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Chemical Compound Review

Detoxepa     1,3-thiazolidine-4-carboxylic acid

Synonyms: Norgamem, Norgamen, Hepaldine, Heparegen, Timonacic, ...
 
 
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Disease relevance of Timonacico [INN-Spanish]

 

High impact information on Timonacico [INN-Spanish]

  • Quantitative replacement of proline with thiaproline was confirmed by mass-spectrometric, amino acid, and x-ray crystallographic analyses [1].
  • Finally, through an examination of the structural and energetic features of binding of a thiazolidinecarboxylic acid inhibitor to the active site dizinc center, a two-step inhibition mechanism involving a protonation-induced ligand exchange reaction is proposed for the inhibitory action of a tight-binding inhibitor possessing a thiol group [5].
  • We here describe a semi-orthogonal strategy for ligating three unprotected peptide segments, two of which contain N-terminal (NT) cysteine, to form in tandem two amide bonds, an Xaa-SPro (thiaproline), and then an Xaa-Cys [6].
  • Here we present data on the same sample of men which definitively demonstrates increased nitrosation of proline and thioproline (thiazolidine-4-carboxylic acid) among infected men compared to uninfected control subjects on a low nitrate diet [7].
  • L-thioproline (thiazolidine-4-carboxylic acid, L-Tp) reduces DNA synthesis in cultured HeLa cells by about 50% when added to synchronized cultures at the beginning of G1 phase [8].
 

Biological context of Timonacico [INN-Spanish]

 

Anatomical context of Timonacico [INN-Spanish]

 

Associations of Timonacico [INN-Spanish] with other chemical compounds

 

Gene context of Timonacico [INN-Spanish]

 

Analytical, diagnostic and therapeutic context of Timonacico [INN-Spanish]

  • Determination of a new antihypertensive agent (2R,4R)-2-(2-hydroxyphenyl)-3-(3-mercaptopropionyl)-4- thiazolidinecarboxylic acid in blood by high-performance liquid chromatography with electrochemical detection [18].
  • This NT-amino acid-specific feature permits the development of a tandem peptide ligation method employing three unprotected peptide segments containing different NT-amino acids to form consecutively two amide bonds, an Xaa-SPro (thiaproline) and then an Xaa-Cys [19].

References

  1. Residue-specific bioincorporation of non-natural, biologically active amino acids into proteins as possible drug carriers: structure and stability of the per-thiaproline mutant of annexin V. Budisa, N., Minks, C., Medrano, F.J., Lutz, J., Huber, R., Moroder, L. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
  2. Thiazolidine-4-carboxylic acid toxicity and glutathione levels in various organs of the rat. Giorgi, G., Martini, P., Micheli, L., Segre, G. Drugs under experimental and clinical research. (1987) [Pubmed]
  3. Thioproline prevents carcinogenesis in the remnant stomach induced by duodenal reflux. Suo, M., Mukaisho, K., Shimomura, A., Sugihara, H., Hattori, T. Cancer Lett. (2006) [Pubmed]
  4. Thioproline (Norgamem): a useless drug in the treatment of squamous cell carcinoma. Alberto, P. European journal of cancer & clinical oncology. (1981) [Pubmed]
  5. Hybrid QM/MM and DFT investigations of the catalytic mechanism and inhibition of the dinuclear zinc metallo-beta-lactamase CcrA from Bacteroides fragilis. Park, H., Brothers, E.N., Merz, K.M. J. Am. Chem. Soc. (2005) [Pubmed]
  6. Tandem ligation of unprotected peptides through thiaprolyl and cysteinyl bonds in water. Tam, J.P., Yu, Q., Yang, J.L. J. Am. Chem. Soc. (2001) [Pubmed]
  7. Thiocyanate-independent nitrosation in humans with carcinogenic parasite infection. Satarug, S., Haswell-Elkins, M.R., Tsuda, M., Mairiang, P., Sithithaworn, P., Mairiang, E., Esumi, H., Sukprasert, S., Yongvanit, P., Elkins, D.B. Carcinogenesis (1996) [Pubmed]
  8. Effect of L-thioproline on the progression and events of the cell cycle of HeLa cells. García Cañero, R., López-Alarcón, L., Veloso, J.J., del Carmen Guijarro, M. Int. J. Cancer (1988) [Pubmed]
  9. Restoration of "contact inhibition" in tumour cells in tissue culture by treatment with thiazolidine-4-carboxylic acid [proceedings]. Gosálvez, M., Vivero, C., Alvarez, I. Biochem. Soc. Trans. (1979) [Pubmed]
  10. Macrophage-mediated N-nitrosation of thioproline and proline. Miwa, M., Tsuda, M., Kurashima, Y., Hara, H., Tanaka, Y., Shinohara, K. Biochem. Biophys. Res. Commun. (1989) [Pubmed]
  11. Thiaproline reduces glomerular basement membrane thickness and collagen accumulation in the db/db mouse. Lubec, B., Rokitansky, A., Hayde, M., Aufricht, C., Wagner, U., Mallinger, W.R., Höger, H., Lubec, G. Nephron (1994) [Pubmed]
  12. Enhancement of leukocyte functions in aged mice supplemented with the antioxidant thioproline. De la Fuente, M., Ferrández, M.D., Del Rio, M., Sol Burgos, M., Miquel, J. Mech. Ageing Dev. (1998) [Pubmed]
  13. Oxidation of L-thiazolidine-4-carboxylate by delta1-pyrroline-5-carboxylate reductase in Escherichia coli. Deutch, C.E., Klarstrom, J.L., Link, C.L., Ricciardi, D.L. Curr. Microbiol. (2001) [Pubmed]
  14. Changes in several functions of murine peritoneal macrophages by N-acetylcysteine and thioproline ingestion. Comparative effect between two strains of mice. Blanco, B., Ferrández, M.D., Correa, R., Del Rio, M., Guaza, C., Hernanz, A., De la Fuente, M. Biofactors (1999) [Pubmed]
  15. Conformational studies of antiradiation agents by NMR: cysteamine and its derivatives. Kulkarni, V.M., Govil, G. Journal of pharmaceutical sciences. (1977) [Pubmed]
  16. Synthesis and some pharmacological properties of oxytocin analogues having L-thiazolidine-4-carboxylic acid in position 7. Rosamond, J.D., Ferger, M.F. J. Med. Chem. (1976) [Pubmed]
  17. Thiazolidine-4-carboxylic acid, a physiologic sulfhydryl antioxidant with potential value in geriatric medicine. Weber, H.U., Fleming, J.F., Miquel, J. Archives of gerontology and geriatrics. (1982) [Pubmed]
  18. Determination of a new antihypertensive agent (2R,4R)-2-(2-hydroxyphenyl)-3-(3-mercaptopropionyl)-4- thiazolidinecarboxylic acid in blood by high-performance liquid chromatography with electrochemical detection. Shimada, K., Tanaka, M., Nambara, T., Imai, Y. Journal of pharmaceutical sciences. (1984) [Pubmed]
  19. Tandem peptide ligation for synthetic and natural biologicals. Tam, J.P., Yu, Q., Lu, Y.A. Biologicals (2001) [Pubmed]
 
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