A comparative molecular field analysis of propafenone-type modulators of cancer multidrug resistance

Quantitative Structure-Activity Relationships

Volumn 17, Issue 4, 1998, Pages 301-312

  Pajeva, Ilza K ^a   Wiese, Michael ^b  

^a BULGARIAN ACADEMY OF SCIENCES   (Bulgaria)

^b MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

Author keywords

CoMFA; Multidrug resistance; Propafenone; Resistance modulator

Indexed keywords

CELL CULTURE; ELECTROSTATICS; MODULATORS;

3D-QSAR; COMFA; COMPARATIVE MOLECULAR FIELD ANALYSIS; HYDROPHOBICS; MULTIDRUG RESISTANCE; MULTIDRUG RESISTANTS; PROPAFENONE; RESISTANCE MODULATOR; RHODAMINE 123; STERICS;

HYDROPHOBICITY;

BENZOFURAN DERIVATIVE; DAUNORUBICIN; PROPAFENONE; RHODAMINE 123;

ARTICLE; CANCER; CONTROLLED STUDY; CYTOTOXICITY; ELECTRICITY; HUMAN; HUMAN CELL; HYDROPHOBICITY; MOLECULAR MODEL; MULTIDRUG RESISTANCE; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; VARIANCE;

EID: 0031664884     PISSN: 09318771     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3838(199808)17:04<301::AID-QSAR301>3.0.CO;2-J     Document Type: Article

References (23)

1. Ford, J. Modulators of multidrug resistance. Hematology/ Oncology Clinics of North America 9 (2), 337-361 (1995).
2. Gottesman, M. M. How cancer cells evade chemotherapy: sixteenth Richard and Hinda Rosenthal Foundation award lecture. Cancer Res. 53, 747-754 (1993).
3. Gottesman, M. M. and Pastan, I. Biochemistry of the multidrug resistance mediated by the multidrug transporter. Ann. Rev. Biochem. 62, 385-427 (1993).
4. Ford, J. M., Prozialeck, W. C. and Hait, W. N. Structural features determining activity of phenothiazine and related drugs for inhibition of cell growth reversal of multidrug resistance. Mol. Pharmacol. 35, 105-115 (1989).
5. Ramu, A and Ramu, N. Reversal of multidrug resistance by phenothiazines and structurally related compounds. Cancer Chemother. Pharmacol. 30, 165-173 (1992).
6. Pearce, H. L., Winter, M. A. and Beck, W. T. Structural characteristics of compounds that modulate P-glycoprotein-associated multidrug resistance. Adv. Enzyme Regulations 30, 357-373 (1990).
7. Pajeva, I. K. and Wiese, M. QSAR and molecular modeling of catamaphilic drugs able to modulate multidrug resistance in tumors. Quant. Struct.-Act. Relat. 16, 1-10 (1997).
8. Wiese, M. and Pajeva, I. K. Molecular modeling study of the multidrug resistance modifiers cis-and trans-flupentixol. Pharmazie 52, 679-685 (1997).
9. Pajeva, I. K. and Wiese, M. Molecular modeling of phenothiazines and related drugs as multidrug resistance modifiers: a comparative molecular field analysis study. J. Med. Chem. 41, 1815-1826 (1998).
10. Ecker, G., Chiba, P., Hitzler, M., Schmid D., Visser, K., Cordes H.-P., Csöllei J., Seydel J. K. and Schaper, K.-J. Structure-Activity Relationship Studies on Benzofuran Analogs of Propafenone-Type Modulators of Tumor Cell Multidrug Resistance. J. Med. Chem. 39, 4767-4774 (1996).
11. Chiba, P., Ecker, G., Schmid, D., Drach, B., Tell, B., Goldenberg, S., and Gekeler, V. Structural Requirements for Acitvity of Propafenone-type Modulators in P-Glycoprotein-Mediated Multidrug Resistance. Mol. Pharmacol. 49, 1122-1130 (1996).
12. Zamora, J. M., Pearce, H. L. Beck, W. T. Physical-Chemical Properties Shared by Compounds that Modulate Multidrug resistance in Human Leukemic Cells. Mol. Pharmacol. 33, 454-462 (1988).
13. Tripos Ass., 1699 Hanley Road. St. Louis, Mo 63144, USA.
14. Kellog, G. E., Semus, S. F. and Abraham, D. J. HINT: A new method for empirical hydrophobic field calculation for CoMFA. J. Comp.-Aided Mol. Design 5, 545-552 (1991).
15. Edusoft, LC, PO Box 1811, Ashland, VA 23005, USA.
16. Cambridge Crystallographic Data Centre, V. 5.13, University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW, U.K.
17. Pajeva, I. K., Wiese, M., Cordes, H.-P. and Seydel, J. K. Membrane interactions of some catamphiphilic drugs and relation to their multidrug-resistance-reversing ability. J. Cancer Res. Clin. Onc. 122, 27-40 (1996).
18. Mauerhofer, E. and Höltje, H.-D. First Workshop on Molecular Modelling, May 1987, Darmstadt.
19. Garnier-Suillerot, A. Impaired accumulation of drug in multidrug resistant cells. What are the respective contributions of the kinetics of uptake of P-glycoprotein-mediated efflux of drug? Curr. Pharmaceut. Design 1, 69-82 (1995).
20. Safa, A. Identification and characterization of the drug-binding sites of P-glycoprotein, in: Gupta, S. and Tsuruo, T. (Eds), Multidrug Resistance in Cancer Cells, J. Wiley & Sons, Chichester 1996, pp. 231-249.
21. Folkers, G., Merz, A. and Rognan, D. CoMFA: Scope and limitations, in: Kubinyi, H. (Ed.) 3D QSAR in Drug Design. Theory, Methods and Application, Escom, Leiden 1993, pp. 583-618.
22. Kroemer, R. T. and Hecht, P. Replacement of steric 6-12 potential-derived interaction energies by atom-based indicator variables in CoMFA leads to models of higher consistency. J. Comp.-Aided Mol. Design 9, 205-212 (1995).
23. Chiba, P., Hitzler, M., Richter, E., Huber, M., Tmej, C., Giovagnoni, E. and Ecker, G. Studies of propafenone-type modulators of multidrug resistance III: variations on the nitrogen Quant. Struct.-Act. Relat. 16, 361-366 (1997).