CURCUMIN-DERIVED TRANSIENTS - A PULSED-LASER AND PULSE-RADIOLYSIS STUDY

被引:81
作者
GORMAN, AA [1 ]
HAMBLETT, I [1 ]
SRINIVASAN, VS [1 ]
WOOD, PD [1 ]
机构
[1] BOWLING GREEN STATE UNIV,CTR PHOTOCHEM SCI,BOWLING GREEN,OH 43403
关键词
D O I
10.1111/j.1751-1097.1994.tb05053.x
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
In this paper we report a time-resolved investigation of transients derived from curcumin, which may be intimately involved in the processes leading to its biological activity. Fluorescence and triplet quantum yields are respectively 0.06 and 0.11. The high percentage of internal conversion is proposed to proceed via H-transfer within the thermodynamically favored enol structure of what is formally a 1,3-diketone. The triplet energy (191 +/- 2 kJ mol(-1)), natural lifetime (1.5 mu s) and self-quenching rate constant (5.0 x 10(8) L mol(-1) s(-1)) have been determined. Oxygen quenching of the triplet leads to the production of singlet oxygen with unit efficiency. Curcumin quenches the latter species very inefficiently (2.5 x 10(5) L mol(-1) s(-1)). The curcumin radical has been produced via three mechanistically distinct methods. This species is unreactive toward oxygen but is repaired by vitamins C and E and anthralin.
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页码:389 / 398
页数:10
相关论文
共 48 条
[1]   STUDIES ON THE CLASTOGENIC EFFECTS OF BIOLOGIC STAINS AND DYES [J].
AU, W ;
HSU, TC .
ENVIRONMENTAL MUTAGENESIS, 1979, 1 (01) :27-35
[2]   PULSE-RADIOLYSIS STUDY OF QUENCHING OF AROMATIC CARBONYL TRIPLETS BY NORBORNADIENES AND QUADRICYCLENES - MECHANISM OF INTERCONVERSION [J].
BARWISE, AJG ;
GORMAN, AA ;
LEYLAND, RL ;
SMITH, PG ;
RODGERS, MAJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (06) :1814-1820
[3]   TRIPLET-TRIPLET EXTINCTION COEFFICIENTS VIA ENERGY TRANSFER [J].
BENSASSON, R ;
LAND, EJ .
TRANSACTIONS OF THE FARADAY SOCIETY, 1971, 67 (583) :1904-+
[4]  
Bensasson R., 1978, PHOTOCH PHOTOBIO SCI, V3, P163
[5]   LUMINESCENCE QUENCHING BY OXYGEN - CYCLOHEXANE-BENZENE-PARA-TERPHENYL [J].
BERRY, PJ ;
BURTON, M .
JOURNAL OF CHEMICAL PHYSICS, 1955, 23 (10) :1969-1970
[6]   RADIATION-INDUCED DIMERIZATION OF TYROSINE AND GLYCYLTYROSINE IN AQUEOUS-SOLUTIONS [J].
BOGUTA, G ;
DANCEWICZ, AM .
INTERNATIONAL JOURNAL OF RADIATION BIOLOGY, 1981, 39 (02) :163-174
[7]   ANTHRALIN-DERIVED TRANSIENTS .2. FORMATION OF THE RADICAL BY SPONTANEOUS FRAGMENTATION OF BOTH SINGLET AND TRIPLET-STATES OF THE 10,10'-DEHYDRODIMER - RADICAL PAIR MULTIPLICITY EFFECTS [J].
BRUCE, JM ;
DODD, NJF ;
GORMAN, AA ;
HAMBLETT, I ;
KERR, CW ;
LAMBERT, C ;
MCNEENEY, SP .
PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1990, 52 (02) :345-351
[8]   ANTHRALIN-DERIVED TRANSIENTS .1. THE TRIPLET-STATE AND THE PRODUCTS OF ITS REACTION WITH OXYGEN IN BENZENE [J].
BRUCE, JM ;
GORMAN, AA ;
HAMBLETT, I ;
KERR, CW ;
LAMBERT, C ;
MCNEENEY, SP .
PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1989, 49 (04) :439-445
[9]   THE AZIDE RADICAL AND ITS REACTION WITH TRYPTOPHAN AND TYROSINE [J].
BUTLER, J ;
LAND, EJ ;
SWALLOW, AJ ;
PRUTZ, W .
RADIATION PHYSICS AND CHEMISTRY, 1984, 23 (1-2) :265-270
[10]   AROMATISCHE KOHLENWASSERSTOFFE .72. DIE ZUSAMMENHANGE ZWISCHEN CHEMISCHER REAKTIVITAT, PHOSPHORESCENZ UND PARA-ABSORPTIONSBANDEN UND DIE WASSERSTOFFAHNLICHKEIT DES OBEREN NIVEAUS DER PARA-BANDEN IN DEN ABSORPTIONSSPEKTREN AROMATISCHER KOHLENWASSERSTOFFE [J].
CLAR, E ;
ZANDER, M .
CHEMISCHE BERICHTE-RECUEIL, 1956, 89 (03) :749-762