ENDOGENOUS ALKALOIDS IN MAN .10. A CHEMICAL CONCEPT FOR THE THERAPY OF GLYOXYLATE-INDUCED OXALURIAS

被引:9
作者
BRINGMANN, G [1 ]
FEINEIS, D [1 ]
HESSELMANN, C [1 ]
SCHNEIDER, S [1 ]
KOOB, M [1 ]
HENSCHLER, D [1 ]
机构
[1] UNIV WURZBURG,INST PHARMACOL & TOXICOL,W-8700 WURZBURG,GERMANY
关键词
D O I
10.1016/0024-3205(92)90445-U
中图分类号
R-3 [医学研究方法]; R3 [基础医学];
学科分类号
1001 ;
摘要
Glyoxylic acid is the toxic principle of acquired and inherited oxalurias. A "chemical", not enzyme-mediated detoxication concept for the trapping of this aldehyde is described, based on a spontaneous formation of alkaloid-type heterocycles by reaction with biogenic amines or amino acids. 5,5-Dimethylthiazolidine-2(R,S)-4(S)-dicarboxylic acid, prepared by the condensation of D(-)-penicillamine with glyoxylic acid, was found to be formed quickly in vitro, to be stable in vivo and of good physiological compatibility. Renal elimination of the unchanged thiazolidine occurs mainly within 24 h, after administration of its calcium salt to NMRI-mice. Recovery up to 85 % of the applied dose was quantitatively monitored by HPLC after derivatization to the corresponding fluorescent dansyl compound, which was unequivocally identified by MS analysis after isolation from mice urine.
引用
收藏
页码:1597 / 1605
页数:9
相关论文
共 23 条
[1]   SYNTHESES IN THE PENICILLIN FIELD .5. THE STRUCTURE AND REDUCTION OF SOME THIAZOLINYLOXALONES [J].
BENTLEY, R ;
COOK, AH ;
ELVIDGE, JA .
JOURNAL OF THE CHEMICAL SOCIETY, 1949, (DEC) :3216-3220
[2]  
BRINGMANN G, 1991, LIEBIGS ANN CHEM, P1189
[3]  
BRINGMANN G, 1986, NACHR CHEM TECH LAB, V34, P222
[4]  
BRINGMANN G, 1991, CHEM TECHN LAB, V57, P73
[5]  
BRINGMANN G, 1992, IN PRESS ANAL LETT, V25
[6]  
BRINGMANN G, 1991, PLANTA MED S1, V57, P73
[7]   D-PENICILLAMINE - ONCE A CONSTITUENT OF PENICILLIN - NOW A POTENT DRUG [J].
LODEMANN, E .
NATURWISSENSCHAFTEN, 1979, 66 (09) :462-466
[8]   STUDIES ON ANTI-TUMOUR ACTIVITY OF ALIPHATIC ALDEHYDES .3. FORMATION OF THIAZOIDINE-4-CARBOXYLIC ACID IN TISSUES [J].
LORETI, L ;
FERIOLI, ME ;
GAZZOLA, GC ;
GUIDOTTI, GG .
EUROPEAN JOURNAL OF CANCER, 1971, 7 (04) :281-&
[9]  
MCMILLAN I, 1968, J CHEM SOC CHEM COMM, P11
[10]   DIVERSION OF ETHANOL-METABOLISM BY SULFHYDRYL AMINO-ACIDS - D-PENICILLAMINE-DIRECTED EXCRETION OF 2,5,5-TRIMETHYL-D-THIAZOLIDINE-4-CARBOXYLIC ACID IN URINE OF RATS AFTER ETHANOL ADMINISTRATION [J].
NAGASAWA, HT ;
GOON, DJW ;
CONSTANTINO, NV ;
ALEXANDER, CS .
LIFE SCIENCES, 1975, 17 (05) :707-714