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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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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 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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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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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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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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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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Differentiation Of Spinal Motor Neurons From Pluripotent Human Stem Cells. Hu, B.Y., and Zhang, S.C. Nat. Protoc. 4, 1295-304, (2009)

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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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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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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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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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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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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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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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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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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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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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Liposomal formulation of retinoids designed for enzyme triggered release. Palle J Pedersen et al J. Med. Chem. 53, 3782-92, (2010)

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Control Of Alpha4β7 Integrin Expression And CD4 T Cell Homing By The β1 Integrin Subunit DeNucci, C., et al. J. Immunol. 184, 2458-2467, (2010)

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

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Kif7 is required for the patterning and differentiation of the diaphragm in a model of syndromic congenital diaphragmatic hernia. Coles GL and Ackerman KG Proc. Natl. Acad. Sci. U. S. A. 110(21), E1898-905, (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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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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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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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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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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Photoaging and tretinoin. Kang S Dermatol. Clin. 16(2), 357-64, (1998)

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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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Transcriptional Activation By MEIS1A In Response To Protein Kinase A Signaling Requires The Transducers Of Regulated CREB Family Of CREB Co-activators. Goh, S.L., et al. J. Thorac. Cardiovasc. Surg. 284, 18904-12, (2009)

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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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Biochemical pathways of retinoid transport, metabolism, and signal transduction. Napoli, J.L. Clin. Immunol. Immunopathol. 80, S52-S62, (1996)

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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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 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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Development: we are what mum eats! Bird L Nat. Rev. Immunol. 14(5), 284-5, (2014)

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In vitro all-trans retinoic acid sensitivity of acute myeloid leukemia blasts with NUP98/RARG fusion gene. Such E, Cordón L, Sempere A, et al. Ann. Hematol. 93(11), 1931-3, (2014)

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

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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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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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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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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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[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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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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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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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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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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Mees lines and Beau lines. Chesnut G, Taylor S, and Belin E Cutis. 91(3), 147, 150-1, (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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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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[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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Generation of dopaminergic neurons from embryonic stem cells. Sasai, Y. J. Neurol. 249, II 41-II 44, (2002)

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Retinoids, apoptosis and cancer. Simoni, D., and Tolomeo, M. Curr. Pharm. Des. 7, 1823-1837, (2001)

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Participation of CYP2C8 in retinoic acid 4-hydroxylation in human hepatic microsomes. Nadin, L Biochem. Pharmacol. 58, 1201-1208, (1999)

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

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

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

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Aldehyde dehydrogenase-1a1 induces oncogene suppressor genes in B cell populations. Yasmeen R, Meyers JM, Alvarez CE, et al. Biochim. Biophys. Acta 1833(12), 3218-27, (2013)

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

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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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Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid. Zebin Xia et al J. Med. Chem. 54, 3793-816, (2011)

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Synthesis and in vitro biological activity of retinyl retinoate, a novel hybrid retinoid derivative. Hyojung Kim et al Bioorg. Med. Chem. 16, 6387-93, (2008)

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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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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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Epimorphic regeneration approach to tissue replacement in adult mammals Agrawal, V., et al. Proc. Natl. Acad. Sci. U. S. A. 107, 3351-5, (2010)

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Lyn Kinase Regulates Mesolimbic Dopamine Release: Implication For Alcohol Reward. Gibb, S.L., et al. J. Neurosci. 31, 2180-7, (2011)

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

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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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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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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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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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All-trans retinoic acid and sodium butyrate enhance natriuretic peptide receptor a gene transcription: role of histone modification. Kumar P, Periyasamy R, Das S, et al. Mol. Pharmacol. 85(6), 946-57, (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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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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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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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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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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