CHARACTERIZATION OF CRYSTALLINE L-CARNOSINE ZN(II) COMPLEX (Z-103), A NOVEL ANTIGASTRIC ULCER AGENT - TAUTOMERIC CHANGE OF IMIDAZOLE MOIETY UPON COMPLEXATION

被引：54

作者：

MATSUKURA, T ^{[1
]}

TAKAHASHI, T ^{[1
]}

NISHIMURA, Y ^{[1
]}

OHTANI, T ^{[1
]}

SAWADA, M ^{[1
]}

SHIBATA, K ^{[1
]}

机构：

[1] OSAKA CITY UNIV, FAC SCI, SUMIYOSHI KU, OSAKA 558, JAPAN

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 1990年 / 38卷 / 11期

关键词：

anti gastric ulcer agent; L-carnosine; solid NMR; tautomeric change; X-ray photoelectron spectrum; Zn(II) complex;

D O I：

10.1248/cpb.38.3140

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A novel crystalline Zn(II) complex of L-carnosine was prepared and evaluated for inhibitory activity against gastric ulceration in rats. The complex was found to be much more active than various other Zn(II) compounds. It was characterized by means of infrared (IR) spectroscopy, solid-state carbon-13 (13C) and nitrogen-15 (15N) 1H-cross-polarization (CP) magic angle spinning (MAS) nuclear magnetic resonance (NMR) spectroscopy and X-ray photoelectron spectroscopy (XPS). The spectroscopic data indicated that L-carnosine coordinates to Zn(II) as a quadridentate ligand. A comparison of the 13C-NMR signals of the imidazole carbons of the complex with those of several histidine derivatives revealed that a tautomeric change of imidazole moiety had occurred upon complexation. The binding mode of the comnlex was considered to be analogous to that of the corresponding Cu(II) complex. © 1990, The Pharmaceutical Society of Japan. All rights reserved.

引用

页码：3140 / 3146

页数：7

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