Human immunodeficiency virus type 1 proteinase resistance to symmetric cyclic urea inhibitor analogs

Antimicrobial Agents and Chemotherapy

Volumn 41, Issue 11, 1997, Pages 2383-2388

  Nillroth, Ulrika ^a   Vrang, Lotta ^a   Markgren, Per Olof ^a   Hultén, Johan ^b   Hallberg, Anders ^b   Danielson, U Helena ^a,c  

^a UPPSALA UNIVERSITY   (Sweden)

^b MEDIVIR AB   (Sweden)

^c UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

4,7 DIBENZYL 2,3,4,5,6,7 HEXAHYDRO 5,6 DIHYDROXY 1,3 BIS[4 (HYDROXYMETHYL)BENZYL] 2H 1,3 DIAZEPIN 2 ONE; A 75925; AHA 008; PHENYL GROUP; PROTEINASE; PROTEINASE INHIBITOR; SAQUINAVIR; UNCLASSIFIED DRUG;

ANTIBIOTIC RESISTANCE; ARTICLE; CELL VIABILITY; CONTROLLED STUDY; DRUG POTENCY; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME KINETICS; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; PRIORITY JOURNAL; VIRUS INHIBITION; VIRUS MUTANT;

EID: 0030664454     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/aac.41.11.2383     Document Type: Article

References (24)

1. Ala, P., E. Huston, R. DeLoskey, J. Duke, B. Korant, and C.-H. Chang. 1996. The molecular basis of HIV-1 protease drug resistance, abstr. Th.A.154. In Abstracts of the XI International Conference on AIDS.
2. Bardsley, W. G., P. B. McGinlay, and M. G. Roig. 1989. Optimal design for model discrimination using the F-test with non-linear biochemical methods. Criteria for choosing the number and spacing of experimental points. J. Theor. Biol. 139:85-102.
3. Coffin, J. M. 1995. HIV population dynamics in vivo: implications for genetic variation pathogenesis, and therapy. Science 267:483-489.
4. Condra, J. H., W. A. Schleif, O. M. Blahy, L. J. Gabryelski, D. J. Graham, J. C. Quintero, A. Rhodes, H. L. Robbins, E. Roth, M. Shivaprakash, D. Titus, T. Yang, H. Teppler, K. E. Squires, P. J. Deutsch, and E. A. Emini. 1995. In vivo emergence of HIV-1 variants resistant to multiple protease inhibitors. Nature 374:569-571.
5. Craig, J. C., I. B. Duncan, D. Hockley, C. Grief, N. A. Roberts, and J. S. Mills. 1991. Antiviral properties of Ro 31-8959, an inhibitor of human immunodeficiency virus (HIV) proteinase. Antiviral Res. 16:295-305.
6. Deeks, S. G., M. Smith, M. Holodniy, and J. O. Kahn. 1997. HIV-1 protease inhibitors. JAMA 277:145-153.
7. Doyon, L., G. Croteau, D. Thiebeault, F. Poulin, L. Pilote, and D. Lamarre. 1996. Second locus involved in human immunodeficiency virus type 1 resistance to protease inhibitors. J. Virol. 70:3763-3769.
8. Gulnik, S. V., L. I. Suvorov, B. Liu, B. Yu, B. Anderson, H. Mitsuya, and J. W. Erickson. 1995. Kinetic characterization and cross-resistance patterns of HIV-1 protease mutants selected under drug pressure. Biochemistry 34: 9282-9287.
9. Hodge, C. N., P. E. Aldrich, L. T. Bacheler, C.-H. Chang, C. J. Eyermann, S. Garber, M. Grubb, D. A. Jackson, P. K. Jadhav, B. Korant, P. Y. S. Lam, M. B. Maurin, J. L. Meek, M. J. Otto, M. M. Rayner, C. Reid, T. R. Sharpe, L. Shum, D. L. Winslow, and S. Erickson-Viitanen. 1996. Improved cyclic urea inhibitors of the HIV-1 protease: synthesis, potency, resistance profile, human pharmacokinetics and X-ray crystal structure of DMP 450. Chem. Biol. 3:301-314.
10. Hultén, J., N. M. Bonham, U. Nillroth, T. Hansson, G. Zuccarello, A. Bouzide, J. Åqvist, B. Classon, U. H. Danielson, A. Karlén, I. Kvarnström, B. Samuelsson, and A. Hallberg. 1997. Cyclic HIV-1 proteinase inhibitors derived from mannitol: synthesis, inhibitory potencies, and computational predictions of binding affinities. J. Med. Chem. 40:885-897.
11. Karlstrom, A. R., and R. L. Levine. 1991. Copper inhibits the protease from human immunodeficiency virus 1 by both cysteine-dependent and cysteine-independent mechanisms. Proc. Natl. Acad. Sci. USA 88:5552-5556.
12. Kempf, D. J., D. W. Norbeck, L. Codacovi, X. C. Wang, W. E. Kohlbrenner, N. E. Wideburg, D. A. Paul, M. F. Knigge, S. Vasavanonda, A. Craig-Kennard, A. Saldivar, W. Roosenbrook, Jr., J. J. Clement, J. J. Plattner, and J. Erickson. 1990. Structure-based, C2 symmetric inhibitors of HIV protease. J. Med. Chem. 33:2687-2689.
13. King, R. W., S. Garber, D. L. Winslow, C. Reid, L. T. Bacheler, E. Anton, and M. J. Otto. 1995. Multiple mutations in the human immunodeficiency virus protease gene are responsible for decreased susceptibility to protease inhibitors. Antivir. Chem. Chemother. 6:80-88.
14. Kohl, N. E., E. A. Emini, W. A. Schleif, L. J. Davis, J. C. Heimbach, R. A. F. Dixon, E. M. Scolnick, and I. S. Sigal. 1988. Active human immunodeficiency virus protease is required for viral infectivity. Proc. Natl. Acad. Sci. USA 85:4686-4690.
15. Lam, P. Y., P. K. Jadhav, C. J. Eyermann, C. N. Hodge, Y. Ru, L. T. Bacheler, J. L. Meek, M. J. Otto, M. M. Rayner, Y. N. Wong, C.-H. Chang, P. C. Weber, D. A. Jackson, T. R. Sharpe, and S. Erickson-Viitanen. 1994. Rational design of potent, bioavailable, nonpeptide cyclic ureas as HIV protease inhibitors. Science263:380-384.
16. Lin, Y., X. Lin, L. Hong, S. Foundling, R. L. Heinrikson, S. Thaisrivongs, W. Leelamanit, D. Raterman, M. Shah, B. M. Dunn, and J. Tang. 1995. Effect of point mutations on the kinetics and the inhibition of human immunodeficiency virus type 1 protease: relationship to drug resistance. Biochemistry 34:1143-1152.
17. 2+ and allosteric interactions. Submitted for publication.
18. Maschera, B., E. Furfine, and E. D. Blair. 1995. Analysis of resistance to human immunodeficiency virus type 1 protease inhibitors by using matched bacterial expression and proviral infection vectors. J. Virol. 69:5431-5436.
19. Nillroth, U., L. Vrang, G. Ahlsén, Y. Besidsky, J. Chattopadhyaya, I. Ugi, and U. H. Danielson. 1995. The use of 5′-phosphate derivatives of nucleoside analogues as inhibitors of HIV-1 replication. Antivir. Chem. Chemother. 6:50-64.
20. Roberts, N. A. 1995. Drug-resistance patterns of saquinavir and other HIV proteinase inhibitors. AIDS 9:S27-S32.
21. Sculley, M. J., and J. F. Morrison. 1986. The determination of kinetic constants governing the slow, tight-binding inhibition of enzyme-catalyzed reactions. Biochim. Biophys. Acta 874:44-53.
22. Tisdale, M., R. E. Myers, B. Maschera, N. R. Parry, N. M. Oliver, and E. D. Blair. 1995. Cross-resistance analysis of human immunodeficiency virus type 1 variants individually selected for resistance to five different protease inhibitors. Antimicrob. Agents Chemother. 39:1704-1710.
23. von der Helm, K., L. Gürtler, J. Eberle, and F. Deinhardt. 1989. Inhibition of HIV replication in cell culture by the specific aspartic protease inhibitor pepstatin A. FEBS Lett. 247:349-352.
24. Weislow, O. S., R. Kiser, D. L. Fine, J. Bader, R. H. Shoemaker, and M. R. Boyd. 1989. New soluble-Formazan assay for HIV-1 cytopathic effects: application to high-flux screening of synthetic and natural products for AIDS-antiviral activity. J. Natl. Cancer Inst. 81:577-586.