Transient free radicals are formed during photolysis of the 1-(2-nitrophenyl) ethyl ester of adenosine triphosphate (caged ATP)

被引:4
作者
Corrie, JET
Baker, J
Ostap, EM
Thomas, DD
Trentham, DR
机构
[1] Natl Inst Med Res, London NW7 1AA, England
[2] Univ Minnesota, Sch Med, Dept Biochem, Minneapolis, MN 55455 USA
基金
美国国家卫生研究院;
关键词
transient free radicals; photolysis; adenosine triphosphate;
D O I
10.1016/S1010-6030(98)00231-7
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Flash photolysis of the P-3-1-(2-nitrophenyl)ethyl ester of ATP (caged ATF) in thr presence of dithiothreitol results in formation of a transient radical species in addition to the known paired-electron aci-nitro anion. The transient radical represents approx, 10% of the reaction flux and is proposed to be the radical anion of the nitroaryl group of caged ATP. The kinetics of its formation suggest that it arises by single electron transfer to the triplet excited state of the nitroarene. The electron donor has not been conclusively identified but tertiary amines present as buffer salts or as impurities are likely candidates. (C) 1998 Elsevier Science S.A. All rights reserved.
引用
收藏
页码:49 / 55
页数:7
相关论文
共 37 条
[1]   CONTROLLING CELL CHEMISTRY WITH CAGED COMPOUNDS [J].
ADAMS, SR ;
TSIEN, RY .
ANNUAL REVIEW OF PHYSIOLOGY, 1993, 55 :755-784
[2]   A TIME-RESOLVED ELECTRON-SPIN-RESONANCE STUDY ON THE PHOTOCHEMICAL REDUCTION OF NITROBENZENE DERIVATIVES IN ALCOHOLIC SOLUTION [J].
AKIYAMA, K ;
IKEGAMI, Y ;
IKENOUE, T ;
TEROKUBOTA, S .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1986, 59 (10) :3269-3270
[3]   SYNTHESIS AND PROPERTIES OF A CONFORMATIONALLY RESTRICTED SPIN-LABELED ANALOG OF ATP AND ITS INTERACTION WITH MYOSIN AND SKELETAL-MUSCLE [J].
ALESSI, DR ;
CORRIE, JET ;
FAJER, PG ;
FERENCZI, MA ;
THOMAS, DD ;
TRAYER, IP ;
TRENTHAM, DR .
BIOCHEMISTRY, 1992, 31 (34) :8043-8054
[4]   Time-resolved infrared spectroscopy of intermediates and products from photolysis of 1-(2-nitrophenyl)ethyl phosphates: Reaction of the 2-nitrosoacetophenone byproduct with thiols [J].
Barth, A ;
Corrie, JET ;
Gradwell, MJ ;
Maeda, Y ;
Mantele, W ;
Meier, T ;
Trentham, DR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (18) :4149-4159
[5]   PHOTOCHEMICAL RELEASE OF ATP FROM CAGED-ATP STUDIED BY TIME-RESOLVED INFRARED-SPECTROSCOPY [J].
BARTH, A ;
HAUSER, K ;
MANTELE, W ;
CORRIE, JET ;
TRENTHAM, DR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (41) :10311-10316
[6]   The direct introduction of the amino and substituted amino groups into the aromatic and heterocyclic nucleus VI The action of alkali diphenylamides on some aromatic nitro compounds [J].
Bergstrom, FW ;
Granara, IM ;
Erickson, V .
JOURNAL OF ORGANIC CHEMISTRY, 1942, 7 (01) :98-102
[7]   CARBANION MECHANISMS .12. PROTON-TRANSFER AND ELECTRON-TRANSFER PROCESSES IN REACTION OF PARA-NITROTOLUENE WITH BASES - A SPECTROPHOTOMETRIC STUDY [J].
BUNCEL, E ;
MENON, BC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (10) :3499-3507
[8]  
CHOW YL, 1982, CHEM AMINO NITR SF 1, P188
[9]  
Corrie JET, 1996, J LABELLED COMPD RAD, V38, P403
[10]   SITE-SPECIFIC LABELING OF CAGED-ATP WITH DEUTERIUM OR O-18 [J].
CORRIE, JET ;
REID, GP .
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1995, 36 (03) :289-300