|
Abe, R., Fujita, Y. & Yamagishi, S. 2007. Angiogenesis and metastasis inhibitors for the treatment of malignant melanoma. Mini Rev Med Chem 7: 649-61. Appendino, G., Mercalli, E., Fuzzati, N., Arnoldi, L., Stavri, M., Gibbons, S., Ballero, M. & Maxia, A. 2004. Antimycobacterial coumarins from the sardinian giant fennel (Ferula communis). J Nat Prod 67: 2108-10. Babior, B. M. 2000. The NADPH oxidase of endothelial cells. IUBMB Life 50: 267-9. Baldi, A., Lombardi, D., Russo, P., Palescandolo, E., De Luca, A., Santini, D., Baldi, F., Rossiello, L., Dell''Anna, M. L., Mastrofrancesco, A., Maresca, V., Flori, E., Natali, P. G., Picardo, M. & Paggi, M. G. 2005. Ferritin contributes to melanoma progression by modulating cell growth and sensitivity to oxidative stress. Clin Cancer Res 11: 3175-83. Bedogni, B., Welford, S. M., Cassarino, D. S., Nickoloff, B. J., Giaccia, A. J. & Powell, M. B. 2005. The hypoxic microenvironment of the skin contributes to Akt-mediated melanocyte transformation. Cancer Cell 8: 443-54. Bedoya, L. M., Beltran, M., Sancho, R., Olmedo, D. A., Sanchez-Palomino, S., del Olmo, E., Lopez-Perez, J. L., Munoz, E., San Feliciano, A. & Alcami, J. 2005. 4-Phenylcoumarins as HIV transcription inhibitors. Bioorg Med Chem Lett 15: 4447-50. Chang, W. S. & Chiang, H. C. 1995. Structure-activity relationship of 48 coumarins in xanthine oxidase inhibition. Anticancer Res 15: 1969-73. Chen, X., Wang, S., Wu, N., Sood, S., Wang, P., Jin, Z., Beer, D. G., Giordano, T. J., Lin, Y., Shih, W. C., Lubet, R. A. & Yang, C. S. 2004. Overexpression of 5-lipoxygenase in rat and human esophageal adenocarcinoma and inhibitory effects of zileuton and celecoxib on carcinogenesis. Clin Cancer Res 10: 6703-9. Chou, D. S., Hsiao, G., Lai, Y. A., Tsai, Y. J. & Sheu, J. R. 2009. Baicalein induces proliferation inhibition in B16F10 melanoma cells by generating reactive oxygen species via 12-lipoxygenase. Free Radic Biol Med 46: 1197-203. Chou, D. S., Hsiao, G., Shen, M. Y., Tsai, Y. J., Chen, T. F. & Sheu, J. R. 2005. ESR spin trapping of a carbon-centered free radical from agonist-stimulated human platelets. Free Radic Biol Med 39: 237-48. Egan, D., O''Kennedy, R., Moran, E., Cox, D., Prosser, E. & Thornes, R. D. 1990. The pharmacology, metabolism, analysis, and applications of coumarin and coumarin-related compounds. Drug Metab Rev 22: 503-29. Farombi, E. O. & Fakoya, A. 2005. Free radical scavenging and antigenotoxic activities of natural phenolic compounds in dried flowers of Hibiscus sabdariffa L. Mol Nutr Food Res 49: 1120-8. Ferrari, A. M., Sgobba, M., Gamberini, M. C. & Rastelli, G. 2007. Relationship between quantum-chemical descriptors of proton dissociation and experimental acidity constants of various hydroxylated coumarins. Identification of the biologically active species for xanthine oxidase inhibition. Eur J Med Chem 42: 1028-31. Finkel, T. 2001. Reactive oxygen species and signal transduction. IUBMB 49 Life 52: 3-6. Finkelstein, E., Rosen, G. M., Rauckman, E. J. & Paxton, J. 1979. Spin trapping of superoxide. Mol Pharmacol 16: 676-85. Forman, H. J. & Torres, M. 2002. Reactive oxygen species and cell signaling: respiratory burst in macrophage signaling. Am J Respir Crit Care Med 166: S4-8. Fruehauf, J. P. & Meyskens, F. L., Jr. 2007. Reactive oxygen species: a breath of life or death? Clin Cancer Res 13: 789-94. Fujita, M., Shiota, S., Kuroda, T., Hatano, T., Yoshida, T., Mizushima, T. & Tsuchiya, T. 2005. Remarkable synergies between baicalein and tetracycline, and baicalein and beta-lactams against methicillin-resistant Staphylococcus aureus. Microbiol Immunol 49: 391-6. Fylaktakidou, K. C., Hadjipavlou-Litina, D. J., Litinas, K. E. & Nicolaides, D. N. 2004. Natural and synthetic coumarin derivatives with anti-inflammatory/ antioxidant activities. Curr Pharm Des 10: 3813-33. Gaggioli, C. & Sahai, E. 2007. Melanoma invasion - current knowledge and future directions. Pigment Cell Res 20: 161-72. Galm, U., Dessoy, M. A., Schmidt, J., Wessjohann, L. A. & Heide, L. 2004. In vitro and in vivo production of new aminocoumarins by a combined biochemical, genetic, and synthetic approach. Chem Biol 11: 173-83. Ghate, M., Kusanur, R. A. & Kulkarni, M. V. 2005. Synthesis and in vivo analgesic and anti-inflammatory activity of some bi heterocyclic coumarin derivatives. Eur J Med Chem 40: 882-7. Ghate, M., Manohar, D., Kulkarni, V., Shobha, R. & Kattimani, S. Y. 2003. 50 Synthesis of vanillin ethers from 4-(bromomethyl) coumarins as anti-inflammatory agents. Eur J Med Chem 38: 297-302. Govindarajan, B., Sligh, J. E., Vincent, B. J., Li, M., Canter, J. A., Nickoloff, B. J., Rodenburg, R. J., Smeitink, J. A., Oberley, L., Zhang, Y., Slingerland, J., Arnold, R. S., Lambeth, J. D., Cohen, C., Hilenski, L., Griendling, K., Martinez-Diez, M., Cuezva, J. M. & Arbiser, J. L. 2007. Overexpression of Akt converts radial growth melanoma to vertical growth melanoma. J Clin Invest 117: 719-29. Hendrix, M. J., Seftor, E. A., Hess, A. R. & Seftor, R. E. 2003. Vasculogenic mimicry and tumour-cell plasticity: lessons from melanoma. Nat Rev Cancer 3: 411-21. Hess, A. R., Seftor, E. A., Seftor, R. E. & Hendrix, M. J. 2003. Phosphoinositide 3-kinase regulates membrane Type 1-matrix metalloproteinase (MMP) and MMP-2 activity during melanoma cell vasculogenic mimicry. Cancer Res 63: 4757-62. Hoult, J. R. & Paya, M. 1996. Pharmacological and biochemical actions of simple coumarins: natural products with therapeutic potential. Gen Pharmacol 27: 713-22. Hsu, S. L., Hsieh, Y. C., Hsieh, W. C. & Chou, C. J. 2001. Baicalein induces a dual growth arrest by modulating multiple cell cycle regulatory molecules. Eur J Pharmacol 425: 165-71. Huang, H. C., Wang, H. R. & Hsieh, L. M. 1994. Antiproliferative effect of baicalein, a flavonoid from a Chinese herb, on vascular smooth muscle cell. Eur J Pharmacol 251: 91-3. Ichihashi, M., Ueda, M., Budiyanto, A., Bito, T., Oka, M., Fukunaga, M., Tsuru, K. & Horikawa, T. 2003. UV-induced skin damage. Toxicology 51 189: 21-39. Ito, C., Itoigawa, M., Mishina, Y., Filho, V. C., Enjo, F., Tokuda, H., Nishino, H. & Furukawa, H. 2003. Chemical constituents of Calophyllum brasiliense. 2. Structure of three new coumarins and cancer chemopreventive activity of 4-substituted coumarins. J Nat Prod 66: 368-71. Jeong, T. S., Kim, K. S., Kim, J. R., Cho, K. H., Lee, S. & Lee, W. S. 2004. Novel 3,5-diaryl pyrazolines and pyrazole as low-density lipoprotein (LDL) oxidation inhibitor. Bioorg Med Chem Lett 14: 2719-23. Jezek, P. & Hlavata, L. 2005. Mitochondria in homeostasis of reactive oxygen species in cell, tissues, and organism. Int J Biochem Cell Biol 37: 2478-503. Justino, G. C., Santos, M. R., Canario, S., Borges, C., Florencio, M. H. & Mira, L. 2004. Plasma quercetin metabolites: structure-antioxidant activity relationships. Arch Biochem Biophys 432: 109-21. Kade, I. J., Paixao, M. W., Rodrigues, O. E., Barbosa, N. B., Braga, A. L., Avila, D. S., Nogueira, C. W. & Rocha, J. B. 2008. Comparative studies on dicholesteroyl diselenide and diphenyl diselenide as antioxidant agents and their effect on the activities of Na+/K+ ATPase and delta-aminolevulinic acid dehydratase in the rat brain. Neurochem Res 33: 167-78. Kakiuchi, Y., Sasaki, N., Satoh-Masuoka, M., Murofushi, H. & Murakami-Murofushi, K. 2004. A novel pyrazolone, 4,4-dichloro-1-(2,4-dichlorophenyl)-3-methyl-5-pyrazolone, as a potent catalytic inhibitor of human telomerase. Biochem Biophys Res Commun 320: 1351-1358. 52 Kanayasu-Toyoda, T., Morita, I. & Murota, S. 1998. Arachidonic acid pretreatment enhances smooth muscle cell migration via increased Ca2+ influx. Prostaglandins Leukot Essent Fatty Acids 58: 25-31. Karihtala, P. & Soini, Y. 2007. Reactive oxygen species and antioxidant mechanisms in human tissues and their relation to malignancies. APMIS 115: 81-103. Khan, I. A., Kulkarni, M. V., Gopal, M., Shahabuddin, M. S. & Sun, C. M. 2005. Synthesis and biological evaluation of novel angularly fused polycyclic coumarins. Bioorg Med Chem Lett 15: 3584-7. Khan, K. M., Saify, Z. S., Khan, M. Z., Zia, U., Choudhary, I. M., Atta Ur, R., Perveen, S., Chohan, Z. H. & Supuran, C. T. 2004. Synthesis of coumarin derivatives with cytotoxic, antibacterial and antifungal activity. J Enzyme Inhib Med Chem 19: 373-9. Kidane, A. G., Salacinski, H., Tiwari, A., Bruckdorfer, K. R. & Seifalian, A. M. 2004. Anticoagulant and antiplatelet agents: their clinical and device application(s) together with usages to engineer surfaces. Biomacromolecules 5: 798-813. Kimura, Y., Matsushita, N. & Okuda, H. 1997. Effects of baicalein isolated from Scutellaria baicalensis on interleukin 1 beta- and tumor necrosis factor alpha-induced adhesion molecule expression in cultured human umbilical vein endothelial cells. J Ethnopharmacol 57: 63-7. Kontogiorgis, C. & Hadjipavlou-Litina, D. 2003. Biological evaluation of several coumarin derivatives designed as possible anti-inflammatory/antioxidant agents. J Enzyme Inhib Med Chem 18: 63-9. 53 Kontogiorgis, C. A. & Hadjipavlou-Litina, D. J. 2004. Synthesis and biological evaluation of novel coumarin derivatives with a 7-azomethine linkage. Bioorg Med Chem Lett 14: 611-4. Kontogiorgis, C. A. & Hadjipavlou-Litina, D. J. 2005. Synthesis and antiinflammatory activity of coumarin derivatives. J Med Chem 48: 6400-8. Kostova, I. 2005. Synthetic and natural coumarins as cytotoxic agents. Curr Med Chem Anticancer Agents 5: 29-46. Lee, B. H., Clothier, M. F., Dutton, F. E., Conder, G. A. & Johnson, S. S. 1998. Anthelmintic beta-hydroxyketoamides (BKAs). Bioorg Med Chem Lett 8: 3317-20. Lee, K. H. 2004. Current developments in the discovery and design of new drug candidates from plant natural product leads. J Nat Prod 67: 273-83. Lin, H. C., Tsai, S. H., Chen, C. S., Chang, Y. C., Lee, C. M., Lai, Z. Y. & Lin, C. M. 2008. Structure-activity relationship of coumarin derivatives on xanthine oxidase-inhibiting and free radical-scavenging activities. Biochem Pharmacol 75: 1416-25. Lin, R., Chiu, G., Yu, Y., Connolly, P. J., Li, S., Lu, Y., Adams, M., Fuentes-Pesquera, A. R., Emanuel, S. L. & Greenberger, L. M. 2007a. Design, synthesis, and evaluation of 3,4-disubstituted pyrazole analogues as anti-tumor CDK inhibitors. Bioorg Med Chem Lett 17: 4557-61. Lin, Y. T., Yang, J. S., Lin, H. J., Tan, T. W., Tang, N. Y., Chaing, J. H., Chang, Y. H., Lu, H. F. & Chung, J. G. 2007b. Baicalein induces apoptosis in SCC-4 human tongue cancer cells via a Ca2+-dependent 54 mitochondrial pathway. In Vivo 21: 1053-8. Liu, H., Colavitti, R., Rovira, II & Finkel, T. 2005. Redox-dependent transcriptional regulation. Circ Res 97: 967-74. Liu, J. J., Huang, T. S., Cheng, W. F. & Lu, F. J. 2003. Baicalein and baicalin are potent inhibitors of angiogenesis: Inhibition of endothelial cell proliferation, migration and differentiation. Int J Cancer 106: 559-65. Liu, Z. Q., Yu, W. & Liu, Z. L. 1999. Antioxidative and prooxidative effects of coumarin derivatives on free radical initiated and photosensitized peroxidation of human low-density lipoprotein. Chem Phys Lipids 103: 125-35. Lloyd, R. V., Hanna, P. M. & Mason, R. P. 1997. The origin of the hydroxyl radical oxygen in the Fenton reaction. Free Radic Biol Med 22: 885-8. Maltese, A., Maugeri, F., Ward, K. W. & Bucolo, C. 2007. Development and validation of an RP-HPLC-UV method for the determination of BOL-303225-A, a new coumarin-based anti-inflammatory drug, in rat plasma. Biomed Chromatogr 21: 351-5. Martins, H. F., Leal, J. P., Fernandez, M. T., Lopes, V. H. & Cordeiro, M. N. 2004. Toward the prediction of the activity of antioxidants: experimental and theoretical study of the gas-phase acidities of flavonoids. J Am Soc Mass Spectrom 15: 848-61. Mates, J. M. & Sanchez-Jimenez, F. M. 2000. Role of reactive oxygen species in apoptosis: implications for cancer therapy. Int J Biochem Cell Biol 32: 157-70. Natarajan, R., Stern, N., Hsueh, W., Do, Y. & Nadler, J. 1988. Role of the lipoxygenase pathway in angiotensin II-mediated aldosterone biosynthesis in human adrenal glomerulosa cells. J Clin Endocrinol 55 Metab 67: 584-91. Nie, D., Krishnamoorthy, S., Jin, R., Tang, K., Chen, Y., Qiao, Y., Zacharek, A., Guo, Y., Milanini, J., Pages, G. & Honn, K. V. 2006. Mechanisms regulating tumor angiogenesis by 12-lipoxygenase in prostate cancer cells. J Biol Chem 281: 18601-9. Nishio, E. & Watanabe, Y. 1997. Role of the lipoxygenase pathway in phenylephrine-induced vascular smooth muscle cell proliferation and migration. Eur J Pharmacol 336: 267-73. Okuda, S., Saito, H. & Katsuki, H. 1994. Arachidonic acid: toxic and trophic effects on cultured hippocampal neurons. Neuroscience 63: 691-9. Postovit, L. M., Seftor, E. A., Seftor, R. E. & Hendrix, M. J. 2006. Influence of the microenvironment on melanoma cell fate determination and phenotype. Cancer Res 66: 7833-6. Raj, H. G., Parmar, V. S., Jain, S. C., Goel, S., Poonam, Himanshu, Malhotra, S., Singh, A., Olsen, C. E. & Wengel, J. 1998. Mechanism of biochemical action of substituted 4-methylbenzopyran-2-ones. Part I: Dioxygenated 4-methyl coumarins as superb antioxidant and radical scavenging agents. Bioorg Med Chem 6: 833-9. Rashba-Step, J., Turro, N. J. & Cederbaum, A. I. 1993. Increased NADPH- and NADH-dependent production of superoxide and hydroxyl radical by microsomes after chronic ethanol treatment. Arch Biochem Biophys 300: 401-8. Rice-Evans, C. A., Miller, N. J. & Paganga, G. 1996. Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radic Biol Med 20: 933-56. Saibara, T., Toda, K., Wakatsuki, A., Ogawa, Y., Ono, M. & Onishi, S. 2003. 56 Protective effect of 3-methyl-1-phenyl-2-pyrazolin-5-one, a free radical scavenger, on acute toxicity of paraquat in mice. Toxicol Lett 143: 51-4. Schuppan, D. & Popov, Y. 2002. Hepatic fibrosis: from bench to bedside. J Gastroenterol Hepatol 17 Suppl 3: S300-5. Sekiya, K. & Okuda, H. 1982. Selective inhibition of platelet lipoxygenase by baicalein. Biochem Biophys Res Commun 105: 1090-5. Sharma, S. D., Rajor, H. K., Chopra, S. & Sharma, R. K. 2005. Studies on structure activity relationship of some dihydroxy-4-methylcoumarin antioxidants based on their interaction with Fe(III) and ADP. Biometals 18: 143-54. Stohs, S. J. & Bagchi, D. 1995. Oxidative mechanisms in the toxicity of metal ions. Free Radic Biol Med 18: 321-36. Tao, J., Hu, S., Pacholec, M. & Walsh, C. T. 2003. Synthesis of proposed oxidation-cyclization-methylation intermediates of the coumarin antibiotic biosynthetic pathway. Org Lett 5: 3233-6. Verhaegen, M., Bauer, J. A., Martin de la Vega, C., Wang, G., Wolter, K. G., Brenner, J. C., Nikolovska-Coleska, Z., Bengtson, A., Nair, R., Elder, J. T., Van Brocklin, M., Carey, T. E., Bradford, C. R., Wang, S. & Soengas, M. S. 2006. A novel BH3 mimetic reveals a mitogen-activated protein kinase-dependent mechanism of melanoma cell death controlled by p53 and reactive oxygen species. Cancer Res 66: 11348-59. Wang, J., Yu, Y., Hashimoto, F., Sakata, Y., Fujii, M. & Hou, D. X. 2004. Baicalein induces apoptosis through ROS-mediated mitochondrial dysfunction pathway in HL-60 cells. Int J Mol Med 14: 627-32. 57 Winer, I., Normolle, D. P., Shureiqi, I., Sondak, V. K., Johnson, T., Su, L. & Brenner, D. E. 2002. Expression of 12-lipoxygenase as a biomarker for melanoma carcinogenesis. Melanoma Res 12: 429-34. Wu, C., Chen, F., Wang, X., Wu, Y., Dong, M., He, G., Galyean, R. D., He, L. & Huang, G. 2007. Identification of antioxidant phenolic compounds in feverfew (Tanacetum parthenium) by HPLC-ESI-MS/MS and NMR. Phytochem Anal 18: 401-10. Wu, W. S. 2006. The signaling mechanism of ROS in tumor progression. Cancer Metastasis Rev 25: 695-705. Xanthoudakis, S., Miao, G., Wang, F., Pan, Y. C. & Curran, T. 1992. Redox activation of Fos-Jun DNA binding activity is mediated by a DNA repair enzyme. EMBO J 11: 3323-35.
|