Stable analogues of geranylgeranyl diphosphate possessing improved geranylgeranyl versus farnesyl protein transferase inhibitory selectivity

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 24, 2003, Pages 4405-4408

  Minutolo, Filippo ^a   Bertini, Simone ^a   Betti, Laura ^a   Danesi, Romano ^a   Gervasi, Gianbattista ^b   Giannaccini, Gino ^a   Papi, Chiara ^a   Placanica, Giorgio ^a   Barontini, Silvia ^a   Rapposelli, Simona ^a   Macchia, Marco ^a  

^a UNIVERSITY OF PISA   (Italy)

^b Laboratori Baldacci SpA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

FARNESYL TRANS TRANSFERASE; GERANYLGERANYL PROTEIN TRANSFERASE 1 INHIBITOR; PROTEIN FARNESYLTRANSFERASE INHIBITOR; TRANSFERASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; DRUG ACTIVITY; DRUG SELECTIVITY; DRUG SYNTHESIS; ENZYME INHIBITION; INHIBITION KINETICS;

OXY;

EID: 0344064836     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2003.09.035     Document Type: Article

References (13)

1. (a) Downward J. Nat. Rev. Cancer. 3:2002;11, and references therein (b) Symons M. TIBS. 21:1996;178.
2. Bos J.L. Cancer Res. 49:1989;4682.
3. Leonard D.M. J. Med. Chem. 40:1997;2971.
4. Whyte D.B., Kirschmeier P., Hockenberry T.N., Nunez-Oliva I., James L., Catino J.J., Bishop W.R., Pai J.-K. J. Biol. Chem. 272:1997;14459.
5. (a) . Some examples are given in: Tucker T.J., Abrams M.T., Buser C.A., Davide J.P., Ellis-Hutchings M., Fernandes C., Gibbs J.B., Graham S.L., Hartman G.D., Huber H.E., Liu D., Lobell R.B., Lumma W.C., Robinson R.G., Sisko J.T., Smith A.M. Bioorg. Med. Chem. Lett. 12:2002;2027 (b) Mu Y.Q., Eubanks L.M., Poulter C.D., Gibbs R.A. Bioorg. Med. Chem. 10:2002;1207 (c) Marson C.M., Rioja A.S., Brooke G., Coombes R.C., Vigushin D.M. Bioorg. Med. Chem. Lett. 12:2002;255 (d) Zahn T.J., Whitney J., Weinbaum C., Gibbs R.A. Bioorg. Med. Chem. Lett. 11:2001;1605 (e) Bergman J.M., Abrams M.T., Davide J.P., Greenberg I.B., Robinson R.G., Buser C.A., Huber H.E., Koblan K.S., Kohl N.E., Lobell R.B., Graham S.L., Hartman G.D., Williams T.M., Dinsmore C.J. Bioorg. Med. Chem. Lett. 11:2001;1411 (f) Gibbs B.S., Zahn T.J., Mu Y.Q., Sebolt-Leopold J.S., Gibbs R.A. J. Med. Chem. 42:1999;3800 (g) Vasudevan A., Qian Y., Vogt A., Blaskovich M.A., Ohkanda J., Sebti S.M., Hamilton A.D. J. Med. Chem. 42:1999;3800 (h) Macchia M., Jannitti N., Gervasi G., Danesi R. J. Med. Chem. 39:1996;1352.
6. (a) Sun J., Blaskovich M.A., Knowles D., Qian Y., Ohkanada J., Bailey R.D., Hamilton A.D., Sebti S.M. Cancer Res. 59:1999;4919 (b) Lobell R.B., Omer C.A., Abrams M.T., Bhimnathwala H.G., Brucker M.J., Buser C.A., Davide J.P., deSolms S.J., Dinsmore C.J., Ellis-Hutchings M.S., Kral A.M., Liu D., Lumma W.C., Machotka S.V., Rands E., Williams T.M., Graham S.L., Hartman G.D., Oliff A.I., Heimbrook D.C., Kohl N.E. Cancer Res. 61:2001;8758 (c) Di Paolo A., Danesi R., Caputo S., Macchia M., Lastella M., Boggi U., Mosca F., Marchetti A., Del Tacca M. Br. J. Cancer. 84:2001;1535.
7. (a) Gibbs R.A. Curr. Opin. Drug Discov. Dev. 3:2000;585 (b) Coxon F.P., Helfrich M.H., Larijani B., Muzylak M., Dunford J.E., Marshall D., McKinnon A.D., Nesbitt S.A., Horton M.A., Seabra M.C., Ebetino F.H., Rogers M.J. J. Biol. Chem. 276:2001;48213 (c) Coxon F.P., Helfrich M.H., Van't Hof R., Sebti S., Ralston S.H., Hamilton A., Rogers M.J. J. Bone Miner. Res. 15:2000;1467 (d) Cohen L.H., Pieterman E., van Leeuwen R.E.W., Overhand M., Burm B.E.A., van der Marel G.A., van Boom J.H. Biochem. Pharmacol. 60:2000;1061.
8. +.
9. +.
10. +.
11. +.
12. (a) Zhang F.L., Moomaw J.F., Casey P.J. J. Biol. Chem. 269:1994;23465 (b) Quian Y., Blaskovich M.A., Saleem M., Seong C.M., Wathen S.P., Hamilton A.D., Sebti S.M. J. Biol. Chem. 268:1994;12410.
13. 3H]FPP and H-Ras-CVLS (FTase), in the presence of different concentrations of inhibitors. After incubation the reaction was stopped and filtered through glass fibre filters to separate free from incorporated label.