Design of anti-HIV ligands by means of minimal topological difference (MTD) method

International Journal of Molecular Sciences

Volumn 7, Issue 11, 2006, Pages 537-555

  Duda Seiman, Corina ^a   Duda Seiman, Daniel ^b   Dragoş, Dan ^b   Medeleanu, Mihai ^c   Careja, Valentin ^d   Putz, Mihai V ^a   Lacrǎmǎ, Ana Maria ^a   Chiriac, Adrian ^a   Nuţiu, Remus ^a   Ciubotariu, Dan ^b  

^a WEST UNIVERSITY OF TIMISOARA   (Romania)

^b VICTOR BABES UNIVERSITY OF MEDICINE AND PHARMACY   (Romania)

^c POLITEHNICA UNIVERSITY OF TIMISOARA   (Romania)

^d ACADEMY OF ROMANIAN SCIENTISTS   (Romania)

Author keywords

Anti HIV ligands; Minimal topological difference (MTD) method; Molecular design

Indexed keywords

1 [(2 HYDROXIETHOXI) METHYL] 6 (PHENYLTHIO)THYMINE; ANTIVIRUS AGENT; LIGAND; RNA DIRECTED DNA POLYMERASE INHIBITOR; UNCLASSIFIED DRUG;

ACQUIRED IMMUNE DEFICIENCY SYNDROME; ARTICLE; BIOLOGICAL ACTIVITY; DRUG STRUCTURE; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS INFECTED PATIENT; METHODOLOGY; MOLECULAR MODEL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; STRUCTURE ACTIVITY RELATION;

HUMAN IMMUNODEFICIENCY VIRUS;

EID: 33947316568     PISSN: None     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/i7110537     Document Type: Article

References (26)

1. Clavel, F.; Guyader, M.; Guetard, M.; Salle, M.; Montagnier, L.; Alizon, M. Molecular cloning and polymorphism of the human immune deficiency virus type 2. Nature 1986, 324, 691-695.
2. Guyader, M.; Emerman, M.; Sonigo, P.; Clavel, F.; Montagnier, M.; Alizon, M. Genome organization and transactivation of the human immunodeficiency virus type 2. Nature 1987, 326, 662-669.
3. Fauci, A.S. The human immunodeficiency virus: infectivity and mechanisms of pathogenesis. Science 1988, 239, 617-622.
4. Barre-Sinoussi, F.; Chermann, J.-C.; Rey, F.; Nugeyre, M.T.; Chamaret, S.; Gruest, J.; Dauguet, C.; Axler-Blin, C.; Vezinet-Brun, F.; Rouzioux, C.; Rozenbaum, W.; Montagnier, L. Isolation of a T-lymphotropic retrovirus from a patient at risk for acquired immune deficiency syndrome (AIDS). Science 1983, 220, 868-871.
5. (a) Popovic, M.; Sarngadharan, M.G.; Read, E.; Gallo, R.C. Detection, isolation, and continuous production of cytopathic retroviruses (HTLV-III) from patients with AIDS and pre-AIDS. Science, 1984, 224, 497-500.;
6. (b) Gallo, R.C.; Salahuddin, S.Z.; Popovic, M.; Shearer, G.M.; Kaplan, M.; Haynes, B.F.; Palker, T.J.; Redfield, R.; Oleske, J.; Safai, B.; White, G.; Foster, P.; Markham, P.D. Frequent detection and isolation of cytopathic retroviruses (HTLV-III) from patients with AIDS and at risk for AIDS. Science 1984, 224, 500-503.
7. th Edition. D. L. Kasper, E. Braunwald, A. S. Fauci, S. L. Hauser, D. L. Longo, J. L. Jameson (Eds.), McGraw-Hill Companies Inc., 2005, p. 1076-1139.
8. De Clercq, E. HIV-1-specific RT inhibitors: highly selective inhibitors of human immunodeficiency virus type 1 that are specifically targeted at the viral reverse transcriptase. Med. Res. Rev. 1993, 13, 229-258.
9. (a) Miyasaka, T.; Tanaka, H.; Baba, M.; Hayakawa, H.; Walker, R.T.; Balzarini, J.; De Clercq, E. A novel lead for specific anti-HIV-1 agents: 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine. J. Med. Chem. 1989, 32, 2507-2509;
10. (b) Baba, M.; Tanaka, H.; De Clercq, E.; Pauwels, R.; Balzarini, J.; Schols, D.; Nakashima, H.; Perno, C.F.; Walker, R.T.; Miyasaka, T. Highly specific inhibition of human immunodeficiency virus type 1 by a novel 6-substituted acyclouridine derivative. Biochem. Biophys. Res. Commun. 1989, 165, 1375-1381.
11. Tanaka, H.; Hirayama, M.; Suzuki, M.; Miyasaka, T.; Matsuda, A.; Ueda, T. A lithiation route to c-5 substitution of an imidazole nucleoside and its application to the synthesis of 3-deazaguanosine. Tetrahedron 1986, 42, 1971-1980.
12. Tanaka, H.; Takashima, H.; Ubasawa, M.; Sekiya, K.; Nitta, I.; Baba, M.; Shigeta, S.; Walker, R.T.; De Clerq, E. Structure-activity relationships of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine analogues: effect of substitutions at the C-6 phenyl ring and at the C-5 position on anti-HIV-1 activity. J. Med. Chem. 1992, 35, 337-345.
13. Balaban, A. T.; Chiriac, A.; Motoc, I; Simon, Z. Steric Fit in QSAR; Springer, Berlin (Lecture Notes in Chemistry Series), 1980.
14. Simon, Z; Chiriac, A.; Holban, S.; Ciubotariu, D.; Mihalas, G. I. Minimum Steric Difference. The MTD Method for QSAR Studies; Res. Studies Press (Wiley), Letchworth, 1984.
15. Ciubotariu, D.; Deretey, E.; Oprea, T. I.; Sulea, T.; Simon, Z.; Kurunczi, L.; Chiriac, A. Multiconformational Minimal Steric Difference. Structure-Acetylcholinesterase Hydrolysis Rates Relations for Acetic Acid Esters. Quant. Struct. Act. Relat. 1993, 12, 367-372.
16. Simon, Z.; Chiriac, A.; Ciubotariu, D.; Muresan, S.; Bologa, C.; Sulea, T.; Kurunczi, L. Metoda MTD (The MTD method). In Relaţii cantitative structurǎ chimicǎ - activitate biologicǎ (QSAR). Metoda MTD (Quantitative chemical structure - biological activity relationships studies (QSAR). The MTD method); Chiriac, A.; Ciubotariu, D.; Simon, Z. (Eds.). Mirton Publishing House, Timişoara, Romania, 1996, Chapter 5.
17. Ciubotariu, D.; Gogonea, V.; Medeleanu, M. in QSAR Studies by Molecular Descriptions; Diudea, M. V. (Editor), Nova Science Publ. Inc., Huntington New York, 2001, Chapter 10.
18. Ciubotariu, D.; Medeleanu, M.; Vlaia, V.; Olariu, T.; Ciubotariu, C.; Dragoş, D.; Seiman, C. Molecular van der Waals Space and Topological Indices from the Distance Matrix. Molecules 2004, 9, 1053-1078.
19. Duda-Seiman C. Doctoral Thesis: QSAR Studies of Pyrimidinic Compounds with Anti-HIV Activity; West University of Timişoara, 2005.
20. Chiriac, A; Ciubotariu, D.; Funar-Timoftei, S.; Kurunczi, L.; Mracec, M.; Mracec, M.; Szabadai, Z.; Seclaman, E.; Simon, Z. QSAR and 3D-QSAR in Timişoara. 1972-2005, Rev. Roum. Chim. 2006, 51, 79-99.
21. Duda-Seiman, C.; Duda-Seiman, D.; Hegheş, A.; Nuţiu, R.; Ciubotariu, D.; Suceveanu, N. Modelarea compuşilor pirimidinici cu activitate anti-HIV (Molecular modeling of pyrimidinic compounds with anti-HIV activity). Revista de Medicinǎ şi Farmacie (Journal of Medicine and Pharmacy) 2004, 50 (Supl. II), 144-149; ISSN 1221-2229.
22. Tanaka, H.; Baba, M.; Ubasawa, M.; Takashima, H.; Sekiya, K.; Nitta, I.; Shigeta, S.; Walker, R.T.; De Clercq, E.; Miyasaka, T. Synthesis and anti-HIV activity of 2-, 3-, and 4-substituted analogues of 1-[(2-hydroxyethoxy)methyl]- 6-(phenylthio)thymine (HEPT). J. Med. Chem. 1991, 34, 1394-1399.
23. Tanaka, H.; Baba, M.; Saito, S.; Miyasaka, T.; Takashima, H.; Sekiya, K.; Ubasawa, M.; Nitta, I.; Walker, R.T.; Nakashima, H.; De Clercq, E. Specific anti-HIV-1 "acyclonucleosides" which cannot be phosphorylated: synthesis of some deoxy analogues of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio) thymine. J. Med. Chem. 1991, 34, 1508-1511.
24. HyperChem 7.01, Program package, Hypercube Inc., 2002.
25. th, 2002, p.55; ISBN 953-6690-22-5.
26. st Ed., Vol. 1, Cambridge University Press, Cambridge, UK, 1987.