Design of new potent hypolipidemic agents with the synergistic structural properties of α-asarone and fibrates

Drug Development Research

Volumn 64, Issue 1, 2005, Pages 28-40

  Zúñiga, Clara ^a   Garduño, Leticia ^a   Cruz, María Del Carmen ^a   Salazar, María ^a   Pérez Pastén, Ricardo ^a   Chamorro, Germán ^a   Labarrios, Fernando ^a   Tamariz, Joaquín ^a  

^a INSTITUTO POLITÉCNICO NACIONAL   (Mexico)

Author keywords

asarone; Ethyl side chain; Fibrates; Hypocholesterolemia; Phenoxyacetic frame

Indexed keywords

2 ACETYLPHENOXYACETIC ACID; 2 ETHYL 4 NITROPHENOXYACETIC ACID; 2 ETHYLPHENOXYACETIC ACID; 3 ACETYLPHENOXYACETIC ACID; 3 ETHYL 4 NITROPHENOXYACETIC ACID; 3 ETHYLPHENOXYACETIC ACID; 4 ACETYLPHENOXYACETIC ACID; 4 ETHYL 2 NITROPHENOXYACETIC ACID; 4 ETHYLPHENOXYACETIC ACID; ALPHA ASARONE; ANTILIPEMIC AGENT; CHOLESTEROL; CLOFIBRATE; ETHYL 2 ACETYLPHENOXYACETATE; ETHYL 2 ETHYLPHENOXYACETATE; ETHYL 3 ACETYLPHENOXYACETATE; ETHYL 3 ETHYLPHENOXYACETATE; ETHYL 4 ACETYLPHENOXYACETATE; ETHYL 4 ETHYL 2 NITROPHENOXYACETATE; ETHYL 4 ETHYLPHENOXYACETATE; FENOFIBRATE; FIBRIC ACID DERIVATIVE; LOW DENSITY LIPOPROTEIN CHOLESTEROL; METHYL 2 ACETYLPHENOXYACETATE; METHYL 2 ETHYLPHENOXYACETATE; METHYL 3 ACETYLPHENOXYACETATE; METHYL 3 ETHYLPHENOXYACETATE; METHYL 4 ACETYLPHENOXYACETATE; METHYL 4 ETHYL 2 NITROPHENOXYACETATE; METHYL 4 ETHYLPHENOXYACETATE; PHENOXYACETIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CHOLESTEROL BLOOD LEVEL; CHOLESTEROL DIET; CONTROLLED STUDY; DOSE RESPONSE; DRUG ACTIVITY; DRUG DESIGN; DRUG POTENCY; DRUG STRUCTURE; MALE; MOUSE; NONHUMAN; PHARMACOPHORE; STRUCTURE ANALYSIS;

EID: 18044385760     PISSN: 02724391     EISSN: None     Source Type: Journal    
DOI: 10.1002/ddr.10418     Document Type: Article

References (40)

1. Byington RP, Jukema JW, Salonen JT, Pitt B, Bruschke AV, Hoen H, Furberg CD, Mancini GB. 1995. Reduction in cardiovascular events during pravastatin therapy. Pooled analysis of clinical events of the pravastatin atherosclerosis intervention program. Circulation 92:2419-2425.
2. Cassani-Galindo ML. 2002. Evaluación genotóxica in vitro de análogos estructurales de la α-asarona. M.S. Thesis, Escuela Nacional de Ciencias Biológicas, IPN. 59 p.
3. Chamorro G, Salazar M, Salazar S, Mendoza T. 1993. Farmacología y toxicología de Guatteria gaumeri. Rev Inv Clin 45:597-604.
4. Chamorro G, Garduño L, Sánchez A, Labarrios F, Salazar M, Martínez E, Díaz F, Tamariz J. 1998. Hypolipidaemic activity of dimethoxy unconjugated propenyl side-chain analogs of α-asarone in mice. Drug Dev Res 43:105-108.
5. Cruz A, Garduño L, Salazar M, Martínez E, Díaz F, Chamorro G, Tamariz J. 2001a. High hypolipidemic activity of saturated side-chain α-asarone analogs. Med Chem Res 10:587-595.
6. Cruz A, Garduño L, Salazar M, Martínez E, Jiménez-Vázquez HA, Díaz F, Chamorro G, Tamariz J. 2001b. Synthesis and hypolipidemic activity of modified side chain α-asarone homologues. Arzneimittel-Forsch 51:535-544.
7. Cruz MC, Salazar M, Garciafigueroa Y, Hernández D, Díaz F, Chamorro G, Tamariz J. 2003. Hypolipidemic activity of new phenoxyacetic derivatives related to α-asarone with minimal pharmacophore features. Drug Dev Res 60:186-195.
8. Díaz F, Muñoz H, Labarrios F, Chamorro G, Salazar M, Morelos ME, Tamariz J. 1993. Synthesis and hypolipidemic activity of some α-asarone analogs. Med Chem Res 3:101-109.
9. Doggrell SA. 2003. Experimental and clinical studies show that the probucol derivative AGI-1007 prevents vascular growth. Expert Opin Invest Drugs 12:1855-1859.
10. Faergeman O. 2000. Hypertriglyceridemia and the fibrate trials. Curr Opin Lipidol 11:609-614.
11. Friedwald WT, Levy RI, Fredrickson DS. 1972. Estimation of the concentration of low-density lipoprotein cholesterol in plasma without use of the preparative ultracentrifuge. Clin Chem 18:499-502.
12. Fruchart JC, Duriez P, Staels B. 1999. Molecular mechanisms of action of the fibrates. J Soc Biol 193:67-75.
13. Fruchart JC. 2002. Statins for cardiovascular prevention. Lowering LDL cholesterol, the primary objective. Presse Med 31:1428-1433.
14. Garduño L, Salazar M, Salazar S, Morelos ME, Labarrios F, Tamariz J, Chamorro GA. 1997. Hypolipidemic activity of α-asarone in mice. J Etlinopharmacol 55:161-163.
15. Hernández D, Bernal P, Cruz A, Garciafigueroa Y, Garduño L, Salazar M, Díaz F, Chamorro G, Tamariz J. 2004. Potent hypolipidemic activity of mimetic amides of fibrates based on the 2-metlioxy-4-(2-propenyl) phenoxyacetic scaffold. Drug Dev Res 61:19-36.
16. Hughes TA, Elan MB, Applegate WB, Bond MG, Hughes SM, Wang X, Tolley EA, Bittle JB, Stentz FB, Kang ES. 1995. Postprandial lipoprotein responses in hypertriglyceridemic subjects with and without cardiovascular disease. Metabolism 44:1082-1098.
17. Ipatieff VN, Pines H, Schmerling L. 1938. Phosphoric acid as catalyst in the ethylation of phenol. J Am Chem Soc 60:1163-1164.
18. Istvan ES, Palnitkar M, Buchanan SK, Deisenhofer J. 2000. Crystal structure of the catalytic portion of human HMG-CoA reductase: insights into regulation of activity and catalysis. EMBO J 19:819-830.
19. Jakobisiak M, Golab J. 2003. Potential antitumor effects of statins (Review). Int J Oncol 23:1055-1069.
20. Kaupmann W, Ohlendorf H, Wolf K-U. 1985. Synthesis of 3-amino-2,3,4,5-tetrahydro-1-benzoxepine-5-ols and their action on gastric motility. Eur J Med Chem 20:207-212.
21. Kealy TJ, Coffman DD. 1961. Thermal addition reactions of monocyclic phenols with ethylene. J Org Chem 26:987-992.
22. Kim SG, Liem A, Stewart BC, Miller SA. 1999. New studies on trans-anethole oxide and trans-asarone oxide. Carcinogenesis 20:1303-1307.
23. Kulkarni SKV, Sattur PB, Nargund KS. 1957. Possible plant hormones. III. 2-Acyl- and 2-Alkyl-4-chlorophenoxyacetic acids. J Karnatak Univ 2:69-78.
24. Labarrios F, Garduño L, Vidal MR, García R, Salazar M, Martínez E, Díaz F, Chamorro G, Tamariz J. 1999. Synthesis and hypolipidaemic activity of a series of α-asarone analogues related to clofibrate in mice. J Pharm Pharmacol 51:1-7.
25. Lehmann JM, Moore LB, Smith Oliver TA. 1995. An antidiabetic thiazolidinedione is a high affinity ligand for peroxisome proliferator- activated receptor gamma (PPAR gamma). J Biol Chem 270:12953-12956.
26. López ML, Hernández A, Chamorro G, Mendoza-Figueroa T. 1993. α-Asarone toxicity in long-term cultures of adult rat hepatocytes. Planta Med 59:115-120.
27. Martínez M. 1992. Las plantas medicinales de México. Mexico City: Botas. p 125-127.
28. Meyers CD, Kashyap ML. 2004. Pharmacological elevation of high-density lipoproteins: recent insights on mechanism of action and atherosclerosis protection. Curr Opin Cardiol 19:366-373.
29. Mieville A. 1977. Pharmaceutical p-acyloximephenoxyacetic acids and their derivatives. Ger. Offen. 2,003,430 (Patent); Chem Abstr 88:22426.
30. Miyazaki A, Koieyuma T, Shimada Y, Kikuchi T, Ito K, Kasanuki N, Koga T. 2004. Pravastatin sodium, an inhibitor of HMG-CoA reductase, decreases HDL cholesterol by transfer of cholesteryl ester from HDL to VLDL in Japanese white rabbits. J Atheroscler Thromb 11:22-28.
31. Rodríguez-Páez L, Juárez-Sanchez, M, Antúnez-Solís J, Baeza I, Wong C. 2003. α-Asarone inhibits HMG-CoA reductase, lowers serum LDL-cholesterol levels and reduces biliary CSI in hypercliolesterolemic rats. Phytomedicine 10:397-404.
32. Sen AB, Joshi KC. 1951. Organic fungicides. IV. Preparation of some aryloxy-fatty acids and their mercury derivatives.
33. Soper QF, Whitehead CW, Behrens OK, Corse JJ, Jones RG. 1948. Biosynthesis of penicillins. VII. Oxy- and mercaptoacetic acids. J Am Chem Soc 70:2849-2855.
34. Suzuki T, Tanemura K, Horaguchi T, Shimizu T, Sakakibara T. 1992. Benzofuran derivatives. Part 4. Synthesis of benzofurans and 2,3,4,5-tetrahydro-1-benzoxepin-3,5-diones. J Heterocycl Chem 29:423-429.
35. Tallarida RJ, Murray RB. 1989. Manual of pharmacological calculations. New York: Springer Verlag. p 150.
36. Tikkanen MT, Helve E, Nikkila EA. 1987. Treatment of familial and non-familial hypercholesterolaemia: a review of HMG-CoA reductase inhibitors and probucol. Eur Heart J 8(suppl E): 97-101.
37. Tyler GJ, Whittaker K. 1959. Some polyamides from dicarboxylic acids containing aromatic ether groups. J Appl Chem 9:594-599.
38. Watts GF, Dimmitt SB. 1999. Fibrates, dyslipoproteinaemia and cardiovascular disease. Curr Opin Lipidol 10:561-574.
39. Wessely F, Schinzel E, Spiteller G, Klezl P. 1959. Reactions of o-quinol acetates with diazoalkanes. Syntheses of 7-hydroxyindazoles. Monatsh Chem 90:96-117.
40. Zhu Z, Espenson JH. 1996. Organic reactions catalyzed by methylrhenium trioxide: reactions of ethyl diazoacetate and organic azides. J Am Chem Soc 118:9901-9907.