title: Novel cross-link breaker based on zwitterion structure: synthesis, structure and druggability studies.
abstract: It has been universally acknowledged that the increase in cardiac and vascular stiffness is due to the formation of advanced glycosylation end-products (AGEs). Research on the stable form of 3-(carboxymethyl)-4-methylthiazol bromide sodium salt (C6H7BrNNaO2S) showed that it had a notable effect on breaking the AGEs. Two compounds with novel structures, zwitterionic 3-(carboxymethyl)-4-methylthiazol (C6H7O2NS) and a dipolymer (C12H15O4N2S2Br) complex, were obtained. When compared with the forms of sodium salt and dipolymer, zwitterion had an obvious advantage in stability, solubility, synthesis and pH, which made the zwitterion a promising drug. The structure of sodium salt, dipolymer and zwitterion was comparatively analyzed by such methods as single crystal X-ray diffraction, ESI-MS, 1H NMR, FT-IR and in situ IR.
authors: Laboratory of Computer-Aided Drug Design & Discovery, Beijing Institute of Pharmacology and Toxicology, 27 Taiping Rd., Beijing 100850, China.
authors: Shuang
authors: S
authors: Cao
authors: Xin-Bo
authors: XB
authors: Zhou
authors: Heng
authors: H
authors: Zhang
authors: Song
authors: S
authors: Li
authors: Wu
authors: W
authors: Zhong
mesh_terms: D018360:Crystallography, X-Ray; D003902:Detergents / Q000737:chemistry / Q000494:pharmacology; D004355:Drug Stability; D017127:Glycation End Products, Advanced / Q000737:chemistry* / Q000187:drug effects; D015394:Molecular Structure; D012995:Solubility; D013844:Thiazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology
chemical_list: C000590552:3-(carboxymethyl)-4-methylthiazole; D003902:Detergents; D017127:Glycation End Products, Advanced; D013844:Thiazoles
keywords: Advanced glycosylation end-products (AGEs); Cross-link breaker; Druggability; In situ IR; X-ray structure; Zwitterion