Nitration and chlorination of folic acid by peroxynitrite and hypochlorous acid, and the selective binding of 10-nitro-folate to folate receptor β
Tài liệu tham khảo
Babior, 2000, Phagocytes and oxidative stress, Am. J. Med., 109, 33, 10.1016/S0002-9343(00)00481-2
Rosen, 1995, Free radicals and phagocytic cells, FASEB J., 9, 200, 10.1096/fasebj.9.2.7540156
Radi, 2001, Unraveling peroxynitrite formation in biological systems, Free Radic. Biol. Med., 30, 463, 10.1016/S0891-5849(00)00373-7
Stanger, 2002, Physiology of folic acid in health and disease, Curr. Drug Metab., 3, 211, 10.2174/1389200024605163
Costi, 2001, Update on antifolate drugs targets, Curr. Drug Targets, 2, 135, 10.2174/1389450013348669
Rosowsky, 1989, Chemistry and biological activity of antifolates, vol. 26, 1
Ross, 1999, Folate receptor type β is a neutrophilic lineage marker and is differentially expressed in myeloid leukemia, Cancer, 85, 348, 10.1002/(SICI)1097-0142(19990115)85:2<348::AID-CNCR12>3.0.CO;2-4
Reddy, 1999, Expression and functional characterization of the β-isoform of the folate receptor on CD34(+) cells, Blood, 93, 3940, 10.1182/blood.V93.11.3940
Nakashima-Matsushita, 1999, Selective expression of folate receptor β and its possible role in methotrexate transport in synovial macrophages from patients with rheumatoid arthritis, Arthritis Rheum., 42, 1609, 10.1002/1529-0131(199908)42:8<1609::AID-ANR7>3.0.CO;2-L
Whiteley, 1981, Structural reassignment of the peroxide oxidation product of 5-methyl-5,6,7,8-tetrahydrofolate, Biochem. Biophys. Res. Commun., 101, 1259, 10.1016/0006-291X(81)91583-7
Lumb, 1988, In vivo oxidation of the methyl group of hepatic 5-methyltetrahydrofolate, J. Clin. Pathol., 41, 1158, 10.1136/jcp.41.11.1158
Joshi, 2001, Free radical scavenging behavior of folic acid: evidence for possible antioxidant activity, Free. Radic. Biol. Med., 30, 1390, 10.1016/S0891-5849(01)00543-3
Brookes, 2002, Oxidation of 10-formyltetrahydrofolate to 10-formyldihydrofolate by complex IV of rat mitochondria, Biochemistry, 41, 5633, 10.1021/bi0120244
Hazen, 1997, p-Hydroxyphenylacetaldehyde, the major product of l-tyrosine oxidation by the myeloperoxidase–H2O2–chloride system of phagocytes, covalently modifies epsilon-amino groups of protein lysine residues, J. Biol. Chem., 272, 16990, 10.1074/jbc.272.27.16990
Reichl, 2000, Reactions of pholasin with peroxidases and hypochlorous acid, Free. Radic. Biol. Med., 28, 1555, 10.1016/S0891-5849(00)00268-9
Eiserich, 1998, Formation of nitric oxide-derived inflammatory oxidants by myeloperoxidase in neutrophils, Nature, 391, 393, 10.1038/34923
Mooradian, 1995, Nitric oxide (NO) donor molecules: effect of NO release rate on vascular smooth muscle cell proliferation in vitro, J. Cardiovasc. Pharmacol., 25, 674, 10.1097/00005344-199504000-00023
Selloum, 2001, Effects of flavonols on the generation of superoxide anion radicals by xanthine oxidase and stimulated neutrophils, Arch. Biochem. Biophys., 395, 49, 10.1006/abbi.2001.2562
Blanchard, 2000, Nitrosation of melatonin by nitric oxide and peroxynitrite, J. Pineal Res., 29, 184, 10.1034/j.1600-079X.2000.290308.x
Hu, 1998, Reaction of cyclohexylamine with hypochlorite and enhancement of oxidation of plasma sulfhydryl groups by hypochlorite in vitro, Food Chem. Toxicol., 36, 755, 10.1016/S0278-6915(98)00060-X
Finglas, 1999, Standardization of HPLC techniques for the determination of naturally occurring folates in food, Food Chem., 64, 245, 10.1016/S0308-8146(98)00171-X
Pfeiffer, 2000, Dityrosine formation outcompetes tyrosine nitration at low steady-state concentrations of peroxynitrite, J. Biol. Chem., 275, 6346, 10.1074/jbc.275.9.6346
Domigan, 1995, Chlorination of tyrosyl residues in peptides by myeloperoxidase and human neutrophils, J. Biol. Chem., 270, 16542, 10.1074/jbc.270.28.16542
Fukui, 1982, Role of frontier orbitals in chemical reactions, Science, 218, 747, 10.1126/science.218.4574.747
Morton, 2002, Evidence for the nitration of γ-tocopherol in vivo: 5-nitro-γ-tocopherol is elevated in the plasma of subjects with coronary heart disease, Biochem. J., 364, 625, 10.1042/bj20020491
Eiserich, 1996, Formation of nitrating and chlorinating species by reaction of nitrite with hypochlorous acid. A novel mechanism for nitric oxide-mediated protein modification, J. Biol. Chem., 271, 19199, 10.1074/jbc.271.32.19199
Koppenol, 1994, Thermodynamic considerations on the formation of reactive species from hypochlorite, superoxide and nitrogen monoxide. Could nitrosyl chloride be produced by neutrophils and macrophages?, FEBS Lett., 347, 5, 10.1016/0014-5793(94)00494-3
She, 1997, Aminobenzoic acid compounds as HOCl traps for activated neutrophils, Free Radic. Biol. Med., 22, 989, 10.1016/S0891-5849(96)00486-8
Liu, 1994, Peroxynitrite a product, of superoxide and nitric oxide, produces coronary vasorelaxation in dogs, J. Pharmacol. Exp. Ther., 268, 1114
Moro, 1995, The formation of nitric oxide donors from peroxynitrite, Br. J. Pharmacol., 116, 1999, 10.1111/j.1476-5381.1995.tb16404.x
Wang, 1998, Folate-mediated targeting of antineoplastic drugs, imaging agents, and nucleic acids to cancer cells, J. Control Release, 53, 39, 10.1016/S0168-3659(97)00236-8
Pan, 2002, Strategy for the treatment of acute myelogenous leukemia based on folate receptor β-targeted liposomal doxorubicin combined with receptor induction using all-trans retinoic acid, Blood, 100, 594, 10.1182/blood.V100.2.594
Lashner, 1989, Effect of folate supplementation on the incidence of dysplasia and cancer in chronic ulcerative colitis. A case-control study, Gastroenterology, 97, 255, 10.1016/0016-5085(89)90058-9