The ability of various aldehydes, some of which are produced in lipid peroxidation, to effect heat-shock gene expression and heat-shock proteins synthesis was evaluated in HeLa cells. Only (E)-4-hydroxyalk-2-enals were active both in racemic and homochiral form. Between the reported primary metabolic products of (E)-4-hydroxynon-2-enal, only the glutathione conjugates were active, whereas (E)-4-hydroxynon-2-enoic acid and 2-nonen-1,4-diol were inactive. Also, unnatural (E)-5-hydroxynon-2-enal and (E)-5-hydroxyhex-2-enal were active, whereas (E)-6-hydroxynon-2-enal was inactive. Thus, it was established that the active aldehydic compounds must possess an (E)-2 double bond and an hydroxy group in a position suitable for the formation of a cyclic hemiacetal in a possible adduct of these aldehydes with proteins. An irreversible binding to proteins could be the first step of the mechanism by which these compounds exert their biological activity.

STRUCTURAL REQUIREMENTS OF ALDEHYDES PRODUCED IN LPO FOR THE ACTIVATION OF THE HEAT-SHOCK GENES IN HELA-CELLS / P. ALLEVI, M. ANASTASIA, F. CAJONE, P. CIUFFREDA, A. SANVITO. - In: FREE RADICAL BIOLOGY & MEDICINE. - ISSN 0891-5849. - 18:1(1995), pp. 107-116.

STRUCTURAL REQUIREMENTS OF ALDEHYDES PRODUCED IN LPO FOR THE ACTIVATION OF THE HEAT-SHOCK GENES IN HELA-CELLS

P. ALLEVI
Primo
;
M. ANASTASIA
Secondo
;
P. CIUFFREDA
Penultimo
;
1995

Abstract

The ability of various aldehydes, some of which are produced in lipid peroxidation, to effect heat-shock gene expression and heat-shock proteins synthesis was evaluated in HeLa cells. Only (E)-4-hydroxyalk-2-enals were active both in racemic and homochiral form. Between the reported primary metabolic products of (E)-4-hydroxynon-2-enal, only the glutathione conjugates were active, whereas (E)-4-hydroxynon-2-enoic acid and 2-nonen-1,4-diol were inactive. Also, unnatural (E)-5-hydroxynon-2-enal and (E)-5-hydroxyhex-2-enal were active, whereas (E)-6-hydroxynon-2-enal was inactive. Thus, it was established that the active aldehydic compounds must possess an (E)-2 double bond and an hydroxy group in a position suitable for the formation of a cyclic hemiacetal in a possible adduct of these aldehydes with proteins. An irreversible binding to proteins could be the first step of the mechanism by which these compounds exert their biological activity.
LIPID PEROXIDATION ; (E)-4-HYDROXYALK-2-ENALS ; (E)-4-HYDROXYNON-2-ENAL ; HYDROXYALDEHYDES ; (E)-4-HYDROXYNON-2-ENOIC ACID ; (E)-5-HYDROXYNON-2-ENAL ; HEAT-SHOCK PROTEINS ; FREE RADICALS
Settore BIO/10 - Biochimica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/183777
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