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Chemical Compound Review

AG-E-59313     5-[(1R,2R,5R)-7-oxo-3-thia- 6,8...

Synonyms: AC1NST2B, CTK1A0983, 21788-37-4, MolPort-002-111-510
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Disease relevance of biotin


Psychiatry related information on biotin


High impact information on biotin


Chemical compound and disease context of biotin


Biological context of biotin


Anatomical context of biotin

  • The modified protein was incorporated into planar lipid membranes, where the introduced biotin moiety served as a site to bind the water-soluble protein streptavidin, added to one side of the membrane or the other [21].
  • An ultrastructural immunostaining method that uses silver-intensified gold was combined with another procedure that uses biotin peroxidase conjugates to allow simultaneous identification of two neurotransmitter-related antigens in the central nervous system [24].
  • In situ hybridization of biotin-substituted pMCT-1 to fixed frozen sections shows that expression of pMCT-1 is seen throughout the tumor and is highly heterogeneous on a cellular basis, while expression is undetectable in any cell in the normal colonic mucosa [25].
  • We have developed an assay for holocarboxylase synthetase in extracts of human fibroblasts using as substrate apopropionyl-CoA carboxylase partially purified from livers of biotin-deficient rats [26].
  • Proteases substituted with biotin were targeted via the cationic protein avidin A, which by virtue of its charge has affinity for the glomerular basement membrane [27].

Associations of biotin with other chemical compounds

  • Here we attach microscopic polystyrene beads to biotin-tagged RecD protein subunits and use tethered-particle light microscopy to observe translocation of single RecBCD molecules (with a precision of up to approximately 30 nm at 2 Hz) and to examine the mechanism by which chi modifies enzyme activity [28].
  • Isolated biotin-resistant 3-methylcrotonyl-CoA carboxylase (MCC) deficiency is an autosomal recessive disorder of leucine catabolism that appears to be the most frequent organic aciduria detected in tandem mass spectrometry-based neonatal screening programs [29].
  • Sodium dodecyl sulfate (SDS) polyacrylamide gel electrophoresis (PAGE)-separated proteins from PMN, ADMC, E+, and E- cells were electrophoretically blotted onto nitrocellulose sheets; a probe of biotin-labeled DNA indicated a single species of DNA-binding molecule migrating in a position consistent with a molecular weight of 30,000 [30].
  • By using biotin-labeled proteoglycan core protein, hyaluronan (hyaluronic acid; HA) was visualized in rat heart grafts at different times (2, 4, and 6 d) after transplantation [31].
  • Transport of the biotin dietary derivative biocytin (N-biotinyl-L-lysine) in rat small intestine [32].

Gene context of biotin

  • To identify the ligand for CD5 we purified the human CD5 protein, labelled it with biotin and used it as a probe [33].
  • The beta-PTyr protein is present on the cell surface, like IFNAR, as shown by extracellular biotin tagging [34].
  • When cell surface proteins are labeled with biotin, a biotinylated FGFR-1 is detected in the nuclear fraction prepared from FGF-2-treated, but not untreated, cells indicating that the nuclear-associated FGFR-1 immunoreactivity derives from the cell surface [35].
  • A 54-kDa protein was isolated by a biotin-high molecular mass kininogen (HK) affinity column that, on aminoterminal sequencing of tryptic digests, was identified as cytokeratin 1 [36].
  • Biotin-responsive basal ganglia disease maps to 2q36.3 and is due to mutations in SLC19A3 [37].

Analytical, diagnostic and therapeutic context of biotin

  • The docking of streptavidin to biotin at liposomal surfaces was confirmed by circular dichroism [38].
  • To further confirm the presence of antihyaluronate antibodies, hyaluronidase-digested streptococcal hyaluronate was conjugated to biotin and used as an antigen in the ELISA [39].
  • This result was further substantiated in experiments where biotin-peptide/class II complexes were extensively dialyzed at low pH followed by analysis on Western blots probed with avidin [40].
  • An enzyme immunoassay was developed to measure the binding of biotin-labeled peptides to purified class II in detergent micelles [41].
  • CD4 internalization was followed using radioiodinated antibodies in an acid-elution endocytosis assay, or by covalently modifying cell surface proteins with biotin and analyzing CD4 distributions by immunoprecipitation; both approaches gave equivalent results [42].


  1. Isolation and characterization of mutations in the human holocarboxylase synthetase cDNA. Suzuki, Y., Aoki, Y., Ishida, Y., Chiba, Y., Iwamatsu, A., Kishino, T., Niikawa, N., Matsubara, Y., Narisawa, K. Nat. Genet. (1994) [Pubmed]
  2. Impaired intestinal absorption of biotin in juvenile multiple carboxylase deficiency. Thoene, J.G., Lemons, R., Baker, H. N. Engl. J. Med. (1983) [Pubmed]
  3. Epstein-Barr virus replication in oropharyngeal epithelial cells. Sixbey, J.W., Nedrud, J.G., Raab-Traub, N., Hanes, R.A., Pagano, J.S. N. Engl. J. Med. (1984) [Pubmed]
  4. Biotin for neurologic disorders of uremia. Yatzidis, H., Koutsicos, D., Alaveras, A.G., Papastephanidis, C., Frangos-Plemenos, M. N. Engl. J. Med. (1981) [Pubmed]
  5. Biotin and the sudden infant death syndrome. Johnson, A.R., Hood, R.L., Emery, J.L. Nature (1980) [Pubmed]
  6. Submicroscopic deletions at the WAGR locus, revealed by nonradioactive in situ hybridization. Fantes, J.A., Bickmore, W.A., Fletcher, J.M., Ballesta, F., Hanson, I.M., van Heyningen, V. Am. J. Hum. Genet. (1992) [Pubmed]
  7. Entrapment of fluorescent signaling DNA aptamers in sol-gel-derived silica. Rupcich, N., Nutiu, R., Li, Y., Brennan, J.D. Anal. Chem. (2005) [Pubmed]
  8. Vicia villosa lectin-positive neurones in human cerebral cortex. Loss in Alzheimer-type dementia. Kobayashi, K., Emson, P.C., Mountjoy, C.Q. Brain Res. (1989) [Pubmed]
  9. Rett syndrome revisited: a patient with biotin dependency. Bachmann, C., Schaub, J., Colombo, J.P., Burri, B.J., Sweetman, L., Wolf, B. Eur. J. Pediatr. (1986) [Pubmed]
  10. Biotin deficiency in an infant fed with amino acid formula and hypoallergenic rice. Higuchi, R., Noda, E., Koyama, Y., Shirai, T., Horino, A., Juri, T., Koike, M. Acta Paediatr. (1996) [Pubmed]
  11. Chromosomal localization of long trinucleotide repeats in the human genome by fluorescence in situ hybridization. Haaf, T., Sirugo, G., Kidd, K.K., Ward, D.C. Nat. Genet. (1996) [Pubmed]
  12. Mutational hotspot in the human biotinidase gene causes profound biotinidase deficiency. Pomponio, R.J., Reynolds, T.R., Cole, H., Buck, G.A., Wolf, B. Nat. Genet. (1995) [Pubmed]
  13. Antisense probing of the human U4/U6 snRNP with biotinylated 2'-OMe RNA oligonucleotides. Blencowe, B.J., Sproat, B.S., Ryder, U., Barabino, S., Lamond, A.I. Cell (1989) [Pubmed]
  14. Interruption of the adipose conversion of 3T3 cells by biotin deficiency: differentiation without triglyceride accumulation. Kuri-Harcuch, W., Wise, L.S., Green, H. Cell (1978) [Pubmed]
  15. Targeting quantum dots to surface proteins in living cells with biotin ligase. Howarth, M., Takao, K., Hayashi, Y., Ting, A.Y. Proc. Natl. Acad. Sci. U.S.A. (2005) [Pubmed]
  16. Structural properties of pyruvate carboxylases from chicken liver and other sources. Barden, R.E., Taylor, B.L., Isoashi, F., Frey, W.H., Zander, G., Lee, J.C., Utter, M.F. Proc. Natl. Acad. Sci. U.S.A. (1975) [Pubmed]
  17. Biochemical characterization of biotin-responsive multiple carboxylase deficiency: heterogeneity within the bio genetic complementation group. Feldman, G.L., Hsia, Y.E., Wolf, B. Am. J. Hum. Genet. (1981) [Pubmed]
  18. Biotinyl 5'-adenylate: corepressor role in the regulation of the biotin genes of Escherichia coli K-12. Prakash, O., Eisenberg, M.A. Proc. Natl. Acad. Sci. U.S.A. (1979) [Pubmed]
  19. Pretargeting radioimmunotherapy of a murine model of adult T-cell leukemia with the alpha-emitting radionuclide, bismuth 213. Zhang, M., Yao, Z., Garmestani, K., Axworthy, D.B., Zhang, Z., Mallett, R.W., Theodore, L.J., Goldman, C.K., Brechbiel, M.W., Carrasquillo, J.A., Waldmann, T.A. Blood (2002) [Pubmed]
  20. The regulatory region of the biotin operon in Escherichia coli. Otsuka, A., Abelson, J. Nature (1978) [Pubmed]
  21. Identification of a translocated protein segment in a voltage-dependent channel. Slatin, S.L., Qiu, X.Q., Jakes, K.S., Finkelstein, A. Nature (1994) [Pubmed]
  22. Structural origins of high-affinity biotin binding to streptavidin. Weber, P.C., Ohlendorf, D.H., Wendoloski, J.J., Salemme, F.R. Science (1989) [Pubmed]
  23. Random peptide libraries: a source of specific protein binding molecules. Devlin, J.J., Panganiban, L.C., Devlin, P.E. Science (1990) [Pubmed]
  24. Silver-intensified gold and peroxidase as dual ultrastructural immunolabels for pre- and postsynaptic neurotransmitters. van den Pol, A.N. Science (1985) [Pubmed]
  25. Biotinated probe containing a long-terminal repeat hybridized to a mouse colon tumor and normal tissue. Royston, M.E., Augenlicht, L.H. Science (1983) [Pubmed]
  26. Mutant holocarboxylase synthetase: evidence for the enzyme defect in early infantile biotin-responsive multiple carboxylase deficiency. Burri, B.J., Sweetman, L., Nyhan, W.L. J. Clin. Invest. (1981) [Pubmed]
  27. Targeted enzyme therapy of experimental glomerulonephritis in rats. White, R.B., Lowrie, L., Stork, J.E., Iskandar, S.S., Lamm, M.E., Emancipator, S.N. J. Clin. Invest. (1991) [Pubmed]
  28. Chi-sequence recognition and DNA translocation by single RecBCD helicase/nuclease molecules. Dohoney, K.M., Gelles, J. Nature (2001) [Pubmed]
  29. The molecular basis of human 3-methylcrotonyl-CoA carboxylase deficiency. Baumgartner, M.R., Almashanu, S., Suormala, T., Obie, C., Cole, R.N., Packman, S., Baumgartner, E.R., Valle, D. J. Clin. Invest. (2001) [Pubmed]
  30. DNA binding to human leukocytes. Evidence for a receptor-mediated association, internalization, and degradation of DNA. Bennett, R.M., Gabor, G.T., Merritt, M.M. J. Clin. Invest. (1985) [Pubmed]
  31. Accumulation of hyaluronan (hyaluronic acid) in myocardial interstitial tissue parallels development of transplantation edema in heart allografts in rats. Hällgren, R., Gerdin, B., Tengblad, A., Tufveson, G. J. Clin. Invest. (1990) [Pubmed]
  32. Transport of the biotin dietary derivative biocytin (N-biotinyl-L-lysine) in rat small intestine. Said, H.M., Thuy, L.P., Sweetman, L., Schatzman, B. Gastroenterology (1993) [Pubmed]
  33. The B-cell surface protein CD72/Lyb-2 is the ligand for CD5. Van de Velde, H., von Hoegen, I., Luo, W., Parnes, J.R., Thielemans, K. Nature (1991) [Pubmed]
  34. Differential tyrosine phosphorylation of the IFNAR chain of the type I interferon receptor and of an associated surface protein in response to IFN-alpha and IFN-beta. Abramovich, C., Shulman, L.M., Ratovitski, E., Harroch, S., Tovey, M., Eid, P., Revel, M. EMBO J. (1994) [Pubmed]
  35. Nuclear Translocation of fibroblast growth factor (FGF) receptors in response to FGF-2. Maher, P.A. J. Cell Biol. (1996) [Pubmed]
  36. Identification of cytokeratin 1 as a binding protein and presentation receptor for kininogens on endothelial cells. Hasan, A.A., Zisman, T., Schmaier, A.H. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
  37. Biotin-responsive basal ganglia disease maps to 2q36.3 and is due to mutations in SLC19A3. Zeng, W.Q., Al-Yamani, E., Acierno, J.S., Slaugenhaupt, S., Gillis, T., MacDonald, M.E., Ozand, P.T., Gusella, J.F. Am. J. Hum. Genet. (2005) [Pubmed]
  38. Attempts to mimic docking processes of the immune system: recognition-induced formation of protein multilayers. Müller, W., Ringsdorf, H., Rump, E., Wildburg, G., Zhang, X., Angermaier, L., Knoll, W., Liley, M., Spinke, J. Science (1993) [Pubmed]
  39. Induction of antibodies to hyaluronic acid by immunization of rabbits with encapsulated streptococci. Fillit, H.M., McCarty, M., Blake, M. J. Exp. Med. (1986) [Pubmed]
  40. Long-lived complexes between peptide and class II major histocompatibility complex are formed at low pH with no requirement for pH neutralization. Jensen, P.E. J. Exp. Med. (1992) [Pubmed]
  41. Enhanced binding of peptide antigen to purified class II major histocompatibility glycoproteins at acidic pH. Jensen, P.E. J. Exp. Med. (1991) [Pubmed]
  42. Differential endocytosis of CD4 in lymphocytic and nonlymphocytic cells. Pelchen-Matthews, A., Armes, J.E., Griffiths, G., Marsh, M. J. Exp. Med. (1991) [Pubmed]
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