67, (2014)

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Potent anticancer activities of novel aminophenol analogues against various cancer cell lines. Toshihiro Ohba et al Bioorg. Med. Chem. 15, 847-53, (2007)

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Epidermal growth factor receptor activity is necessary for mouse basal cell proliferation. Brechbuhl HM, Li B, Smith RW, et al. Am. J. Physiol. Lung Cell. Mol. Physiol. 307(10), L800-10, (2014)

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Potential for all-trans retinoic acid (tretinoin) to enhance interferon-alpha treatment response in chronic myelogenous leukemia, melanoma, myeloma and renal cell carcinoma. Kast RE Cancer Biol. Ther. 7(10), 1515-9, (2008)

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BBS4 is necessary for ciliary localization of TrkB receptor and activation by BDNF. Leitch CC and Zaghloul NA PLoS ONE 9(5), e98687, (2014)

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All-trans retinoic acid modulates mitogen-activated protein kinase pathway activation in human scleral fibroblasts through retinoic acid receptor beta. Huo L, Cui D, Yang X, et al. Mol. Vis. 19, 1795-803, (2013)

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Explant cultures of Rpe65-/- mouse retina: a model to investigate cone opsin trafficking. Bandyopadhyay M, Kono M, and Rohrer B Mol. Vis. 19, 1149-57, (2013)

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Arsenite retards the cardiac differentiation of rat cardiac myoblast H9c2 cells. Sumi D, Abe K, and Himeno S Biochem. Biophys. Res. Commun. 436(2), 175-9, (2013)

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Predictive factors for all-trans retinoic acid-related differentiation syndrome in patients with acute promyelocytic leukemia. Leblebjian H, DeAngelo DJ, Skirvin JA, et al. Leuk. Res. 37(7), 747-51, (2013)

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Efficient synthesis and biological evaluation of demethyl geranylgeranoic acid derivatives. Akimori Wada et al Bioorg. Med. Chem. 18, 5795-806, (2010)

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Interplay between estrogen and retinoid signaling in breast cancer--current and future perspectives. Ribeiro MP, Santos AE, and Custódio JB Cancer Lett. 353(1), 17-24, (2014)

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Retinoic acid regulates several genes in bile acid and lipid metabolism via upregulation of small heterodimer partner in hepatocytes. Mamoon A, Subauste A, Subauste MC, et al. Gene 550(2), 165-70, (2014)

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All-trans-retinoic acid improves cholestasis in α-naphthylisothiocyanate-treated rats and Mdr2-/- mice. Cai SY, Mennone A, Soroka CJ, et al. J. Pharmacol. Exp. Ther. 349(1), 94-8, (2014)

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Nitric oxide and interleukin-1β stimulate the proteasome-independent degradation of the retinoic acid hydroxylase CYP2C22 in primary rat hepatocytes. Lee CM, Lee BS, Arnold SL, et al. J. Pharmacol. Exp. Ther. 348(1), 141-52, (2014)

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Effect of conjugates of all-trans-retinoic acid and shorter polyene chain analogues with amino acids on prostate cancer cell growth. Eldem Sadikoglou et al Eur. J. Med. Chem. 44, 3175-87, (2009)

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PMA withdrawal in PMA-treated monocytic THP-1 cells and subsequent retinoic acid stimulation, modulate induction of apoptosis and appearance of dendritic cells. Spano A, Barni S, and Sciola L Cell Prolif. 46(3), 328-47, (2013)

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Biological functional annotation of retinoic acid alpha and beta in mouse liver based on genome-wide binding. He Y, Tsuei J, and Wan YJ Am. J. Physiol. Gastrointest. Liver Physiol. 307(2), G205-18, (2014)

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A novel RARα/CAR-mediated mechanism for regulation of human organic solute transporter-β gene expression. Xu S, Sun AQ, and Suchy FJ Am. J. Physiol. Gastrointest. Liver Physiol. 306(2), G154-62, (2014)

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CTCF controls HOXA cluster silencing and mediates PRC2-repressive higher-order chromatin structure in NT2/D1 cells. Xu M, Zhao GN, Lv X, et al. Mol. Cell. Biol. 34(20), 3867-79, (2014)

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Neuronal hypoxia in vitro: investigation of therapeutic principles of HUCB-MNC and CD133+ stem cells. Doreen M Reich et al BMC Neurosci. 9, 91, (2008)

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Acetylcholine receptors regulate gene expression that is essential for primitive streak formation in murine embryoid bodies. Arima N, Uchida Y, Yu R, et al. Biochem. Biophys. Res. Commun. 435(3), 447-53, (2013)

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Decreased SIRT2 activity leads to altered microtubule dynamics in oxidatively-stressed neuronal cells: implications for Parkinson's disease. Patel VP and Chu CT Exp. Neurol. 257, 170-81, (2014)

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Novel non-carboxylic acid retinoids: 1,2,4-oxadiazol-5-one derivatives. Julie Charton et al Bioorg. Med. Chem. Lett. 19, 489-92, (2009)

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Retinoic acid plays an evolutionarily conserved and biphasic role in pancreas development. Huang W, Wang G, Delaspre F, et al. Dev. Biol. 394(1), 83-93, (2014)

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Retinoic acid isomers facilitate apolipoprotein E production and lipidation in astrocytes through the retinoid X receptor/retinoic acid receptor pathway. Zhao J, Fu Y, Liu CC, et al. J. Biol. Chem. 289(16), 11282-92, (2014)

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Treatment of multiple miliary osteoma cutis of the face with local application of tretinoin (all-trans-retinoic acid): a case report and review of the literature. Cohen AD, Chetov T, Cagnano E, et al. J. Dermatolog. Treat. 12(3), 171-3, (2001)

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Diagnostic immunophenotype of acute promyelocytic leukemia before and early during therapy with all-trans retinoic acid. Horna P, Zhang L, Sotomayor EM, et al. Am. J. Clin. Pathol. 142(4), 546-52, (2014)

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The influence of retinoic Acid and thalidomide on the radiosensitivity of u343 glioblastoma cells. Milanović D, Maier P, Schanne DH, et al. Anticancer Res. 34(4), 1885-91, (2014)

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Retinoic acid signaling in spinal cord development. Lara-Ramírez R, Zieger E, and Schubert M Int. J. Biochem. Cell Biol. 45(7), 1302-13, (2013)

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Computational prediction and in vitro analysis of potential physiological ligands of the bile acid binding site in cytochrome c oxidase. Buhrow L, Hiser C, Van Voorst JR, et al. Biochemistry 52(40), 6995-7006, (2013)

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Effect of all-trans-retinoic acid on enterovirus 71 infection in vitro. Chen S, Yang Y, Xu J, et al. Br. J. Nutr. 111(9), 1586-93, (2014)

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Mequinol 2%/tretinoin 0.01% topical solution for the treatment of melasma in men: a case series and review of the literature. Keeling J, Cardona L, Benitez A, et al. Cutis. 81(2), 179-83, (2008)

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Small ubiquitin-related modifier-1 modification regulates all-trans-retinoic acid-induced differentiation via stabilization of retinoic acid receptor α. Zhou Q, Zhang L, Chen Z, et al. FEBS J. 281(13), 3032-47, (2014)

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Effects of hyperbaric oxygen treatment on antimicrobial function and apoptosis of differentiated HL-60 (neutrophil-like) cells. Almzaiel AJ, Billington R, Smerdon G, et al. Life Sci. 93(2-3), 125-31, (2013)

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Effects of all-trans-retinoic acid on the permeability transition and bioenergetic functions of rat liver mitochondria in combination with endoxifen. Ribeiro MP, Santos AE, Santos MS, et al. Life Sci. 93(2-3), 96-107, (2013)

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Retinoic acid prevents Chlamydia pneumoniae-induced foam cell development in a mouse model of atherosclerosis. Jiang SJ Microbes Infect. 10(12-13), 1393-7, (2008)

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3-[6-(2-Dimethylamino-1-imidazol-1-yl-butyl)-naphthalen-2-yloxy]-2,2-dimethyl-propionic acid as a highly potent and selective retinoic acid metabolic blocking agent. Mark J Mulvihill et al Bioorg. Med. Chem. Lett. 16, 2729-33, (2006)

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BCL-xL/MCL-1 inhibition and RARγ antagonism work cooperatively in human HL60 leukemia cells. Perri M, Yap JL, Yu J, et al. Exp. Cell Res. 327(2), 183-91, (2014)

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Foxa1 contributes to the repression of Nanog expression by recruiting Grg3 during the differentiation of pluripotent P19 embryonal carcinoma cells. Chen T, He S, Zhang Z, et al. Exp. Cell Res. 326(2), 326-35, (2014)

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Src family kinase inhibitor PP2 enhances differentiation of acute promyelocytic leukemia cell line induced by combination of all-trans-retinoic acid and arsenic trioxide. Jung YS, Cheong HJ, Kim SJ, et al. Leuk. Res. 38(8), 977-82, (2014)

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Synthesis and in vitro biological activity of retinyl polyhydroxybenzoates, novel hybrid retinoid derivatives. Sungbum Kim et al Bioorg. Med. Chem. Lett. 19, 508-12, (2009)

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Superficial dermabrasion versus topical tretinoin on early striae distensae: a randomized, pilot study. Hexsel D, Soirefmann M, Porto MD, et al. Dermatol. Surg. 40(5), 537-44, (2014)

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Role of cell cycle regulatory molecules in retinoic acid- and vitamin D3-induced differentiation of acute myeloid leukaemia cells. Hu XT and Zuckerman KS Cell Prolif. 47(3), 200-10, (2014)

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Conservation of position-specific gene expression in axolotl limb skin. Satoh A and Makanae A Zoolog. Sci. 31(1), 6-13, (2014)

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Oroxylin A inhibits ATRA-induced IL-6 expression involved in retinoic acid syndrome by down-regulating CHOP. Hui H, Yang H, Dai Q, et al. Gene 551(2), 230-5, (2014)

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The effect to IL-3Ralpha, downstream PI3k/Akt signaling of all-trans retinoic acid and arsenic trioxide in NB4 cells. Chen P, Wu JY, Huang HF, et al. Pharmazie 69(4), 297-300, (2014)

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Retinoic acid generates regulatory T cells in experimental transplantation. Moore C, Fuentes C, Sauma D, et al. Transplant. Proc. 43(6), 2334-7, (2011)

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Clindamycin phosphate 1.2%- tretinoin 0.025% gel: vehicle characteristics, stability, and tolerability. Del Rosso JQ, Jitpraphai W, Bhambri S, et al. Cutis. 81(5), 405-8, (2008)

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Resolution of radiation-induced acneform eruption following treatment with tretinoin and minocycline: a case report. Parr K, Mahmoudizad R, and Grimwood R Cutis. 92(1), 27-8, (2013)

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Alitretinoin: a new treatment option for hereditary punctate palmoplantar keratoderma (Brauer-Buschke-Fischer syndrome). Raone B, Raboni R, and Patrizi A J. Am. Acad. Dermatol. 71(2), e48-9, (2014)

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Efficacy of oral alitretinoin for the treatment of Darier disease: a case report. Anuset D, Goutorbe C, Bernard P, et al. J. Am. Acad. Dermatol. 71(2), e46-8, (2014)

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Immunology: A is for immunity. Eberl G Nature 508(7494), 47-8, (2014)

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Successful treatment of high-risk acute promyelocytic leukemia in very elderly patients using all-trans retinoic acid plus reduced-dose idarubicin. Fujisawa T, Takeda J, Aoki K, et al. Ann. Hematol. 93(9), 1621-3, (2014)

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Treatment of acute promyelocytic leukemia. Miura Y, Suyama K, and Takano T N. Engl. J. Med. 369(15), 1471-2, (2013)

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Treatment of acute promyelocytic leukemia. Lo-Coco F, Orlando SM, and Platzbecker U N. Engl. J. Med. 369(15), 1472, (2013)

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All-transretinoic acid regulates Th1/Th2 balance in CD4+ T cells when GATA-3 is deficient. Zhu YF, Hu JZ, Zhao PN, et al. Biomed. Environ. Sci. 26(9), 774-7, (2013)

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Targeting agents alone to cure acute promyelocytic leukemia. Chen SJ and Chen Z N. Engl. J. Med. 369(2), 186-7, (2013)

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Vitamin A notches up CD11b hi DC development. Stock AT and Bedoui S Eur. J. Immunol. 43(6), 1441-4, (2013)

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Mees lines and Beau lines. Chesnut G, Taylor S, and Belin E Cutis. 91(3), 147, 150-1, (2013)

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Another approach to actinic keratosis management using nonablative fractional laser. Pearce DJ and Williford PM J. Dermatolog. Treat. 25(4), 298, (2014)

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Merck 14,8165

Beil. 9,IV,2387

Aldrich MSDS 1, 1587:C / Corp MSDS 1 (2), 3045:B / FT-IR 2 (1), 839:C / FT-IR 1 (1), 505:A / FT-NMR 1 (1), 790:A / IR-Spectra (3), 296:E / NMR-Reference 2 (1), 438:C / RegBook 1 (1), 553:J / Sax 6, 2364 / Sigma FT-IR 1 (2), 881:D / Structure Index 1, 84:C:4

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