Antiviral activity; Herpes simplex virus type 1; 5-(2-Bromovinyl)-2'-deoxyuridine analogue; Single crystal X-ray diffraction; MO calculation
Abstract :
[en] Structural and electronic characteristics of 5-(5-chlorothien-2-yl)-2′-deoxyuridine (I), 5-(furan-2-yl)-2′-deoxyuridine (II), 5-(5-bromofuran-2-yl)-2′-deoxyuridine (III), 5-(3-bromoisoxazol-5-yl)-2′-deoxyuridine (V) and 5-(isoxazol-5-yl)-2′-deoxyuridine (IV) have been determined and compared to the BVDU (VI) characteristics in order to explain their respective affinity for the herpes simplex virus type 1 thymidine kinase (TK). Molecular structure of 5-(5-chlorothien-2-yl)-2′-deoxyuridine has been obtained using single crystal X-ray crystallography. Electrostatic potential maps, energy and topology of frontier orbitals were computed at the ab initio MO STO-3G and STO-3G* level. These studies reveal that the electrostatic potential energy maps are clearly dependent on the affinity of the compound for the enzyme.
Disciplines :
Biochemistry, biophysics & molecular biology
Author, co-author :
Olivier, Anne; Facultés Universitaires Notre-Dame de la Paix - Namur - FUNDP > Département de Chimie > Laboratoire de Chimie Moléculaire Structurale
Creuven, Isabelle; Facultés Universitaires Notre-Dame de la Paix - Namur - FUNDP > Département de Chimie > Laboratoire de Chimie Moléculaire Structurale
Evrard, Christine ; Facultés Universitaires Notre-Dame de la Paix - Namur - FUNDP > Département de Chimie > Laboratoire de Chimie Moléculaire Structurale
Evrard, Guy; Facultés Universitaires Notre-Dame de la Paix - Namur - FUNDP > Département de Chimie > Laboratoire de Chimie Moléculaire Structurale
Dory, Magdalena; Facultés Universitaires Notre-Dame de la Paix - Namur - FUNDP > Département de Chimie > Laboratoire de Chimie Moléculaire Structurale
van Aerschot, Arthur; Katholieke Universiteit Leuven - KUL
Wigerinck, Piet; Katholieke Universiteit Leuven - KUL
Herdewijn, Piet; Katholieke Universiteit Leuven - KUL
Durant, François; Facultés Universitaires Notre-Dame de la Paix - Namur - FUNDP > Département de Chimie > Laboratoire de Chimie Moléculaire Structurale
Language :
English
Title :
Stereoelectronic properties of five anti-HSV-1 2′-deoxynucleosides analogues with heterocyclic substituents in the 5-position: A comparison with BVDU
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