Selective fluorescence quenching of 2,3-diazabicyclo[2.2.2]oct-2-ene by nucleotides

被引:45
作者
Marquez, C
Pischel, U
Nau, WM
机构
[1] Int Jacobs Univ Bremen, Sch Sci & Engn, D-28759 Bremen, Germany
[2] Univ Porto, Dept Quim, REQUIMTE, P-4169007 Oporto, Portugal
关键词
D O I
10.1021/ol035454q
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The fluorescence quenching of 2,3-diazabicyclo[2.2.2]oct-2-ene (DBO) by nucleotides has been studied. The quenching mechanism was analyzed on the basis of deuterium isotope effects, tendencies for exciplex formation, and the quenching efficiency in the presence of a molecular container (cucurbit[7]uril). Exciplex-induced quenching appears to prevail for adenosine, cytidine, and uridine, while hydrogen abstraction becomes competitive for thymidine and guanosine. Compared to other fluorescent probes, DBO responds very selectively to the type of nucleotide.
引用
收藏
页码:3911 / 3914
页数:4
相关论文
共 54 条
[1]   Photooxidative damage of guanine in DG and DNA by the radicals derived from the α cleavage of the electronically excited carbonyl products generated in the thermolysis of alkoxymethyl-substituted dioxetanes and the photolysis of alkoxyacetones [J].
Adam, W ;
Arnold, MA ;
Saha-Möller, CR .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (02) :597-604
[2]   Energetics and rate of electron transfer in DNA from base radical anions to electron-affinic intercalators in aqueous solution [J].
Anderson, RF ;
Wright, GA .
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 1999, 1 (20) :4827-4831
[3]   RAMAN SPECTRAL STUDIES NUCLEIC-ACIDS .24. MOLECULAR-CONFORMATIONS AND 8-CH EXCHANGE-RATES OF PURINE RIBONUCLEOTIDES AND DEOXYRIBONUCLEOTIDES - INVESTIGATION BY RAMAN-SPECTROSCOPY [J].
BENEVIDES, JM ;
LEMEUR, D ;
THOMAS, GJ .
BIOPOLYMERS, 1984, 23 (06) :1011-1024
[4]  
Cosa G, 2001, PHOTOCHEM PHOTOBIOL, V73, P585, DOI 10.1562/0031-8655(2001)073<0585:PPOFDD>2.0.CO
[5]  
2
[6]   Proton-coupled electron transfer [J].
Cukier, RI ;
Nocera, DG .
ANNUAL REVIEW OF PHYSICAL CHEMISTRY, 1998, 49 :337-369
[7]   Photosensitization of thymine nucleobase by benzophenone through energy transfer, hydrogen abstraction and one-electron oxidation [J].
Delatour, T ;
Douki, T ;
D'Ham, C ;
Cadet, J .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY B-BIOLOGY, 1998, 44 (03) :191-198
[8]   PROTON-TRANSFER FROM HETEROCYCLIC-COMPOUNDS .4. GUANINE, GUANOSINE, HYPOXANTHINES, AND INOSINE [J].
ELVIDGE, JA ;
JONES, JR ;
OBRIEN, C ;
EVANS, EA ;
SHEPPARD, HC .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1974, (02) :174-176
[9]   THROUGH-SPACE TRIPLET ENERGY-TRANSFER - MOVEMENT OF ELECTRONS THROUGH THE HEMICARCERAND SKELETON [J].
FARRAN, A ;
DESHAYES, K ;
MATTHEWS, C ;
BALANESCU, I .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (37) :9614-9615
[10]   Free energy dependence of intermolecular triplet energy transfer: Observation of the inverted region [J].
Farran, A ;
Deshayes, KD .
JOURNAL OF PHYSICAL CHEMISTRY, 1996, 100 (09) :3305-3307