5-Acyloxy-5-hydroxymethyltetrahydro-2-furancarboxylate as a novel template for protein kinase C (PKC) binding

Farmaco

Volumn 56, Issue 3, 2001, Pages 203-210

  Lee, Jeewoo ^a   Han, Kee Chung ^a   Lee, Sang Yoon ^a   Kim, Su Yeon ^a   Kang, Ji Hye ^a   Lewin, Nancy E ^b   Best, Lionel S ^b   Blumberg, Peter M ^b   Marquez, Victor E ^c  

^a Seoul National University   (South Korea)

^b NATIONAL CANCER INSTITUTE   (United States)

^c Div Basic Sci Natl Cancer I   (United States)

Author keywords

Diacylglycerol lactones; Pharmacophore model; Phorbol ester; PKC ligands; Protein kinase C

Indexed keywords

5 HYDROXYMETHYLTETRAHYDRO 2 FURANCARBOXYLATE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; ETHER DERIVATIVE; GLYCIDYL 4 METHOXYPHENYL ETHER; METHYL 5 (HYDROXYMETHYL) 5 [(TETRADECANOYLOXY)METHYL]TETRAHYDRO 2 FURANCARBOXYLATE; PHORBOL ESTER; PROTEIN KINASE C; PROTEIN KINASE C INHIBITOR; TETRADECYL 5 [(HEXANOYLOXY)METHYL] 5 (HYDROXYMETHYL)TETRAHYDRO 2 FURANCARBOXYLATE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME BINDING; PHARMACOPHORE;

BINDING, COMPETITIVE; CARBOXYLIC ACIDS; FURANS; KINETICS; LIGANDS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PHORBOL 12,13-DIBUTYRATE; PROTEIN BINDING; PROTEIN KINASE C; TEMPLATES, GENETIC;

EID: 0035304628     PISSN: 0014827X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0014-827X(01)01077-1     Document Type: Article

References (21)

1. Nishizuka Y. The molecular heterogeneity of protein kinase C and its implications for cellular regulation. Nature. 334:1988;661-665.
2. D.S. Lester, R.M. Espand (Eds.), Protein Kinase C. Current and Future Perspectives, Ellis Horwood, New York, 1992.
3. Goekjian P.G., Jirousek M.R. Protein kinase C in the treatment of disease: signal transduction pathways, inhibitors, and agents in development. Curr. Med. Chem. 6:1999;877-903.
4. Kazanietz M.G., Areces L.B., Bahador A., Mischak H., Goodnight J., Mushinsky J.F., Blumberg P.M. Characterization of ligand and substrate specificity for the calcium-dependent and calcium-independent protein kinase C isozymes. Mol. Pharmacol. 44:1993;298-307.
5. Ono Y., Fujii T., Igarashi K., Kuno T., Tanaka C., Kikkawa U., Nishizuka Y. Phorbol ester binding to protein kinase C requires a cysteine-rich zinc finger-like sequence. Proc. Natl. Acad. Sci. USA. 86:1989;4868-4871.
6. P.A. Wender, J. De Brabander, P.G. Harran, J.-M. Jimenez, M.F.T. Koehler, B. Lippa, C.-M. Park, C. Siedenbiedel, G.R. Pettit, The design, computer modeling, solution structure, and biological evaluation of synthetic analogues of bryostatic 1. Proc. Natl. Acad. Sci. USA 95 (1998) 6624-9 and refs. therein.
7. Wender P.A., Cribbs C.M. Structural Design in Antitumor Compounds in Molecular Mechanisms and their Clinical Applications in Malignancies, Ch. 13. 1991;Academic Press, New York.
8. Itai A., Kato Y., Tomioka N., Iitaka Y., Endo Y., Hasegawa M., Shudo K., Fujuki H., Sakai S.-I. A receptor model for tumor promotors: Rational superposition of teleocidins and phorbol esters. Proc. Natl. Acad. Sci. USA. 85:1988;3688-3692.
9. Jeffrey A.M., Liskamp R.M.J. Computer-assisted molecular modeling of tumor promotors: Rationale for the activity of phorbol esters, teleocidin B and aplysiatoxin. Proc. Natl. Acad. Sci. USA. 83:1986;241-245.
10. Nakamura H., Kishi Y., Pajares M.A., Rando R.R. Structural basis of protein kinase C activation by tumor promotors. Proc. Natl. Acad. Sci. USA. 86:1989;9672-9676.
11. Wang S., Kazanietz M.G., Blumberg P.M., Marquez V.E., Milne G.W.A. Molecular modeling and site-directed mutagenesis studies of a phorbol ester-binding site in protein kinase C. J. Med. Chem. 39:1996;2541-2553.
12. Zhang G.G., Kazanietz M.G., Blumberg P.M., Hurley J.H. Crystal structure of the cys2 activator-binding domain of protein kinase Cδ in complex with phorbol ester. Cell. 81:1995;917-924.
13. Marquez V.E., Nacro K., Benzaria S., Lee J., Sharma R., Teng K., Milne G.W.A., Bienfait B., Wang S., Lewin N.E., Blumberg P.M. The transition from a pharmacophore-guided approach to a receptor-guided approach in the design of potent protein kinase C ligands. Pharmacol. Ther. 82:1999;251-261.
14. Nacro K., Bienfait B., Lee J., Han K.-C., Kang J.-H., Benzaria S., Lewin N.E., Bhattacharyya D.K., Blumberg P.M., Marquez V.E. Conformationally constrained analogues of diacylglycerol (DAG). 16. How much structural complexity is necessary for recognition and high binding affinity to protein kinase C? J. Med. Chem. 43:2000;921-944.
15. Krauser G., Von Der Lieth C.-W., Schmidt R., Hecker E. Structure/activity relationships of polyfunctional diterpenes of the tigilance type: a pharmacophore model for protein-kinase C activators based on structure/activity studies and molecular modeling of the tumor promotors 12-O-tetradecanoyl phorbol 13-acetate and 3-O-tetradecanoylingenol. Eur. J. Biochem. 242:1996;417-427.
16. Sugita K., Neville C.F., Sodeoka M., Sasai H., Shibasaki M. Stereocontrolled syntheses of phorbol analogues and evaluation of their binding affinity to PKC. Tetrahedron Lett. 36:1995;1067-1070.
17. Lee J., Kang J.-H., Lee S.-Y., Han K.-C., Torres C.M., Bhattacharyya D.K., Blumberg P.M., Marquez V.E. Protein kinase C ligands based on tetrahydrofuran templates containing a new set of phorbol ester pharmacophores. J. Med. Chem. 42:1999;4129-4139.
18. W.M. Meylan, P.H. Howard, Atom/fragment contribution method for estimating octanol-water partition coefficients, J. Pharm. Sci. 84 (1995) 83-92. KOWWIN 1.63, Syracuse Research Corp., http://esc.syrres.com/.
19. Marquez V.E., Lee J., Sharma R., Teng K., Wang S., Lewin N.E., Bahador A., Kazanietz M.G., Blumberg P.M. Conformationally constrained analogues of diacylglycerol. 6. Changes in PK-C binding affinity for 3-O-acyl-2-deoxy-l-ribonolactones bearing different acyl chains. Bioorg. Med. Chem. Lett. 4:1994;355-360.
20. Lee J., Sharma R., Wang S., Milne G.W.A., Lewin N.E., Szallasi Z., Blumberg P.M., George C., Marquez V.E. Conformationally constrained analogues of diacylglycerol. 12. Ultrapotent protein kinase C ligands based on a chiral 5-disubstituted heptono-1,4-lactone template. J. Med. Chem. 39:1996;36-45.
21. Teng K., Marquez V.E., Milne G.W.A., Barchi J.J. Jr, Kazanietz M.G., Lewin N.E. Conformationally constrained analogues of diacylglycerol. 1. Interaction of γ-lactone with the phorbol ester receptor of protein kinase C. J. Am. Chem. Soc. 114:1992;1059-1070.