Inhibition of protein prenylation by metabolites of limonene

Biochemical Pharmacology

Volumn 57, Issue 7, 1999, Pages 801-809

  Hardcastle, Ian R ^a   Rowlands, Martin G ^a   Moreno Barber, Amelia ^a   Grimshaw, Rachel M ^a   Mohan, Mukesh K ^a   Nutley, Bernard P ^a   Jarman, Michael ^a  

^a IMPERIAL CANCER RESEARCH FUND   (United Kingdom)

Author keywords

Antitumour; Inhibitor; Isoprenylation; Limonene; Metabolism; Monoterpenes

Indexed keywords

DRUG METABOLITE; FARNESYL TRANS TRANSFERASE; LIMONENE; PERILLIC ACID; PERILLYL ALCOHOL; TRANSFERASE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CLINICAL TRIAL; CONTROLLED CLINICAL TRIAL; CONTROLLED STUDY; DRUG BLOOD LEVEL; DRUG DETERMINATION; DRUG SYNTHESIS; ENANTIOMER; HUMAN; ISOPRENYLATION; NONHUMAN; ORAL DRUG ADMINISTRATION; PRENYLATION; PRIORITY JOURNAL; RAT;

ALKYL AND ARYL TRANSFERASES; ANIMALS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; BRAIN; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYCLOHEXENES; CYTOSOL; ENZYME INHIBITORS; FARNESYLTRANSTRANSFERASE; HUMANS; MASS SPECTROMETRY; MONOTERPENES; NERVE TISSUE PROTEINS; PROTEIN ISOPRENYLATION; RATS; TERPENES;

EID: 0032965988     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-2952(98)00349-9     Document Type: Article

References (35)

1. Crowell P.L., Gould M.N. Chemoprevention and therapy of cancer by d-limonene. Crit Rev Oncol. 5:1994;1-22.
2. Elegbede J.A., Elson C.E., Tanner M.A., Qureshi A., Gould M.N. Regression of rat primary mammary tumors following dietary d-limonene. J Natl Cancer Inst. 76:1986;323-325.
3. Haag J.D., Lindstrom M.J., Gould M.N. Limonene-induced regression of mammary carcinomas. Cancer Res. 52:1992;4021-4026.
4. Chander S.K., Lansdown A.G.B., Luqmani Y.A., Gomm J.J., Coope R.C., Gould N., Coombes R.C. Effectiveness of combined limonene and 4-hydroxyandrostenedione in the treatment of NMU-induced rat mammary cancers. Br J Cancer. 69:1994;879-882.
5. Igimi H., Nishimura R., Kodama R., Ide H. Studies on the metabolism of d-limonene (p-mentha-1,8-diene). I. The absorption, distribution and excretion of d-limonene in rats. Xenobiotica. 4:1974;77-82.
6. Crowell P.L., Elson C.E., Bailey H.H., Elegbede A., Haag J.D., Gould M.N. Human metabolism of the experimental cancer therapeutic agent d-limonene. Cancer Chemother Pharmacol. 35:1994;31-37.
7. Crowell P.L., Lin S., Vedejs E., Gould M.L. Identification of metabolites of the antitumor agent d-limonene capable of inhibiting protein isoprenylation and cell growth. Cancer Chemother Pharmacol. 31:1992;205-212.
8. Poon G.K., Vigushin D., Griggs L.J., Rowlands M.G., Coombes R.C., Jarman M. Identification and characterization of limonene metabolites in patients with advanced cancer by liquid chromatography/mass spectrometry. Drug Metab Dispos. 24:1996;565-571.
9. Haag J.D., Gould M.N. Mammary carcinoma regression induced by perillyl alcohol a hydroxylated analog of limonene. Cancer Chemother Pharmacol. 34:1994;477-483.
10. Stark M.J., Burke Y.D., McKinzie J.H., Ayoubi A.S., Crowell P.L. Chemotherapy of pancreatic cancer with the monoterpene perillyl alcohol. Cancer Lett. 96:1995;15-21.
11. Ripple G., Gould M., Stewart J., Tutsch K., Alberti D., Feierabend C., Simon K., Arzoomanian R., Pomplun M., Wilding G., Bailey H. Phase I trial of perillyl alcohol administered daily. Proc Natl Acad Sci USA. 37:1997;221.
12. Clinical development plan l-perillyl alcohol . J Cell Biochem. 26S:1996;137-148.
13. Vigushin D.M., Poon G.K., Boddy A., English J., Halbert G.W., Pagonis C., Jarman M., Coombes R.C. Phase I and pharmacokinetic study of d-limonene in patients with advanced cancer. Cancer Chemother Pharmacol. 42:1998;111-117.
14. Hall A. A biochemical function for Ras - at last. Science. 264:1994;1413-1414.
15. Rodenhuis S. Ras and human tumors. Semin Cancer Biol. 3:1992;241-247.
16. Gelb M.H. Protein prenylation, et cetera signal transduction in two dimensions . Science. 275:1997;1750-1751.
17. Graham S.L. Inhibitors of protein farnesylation a new approach to cancer chemotherapy . Exp Opin Ther Patents. 5:1995;1269-1285.
18. Leonard D.M. Ras Farnesyltransferase a new therapeutic target . J Med Chem. 40:1997;2971-2990.
19. Crowell P.L., Chang R.R., Ren Z., Elson C.E., Gould M.N. Selective inhibition of isoprenylation of 21-26-kDa proteins by the anticarcinogen d-limonene and its metabolites. J Biol Chem. 26:1991;17679-17685.
20. Crowell P.L., Ren Z., Lin S., Vedejs E., Gould M. Structure-activity relationships among monoterpene inhibitors of protein isoprenylation and cell proliferation. Biochem Pharmacol. 47:1994;1405-1415.
21. Gelb M.H., Tamanoi F., Yokoyama K., Ghomashchi F., Esson K. The inhibition of protein prenyltransferases by oxygenated metabolites of limonene and perillyl alcohol. Cancer Lett. 91:1995;169-175.
22. Ren Z., Elson C.E., Gould M.N. Inhibition of type I and type II geranylgeranyl-protein transferase by the monoterpene perillyl alcohol in NIH3T3 cells. Biochem Pharmacol. 54:1997;113-120.
23. Clegg R.J., Middleton B., Bell G.D., White D.A. Inhibition of hepatic cholesterol synthesis and S-3-hydroxy-3-methylglutaryl-CoA reductase by mono- and bicyclic monoterpenes administered in vivo. Biochem Pharmacol. 29:1980;2125-2127.
24. Ren Z., Gould M.N. Inhibition of ubiquinone and cholesterol synthesis by the monoterpene perillyl alcohol. Cancer Lett. 76:1994;185-190.
25. Schulz S., Reinhold D., Schmidt H., Ansorge S., Holt V. Perillic acid inhibits Ras/MAP kinase-driven IL-2 production in human T lymphocytes. Biochem Biophys Res Commun. 241:1997;720-725.
26. Ruch R.J., Sigler K. Growth inhibition of rat liver epithelial tumor cells by monoterpenes does not involve Ras plasma membrane association. Carcinogenesis. 15:1994;787-789.
27. Mills J.J., Chari R.S., Boyer I.J., Gould M.N., Jirtle R.L. Induction of apoptosis in liver tumors by the monoterpene perillyl alcohol. Cancer Res. 55:1995;979-983.
28. Harwood H.J. Protein farnesyltransferase measurement of enzymatic activity in 96-well format using Topcount microplate scintillation counting technology . Anal Biochem. 226:1995;268-278.
29. Moores S.L., Schaber M.D., Mosser S.D., Rands E., O'Hara M.B., Garsky V.M., Marshall M.S., Pompaliano D.L., Gibbs J.B. Sequence dependency of protein isoprenylation. J Biol Chem. 266:1991;14603-14610.
30. Seabra M.C., Reis Y., Casey P.J., Brown M.S., Goldstein J.L. Protein farnesyl transferase and gerenylgeranyltransferase share a common α subunit. Cell. 65:1991;429-434.
31. Pompliano D.L., Rands E., Schaber M.D., Mosser S.D., Anthony N.J., Gibbs J.B. Steady-state kinetic mechanism of ras farnesyl protein transferase. Biochemistry. 31:1992;3800-3807.
32. Gibbs J.B., Pompliano D.L., Mosser S.D., Rands E., Lingham R.B., Singh S.B., Scolnick E.M., Kohl N.E., Oliff A. Selective inhibition of farnesyl-protein transferase blocks Ras processing in vivo. J Biol Chem. 269:1993;7617-7620.
33. Tamanoi F. Inhibitors of ras farnesyltransferases. TIBS. 18:1993;349-353.
34. Kohl N.E., Wilson F.R., Mosser S.D., Giuliani E., DeSolms S.J., Conner M.W., Anthony N.J., Holtz W.J., Gomez R.P., Lee T.-J., Smith R.L., Graham S.L., Hartman G.D., Gibbs J.B., Oliff A. Protein farnesyltransferase inhibitors block the growth of ras-dependent tumors in nude mice. Proc Natl Acad Sci USA. 91:1994;9141-9145.
35. Park H.W., Boduluri S.R., Moomaw J.F., Casey P.J., Beese L.S. Crystal structure of protein farnesyl transferase at 2.25 Angstrom resolution. Science. 275:1997;1800-1804.