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Journal articles
Phosphorylation of dGMP analogs by vaccinia virus TMP kinase and human GMP kinase.
Constance Auvynet
1
Dimitri Topalis
2
Christophe Caillat
3
Hélène Munier-Lehmann
4
Edward Seclaman
4
Jan Balzarini
5
Luigi André Agrofoglio
6
7
Philippe Meyer
8
Dominique Deville-Bonne
2
Chahrazade El Amri
9, *
*
Corresponding author
Constance Auvynet 1
Author
Dimitri Topalis 2
Author
Christophe Caillat 3
Author
Hélène Munier-Lehmann 4
Author IdHAL : helene-munier-lehmann ORCID : https://orcid.org/0000-0001-7579-8561
1
FRE 2852 - Peptidome de la Peau des Amphibiens (Tour 43, 2 place Jussieu, 75251 Paris Cedex 05 - France)
- UPMC - Université Pierre et Marie Curie - Paris 6 (4 place Jussieu - 75005 Paris - France)
2
Laboratoire d'Enzymologie Moléculaire (France)
- UPMC - Université Pierre et Marie Curie - Paris 6 (4 place Jussieu - 75005 Paris - France)
- CNRS - Centre National de la Recherche Scientifique : FRE2852 (France)
3
LEBS - Laboratoire d'Enzymologie et Biochimie Structurales (91 198 Gif-sur-Yvette Cedex - France)
- CNRS - Centre National de la Recherche Scientifique : UPR3082 (France)
4
Chimie Organique (28 rue du Docteur Roux 75724 Paris Cedex 15 - France)
- Institut Pasteur [Paris] (25-28, rue du docteur Roux, 75724 Paris cedex 15 - France)
- CNRS - Centre National de la Recherche Scientifique : URA2128 (France)
5
Rega Institute for Medical Research [Leuven, België] (Minderbroedersstraat 10, B 3000 Leuven - Belgium)
- KU Leuven - Catholic University of Leuven - Katholieke Universiteit Leuven (Oude Markt 13 - bus 5005, 3000 Leuven - Belgium)
6
ICOA - Institut de Chimie Organique et Analytique (UFR Sciences Rue de Chartres - BP 6759 - 45067 ORLEANS CEDEX 2 - France)
- INC - Institut de Chimie du CNRS (3 Rue Michel-Ange 75 016 Paris - France)
- UO - Université d'Orléans : UMR6005 (Château de la Source - Avenue du Parc Floral - BP 6749 - 45067 Orléans cedex 2 - France)
- INSERM - Institut National de la Santé et de la Recherche Médicale : UMR6005 (101, rue de Tolbiac, 75013 Paris - France)
- CNRS - Centre National de la Recherche Scientifique : UMR6005 (France)
7
Department of Molecular and Optical Physics (79104 Freibourg - Germany)
- Albert-Ludwigs-Universität Freiburg (Georges-Köhler Allee 51 79110 Freiburg im Breisgau (Germany) - Germany)
8
IRFU - Institut de Recherches sur les lois Fondamentales de l'Univers (CEA Saclay
F-91191 Gif sur Yvette cedex - France)
- CEA - Commissariat à l'énergie atomique et aux énergies alternatives : DRF/IRFU (Centre de Saclay Centre de Grenoble Centre de Cadarache etc - France)
- Université Paris-Saclay (Bâtiment Bréguet, 3 Rue Joliot Curie 2e ét, 91190 Gif-sur-Yvette - France)
9
UPMC - Université Pierre et Marie Curie - Paris 6 (4 place Jussieu - 75005 Paris - France)
Abstract : Vaccinia virus thymidylate kinase, although similar in sequence to human TMP kinase, has broader substrate specificity and phosphorylates (E)-5-(2-bromovinyl)-dUMP and dGMP. Modified guanines such as glyoxal-dG, 8-oxo-dG, O(6)-methyl-dG, N(2)-ethyl-dG and N(7)-methyl-dG were found present in cancer cell DNA. Alkylated and oxidized dGMP analogs were examined as potential substrates for vaccinia TMP kinase and also for human TMP and GMP kinases. Molecular models obtained from structure-based docking rationalized the enzymatic data. All tested nucleotides are found surprisingly substrates of vaccinia TMP kinase and also of human GMP kinase. Interestingly, O(6)-methyl-dGMP is the only analog specific for the vaccinia enzyme. Thus, O(6)-Me-dGMP could be useful for designing new compounds of medical interest either in antipoxvirus therapy or in experimental combined gene/chemotherapy of cancer. These results also provide new insights regarding dGMP analog reaction with human GMP kinase and their slow recycling by salvage pathway nucleotide kinases.
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Journal articles
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https://hal-pasteur.archives-ouvertes.fr/pasteur-00417244
Contributor : Alexandre Kaminski Connect in order to contact the contributor
Submitted on : Tuesday, September 15, 2009 - 4:30:30 PM
Last modification on : Thursday, May 5, 2022 - 3:18:01 PM
Long-term archiving on: : Saturday, November 26, 2016 - 12:34:48 PM
Contributor : Alexandre Kaminski Connect in order to contact the contributor
Submitted on : Tuesday, September 15, 2009 - 4:30:30 PM
Last modification on : Thursday, May 5, 2022 - 3:18:01 PM
Long-term archiving on: : Saturday, November 26, 2016 - 12:34:48 PM
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Identifiers
- HAL Id : pasteur-00417244, version 1
- DOI : 10.1016/j.bbrc.2009.07.089
- PUBMED : 19631609
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PASTEUR | CNRS | UNIV-ORLEANS | ICOA | THESE-UNIV-ORLEANS | UPMC | CEA | DSM-IRFU | CEA-DRF | SORBONNE-UNIVERSITE | SU-SCIENCES | SU-TI | INC-CNRS
Citation
Constance Auvynet, Dimitri Topalis, Christophe Caillat, Hélène Munier-Lehmann, Edward Seclaman, et al.. Phosphorylation of dGMP analogs by vaccinia virus TMP kinase and human GMP kinase.. Biochemical and Biophysical Research Communications, Elsevier, 2009, 388 (1), pp.6-11. ⟨10.1016/j.bbrc.2009.07.089⟩. ⟨pasteur-00417244⟩
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