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Chemical Compound Review

THIAZOLIDINE     1,3-thiazolidine

Synonyms: SureCN7360, SureCN131493, ACMC-1AO0M, CCRIS 4275, AG-F-69755, ...
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Disease relevance of thiazolidine

  • Fate of thiazolidine ring during fragmentation of penicillin by exocellular DD-carboxypeptidase-transpeptidase of Streptomyces R61 [1].
  • This thiazolidine may be useful in the treatment of other toxicities and in the treatment of certain diseases [2].
  • The mechanisms for the insulin resistance induced by hyperglycemia were investigated by studying the effect of high glucose concentration (HG) and its modulation by thiazolidine derivatives, on insulin signaling using Rat 1 fibroblasts expressing human insulin receptors (HIRc) [3].
  • We therefore suggest that nuclear signaling via RZR/RORalpha is a key mechanism in mediating the antiarthritic effects of these thiazolidine diones and may open a novel therapeutic approach for the treatment of rheumatoid arthritis and other autoimmune diseases [4].
  • We reported earlier that OPB-9195, a synthetic thiazolidine derivative and novel inhibitor of advanced glycation, prevented progression of diabetic glomerulosclerosis by lowering serum concentrations of advanced glycation end products and reducing their deposition in the glomeruli [5].

High impact information on thiazolidine

  • In conclusion, exposing cells to high glucose levels desensitizes insulin receptor function, and thiazolidine derivatives can reverse the process via the normalization of cytosolic PTPase, but not of protein kinase C [3].
  • Protein-splicing reaction via a thiazolidine intermediate: crystal structure of the VMA1-derived endonuclease bearing the N and C-terminal propeptides [6].
  • The dimethylated thiazolidine- and oxazolidine-containing [D-Phe(3)]morphiceptin- and endomorphin-2 analogues (R(1), R(2) = CH(3)) all retained full mu agonist potency in the GPI assay and displayed mu receptor binding affinities in the nanomolar range and high mu receptor selectivity [7].
  • As assessed by Fisher's exact test, tumor incidences were significant in the TZ (0.01 less than P less than 0.05) and DMBA (P less than 0.01) groups as compared with the dimethylsulfoxide (DMSO) followed by TPA groups (5%, 0.05/mouse) [8].
  • Background and purpose:The thiazolidine carboxylic acid, BML-241, has been proposed as a lead compound in development of selective antagonists at the sphingosine-1-phosphate receptor (S1P(3)), based on its inhibition of the rise in intracellular calcium concentrations ([Ca(2+)](i)) in HeLa cells overexpressing S1P receptors [9].

Chemical compound and disease context of thiazolidine


Biological context of thiazolidine

  • Thiazolidine prodrugs as protective agents against gamma-radiation-induced toxicity and mutagenesis in V79 cells [15].
  • Non-enzymatic hydrolysis of TDs depended on the chemical nature of the substituents in the thiazolidine (Th) ring [16].
  • Quantitative hapten inhibition studies revealed that the combining sites of the former antibodies were complementary to amoxicillin in a form that permits binding to the hydroxyaminobenzyl side-chain and the thiazolidine ring carboxyl [17].
  • NTHZ was prepared in 99 + % purity by the nitrosation of the cysteamine-formaldehyde reaction mixture without isolation and purification of the resulting amine, and from thiazolidine, directly [18].
  • Apoptosis was not induced by either a 60-min or 20-h exposure to 10 mM of the thiazolidine prodrugs ribose-cysteine (RibCys) or ribose-cysteamine (RibCyst) [19].

Anatomical context of thiazolidine


Associations of thiazolidine with other chemical compounds


Gene context of thiazolidine


Analytical, diagnostic and therapeutic context of thiazolidine

  • This thiazolidine ligation approach is performed with stoichiometric amounts of fully unprotected MPS and functional peptide in an aqueous buffered solution, eliminating the need for additional chemical manipulation and purification prior to use in bioassays [33].
  • However, the C-terminal peptide was blocked at its N terminal by a thiazolidine ring and hence could not be used for Edman degradation sequence analysis [34].
  • Immobilization by thiazolidine ring and oxime bond formation were the preferred methods, given the stability of the linkages formed, their compatibility with aqueous solvents, the few number of steps required, and their potential for application to larger pectin fragments [35].
  • Determination of aliphatic aldehydes as their thiazolidine derivatives in foods by gas chromatography with flame photometric detection [36].
  • We were able to identify three separate groups of patients on the basis of clinical history, patch-test, and tolerance challenge pattern: allergy to the side chain of aminopenicillins in 16 patients (53.3%); allergy to the thiazolidine ring in 3 patients (10.0%); undetermined specificity in the remainder 11 patients (36.7%) [37].


  1. Fate of thiazolidine ring during fragmentation of penicillin by exocellular DD-carboxypeptidase-transpeptidase of Streptomyces R61. Frere, J., Ghuysen, J., Vanderhaeghe, H., Adriaens, P., Degelaen, J., De Graeve, J. Nature (1976) [Pubmed]
  2. Intracellular cysteine delivery system that protects against toxicity by promoting glutathione synthesis. Williamson, J.M., Boettcher, B., Meister, A. Proc. Natl. Acad. Sci. U.S.A. (1982) [Pubmed]
  3. Thiazolidine derivatives ameliorate high glucose-induced insulin resistance via the normalization of protein-tyrosine phosphatase activities. Maegawa, H., Ide, R., Hasegawa, M., Ugi, S., Egawa, K., Iwanishi, M., Kikkawa, R., Shigeta, Y., Kashiwagi, A. J. Biol. Chem. (1995) [Pubmed]
  4. Thiazolidine diones, specific ligands of the nuclear receptor retinoid Z receptor/retinoid acid receptor-related orphan receptor alpha with potent antiarthritic activity. Missbach, M., Jagher, B., Sigg, I., Nayeri, S., Carlberg, C., Wiesenberg, I. J. Biol. Chem. (1996) [Pubmed]
  5. Suppression of transforming growth factor beta and vascular endothelial growth factor in diabetic nephropathy in rats by a novel advanced glycation end product inhibitor, OPB-9195. Tsuchida, K., Makita, Z., Yamagishi, S., Atsumi, T., Miyoshi, H., Obara, S., Ishida, M., Ishikawa, S., Yasumura, K., Koike, T. Diabetologia (1999) [Pubmed]
  6. Protein-splicing reaction via a thiazolidine intermediate: crystal structure of the VMA1-derived endonuclease bearing the N and C-terminal propeptides. Mizutani, R., Nogami, S., Kawasaki, M., Ohya, Y., Anraku, Y., Satow, Y. J. Mol. Biol. (2002) [Pubmed]
  7. Pseudoproline-containing analogues of morphiceptin and endomorphin-2: evidence for a cis Tyr-Pro amide bond in the bioactive conformation. Keller, M., Boissard, C., Patiny, L., Chung, N.N., Lemieux, C., Mutter, M., Schiller, P.W. J. Med. Chem. (2001) [Pubmed]
  8. Initiating activity of eight pyrolysates of carbohydrates in a two-stage mouse skin tumorigenesis model. Miyakawa, Y., Nishi, Y., Kato, K., Sato, H., Takahashi, M., Hayashi, Y. Carcinogenesis (1991) [Pubmed]
  9. BML-241 fails to display selective antagonism at the sphingosine-1-phosphate receptor, S1P(3). Jongsma, M., Hendriks-Balk, M.C., Michel, M.C., Peters, S.L., Alewijnse, A.E. Br. J. Pharmacol. (2006) [Pubmed]
  10. Vasculo-protective effects of insulin sensitizing agent pioglitazone in neointimal thickening and hypertensive vascular hypertrophy. Yoshimoto, T., Naruse, M., Shizume, H., Naruse, K., Tanabe, A., Tanaka, M., Tago, K., Irie, K., Muraki, T., Demura, H., Zardi, L. Atherosclerosis (1999) [Pubmed]
  11. Novel hepatitis C virus protease inhibitors: thiazolidine derivatives. Sudo, K., Matsumoto, Y., Matsushima, M., Fujiwara, M., Konno, K., Shimotohno, K., Shigeta, S., Yokota, T. Biochem. Biophys. Res. Commun. (1997) [Pubmed]
  12. Bacterial formation of N-nitroso compounds in the rat stomach after omeprazole-induced achlorhydria. Calmels, S., Béréziat, J.C., Ohshima, H., Bartsch, H. IARC Sci. Publ. (1991) [Pubmed]
  13. Experimental studies on the effect of hepatoprotective compounds. Lapis, K., Jeney, A., Divald, A., Vajta, G., Zalatnai, A., Schaff, Z. Tokai J. Exp. Clin. Med. (1986) [Pubmed]
  14. Dehydrotrametenolic acid induces preadipocyte differentiation and sensitizes animal models of noninsulin-dependent diabetes mellitus to insulin. Sato, M., Tai, T., Nunoura, Y., Yajima, Y., Kawashima, S., Tanaka, K. Biol. Pharm. Bull. (2002) [Pubmed]
  15. Thiazolidine prodrugs as protective agents against gamma-radiation-induced toxicity and mutagenesis in V79 cells. Wilmore, B.H., Cassidy, P.B., Warters, R.L., Roberts, J.C. J. Med. Chem. (2001) [Pubmed]
  16. Thiazolidine derivatives as source of free L-cysteine in rat tissue. Wlodek, L., Rommelspacher, H., Susilo, R., Radomski, J., Höfle, G. Biochem. Pharmacol. (1993) [Pubmed]
  17. Fine structural recognition specificities of IgE antibodies distinguishing amoxicilloyl and amoxicillanyl determinants in allergic subjects. Zhao, Z., Baldo, B.A., Baumgart, K.W., Mallon, D.F. J. Mol. Recognit. (2001) [Pubmed]
  18. Apparent mutagenicity of N-nitrosothiazolidine caused by a trace contaminant. Miller, A.J., Pensabene, J.W., Doerr, R.C., Fiddler, W. Mutat. Res. (1985) [Pubmed]
  19. Modulation of radiation-induced apoptosis by thiolamines. Warters, R.L., Roberts, J.C., Wilmore, B.H., Kelley, L.L. Int. J. Radiat. Biol. (1997) [Pubmed]
  20. Peroxisomal oxidation of thiazolidine carboxylates in firefly fat body, frog retina, and rat liver and kidney. St Jules, R., Kennard, J., Setlik, W., Holtzman, E. Eur. J. Cell Biol. (1991) [Pubmed]
  21. Metabolism of 7-(1,3-thiazolidin-2-ylmethyl)theophylline by rat liver microsomes. Evidence for a monooxygenase-dependent step in 1,3-thiazolidine ring cleavage. Grosa, G., Caputo, O., Ceruti, M., Biglino, G. Drug Metab. Dispos. (1992) [Pubmed]
  22. Characterization of the increased binding of acetaldehyde to red blood cells in alcoholics. Hernández-Muñoz, R., Baraona, E., Blacksberg, I., Lieber, C.S. Alcohol. Clin. Exp. Res. (1989) [Pubmed]
  23. Enzymatic activity of DPIV/CD26 is involved in PMA-induced hyperphosphorylation of p56lck. Kähne, T., Neubert, K., Ansorge, S. Immunol. Lett. (1995) [Pubmed]
  24. Synthesis, isolation and characterization of Plasmodium falciparum antigenic tetrabranched peptide dendrimers obtained by thiazolidine linkages. Chaves, F., Calvo, J.C., Carvajal, C., Rivera, Z., Ramírez, L., Pinto, M., Trujillo, M., Guzmán, F., Patarroyo, M.E. J. Pept. Res. (2001) [Pubmed]
  25. Impairment of mitochondrial membrane by ethanol and protective effect of a thiazolidine compound in in vitro and in vivo experiments. Lamboeuf, Y., de Saint Blanquat, G., Roumec, C., Alary, J., Carrera, G., Faurie, M. Food additives and contaminants. (1990) [Pubmed]
  26. Antihypertensive and vasculo- and renoprotective effects of pioglitazone in genetically obese diabetic rats. Yoshimoto, T., Naruse, M., Nishikawa, M., Naruse, K., Tanabe, A., Seki, T., Imaki, T., Demura, R., Aikawa, E., Demura, H. Am. J. Physiol. (1997) [Pubmed]
  27. Monitoring endogenous nitrosamine formation in man. Ohshima, H., Bartsch, H. IARC Sci. Publ. (1984) [Pubmed]
  28. Metabolism of glucagon by dipeptidyl peptidase IV (CD26). Pospisilik, J.A., Hinke, S.A., Pederson, R.A., Hoffmann, T., Rosche, F., Schlenzig, D., Glund, K., Heiser, U., McIntosh, C.H., Demuth, H. Regul. Pept. (2001) [Pubmed]
  29. Protein splicing of yeast VMA1-derived endonuclease via thiazolidine intermediates. Mizutani, R., Anraku, Y., Satow, Y. Journal of synchrotron radiation. (2004) [Pubmed]
  30. Anti-ampicillin monoclonal antibodies and their cross-reactivities to various beta-lactams. Nagakura, N., Souma, S., Shimizu, T., Yanagihara, Y. J. Antimicrob. Chemother. (1991) [Pubmed]
  31. Thiazolidine-2-carboxylate derivatives formed from glyoxylate and L-cysteine or L-cysteinylglycine as possible physiological substrates for D-aspartate oxidase. Burns, C.L., Main, D.E., Buckthal, D.J., Hamilton, G.A. Biochem. Biophys. Res. Commun. (1984) [Pubmed]
  32. Thiazolidine derivatives as potent inhibitors specific for prolyl endopeptidase. Tsuru, D., Yoshimoto, T., Koriyama, N., Furukawa, S. J. Biochem. (1988) [Pubmed]
  33. Preparation of functionally active cell-permeable peptides by single-step ligation of two peptide modules. Zhang, L., Torgerson, T.R., Liu, X.Y., Timmons, S., Colosia, A.D., Hawiger, J., Tam, J.P. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
  34. Generation of a free alpha-amino group by Raney nickel after 2-nitro-5-thiocyanobenzoic acid cleavage at cysteine residues: application to automated sequencing. Otieno, S. Biochemistry (1978) [Pubmed]
  35. Immobilization of pectin fragments on solid supports: novel coupling by thiazolidine formation. Guillaumie, F., Thomas, O.R., Jensen, K.J. Bioconjug. Chem. (2002) [Pubmed]
  36. Determination of aliphatic aldehydes as their thiazolidine derivatives in foods by gas chromatography with flame photometric detection. Kataoka, H., Sumida, A., Nishihata, N., Makita, M. Journal of chromatography. A. (1995) [Pubmed]
  37. Clinical usefulness of patch and challenge tests in the diagnosis of cell-mediated allergy to betalactams. Patriarca, G., D'Ambrosio, C., Schiavino, D., Larocca, L.M., Nucera, E., Milani, A. Ann. Allergy Asthma Immunol. (1999) [Pubmed]
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