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S-fluorenylmethoxycarbonyl glutathione and diesters: inhibition of mammalian glyoxalase II.

Abstract
Inhibitors having high specificity toward mammalian glyoxalase II, but not glyoxalase I, were sought as part of a program to study glyoxalase enzyme function in mammalian cells. The compound, S-fluorenylmethoxycarbonyl glutathione (FMOC-G), was synthesized and found to be a competitive inhibitor of purified calf liver glyoxalase II (Ki = 2.1 mumol/l). Inhibition constants (Ki values) for the other glyoxalase enzyme, glyoxalase I, and the glutathione-requiring enzyme, glutathione S-transferase, from other sources, were found to be 17 and 25 mumol/l, respectively. FMOC-G is a very poor inhibitor of glutathione reductase and glutathione peroxidase. Diesters (dimethyl, diethyl, diisopropyl) of FMCO-G were also synthesized, as proinhibitors, to improve transport of FMOC-G into mammalian tumor cells (rat adrenal pheochromocytoma, PC-12) in culture. The diesters were inhibitory to cell growth and variability; the most effective of these, diisopropyl FMOC-G, exhibited an [I]0.5 value of approximately 275 mumol/l. Diesters of FMOC-G may be useful in studies of the glyoxalase enzyme system in cultured mammalian cells.
AuthorsM K Chyan, A C Elia, G B Principato, E Giovannini, G Rosi, S J Norton
JournalEnzyme & protein (Enzyme Protein) 1994-1995 Vol. 48 Issue 3 Pg. 164-73 ISSN: 1019-6773 [Print] Switzerland
PMID8589803 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
Chemical References
  • Enzyme Inhibitors
  • Esters
  • Fluorenes
  • S-fluorenylmethoxycarbonylglutathione
  • Glutathione Peroxidase
  • Glutathione Reductase
  • Glutathione Transferase
  • Thiolester Hydrolases
  • hydroxyacylglutathione hydrolase
  • Lactoylglutathione Lyase
  • Glutathione
Topics
  • Animals
  • Cattle
  • Cell Division (drug effects)
  • Cell Survival (drug effects)
  • Enzyme Inhibitors (pharmacology)
  • Esters
  • Fluorenes (chemical synthesis, pharmacology)
  • Glutathione (analogs & derivatives, chemical synthesis, pharmacology)
  • Glutathione Peroxidase (metabolism)
  • Glutathione Reductase (metabolism)
  • Glutathione Transferase (metabolism)
  • Kinetics
  • Lactoylglutathione Lyase (antagonists & inhibitors, metabolism)
  • Liver (enzymology)
  • Magnetic Resonance Spectroscopy
  • PC12 Cells
  • Rats
  • Thiolester Hydrolases (antagonists & inhibitors, metabolism)

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