A GENERAL PROCEDURE FOR ISOTOPIC (DEUTERIUM) LABELING OF NONSTEROIDAL ANTIINFLAMMATORY 2-ARYLPROPIONIC ACIDS

被引:19
作者
CASTELL, JV
MARTINEZ, LA
MIRANDA, MA
TARREGA, P
机构
[1] HOSP UNIV LA FE,CTR INVEST,AVE CAMPANAR 21,E-46009 VALENCIA,SPAIN
[2] UNIV POLITECN VALENCIA,CSIC,INST TECNOL QUIM,DEPT QUIM,E-46071 VALENCIA,SPAIN
关键词
2-ARYLPROPIONIC ACIDS; DEUTERIUM LABELING; PHOTOALLERGY; PHOTOCHEMISTRY;
D O I
10.1002/jlcr.2580340113
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
Alkaline treatment of nonsteroidal antiinflammatory 2-arylpropionic acids in deuterium oxide led in all cases to isotopic exchange of the proton located at the alpha-position of the side chain. Monodeuteration was observed in the case of carprofen, ibuprofen, ketoprofen, fenoprofen, flurbiprofen and naproxen. Additional exchange of one or two protons of the heterocyclic ring occurred in indoprofen, suprofen and tiaprofenic acid. The isotopic labelling survived under the conditions required to perform in vitro photoallergic studies (photolysis in non-deuterated aqueous media).
引用
收藏
页码:93 / 100
页数:8
相关论文
共 12 条
  • [1] PHOTOLYTIC DEGRADATION OF IBUPROFEN - TOXICITY OF THE ISOLATED PHOTOPRODUCTS ON FIBROBLASTS AND ERYTHROCYTES
    CASTELL, JV
    GOMEZ, MJ
    MIRANDA, MA
    MORERA, IM
    [J]. PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1987, 46 (06) : 991 - 996
  • [2] INVOLVEMENT OF DRUG-DERIVED PEROXIDES IN THE PHOTOTOXICITY OF NAPROXEN AND TIAPROFENIC ACID
    CASTELL, JV
    GOMEZLECHON, MJ
    GRASSA, C
    MARTINEZ, LA
    MIRANDA, MA
    TARREGA, P
    [J]. PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1993, 57 (03) : 486 - 490
  • [3] CHEN CS, 1990, J LABELLED COMPD RAD, V28, P1019
  • [4] SYNTHESIS OF DEUTERATED ARYLALKANOIC ACIDS FOR USE AS INTERNAL STANDARDS IN GAS CHROMATOGRAPHY/MASS SPECTROMETRY ASSAYS FOR NON-STEROIDAL ANTI-INFLAMMATORY DRUGS
    DAWSON, M
    MCGEE, CM
    SMITH, MD
    VINE, JH
    [J]. JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1989, 27 (06) : 707 - 714
  • [5] RADIOCHEMICAL SYNTHESIS .4. SYNTHESIS OF LABELED ANTIINFLAMMATORY AGENTS
    HAFFERL, W
    HARY, A
    [J]. JOURNAL OF LABELLED COMPOUNDS, 1973, 9 (02): : 293 - 300
  • [6] KELLOGG MR, 1984, COMPREHENSIVE HETE 3, V4, P719
  • [7] PHOTOTOXICITY OF NONSTEROIDAL INFLAMMATORY DRUGS - COINCIDENCE OR SPECIFIC MECHANISM
    KOCHEVAR, IE
    [J]. ARCHIVES OF DERMATOLOGY, 1989, 125 (06) : 824 - 826
  • [8] MIRANDA MA, 1992, IN VITRO ALTERNATIVE, P239
  • [9] MIRANDA MA, 1993, IN PRESS TOXICOL INV
  • [10] Mori Y, 1983, Radioisotopes, V32, P533