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47868 Supelco

D-Biotin

analytical standard

Synonym: D-Biotin, Bios II, Biotin, Coenzyme R, Vitamin B7, Vitamin H

  • CAS Number 58-85-5

  • Empirical Formula (Hill Notation) C10H16N2O3S

  • Molecular Weight 244.31

  •  Beilstein Registry Number 86838

  •  EC Number 200-399-3

  •  MDL number MFCD00005541

  •  PubChem Substance ID 24871542

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Properties

Related Categories Additional Standards, Analytical Standards, Analytical/Chromatography, Application Areas and Market Segments, Cell Biology,
grade   analytical standard
form   neat
feature   standard type water soluble vitamin
packaging   ampule of 100 mg
mp   231-233 °C(lit.)
format   neat
storage temp.   2-8°C

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Safety & Documentation

Safety Information

WGK Germany 
1
RTECS 
XJ9088200

Protocols & Articles

Peer-Reviewed Papers

References

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Methylation-dependent and -independent genomic targeting principles of the MBD protein family. Baubec T, Ivánek R, Lienert F, et al. Cell 153(2), 480-92, (2013)

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Imaging of neural ensemble for the retrieval of a learned behavioral program. Aoki T, Kinoshita M, Aoki R, et al. Neuron 78(5), 881-94, (2013)

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Evolutionary origin of insect-Wolbachia nutritional mutualism. Nikoh N, Hosokawa T, Moriyama M, et al. Proc. Natl. Acad. Sci. U. S. A. 111(28), 10257-62, (2014)

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Reward-modulated motor information in identified striatum neurons. Isomura Y, Takekawa T, Harukuni R, et al. J. Neurosci. 33(25), 10209-20, (2013)

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Pattern of innervation and recruitment of different classes of motoneurons in adult zebrafish. Ampatzis K, Song J, Ausborn J, et al. J. Neurosci. 33(26), 10875-86, (2013)

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Layer-by-layer construction of protein architectures through avidin-biotin and lectin-sugar interactions for biosensor applications. Takahashi S, Sato K, and Anzai J Anal. Bioanal. Chem 402(5), 1749-58, (2012)

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Dopamine differentially modulates the excitability of striatal neurons of the direct and indirect pathways in lamprey. Ericsson J, Stephenson-Jones M, Pérez-Fernández J, et al. J. Neurosci. 33(18), 8045-54, (2013)

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Inherently electroactive graphene oxide nanoplatelets as labels for specific protein-target recognition. Loo AH, Bonanni A, and Pumera M Nanoscale 5(17), 7844-8, (2013)

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Reversible lactic acidosis in a newborn with thiamine transporter-2 deficiency. Pérez-Dueñas B, Serrano M, Rebollo M, et al. Pediatrics 131(5), e1670-5, (2013)

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Network state-dependent inhibition of identified hippocampal CA3 axo-axonic cells in vivo. Viney TJ, Lasztoczi B, Katona L, et al. Nat. Neurosci. 16(12), 1802-11, (2013)

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Circuits for grasping: spinal dI3 interneurons mediate cutaneous control of motor behavior. Bui TV, Akay T, Loubani O, et al. Neuron 78(1), 191-204, (2013)

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Comparison of peptide-major histocompatibility complex tetramers and dextramers for the identification of antigen-specific T cells. Dolton G, Lissina A, Skowera A, et al. Clin. Exp. Immunol. 177(1), 47-63, (2014)

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Efferent connections of the parvalbumin-positive (PV1) nucleus in the lateral hypothalamus of rodents. Celio MR, Babalian A, Ha QH, et al. J. Comp. Neurol. 521(14), 3133-53, (2013)

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Distinct dendritic arborization and in vivo firing patterns of parvalbumin-expressing basket cells in the hippocampal area CA3. Tukker JJ, Lasztóczi B, Katona L, et al. J. Neurosci. 33(16), 6809-25, (2013)

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Simultaneous monitoring of presynaptic transmitter release and postsynaptic receptor trafficking reveals an enhancement of presynaptic activity in metabotropic glutamate receptor-mediated long-term depression. Xu W, Tse YC, Dobie FA, et al. J. Neurosci. 33(13), 5867-77, (2013)

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Pyridoxal-5'-phosphate-dependent enzymes involved in biotin biosynthesis: structure, reaction mechanism and inhibition. Mann S and Ploux O Biochim. Biophys. Acta 1814(11), 1459-66, (2011)

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Proliferation and differentiation of cultured human follicular keratinocytes are not influenced by biotin. Limat A, Suormala T, Hunziker T, et al. Arch. Dermatol. Res. 288(1), 31-8, (1996)

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Dynamic tuning of electrical and chemical synaptic transmission in a network of motion coding retinal neurons. Trenholm S, McLaughlin AJ, Schwab DJ, et al. J. Neurosci. 33(37), 14927-38, (2013)

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Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Sreekumar A, Poisson LM, Rajendiran TM, et al. Nature 457(7231), 910-4, (2009)

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In HepG2 cells, coexisting carnitine deficiency masks important indicators of marginal biotin deficiency. Bogusiewicz A, Boysen G, and Mock DM J. Nutr. 145(1), 32-40, (2015)

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Endogenous S-sulfhydration of PTEN helps protect against modification by nitric oxide. Ohno K, Okuda K, and Uehara T Biochem. Biophys. Res. Commun. 456(1), 245-9, (2015)

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Benefit of supplements in functional dyspepsia after treatment of Helicobacter pylori. Pellicano R, Ribaldone DG, Saracco GM, et al. Minerva Gastroenterol. Dietol. 60(4), 263-8, (2014)

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Structure and function of a single-chain, multi-domain long-chain acyl-CoA carboxylase. Tran TH, Hsiao YS, Jo J, et al. Nature 518(7537), 120-4, (2015)

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Adequate intake of biotin in pregnancy: why bother? Mock DM J. Nutr. 144(12), 1885-6, (2014)

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Pregnancy and lactation alter biomarkers of biotin metabolism in women consuming a controlled diet. Perry CA, West AA, Gayle A, et al. J. Nutr. 144(12), 1977-84, (2014)

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[Prospective study of biotin treatment in patients with erythema due to gefitinib or erlotinib]. Ogawa Y, Kiba T, Nakano K, et al. Gan To Kagaku Ryoho. 41(4), 517-22, (2014)

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Hair-shaft abnormality in a 7-year-old girl. Trichorrhexis nodosa dueto biotinidase deficiency. Lünnemann L, Vogt A, Blume-Peytavi U, et al. JAMA Dermatol. 149(3), 357-63, (2013)

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[New approaches in the treatment of deep vein thrombosis]. Nieto Rodríguez JA Med. Clin. (Barc.) 139 Suppl 2, 19-23, (2012)

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A newly discovered function of peroxisomes: involvement in biotin biosynthesis. Maruyama J, Yamaoka S, Matsuo I, et al. Plant Signal Behav. 7(12), 1589-93, (2012)

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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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Avidin-biotin technology in targeted therapy. Lesch HP, Kaikkonen MU, Pikkarainen JT, et al. Expert Opin. Drug Deliv. 7(5), 551-64, (2010)

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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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Chemiluminescence analysis for HBV-DNA hybridization detection with magnetic nanoparticles based DNA extraction from positive whole blood samples. He N, Wang F, Ma C, et al. J. Biomed. Nanotechnol. 9(2), 267-73, (2013)

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Measuring membrane protein stability under native conditions. Chang YC and Bowie JU Proc. Natl. Acad. Sci. U. S. A. 111(1), 219-24, (2014)

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Structure and function of biotin-dependent carboxylases. Tong L Cell. Mol. Life Sci. 70(5), 863-91, (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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Uptake, localization, and noncarboxylase roles of biotin. Zempleni J Annu. Rev. Nutr. 25, 175-96, (2005)

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Allosteric regulation of the biotin-dependent enzyme pyruvate carboxylase by acetyl-CoA. Adina-Zada A, Zeczycki TN, St Maurice M, et al. Biochem. Soc. Trans. 40(3), 567-72, (2012)

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A rapid approach for the detection, quantification, and discovery of novel sulfenic acid or S-nitrosothiol modified proteins using a biotin-switch method. Burgoyne JR and Eaton P Meth. Enzymol. 473, 281-303, (2010)

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Synthetic oligosaccharides as active pharmaceutical ingredients: lessons learned from the full synthesis of one heparin derivative on a large scale. Driguez PA, Potier P, and Trouilleux P Nat. Prod. Rep. 31(8), 980-9, (2014)

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Molecular genetics of biotin metabolism: old vitamin, new science. Gravel RA and Narang MA J. Nutr. Biochem. 16(7), 428-31, (2005)

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A novel growth-promoting pathway formed by GDNF-overexpressing Schwann cells promotes propriospinal axonal regeneration, synapse formation, and partial recovery of function after spinal cord injury. Deng LX, Deng P, Ruan Y, et al. J. Neurosci. 33(13), 5655-67, (2013)

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Triple cysteine module within M-type K+ channels mediates reciprocal channel modulation by nitric oxide and reactive oxygen species. Ooi L, Gigout S, Pettinger L, et al. J. Neurosci. 33(14), 6041-6, (2013)

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A cytometric bead assay for sensitive DNA detection based on enzyme-free signal amplification of hybridization chain reaction. Ren W, Liu H, Yang W, et al. Biosens. Bioelectron. 49, 380-6, (2013)

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Transport of biotin in human keratinocytes. Grafe F, Wohlrab W, Neubert RH, et al. J. Invest. Dermatol. 120(3), 428-33, (2003)

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Evaluating the sensitivity of Mycobacterium tuberculosis to biotin deprivation using regulated gene expression. Woong Park S PLoS Pathog. 7(9), e1002264, (2011)

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Synthesis of the α,ω-dicarboxylic acid precursor of biotin by the canonical fatty acid biosynthetic pathway. Cronan JE and Lin S Curr. Opin. Chem. Biol. 15(3), 407-13, (2011)

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Streptavidin-biotin technology: improvements and innovations in chemical and biological applications. Dundas CM, Demonte D, and Park S Appl. Microbiol. Biotechnol. 97(21), 9343-53, (2013)

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Biotin dependency due to a defect in biotin transport. Mardach R, Zempleni J, Wolf B, et al. J. Clin. Invest. 109(12), 1617-23, (2002)

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Plug-and-play pairing via defined divalent streptavidins. Fairhead M, Krndija D, Lowe ED, et al. J. Mol. Biol. 426(1), 199-214, (2014)

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Biotin-responsive basal ganglia disease should be renamed biotin-thiamine-responsive basal ganglia disease: a retrospective review of the clinical, radiological and molecular findings of 18 new cases. Alfadhel M, Almuntashri M, Jadah RH, et al. Orphanet J. Rare Dis. 8, 83, (2013)

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A substrate-induced biotin binding pocket in the carboxyltransferase domain of pyruvate carboxylase. Lietzan AD and St Maurice M J. Biol. Chem. 288(27), 19915-25, (2013)

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Paraventricular hypothalamic regulation of trigeminovascular mechanisms involved in headaches. Robert C, Bourgeais L, Arreto CD, et al. J. Neurosci. 33(20), 8827-40, (2013)

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Nanoscale adhesion forces between enamel pellicle proteins and hydroxyapatite. Vukosavljevic D, Hutter JL, Helmerhorst EJ, et al. J. Dent. Res. 93(5), 514-9, (2014)

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Lhx3-Chx10 reticulospinal neurons in locomotor circuits. Bretzner F and Brownstone RM J. Neurosci. 33(37), 14681-92, (2013)

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Characterization of SMG-9, an essential component of the nonsense-mediated mRNA decay SMG1C complex. Fernández IS, Yamashita A, Arias-Palomo E, et al. Nucleic Acids Res. 39(1), 347-58, (2011)

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Degradable and biocompatible nanoparticles decorated with cyclic RGD peptide for efficient drug delivery to hepatoma cells in vitro. Loyer P, Bedhouche W, Huang ZW, et al. Int. J. Pharm. 454(2), 727-37, (2013)

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Qualitative and quantitative evaluation of derivatization reagents for different types of protein-bound carbonyl groups. Bollineni RC, Fedorova M, and Hoffmann R Analyst 138(17), 5081-8, (2013)

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A new method for the detection of adenosine based on time-resolved fluorescence sensor. Zhang K, Wang K, Xie M, et al. Biosens. Bioelectron. 49, 226-30, (2013)

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The N and C termini of ZO-1 are surrounded by distinct proteins and functional protein networks. Van Itallie CM, Aponte A, Tietgens AJ, et al. J. Biol. Chem. 288(19), 13775-88, (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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Monosynaptic convergence of chorda tympani and glossopharyngeal afferents onto ascending relay neurons in the nucleus of the solitary tract: a high-resolution confocal and correlative electron microscopy approach. Corson JA and Erisir A J. Comp. Neurol. 521(13), 2907-26, (2013)

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A re-assessment of long distance growth and connectivity of neural stem cells after severe spinal cord injury. Sharp KG, Yee KM, and Steward O Exp. Neurol. 257, 186-204, (2014)

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Closing in on complete pathways of biotin biosynthesis. Lin S and Cronan JE Mol. Biosyst. 7(6), 1811-21, (2011)

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Biotin. Zempleni J, Wijeratne SS, and Hassan YI Biofactors 35(1), 36-46, (2009)

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Neuronal mechanisms of respiratory pattern generation are evolutionary conserved. Cinelli E, Robertson B, Mutolo D, et al. J. Neurosci. 33(21), 9104-12, (2013)

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Nitric oxide synthesis and cGMP production is important for neurite growth and synapse remodeling after axotomy. Cooke RM, Mistry R, Challiss RA, et al. J. Neurosci. 33(13), 5626-37, (2013)

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Biotin synthase: insights into radical-mediated carbon-sulfur bond formation. Fugate CJ and Jarrett JT Biochim. Biophys. Acta 1824(11), 1213-22, (2012)

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QSPR modeling of octanol/water partition coefficient for vitamins by optimal descriptors calculated with SMILES. A A Toropov et al Eur. J. Med. Chem. 43, 714-40, (2008)

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Mechanisms of coordination in distributed neural circuits: encoding coordinating information. Smarandache-Wellmann C and Grätsch S J. Neurosci. 34(16), 5627-39, (2014)

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Biotin requirements for DNA damage prevention. Zempleni J, Teixeira DC, Kuroishi T, et al. Mutat. Res. 733(1-2), 58-60, (2012)

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S-nitrosylation influences the structure and DNA binding activity of AtMYB30 transcription factor from Arabidopsis thaliana. Tavares CP, Vernal J, Delena RA, et al. Biochim. Biophys. Acta 1844(4), 810-7, (2014)

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Implementation of a SPR immunosensor for the simultaneous detection of the 22K and 20K hGH isoforms in human serum samples. de Juan-Franco E, Rodríguez-Frade JM, Mellado M, et al. Talanta 114, 268-75, (2013)

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Vocal corollary discharge communicates call duration to vertebrate auditory system. Chagnaud BP and Bass AH J. Neurosci. 33(48), 18775-80, (2013)

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Functionally diverse biotin-dependent enzymes with oxaloacetate decarboxylase activity. Lietzan AD and St Maurice M Arch. Biochem. Biophys. 544, 75-86, (2014)

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Engineering oscillating microtubule bundles. Sanchez T and Dogic Z Meth. Enzymol. 524, 205-24, (2013)

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Prenatal diagnosis and treatment of holocarboxylase synthetase deficiency. Thuy LP, Belmont J, and Nyhan WL Prenat. Diagn. 19(2), 108-12, (1999)

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A simplified method to attach antibodies on liposomes by biotin-streptavidin affinity for rapid and economical screening of targeted liposomes. Papadia K, Markoutsa E, and Antimisiaris SG J. Biomed. Nanotechnol. 10(5), 871-6, (2014)

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Solitary BioY proteins mediate biotin transport into recombinant Escherichia coli. Finkenwirth F, Kirsch F, and Eitinger T J. Bacteriol. 195(18), 4105-11, (2013)

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Effect of biotin on milk performance of dairy cattle: a meta-analysis. Chen B, Wang C, Wang YM, et al. J. Dairy Sci. 94(7), 3537-46, (2011)

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Histoplasma capsulatum depends on de novo vitamin biosynthesis for intraphagosomal proliferation. Garfoot AL, Zemska O, and Rappleye CA Infect. Immun. 82(1), 393-404, (2014)

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Synthesis of a biotin derivative of iberiotoxin: binding interactions with streptavidin and the BK Ca2+-activated K+ channel expressed in a human cell line. Bingham JP, Bian S, Tan ZY, et al. Bioconjug. Chem. 17(3), 689-99, (2006)

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Biotin status: which are valid indicators and how do we know? Mock DM J. Nutr. 129(2S Suppl), 498S-503S, (1999)

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The enzymes of biotin dependent CO₂ metabolism: what structures reveal about their reaction mechanisms. Waldrop GL, Holden HM, and St Maurice M Protein Sci. 21(11), 1597-619, (2012)

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A protein nanofiber hydrogel for sensitive immunoassays. Lee DS, Park JS, Lee EJ, et al. Analyst 138(17), 4786-94, (2013)

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3'-Biotin-tagged microRNA-27 does not associate with Argonaute proteins in cells. Guo YE and Steitz JA RNA 20(7), 985-8, (2014)

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Brucella BioR regulator defines a complex regulatory mechanism for bacterial biotin metabolism. Feng Y, Xu J, Zhang H, et al. J. Bacteriol. 195(15), 3451-67, (2013)

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Human placental biotin transport: normal characteristics and effect of ethanol. Schenker S, Hu ZQ, Johnson RF, et al. Alcohol. Clin. Exp. Res. 17(3), 566-75, (1993)

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A new immunochemical assay for biotin. Thuy LP, Sweetman L, and Nyhan WL Clin. Chim. Acta 202(3), 191-7, (1991)

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Biotin biosynthesis in Mycobacterium tuberculosis: physiology, biochemistry and molecular intervention. Salaemae W, Azhar A, Booker GW, et al. Protein Cell. 2(9), 691-5, (2011)

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Biotin deficiency in an infant fed with amino acid formula. Fujimoto W, Inaoki M, Fukui T, et al. J. Dermatol. 32(4), 256-61, (2005)

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Biotin derivatives carrying two chelating DOTA units. Synthesis, in vitro evaluation of biotinidases resistance, avidin binding, and radiolabeling tests. Alessandro Pratesi et al J. Med. Chem. 53, 432-40, (2010)

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Determination of water-soluble vitamins in infant milk and dietary supplement using a liquid chromatography on-line coupled to a corona-charged aerosol detector. Márquez-Sillero I, Cárdenas S, and Valcárcel M J. Chromatogr. A 1313, 253-8, (2013)

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Synthesis and possible applications of biotin-linked copper clusters. Bigham SL, Ballard JD, Giles KD, et al. Physiol. Chem. Phys. Med. NMR 22(2), 63-72, (1990)

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High dietary levels of biotin and zinc to improve health of foot pads in broilers exposed experimentally to litter with critical moisture content. Abd El-Wahab A, Radko D, and Kamphues J Poult. Sci. 92(7), 1774-82, (2013)

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A hypersensitive biotin-avidin-TRFIA for quantitative detection of ANA-Ig(GAM) and its clinical application. Liu J, Ye Y, Hu Z, et al. J. Immunoassay Immunochem. 34(2), 197-207, (2013)

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A direct streptavidin-binding assay does not accurately quantitate biotin in human urine. Mock DM, Nyalala JO, and Raguseo RM J. Nutr. 131(8), 2208-14, (2001)

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Protein expression profiling during wallerian degeneration after rat sciatic nerve injury. Li M, Zhang P, Guo W, et al. Muscle Nerve 50(1), 73-8, (2014)

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Biotin accounts for less than half of all biotin and biotin metabolites in the cerebrospinal fluid of children. Bogusiewicz A, Stratton SL, Ellison DA, et al. Am. J. Clin. Nutr. 88(5), 1291-6, (2008)

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Nucleoside analogues with a 1,3-diene-Fe(CO)3 substructure: stereoselective synthesis, configurational assignment, and apoptosis-inducing activity. Hirschhäuser C, Velcicky J, Schlawe D, et al. Chemistry 19(39), 13017-29, (2013)

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Design, synthesis, and biological evaluations of tumor-targeting dual-warhead conjugates for a taxoid-camptothecin combination chemotherapy. Vineberg JG, Zuniga ES, Kamath A, et al. J. Med. Chem. 57(13), 5777-91, (2014)

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Molecular modulation of the copper and cisplatin transport function of CTR1 and its interaction with IRS-4. Tsai CY, Larson CA, Safaei R, et al. Biochem. Pharmacol. 90(4), 379-87, (2014)

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Design and synthesis of a biotinylated probe of COX-2 inhibitor nimesulide analog JCC76. Bo Zhong et al Bioorg. Med. Chem. Lett. 21, 5324-7, (2011)

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Tumor cell-derived exosome-targeted dendritic cells stimulate stronger CD8+ CTL responses and antitumor immunities. Yao Y, Chen L, Wei W, et al. Biochem. Biophys. Res. Commun. 436(1), 60-5, (2013)

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Determination of biotin levels in cerebrospinal fluid samples. Livaniou E, Nyalala JO, Anagnostouli M, et al. J. Pharm. Biomed. Anal. 21(4), 875-9, (1999)

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Cerebrospinal fluid levels of biotin in various neurological disorders. Anagnostouli M, Livaniou E, Nyalala JO, et al. Acta Neurol. Scand 99(6), 387-92, (1999)

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Labeling study of avidin by modular method for affinity labeling (MoAL). Shuichi Nakanishi et al Bioorg. Med. Chem. Lett. 20, 7050-3, (2010)

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A large solvent isotope effect on protein association thermodynamics. Eginton C and Beckett D Biochemistry 52(38), 6595-600, (2013)

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Protein:protein interactions in control of a transcriptional switch. Adikaram PR and Beckett D J. Mol. Biol. 425(22), 4584-94, (2013)

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Structural investigation of the interactions of biotinylruthenocene with avidin. Strzelczyk P, Bujacz A, Plażuk D, et al. Chem. Biol. Interact. 204(1), 6-12, (2013)

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New anticoagulants for the treatment of venous thromboembolism. Prandoni P, Dalla Valle F, Piovella C, et al. Minerva Med. 104(2), 131-39, (2013)

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Toxoplasma gondii binds sheep prolactin. Dzitko K, Dziadek B, Gatkowska J, et al. Exp. Parasitol. 134(2), 216-9, (2013)

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Biotin-responsive basal ganglia disease: case report and review of the literature. El-Hajj TI, Karam PE, and Mikati MA Neuropediatrics 39(5), 268-71, (2008)

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Selection and characterization of single stranded DNA aptamers for the hormone abscisic Acid. Grozio A, Gonzalez VM, Millo E, et al. Nucleic Acid Ther. 23(5), 322-31, (2013)

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Luminescence stability improvement in liposome-based homogeneous luminescence resonance energy transfer. Pihlasalo S, Granberg J, Hänninen P, et al. Anal. Biochem. 440(1), 6-8, (2013)

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High incidence of partial biotinidase deficiency cases in newborns of Greek origin. Thodi G, Schulpis KH, Molou E, et al. Gene 524(2), 361-2, (2013)

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Quantification of α-tubulin isotypes by sandwich ELISA with signal amplification through biotinyl-tyramide or immuno-PCR. Dráberová E, Stegurová L, Sulimenko V, et al. J. Immunol. Methods 395(1-2), 63-70, (2013)

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Epigenetic synergies between biotin and folate in the regulation of pro-inflammatory cytokines and repeats. Xue J and Zempleni J Scand. J. Immunol. 78(5), 419-25, (2013)

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Question 2. What is the incidence of biotin deficiency in preschool children with global developmental delay? Ogundele MO Arch. Dis. Child. 96(9), 895-7, (2011)

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Merck 14,1231

Beil. 27,IV,7979

Corp MSDS 1, 414:D / FT-IR 2 (1), 1372:C / FT-IR 1 (1), 809:C / FT-NMR 1 (1), 1317:C / IR-Spectra (3), 480:A / RegBook 1 (1), 949:G / Sigma FT-IR 1 (1), 627:A / Structure Index 1, 147:D:7

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