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
scite shows how a scientific paper has been cited by providing the context of the citation, a classification describing whether it supports, mentions, or contrasts the cited claim, and a label indicating in which section the citation was made.
Bibliography
Angyan, Poirier, Kucsman, Csizmadia (1987) Bonding between nonbonded sulfur and oxygen atoms in selected organic molecules (a quantum chemical study). Journal of the American Chemical Society 109:2237-2245.
Baudoux, Vercauteren CPS, a contouring plotting system, Facultés Universitaires Notre-Dame de la paix, Namur; 1989.
Bohman, Balzarini, Wigerinck, Van Aerschot, Herdewijn, De Clercq (1993) Mechanistic study on the antiviral and cytostatic effects of 5-thien-2-yl and 5-furan-2-yl substituted pyrimidine nucleoside analogues. 4th Symposium of the European Society for the study of Purine and Pyrimidine Metabolism in Man, Nijmegen, The Netherlands, 31 Aug.–3 Sept; .
Bradshaw, Deininger (1984) Human thymidine kinase gene: molecular cloning and nucleotide sequences of a cDNA expressible in mammalian cells. Mol. Cell. Biol. 4:2316-2320.
Coen (1991) The implication of resistance to antiviral agents for herpes virus drug targets and drug therapy. Antiviral Res. 15:187-300.
Collins, Schleyer, Binkley, Pople (1976) Self-consistent molecular orbital methods. XVII. Geometries and binding energies of second-row molecules. A comparison of three basis sets , J. Chem. Phys.; 64:5142-5151.
Enquist, Vandewoude, Wagner, Smiley, Summers (1979) Construction and characterization of a recombinant plasmid encoding the gene for the thymidine kinase of herpes simplex type 1 virus. Gene 7:335-342.
Folkers, Trumpp-kallmeyer, Gutbrod, Krickl, Fetzer, Keil (1991) Computer-aided active-site-directed modeling of the Herpes Simplex Virus 1 and human thymidine kinase. Journal of Computer-Aided Molecular Design 5:387-404.
Flemington, Bradshaw, Traina-Dorge, Slagel, Deininger (1987) Sequence, structure and promotor characterization of the thymidine kinase gene. Gene 52:267-277.
Hehre, Stewart, Pople (1969) Self-consistent Molecular-Orbital Methods. I. Use of Gaussian Expansions of Slater-type Atomic Orbitals. J. Chem. Phys. 51:2657-2664.
Hinde, Luken, Chin (1988) “Moplot”. IBM Kingston Technical Report KGN-141, New York; .
Johnson ORTEP Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, Tennesse, USA; 1976.
Kalman, Parkanyi (1980) Structure of 2-benzoylimino-3-methyl-1,3-thiazolidine: a comparison of intramolecular X–S.O = Y interactions. Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry 36 B:2372-2378.
Leib, Ruffner, Hildebrand, Schaffer, Wright, Coen (1990) Specific inhibitors of herpes simplex thymidine kinase diminish reactivation of latent virus from explanted murine ganglia. Antimicr. Ag. Chemother. 34:1285-1286.
Lozac'h (1971) Adv. Heterocycl. Chem. 13:161-234.
Parkanyi, Kalman, Kovacs, Szaboles, Otvos (1983) Crystal and molecular structure of (E)-5-(2-bromoviayl-2′-deoxyuridine). Nucleic Acids Research 11:7999.
Parkanyi, Kalman, Czugler, Kovacs, Walker (1987) A comparison of the conformations adopted by some 5-bromovinyl-2'-deoxyuridines and a correlation with their antiviral properties: an X-ray study. Nucleic Acids Research 15:4111-4121.
Sanderson, Freemont, Murthy, Krane, Summers, Steitz (1988) Purification and crystallization of thymidine kinase from herpes simplex virus type 1. J. Mol. Biol. 202:917-919.
Sheldrick (1976) SHELX76. Program for crystal structure determination, Univ. of Cambridge, UK; .
Sheldrick (1986) SHELX86. Program for the solution of crystal structures, Institut für Anorganische Chemie der Universität, Göttingen, Germany; .
Spek (1990) PLATON92. Acta Cryst 46 A:C3.
Vanderveken, Vercauteren KEMIT, a Molecular Graphics System, Rel 1.2., Facultés Universitaires Notre-Dame de la Paix, Namur; 1989.
Wigerinck, Pannecouque, Snoeck, Claes, De Clercq, Herdewijn (1991) 5-(5-Bromothien-2-yl)-2′-deoxyuridine and 5-(5-chlorothien-2-yl)-2′-deoxyuridine are equipotent to (E)-5-(2-bromovinyl)-2′-deoxyuridine in the inhibition of herpes simplex virus type-1 replication. J. Med. Chem. 34:2383-2389.
Wigerinck, Snoeck, Claes, De Clercq, Herdewijn (1991) Synthesis and antiviral activity of 5-heteroaryl substituted 2′-deoxyuridine. J. Med. Chem. 34:1767-1772.
Wigerinck, Kerremans, Claes, Snoeck, Maudgal, De Clercq, Herdewijn (1993) Synthesis and antiviral activity of 5-thien-2-yl-2'-deoxyuridine analogs. Journal of Medicinal Chemistry 31:538-543.
Similar publications
Sorry the service is unavailable at the moment. Please try again later.
This website uses cookies to improve user experience. Read more
Save & Close
Accept all
Decline all
Show detailsHide details
Cookie declaration
About cookies
Strictly necessary
Performance
Strictly necessary cookies allow core website functionality such as user login and account management. The website cannot be used properly without strictly necessary cookies.
This cookie is used by Cookie-Script.com service to remember visitor cookie consent preferences. It is necessary for Cookie-Script.com cookie banner to work properly.
Performance cookies are used to see how visitors use the website, eg. analytics cookies. Those cookies cannot be used to directly identify a certain visitor.
Used to store the attribution information, the referrer initially used to visit the website
Cookies are small text files that are placed on your computer by websites that you visit. Websites use cookies to help users navigate efficiently and perform certain functions. Cookies that are required for the website to operate properly are allowed to be set without your permission. All other cookies need to be approved before they can be set in the browser.
You can change your consent to cookie usage at any time on our Privacy Policy page.
