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

References

• Vijayalaxmi TCR, Thomas CRJr, Reiter RJ, Herman TS. Melatonin: From basic research to cancer treatment clinics. J Clin Oncol 2002; 20: 2575–2601
   PubMed Web of Science ®Google Scholar
• Delagrange P, Guardiola-Lemaitre B, Delagrange P, Guardiola-Lemaitre B. Melatonin, its receptors, and relationships with biological rhythm disorders. Clin Neuropharmacol 1997; 20: 482–510
   PubMed Web of Science ®Google Scholar
• Tan DX, Chen LD, Poeggeler B, Manchester LC, Reiter R. Melatonin: A potent endogenous hydroxyl radical scavenger. Endocrinol J 1993; 1: 215–218
   Google Scholar
• Stasica P, Ulanski P, Rosiak JM. Melatonin as a hydroxyl radical scavenger. J Pineal Res 1998; 25: 65–66
   PubMed Web of Science ®Google Scholar
• Tan DX, Poeggeler B, Reiter RJ, Chen LD, Chen S, Manchester LC, Barlow-Walden LR. The pineal hormone melatonin inhibits DNA-adduct formation induced by the chemical carcinogen safrole in vivo. Cancer Lett 1993; 70: 65–71
   PubMed Web of Science ®Google Scholar
• Tan DX, Reiter RJ, Chen LD, Poeggeler B, Manchester LC, Barlow-Walden LR. Both physiological and pharmacological levels of melatonin reduce DNA adduct formation induced by the carcinogen safrole. Carcinogenesis 1994; 15: 215–218
   PubMed Web of Science ®Google Scholar
• Melchiorri D, Reiter RJ, Attia AM, Hara M, Burgos A, Nistico G. Potent protective effect of melatonin on in vivo paraquat-induced oxidative damage in rats. Life Sci 1995; 56: 83–89
   PubMed Web of Science ®Google Scholar
• Melchiorri D, Reiter RJ, Severynek E, Chen LD, Nistico G. Melatonin reduces kainate-induced lipid peroxidation in homogenates of different brain regions. FASEB J 1995; 9: 1205–1210
   PubMed Web of Science ®Google Scholar
• Reiter RJ, Tan DX, Cabrera J, D'Arpa D. Melatonin and tryptophan derivatives as free radical scavengers and antioxidants. Adv Exp Med Biol 1999; 467: 379–387
   PubMed Web of Science ®Google Scholar
• Matuszak Z, Reszak KJ, Chignell CF. Reaction of melatonin and related indoles with hydroxyl radicals: EPR and spin trapping investigations. Free Radical Bio Med 1997; 23: 367–372
   PubMed Web of Science ®Google Scholar
• Stolc S. Indole derivatives as neuroprotectants. Life Sci 1999; 65: 1943–1950
   PubMed Web of Science ®Google Scholar
• Gozzo A, Lesieur D, Duriez P, Fruchart JC, Teissier E. Structure-activity relationships in a series of melatonin analogues with the low-density lipoprotein oxidation model. Free Radical Bio Med 1999; 26: 1538–1543
   PubMed Web of Science ®Google Scholar
• Tailleux A, Gozzo A, Torpier G, Martin-Nizard F, Bonnefont-Rousselot D, Lemdani M, Furman C, Foricher R, Chevé G, Yous S, Micard F, Bordet R, Gardès-Albert M, Lesieur D, Teissier E, Fruchart JC, Fiévet C, Duriez P. 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 2005; 46: 241–249
   PubMed Web of Science ®Google Scholar
• 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, Gardès-Albert M. Melatonin related compounds inhibit lipid peroxidation during copper or free radical-induced LDL oxidation. J Pineal Res 2002; 33: 107–117
   Google Scholar
• Chevé G, Duriez P, Fruchart JC, Teissier E, Poupaert J, Lesieur D. Antioxidant activity of pinolines analogues in the LDL oxidation model. Med Chem Res 2003; 11: 361–379
   Google Scholar
• Mekhloufi J, Bonnefont-Rousselot D, Yous S, Lesieur D, Couturier M, Thérond P, Legrand A, Jore D, Gardès-Albert M. Antioxidant activity of melatonin and a pinoline derivative on linoleate model system. J Pineal Res 2005; 39: 27–33
   PubMedGoogle Scholar
• Peura P, Johnson JV, Yost RA, Faull KF. Concentrations of tryptoline and methtryptoline in rat brain. J Neurochem 1989; 52: 847–852
   PubMedGoogle Scholar
• Kari I. 6-methoxy-1 2,3,4-tetrahydro-(-carboline in pineal gland of chicken and cock. FEBS Lett 1981; 127: 277–280
   PubMedGoogle Scholar
• Callaway JC, Ghynther J, Poso A, Vepsalainen J, Airaksinen MM. The Pictet-Spengler reaction and biogenic tryptamines: Formation of tetrahydro-(-carbolines at physiological pH. J Het Chem 1994; 31: 431–435
   Web of Science ®Google Scholar
• Airaksinen MM, Kari I. (-carbolines, psychoactive compounds in the mammalian body. Part I: Occurrence, origin and metabolism. Med Biol 1981; 59: 21–34
   PubMedGoogle Scholar
• Pähkla R, Zilmer M, Kullisaar T, Rägo L. Comparison of the antioxidant activity of melatonin and pinoline in vitro. J Pineal Res; 1998; 24: 96–101
   PubMed Web of Science ®Google Scholar
• Pless G, Frederiksen TJ, Garcia JJ, Reiter RJ. 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 1999; 26: 236–246
   PubMedGoogle Scholar
• Pless G, Frederiksen TJP, Garcia JJ, Reiter RJ. 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 1999; 26: 236–246
   PubMedGoogle Scholar
• Garcia JJ, Martinez-Ballain E, Robinson M, Allué JL, Reiter RJ, Osuna C, Acuña-Castroviejo D. Protective effect of β-carbolines and other antioxidants on lipid peroxidation due to hydrogen peroxide in rat brain homogenates. Neurosci Lett 2000; 29: 1–4
   Google Scholar
• Siu AW, Reiter RJ, To CH. Pineal indoleamines and vitamin E reduce nitric oxide-induced lipid peroxidation in rat retinal homogenates. J Pineal Res 1999; 27: 122–128
   PubMed Web of Science ®Google Scholar
• Qi W, Reiter RJ, Tan DX, Manchester LC, Siu AW, Garcia JJ. Increased levels of oxidatively damaged DNA induced by chromium(III) and H2O2: Protection by melatonin and related molecules. J Pineal Res 2000; 29: 54–61
   PubMed Web of Science ®Google Scholar
• Garcia JJ, Reiter RJ, Pie J, Ortiz GG, Cabrera J, Sainz RM, Acuña-Castroviejo D. Role of pinoline and melatonin in stabilizing hepatic microsomal membranes against oxidative stress. J Bioenerg Biomembr 1999; 31: 609–616
   PubMedGoogle Scholar
• Rackova L, Snirc V, Majekova M, Majek P, Stefek M. Free radical scavenging and antioxidant activies of substituted hexahydropyridoindoles. Quantitative structure-activity relationships. J Med Chem 2006; 49: 2543–2548
   PubMed Web of Science ®Google Scholar
• Rackova L, Firakova S, Kostalova D, Stefek M, Sturdik E, Majekova M. Oxidation of liposomal membrane suppressed by flavonoids: Quantitative structure-activity relationships. Bioorg Med Chem 2005; 13: 6477–6484
   PubMed Web of Science ®Google Scholar
• Oprea TI, Waller CL, Marshall GR. 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 1994; 37: 2206–2215
   PubMed Web of Science ®Google Scholar
• SYBYL, 6.9 ed., Tripos Associates In., 1699 South Hanley Road, St. Louis, MO 63144
   Google Scholar
• Stewart JJP. MOPAC: A semi-empirical molecular orbital program. J Comput Aid Mol Des 1990; 4: 1–103
   PubMed Web of Science ®Google Scholar
• Todeschini R, Consonni V. Handbook of molecular descriptors. Wiley-VCH, Weinheim 2000; 667
   Google Scholar
• Clark M, Cramer V, III RD. Validation of the general purpose tripos 5.2 force field. Quant Struct-Act Rel 1993; 12: 137–145
   Web of Science ®Google Scholar