Antioxidant and cytotoxic activity of new di- and polyamine caffeine analogues

References

• Knekt P, Reunanen A, Takkunen H, et al. Body iron stores and risk of cancer. Int J Cancer. 1994;56(3):379–382.
   PubMed Web of Science ®Google Scholar
• Omenn GS, Goodman GE, Thornquist MD, et al. Effects of a combination of beta carotene and vitamin A on lung cancer and cardiovascular disease. N Engl J Med. 1996;334(18):1150–1155.
   PubMed Web of Science ®Google Scholar
• Street DA, Comstock GW, Salkeld RM, et al. Serum antioxidants and myocardial infarction. Are low levels of carotenoids and alpha-tocopherol risk factors for myocardial infarction? Circulation. 1994;90(3):1154–1161.
   PubMed Web of Science ®Google Scholar
• Kushi LH, Folsom AR, Prineas RJ, et al. Dietary antioxidant vitamins and death from coronary heart disease in postmenopausal women. N Engl J Med. 1996;334(18):1156–1162.
   PubMed Web of Science ®Google Scholar
• Janero DR. Therapeutic potential of vitamin E in the pathogenesis of spontaneous atherosclerosis. Free Radic Biol Med. 1991;11(1):129–144.
   PubMed Web of Science ®Google Scholar
• Butterfield DA, Martin L, Carney JM, et al. Aβ(25–35) peptide displays H2O2-like reactivity towards aqueous FE2+, nitroxide spin probes, and synaptosomal membrane proteins. Life Sci. 1996;58(3):217–228.
   PubMed Web of Science ®Google Scholar
• Butterfield DA. β-Amyloid-associated free radical oxidative stress and neurotoxicity: implications for Alzheimer’s disease. Chem Res Toxicol. 1997;10(5):495–506.
   PubMed Web of Science ®Google Scholar
• Rice-Evans C, Halliwell B, Lunt GG, editors. Free radical and oxidative stress: environment, drugs and food additives. London: Portland Press; 1995. p. 103–116.
   Google Scholar
• Arendash GW, Mori T, Cao Ch, et al. Caffeine reverses cognitive impairment and decreases brain amyloid-β levels in aged Alzheimer’s disease mice. JAD. 2009;17(3):661–680.
   Google Scholar
• Arendash GW, Chuanhai C. Caffeine and coffee as therapeutics against Alzheimer’s disease. J Alzheimers Dis. 2010;20:S117–S126.
   PubMed Web of Science ®Google Scholar
• Nehlig A, Daval JL, Debry G. Caffeine and the central nervous system: mechanisms of action, biochemical, metabolic and psychostimulant effects. Brain Res Brain Res Rev. 1992;17(2):139–170.
   PubMed Web of Science ®Google Scholar
• Devasagayam TPA, Kamat JP, Mohan H, et al. Caffeine as an antioxidant: inhibition of lipid peroxidation induced by reactive oxygen species. Biochim Biophys Acta. 1996;1282(1):63–70.
   PubMed Web of Science ®Google Scholar
• Devasagayam TPA, Kesavan PC. Radioprotective and antioxidant action of caffeine: mechanistic considerations. Indian J Exp Biol. 1996;34(4):291–297.
   PubMedGoogle Scholar
• Kesavan PC. Protection by caffeine against oxic radiation damage and chemical carcinogens: mechanistic considerations. Curr Sci. 1992;62:791–797.
   Web of Science ®Google Scholar
• Kumar MR, Rao MT, Adinarayana M. Phosphate radical induced oxidation of pyrimidine bases in aqueous solution. Indian J Biochem Biophys. 2000;37(1):13–17.
   PubMed Web of Science ®Google Scholar
• Jasiewicz B, Sierakowska A, Wandyszewska N, et al. Antioxidant properties of thio-caffeine derivatives: identification of the newly synthesized 8-[(pyrrolidin-1-ylcarbonothioyl) sulfanyl] caffeine as antioxidant and highly potent cytoprotective agent. Bioorg Med Chem Lett. 2016;26(16):3994–3998.
   PubMed Web of Science ®Google Scholar
• Wallace HM, Fraser AV, Hughes A. A perspective of polyamine metabolism. Biochem J. 2003;376(1):1–14.
   PubMed Web of Science ®Google Scholar
• Drolet G, Dumbroff EB, Legge RL, et al. Radical scavenging properties of polyamines. Phytochemistry. 1986;25(2):367–371.
   Web of Science ®Google Scholar
• Kostopoulou ON, Kouvela EC, Magoulas GE, et al. Conjugation with polyamines enhances the antibacterial and anticancer activity of chloramphenicol. Nucleic Acids Res. 2014;42(13):8621–8634.
   PubMed Web of Science ®Google Scholar
• Phillips JC, Braun R, Wang W, et al. Scalable molecular dynamics with NAMD. J Comput Chem. 2005;26(16):1781–1802.
   PubMed Web of Science ®Google Scholar
• Best RB, Zhu X, Shim J, et al. Optimization of the additive CHARMM all-atom protein force field targeting improved sampling of the backbone φ, ψ and side-chain χ1 and χ2 dihedral angles. J Chem Theory Comput. 2012;8(9):3257–3273.
   PubMed Web of Science ®Google Scholar
• Saam J, Ivanov I, Walther M, et al. Molecular dioxygen enters the active site of 12/15-lipoxygenase via dynamic oxygen access channels. Proc Natl Acad Sci USA. 2007;104(33):13319–13324.
   PubMed Web of Science ®Google Scholar
• Humphrey W, Dalke A, Schulten K. VMD: visual molecular dynamics. J Mol Graph. 1996;14(1):27, 33–8.
   PubMedGoogle Scholar
• Becke AD. Density-functional exchange-energy approximation with correct asymptotic behavior. Phys Rev A. 1988;38(6):3098–3100.
   PubMed Web of Science ®Google Scholar
• Ditchfield R, Hehre WJ, Pople JA. Self-consistent molecular-orbital methods. IX. An extended Gaussian-type basis for molecular-orbital studies of organic molecules. J Chem Phys. 1971;54(2):724–728.
   Web of Science ®Google Scholar
• Reed AE, Weinstock RB, Weinhold F. Natural population analysis. J Chem Phys. 1985;83(2):735–746.
   Web of Science ®Google Scholar
• Frisch MJ, Trucks GW, Schlegel HB, et al. Gaussian 09, revision A.1. Wallingford (CT): Gaussian, Inc; 2009.
   Google Scholar
• Kirkpatrick S, Gelatt CD, Vecchi MP. Optimization by simulated annealing. Science. 1983;220(4598):671–680.
   PubMed Web of Science ®Google Scholar
• Allen MP, Tildesley DJ. Computer simulation of liquids. Oxford: Clarendon Press; 1987.
   Google Scholar
• Kozanecka W, Mrówczyńska L, Pospieszny T, et al. Synthesis, spectroscopy, theoretical and biological studies of new gramine-steroids salts and conjugates. Steroids. 2015;98:92–99.
   PubMed Web of Science ®Google Scholar
• Carmichael J, DeGraff WG, Gazdar AF, et al. Evaluation of a tetrazolium-based semiautomated colorimetric assay: assessment of chemosensitivity testing. Cancer Res. 1987;47(4):936–942.
   PubMed Web of Science ®Google Scholar
• Coutsias EA, Seok C, Dill KA. Using quaternions to calculate RMSD. J Comput Chem. 2004;25(15):1849–1857.
   PubMed Web of Science ®Google Scholar
• Mrówczyńska L, Hägerstrand H. Platelet-activating factor interaction with the human erythrocyte membrane. J Biochem Mol Toxicol. 2009;23(5):345–348.
   PubMed Web of Science ®Google Scholar
• Wang YQ, Zhang HM, Zhou QH. Studies on the interaction of caffeine with bovine hemoglobin. Eur J Med Chem. 2009;44(5):2100–2105.
   PubMed Web of Science ®Google Scholar
• Ajila CM, Prasada Rao UJS. Protection against hydrogen peroxide induced oxidative damage in rat erythrocytes by Mangifera indica L. peel extract. Food Chem Toxicol. 2008;46(1):303–309.
   PubMed Web of Science ®Google Scholar
• Rosendahl AH, Perks CM, Zeng L, et al. Caffeine and caffeic acid inhibit growth and modify estrogen receptor and insulin-like growth factor I receptor levels in human breast cancer. Clin Cancer Res. 2015;21(8):1877–1887.
   PubMed Web of Science ®Google Scholar
• Kaplánek R, Jakubek M, Rak J, et al. Caffeine–hydrazones as anticancer agents with pronounced selectivity toward T-lymphoblastic leukaemia cells. Bioorg Chem. 2015;60:19–29.
   PubMed Web of Science ®Google Scholar