Quantitative structure-activity relationships studies of antiocidant hexahydropyridoindoles and flavonoid derivatives

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 22, Issue 5, 2007, Pages 556-562

  Durand, Anne Catherine ^a   Farce, Amaury ^a   Carato, Pascal ^a   Dilly, Sebastien ^a   Yous, Said ^a   Berthelot, Pascal ^a   Chavatte, Philippe ^a  

^a UNIV LILLE   (France)

Author keywords

carbolines; 2D QSAR; Antioxidant; Flavonoids; Hexahydropyridoindoles; Melatonin; Pinoline

Indexed keywords

6 METHOXYTRYPTOLINE; CARBOLINE DERIVATIVE; DIOLEOYLPHOSPHATIDYLCHOLINE; FLAVONOID; LIPID; TRYPTOLINE DERIVATIVE;

ANTIOXIDANT ACTIVITY; ARTICLE; COMPUTER PROGRAM; CONTROLLED STUDY; CORRELATION ANALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; EXPERIMENTAL MODEL; IC 50; LIPID PEROXIDATION; MOLECULAR MODEL; PREDICTION; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

ANTIOXIDANTS; CARBOLINES; COMPUTER SIMULATION; FLAVONOIDS; INDOLES; INHIBITORY CONCENTRATION 50; MODELS, CHEMICAL; MOLECULAR STRUCTURE; PREDICTIVE VALUE OF TESTS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; REPRODUCIBILITY OF RESULTS;

EID: 35348958431     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.1080/14756360701425238     Document Type: Article

References (33)

1. Vijayalaxmi, TCR, Thomas, CRJr, Reiter, RJ and Herman, TS (2002) Melatonin: From basic research to cancer treatment clinics. J Clin Oncol, 20, pp. 2575-2601.
2. Delagrange, P., Guardiola-Lemaitre, B., Delagrange, P. and Guardiola-Lemaitre, B. (1997) Melatonin, its receptors, and relationships with biological rhythm disorders. Clin Neuropharmacol, 20, pp. 482-510.
3. Tan, DX, Chen, LD, Poeggeler, B., Manchester, LC and Reiter, R. (1993) Melatonin: A potent endogenous hydroxyl radical scavenger. Endocrinol J, 1, pp. 215-218.
4. Stasica, P., Ulanski, P. and Rosiak, JM (1998) Melatonin as a hydroxyl radical scavenger. J Pineal Res, 25, pp. 65-66.
5. Tan, DX, Poeggeler, B., Reiter, RJ, Chen, LD, Chen, S., Manchester, LC and Barlow-Walden, LR (1993) The pineal hormone melatonin inhibits DNA-adduct formation induced by the chemical carcinogen safrole in vivo. Cancer Lett, 70, pp. 65-71.
6. Tan, DX, Reiter, RJ, Chen, LD, Poeggeler, B., Manchester, LC and Barlow-Walden, LR (1994) Both physiological and pharmacological levels of melatonin reduce DNA adduct formation induced by the carcinogen safrole. Carcinogenesis, 15, pp. 215-218.
7. Melchiorri, D., Reiter, RJ, Attia, AM, Hara, M., Burgos, A. and Nistico, G. (1995) Potent protective effect of melatonin on in vivo paraquat-induced oxidative damage in rats. Life Sci, 56, pp. 83-89.
8. Melchiorri, D., Reiter, RJ, Severynek, E., Chen, LD and Nistico, G. (1995) Melatonin reduces kainate-induced lipid peroxidation in homogenates of different brain regions. FASEB J, 9, pp. 1205-1210.
9. Reiter, RJ, Tan, DX, Cabrera, J. and D'Arpa, D. (1999) Melatonin and tryptophan derivatives as free radical scavengers and antioxidants. Adv Exp Med Biol, 467, pp. 379-387.
10. Matuszak, Z., Reszak, KJ and Chignell, CF (1997) Reaction of melatonin and related indoles with hydroxyl radicals: EPR and spin trapping investigations. Free Radical Bio Med, 23, pp. 367-372.
11. Stolc, S. (1999) Indole derivatives as neuroprotectants. Life Sci, 65, pp. 1943-1950.
12. Gozzo, A., Lesieur, D., Duriez, P., Fruchart, JC and Teissier, E. (1999) Structure-activity relationships in a series of melatonin analogues with the low-density lipoprotein oxidation model. Free Radical Bio Med, 26, pp. 1538-1543.
13. Tailleux, A., Gozzo, A., Torpier, G., Martin-Nizard, F., Bonnefont-Rousselot, D., Lemdani, M., Furman, C., Foricher, R., Chevwé, G., Yous, S., Micard, F., Bordet, R., Gardès-Albert, M., Lesieur, D., Teissier, E., Fruchart, JC, Fiévet, C. and Duriez, P. (2005) Increased susceptibility of low-density lipoprotein to ex vivo oxidation in mice transgenic for human apolipoprotein B treated with 1 melatonin-related compound is not associated with atherosclerosis progression. J Cardiovasc Pharm, 46, pp. 241-249.
14. Bonnefont-Rousselot, D., Chevé, G., Gozzo, A., Tailleux, A., Guilloz, V., Caisey, S., Teissier, E., Fruchart, JC, Delattre, J., Jore, D., Lesieur, D., Duriez, P. and Gardès-Albert, M. (2002) Melatonin related compounds inhibit lipid peroxidation during copper or free radical-induced LDL oxidation. J Pineal Res, 33, pp. 107-117.
15. Chevé, G., Duriez, P., Fruchart, JC, Teissier, E., Poupaert, J. and Lesieur, D. (2003) Antioxidant activity of pinolines analogues in the LDL oxidation model. Med Chem Res, 11, pp. 361-379.
16. Mekhloufi, J., Bonnefont-Rousselot, D., Yous, S., Lesieur, D., Couturier, M., Thérond, P., Legrand, A., Jore, D. and Gardès-Albert, M. (2005) Antioxidant activity of melatonin and a pinoline derivative on linoleate model system. J Pineal Res, 39, pp. 27-33.
17. Peura, P., Johnson, JV, Yost, RA and Faull, KF (1989) Concentrations of tryptoline and methtryptoline in rat brain. J Neurochem, 52, pp. 847-852.
18. Kari, I. (1981) 6-methoxy-1 2,3,4-tetrahydro-(-carboline in pineal gland of chicken and cock. FEBS Lett, 127, pp. 277-280.
19. Callaway, JC, Ghynther, J., Poso, A., Vepsalainen, J. and Airaksinen, MM (1994) The Pictet-Spengler reaction and biogenic tryptamines: Formation of tetrahydro-(-carbolines at physiological pH. J Het Chem, 31, pp. 431-435.
20. Airaksinen, MM and Kari, I. (1981) (-carbolines, psychoactive compounds in the mammalian body. Part I: Occurrence, origin and metabolism. Med Biol, 59, pp. 21-34.
21. Pähkla, R., Zilmer, M., Kullisaar, T. and Rägo, L. (1998) Comparison of the antioxidant activity of melatonin and pinoline in vitro. J Pineal Res;, 24, pp. 96-101.
22. Pless, G., Frederiksen, TJ, Garcia, JJ and Reiter, RJ (1999) Pharmacological aspects of N-acetyl-5-methoxytryptamine (melatonin) and 6-methoxy-1,2,3,4-tetrahydro-beta-carboline (pinoline) as antioxidants: Reduction of oxidative damage in brain region homogenates. J Pineal Res, 26, pp. 236-246.
23. Pless, G., Frederiksen, TJP, Garcia, JJ and Reiter, RJ (1999) Pharmacological aspects of N-acetyl-5-methoxytryptamine (melatonin) and 6-methoxy-1,2,3,4-tetrahydro-(-carboline (pinoline) as antioxidants: Reduction of oxidative damage in brain region homogenates. J Pineal Res, 26, pp. 236-246.
24. Garcia, JJ, Martinez-Ballain, E., Robinson, M., Allué, JL, Reiter, RJ, Osuna, C. and Acuña-Castroviejo, D. (2000) Protective effect of β-carbolines and other antioxidants on lipid peroxidation due to hydrogen peroxide in rat brain homogenates. Neurosci Lett, 29, pp. 1-4.
25. Siu, AW, Reiter, RJ and To, CH (1999) Pineal indoleamines and vitamin E reduce nitric oxide-induced lipid peroxidation in rat retinal homogenates. J Pineal Res, 27, pp. 122-128.
26. 2: Protection by melatonin and related molecules. J Pineal Res, 29, pp. 54-61.
27. Garcia, JJ, Reiter, RJ, Pie, J., Ortiz, GG, Cabrera, J., Sainz, RM and Acuña-Castroviejo, D. (1999) Role of pinoline and melatonin in stabilizing hepatic microsomal membranes against oxidative stress. J Bioenerg Biomembr, 31, pp. 609-616.
28. Rackova, L., Snirc, V., Majekova, M., Majek, P. and Stefek, M. (2006) Free radical scavenging and antioxidant activies of substituted hexahydropyridoindoles. Quantitative structure-activity relationships. J Med Chem, 49, pp. 2543-2548.
29. Rackova, L., Firakova, S., Kostalova, D., Stefek, M., Sturdik, E. and Majekova, M. (2005) Oxidation of liposomal membrane suppressed by flavonoids: Quantitative structure-activity relationships. Bioorg Med Chem, 13, pp. 6477-6484.
30. Oprea, TI, Waller, CL and Marshall, GR (1994) Three-dimensional quantitative structure-activity relationship of human immunodeficiency virus (I) protease inhibitors. 2. Predictive power using limited exploration of alternate binding modes. J Med Chem, 37, pp. 2206-2215.
31. Stewart, JJP (1990) MOPAC: A semi-empirical molecular orbital program. J Comput Aid Mol Des, 4, pp. 1-103.
32. Todeschini, R. and Consonni, V. (2000) Handbook of molecular descriptors, p. 667. Wiley-VCH, Weinheim
33. Clark, M. and Cramer III RD, V. (1993) Validation of the general purpose tripos 5.2 force field. Quant Struct-Act Rel, 12, pp. 137-145.