Evaluation of the inhibitory activity on serine and aspartic proteases of 4-amino-4H-1,2,4-triazole and 5-aminothiazole derivatives structurally related to β-lactam antibiotics
Vilain, A. C.; Pirotte, Bernard; Vergely, I.et al.
1993 • In Journal of Pharmacy and Pharmacology, 45, p. 466-472
Pirotte, Bernard ; Université de Liège - ULiège > Département de pharmacie > Chimie pharmaceutique
Vergely, I.
Boggetto, N.
Masereel, B.
Schynts, M.
Delarge, J.
Reboud-Ravaux, M.
Language :
English
Title :
Evaluation of the inhibitory activity on serine and aspartic proteases of 4-amino-4H-1,2,4-triazole and 5-aminothiazole derivatives structurally related to β-lactam antibiotics
Begtrup M. (1979) Cyclisation of N‐formyl‐ and N‐thioformylsarcosine‐N‐methylamide into methylaminothiazolium and anhydro‐mercaptoimidazolium hydroxide derivatives. Journal of the Chemical Society, Perkin Transactions 1 1:1132-1136.
Bender J.G., Van Epps D.E., Searles R., Williams R.C. (1986) Altered function of synovial fluid granulocytes in patients with acute inflammatory arthritis, evidence of action of neutrophils and its mediation by a factor present in synovial fluid. Inflammation 10:443-453.
Bender M.L., Begue‐Canton M.L., Blakely R.L., Brubacher L.J., Feder J., Gunter C.R., Kezdy F.J., Killheffer J.V., Marshall T.H., Miller C.G., Roeske R.W., Stoops J.K. (1966) The determination of the concentration of hydrolytic enzyme solutions: α‐chymotrypsin, trypsin, papain, elastase, subtilisin, and acetylcholinesterase. J. Am. Chem. Soc. 88:5890-5913.
Chase T., Shaw E. (1970) Titration of trypsin, plasmin, and thrombin with p‐nitrophenyl and p′‐guanidinobenzoate HCl. Methods Enzymol. 19:20-27.
Doherty J.B., Ashe B.M., Argenbright L.W., Barker P.L., Bonney R.L., Chandler G.O., Dahlgren M.E., Dorn C.P., Finke P.E., Firestone R.A., Fletcher D., Hagmann W.K., Mumford R., O'Grady L., Maycock A.L., Pisano J.M., Shah S.K., Thompson K.V., Zimmerman M. (1986) Cephalosporin antibiotics can be modified to inhibit human leukocyte elastase. Nature 322:192-194.
Dupaix A., Béchet J.‐J., Roucous C. (1970) Separation of polar, steric and specific effects in the α‐chymotrypsin‐catalyzed hydrolysis of acyl‐substituted p‐nitrophenyl esters. Biochem. Biophys. Res. Commun. 41:464-470.
Finke P.E., Ashe B.M., Knight W.B., Maycock A.L., Navia M.A., Shah S.K., Thompson K.R., Underwood D.J., Weston H., Zimmerman M., Doherty J.B. (1990) Inhibition of human leukocyte elastase. 2. Inhibition by substituted cephalosporin esters and amides. J. Med. Chem. 33:2522-2528.
Firestone R.A., Barker P.L., Pisano J.M., Ashe B.M., Dahlgren M. (1990) Monocyclic β‐lactams inhibitors of leukocyte elastase. Tetrahedron 46:2255-2262.
Keeley F.W., Todorovitch L., Rabinovitch M. (1989) Elastin and elastases in the pathology of the arterial wall. Elastin and Elastases , Robert, L., Hornebeck, W., (eds), CRC Press, Boca Raton, Florida, pp; 2:169-184.
Kettner C., Shenvi A.B. (1984) Inhibition of serine proteases leukocyte elastase, cathepsin G., and chymotrypsin by peptide boronic acids. J. Biol. Chem. 259:15106-15114.
Kuramochi H., Nakata H., Ishii S.‐I. (1979) Mechanism of association of a specific aldehyde inhibitor, leupeptin, with bovine trypsin. J. Biochem. 80:1403-1410.
Janoff A. (1985) Elastase and emphysema‐current assessment of the protease‐anti‐protease hypothesis. Am. Rev. Respir. Dis. 132:417-433.
Maillard J.L., Favreau C., Reboud‐Ravaux M., Kobaiter R., Joyeau R., Wakselman M. (1990) Biological evaluation of the inhibition of neutrophil elastase by a synthetic β‐lactam derivative. Eur. J. Cell Biol. 52:213-218.
Pirotte B. (1990) Synthesis and biological evaluation of 5‐amino‐thiazole and 4‐amino‐1,2,4‐triazole derivatives, potential inhibitors of bacterial serine enzymes. Dissert. Abstr. Int. 1:109-110.
Pirotte B., Delarge J. (1990) 5‐Phenylacetylaminothiazolium salts and their reactions with nucleophiles. J. Chem. Res. (S) 208-209.
Pirotte B., Delarge J., Coyette J.‐M., Frère J.‐M. (1991) Antibacterial activity of 5‐acylaminothiazole derivatives, synthetic drugs related to β‐lactam antibiotics. J. Antibiotics 44:844-853.
Pirotte B., Dive G., Delarge J., Masereel B., Dupont L., Thunus L., Schynts M., Coyette J., Frère J.‐M. (1992) Synthèse, étude théorique et évalulation biologique de dérivés du 4‐amino‐4H‐1,2,4‐triazole analogues des antibiotiques β‐lactimiques. Eur. J. Med. Chem. 27:193-205.
Pohl J., Zaoral M., Jindra A., Kosta V. (1984) Purifications of pepsins and cathepsin D by affinity chromatography on sepharose 4B with an immobilized synthetic inhibitor. Anal. Biochem. 139:265-271.
Powers J.C., Gupton B.F. (1977) Reaction of serine proteases with aza‐amino acid and azapeptide derivatives. Methods Enzymol. 46:208-216.
Wakselman M., Joyeau R., Kobaiter R., Boggetto N., Vergely I., Maillard J., Okochi V., Montagne J.‐J., Reboud‐Ravaux M. (1991) Functionalized N‐aryl azetidinones as novel mechanism‐based inhibitors of neutrophil elastase. FEBS Lett. 282:377-381.
Zerner B., Bender M.L. (1964) The kinetic consequence of the acyl‐enzyme mechanism for the reactions of specific substrates with chymotrypsin. J. Am. Chem. Soc. 86:3669-3674.
