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

• This study was undertaken to examine the in vivo effects of the thiazolidine compound pioglitazone (PIO) on carotid neointimal thickening, after endothelial injury in Wistar rats and vascular hypertrophy in stroke-prone spontaneously hypertensive rats (SHR-SP/Izm) [10].
• This study evaluated the inhibitory effects of thiazolidine derivatives on hepatitis C virus (HCV) protease and other human serine proteases [11].
• When rats were given both thiazolidine 4-carboxylic acid and nitrate, greater endogenous nitrosamine formation was observed in rats receiving omeprazole and an E. coli suspension than in control or omeprazole-treated rats [12].
• The induction of cirrhosis could be modified by the simultaneous treatment with PGI2 or by the thiazolidine compound but the fully developed cirrhosis was not affected [13].
• These terpenoids and thiazolidine type of antidiabetic agents such as Ciglitazone, although structurally unrelated, share many biological activities: both induce adipose conversion, activate peroxisome proliferator-activated receptor gamma (PPAR gamma) in vitro, and reduce hyperglycemia in animal models of NIDDM [14].

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

• A novel insulin sensitizing agent, thiazolidine, has been demonstrated to inhibit the growth of cultured vascular smooth muscle cells (VSMC) in vitro [10].
• Peroxisomal oxidation of thiazolidine carboxylates in firefly fat body, frog retina, and rat liver and kidney [20].
• 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 [21].
• This binding (possibly due to thiazolidine formation with cysteine) was enhanced in alcoholics, whose red blood cell cysteine content was doubled [22].
• Interestingly, both with the thiazolidine compounds and with more traditional D-amino acid oxidase substrates, the fireflies' photocyte granules, which are peroxisomes, lack activity [20].

Associations of thiazolidine with other chemical compounds

• Free thiazolidine and piperidine, used in control experiments, neither inhibit DPIV enzyme activity nor PMA-induced hyperphosphorylation [23].
• The antigen-core ligation alternatives, studied by indirect synthesis, were the formation of oxime, hydrazone and thiazolidine linkages, making use of the reaction between a weak base (acting as nucleophile) and an alkyl aldehyde [24].
• Impairment of mitochondrial membrane by ethanol and protective effect of a thiazolidine compound in in vitro and in vivo experiments [25].
• In the present study, we investigated the effects of a thiazolidine derivative, pioglitazone, and examined the insulin-sensitizing action on blood pressure, nephropathy, and vascular changes in genetically obese diabetic Wistar fatty (WF) rats [26].
• As the respective amino precursors (thiazolidine 4-carboxylic acids) can be formed by reaction of formaldehyde or acetaldehyde with cysteine, measurement of NTCA and NMTCA in urine may provide a further index for endogenous nitrosation in the human body and may also allow monitoring of exposure of human subjects to aldehydes, nitrate and nitrite [27].

Gene context of thiazolidine

• Degradation, monitored by mass spectrometry and bioassay, was blocked by the specific DP IV inhibitor, isoleucyl thiazolidine [28].
• Protein splicing of yeast VMA1-derived endonuclease via thiazolidine intermediates [29].
• These data suggest that Abp4 recognizes the thiazolidine ring and Abp7 recognizes the acyl side chain [30].
• The results imply that these thiazolidine derivatives are the likely physiological reactants for mammalian D-aspartate oxidase [31].
• Thiazolidine derivatives as potent inhibitors specific for prolyl endopeptidase [32].

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].

References