A Critical Overview of the Chemistry of Copper-Dependent Low Density Lipoprotein Oxidation: Roles of Lipid Hydroperoxides, α-Tocopherol, Thiols, and Ceruloplasmin

Archives of Biochemistry and Biophysics - Tập 394 Số 1 - Trang 117-135 - 2001
Mark J. Burkitt1
1Gray Cancer Institute, Mount Vernon Hospital, Northwood, Middlesex HA6 2JR, United Kingdom.

Tóm tắt

Từ khóa


Tài liệu tham khảo

Steinbrecher, 1984, Proc. Natl. Acad. Sci. USA, 81, 3883, 10.1073/pnas.81.12.3883

Parthasarathy, 1986, Arteriosclerosis, 6, 505, 10.1161/01.ATV.6.5.505

Steinberg, 1989, New Engl. J. Med., 320, 915, 10.1056/NEJM198901053200122

Chisolm, 2000, Free Rad. Biol. Med., 28, 1815, 10.1016/S0891-5849(00)00344-0

Bowry, 1992, Biochem. J., 288, 341, 10.1042/bj2880341

Bowry, 1993, J. Am. Chem. Soc., 115, 6029, 10.1021/ja00067a019

Ingold, 1993, Proc. Natl. Acad. Sci. USA, 90, 45, 10.1073/pnas.90.1.45

Iwatsuki, 1995, FEBS Lett., 360, 271, 10.1016/0014-5793(95)00122-P

Lynch, 1995, J. Biol. Chem., 270, 5158, 10.1074/jbc.270.10.5158

Ehrenwald, 1994, J. Clin. Invest., 93, 1493, 10.1172/JCI117127

Mukhopadhyay, 1996, J. Biol. Chem., 271, 14773, 10.1074/jbc.271.25.14773

Mukhopadhyay, 1998, Biochemistry, 37, 14222, 10.1021/bi981137t

Laranjinha, 1996, Biochem. Pharmacol., 51, 395, 10.1016/0006-2952(95)02171-X

Witting, 1999, Chem. Res. Toxicol., 12, 1173, 10.1021/tx9900472

Santanam, 1995, J. Clin. Invest., 95, 2594, 10.1172/JCI117961

Kalyanaraman, 1995, J. Lipid Res., 36, 1037, 10.1016/S0022-2275(20)39861-8

Witting, 1997, Biochemistry, 36, 1251, 10.1021/bi962493j

Rubbo, 1995, Arch. Biochem. Biophys., 324, 12, 10.1006/abbi.1995.9935

Upston, 1996, J. Lipid Res., 37, 2650, 10.1016/S0022-2275(20)37468-X

Upston, 1997, J. Biol. Chem., 272, 30067, 10.1074/jbc.272.48.30067

Darley-Usmar, 1992, Free Rad. Res. Commun., 17, 9, 10.3109/10715769209061085

Graham, 1993, FEBS Lett., 330, 181, 10.1016/0014-5793(93)80269-Z

Thomas, 1998, Chem. Res. Toxicol., 11, 484, 10.1021/tx970173a

Kritharides, 1995, Arch. Biochem. Biophys., 323, 127, 10.1006/abbi.1995.0018

Müller, 1998, Free Rad. Res., 29, 207, 10.1080/10715769800300241

Baoutina, 1998, J. Lipid Res., 39, 114, 10.1016/S0022-2275(20)34208-5

Kritharides, 1995, Free Rad. Res., 22, 399, 10.3109/10715769509147549

Garner, 1997, J. Biol. Chem., 272, 6927, 10.1074/jbc.272.11.6927

Smith, 1992, Biochem. J., 286, 901, 10.1042/bj2860901

Ueda, 1998, Arch. Biochem. Biophys., 357, 231, 10.1006/abbi.1998.0811

Maiorino, 1995, Free Rad. Biol. Med., 18, 67, 10.1016/0891-5849(94)00103-Q

Abuja, 1997, Chem. Res. Toxicol., 10, 644, 10.1021/tx9700073

Grossi, 1998, J. Org. Chem., 63, 8366, 10.1021/jo9812678

Qian, 2000, Free Rad. Biol. Med., 29, 568, 10.1016/S0891-5849(00)00407-X

Abuja, 1995, Chem. Res. Toxicol., 8, 753, 10.1021/tx00047a016

Small, 1979, Photochem. Photobiol., 29, 49, 10.1111/j.1751-1097.1979.tb09258.x

Esterbauer, 1992, Free Rad. Biol. Med., 13, 341, 10.1016/0891-5849(92)90181-F

Koppenol, 1985, Adv. Free Rad. Biol. Med., 1, 91, 10.1016/8755-9668(85)90005-5

Yoshida, 1993, Biochim. Biophys. Acta, 1210, 81, 10.1016/0005-2760(93)90052-B

Buettner, 1993, Arch. Biochem. Biophys., 300, 535, 10.1006/abbi.1993.1074

Das, 1998, J. Phys. Chem., 102, 280, 10.1021/jp972903t

Patel, 1997, Biochem. J., 322, 425, 10.1042/bj3220425

Sayre, 1996, Science, 274, 1933, 10.1126/science.274.5294.1933

Cadenas, 1998, Free Rad. Res., 28, 601, 10.3109/10715769809065816

Bossu, 1977, J. Am. Chem. Soc., 99, 2195, 10.1021/ja00449a028

Lappin, 1980, Inorg. Chem., 19, 407, 10.1021/ic50204a025

Koppenol, 1990, FEBS Lett., 264, 165, 10.1016/0014-5793(90)80239-F

Burton, 1986, Acc. Chem. Res., 19, 194, 10.1021/ar00127a001

Esterbauer, 1987, J. Lipid Res., 28, 495, 10.1016/S0022-2275(20)38678-8

Kagan, 1992, J. Lipid Res., 33, 385, 10.1016/S0022-2275(20)41529-9

Barclay, 1997, J. Am. Chem. Soc., 119, 5764, 10.1021/ja9705856

Frei, 1993, J. Lipid Res., 34, 2135, 10.1016/S0022-2275(20)35354-2

Thomas, 1994, Arch. Biochem. Biophys., 315, 244, 10.1006/abbi.1994.1496

Yoshida, 1994, Biochim. Biophys. Acta, 1200, 85, 10.1016/0304-4165(94)90121-X

Maiorino, 1993, FEBS Lett., 330, 174, 10.1016/0014-5793(93)80267-X

Witting, 1995, FEBS Lett., 375, 45, 10.1016/0014-5793(95)01172-B

Proudfoot, 1997, Free Rad. Biol. Med., 23, 720, 10.1016/S0891-5849(97)00015-4

Yamamoto, 1988, Biochim. Biophys. Acta, 958, 19, 10.1016/0005-2760(88)90241-X

Yang, 1990, Proc. Natl. Acad. Sci. USA, 87, 5523, 10.1073/pnas.87.14.5523

Davis, 1983, J. Chem. Soc. Perkin Trans., 2, 1763, 10.1039/p29830001763

Kachur, 1999, Free Rad. Res., 31, 23, 10.1080/10715769900300571

Blumberg, 1968, J. Chem. Phys., 49, 1793, 10.1063/1.1670309

Gilbert, 1997, 49

Burkitt, 2000, Arch. Biochem. Biophys., 381, 253, 10.1006/abbi.2000.1973

Saez, 1982, Biochim. Biophys. Acta, 719, 24, 10.1016/0304-4165(82)90302-6

Gilbert, 1999, J. Chem. Soc., Perkin Trans., 2, 1115, 10.1039/a901179j

Hemmerich, 1966, Angew. Chem. Int. Ed. Engl., 5, 422, 10.1002/anie.196604222

Kroneck, 1971, Inorg. Nucl. Chem. Lett., 7, 659, 10.1016/0020-1650(71)80052-1

Kuzuya, 1992, Biochim. Biophys. Acta, 1123, 334, 10.1016/0005-2760(92)90015-N

Chen, 1997, Redox Rep., 3, 175, 10.1080/13510002.1997.11747106

Retsky, 1999, Free Rad. Biol. Med., 26, 90, 10.1016/S0891-5849(98)00151-8

Ueda, 1995, Free Rad. Biol. Med., 18, 929, 10.1016/0891-5849(94)00213-4

Kaim, 1996, Angew. Chem. Int. Ed. Engl., 35, 43, 10.1002/anie.199600431

Fergusson, 1997, Free Rad. Biol. Med., 341, 287

Gey, 1993, Brit. Med. Bull., 49, 679, 10.1093/oxfordjournals.bmb.a072640

Thomas, 1998, Chem. Res. Toxicol., 11, 484, 10.1021/tx970173a

Thomas, 2000, Free Rad. Biol. Med., 28, 1795, 10.1016/S0891-5849(00)00236-7

Neužil, 1997, Free Rad. Biol. Med., 22, 57, 10.1016/S0891-5849(96)00224-9

Kontush, 1996, J. Lipid Res., 37, 1436, 10.1016/S0022-2275(20)39128-8

Aihara, 1990, Biochem. Biophys. Res. Commun., 168, 169, 10.1016/0006-291X(90)91689-P

Urano, 1993, Biochem. Biophys. Res. Commun., 192, 568, 10.1006/bbrc.1993.1453

Aihara, 1993, J. Chem. Soc., Perkin Trans., 2, 2165, 10.1039/P29930002165

Bielski, 1985, J. Phys. Chem. Ref. Data, 14, 1041, 10.1063/1.555739

Pecci, 1997, Biochem. Biophys. Res. Commun., 235, 264, 10.1006/bbrc.1997.6756

Klug, 1972, J. Biol. Chem., 247, 4839, 10.1016/S0021-9258(19)44987-9

Thomas, 1992, Biochim. Biophys. Acta, 1128, 50, 10.1016/0005-2760(92)90256-U

Lynch, 1993, J. Lipid Res., 34, 1745, 10.1016/S0022-2275(20)35737-0

Udenfriend, 1954, J. Biol. Chem., 208, 731, 10.1016/S0021-9258(18)65598-X

Burkitt, 1990, Free Rad. Res. Commun., 10, 265, 10.3109/10715769009149895

Masarwa, 1988, J. Am. Chem. Soc., 110, 4293, 10.1021/ja00221a031

Sagripanti, 1989, J. Biol. Chem., 264, 1729, 10.1016/S0021-9258(18)94247-X

Stoewe, 1987, Free Rad. Biol. Med., 3, 97, 10.1016/S0891-5849(87)80003-5

Aruoma, 1991, Biochem. J., 273, 601, 10.1042/bj2730601

Gunther, 1995, Arch. Biochem. Biophys., 316, 515, 10.1006/abbi.1995.1068

Oikawa, 1996, Biochemistry, 35, 4584, 10.1021/bi9527000

Burkitt, 1995, Arch. Biochem. Biophys., 323, 63, 10.1006/abbi.1995.0010

Morgan, 1976, Nucleic Acids Res., 3, 1139, 10.1093/nar/3.5.1139

Que, 1980, Biochemistry, 19, 5987, 10.1021/bi00567a007

Dizdaroglu, 1990, Biochemistry, 29, 8447, 10.1021/bi00488a035

Burkitt, 1996, FEBS Lett., 379, 51, 10.1016/0014-5793(95)01481-0

Yamashita, 1998, Chem. Res. Toxicol., 11, 855, 10.1021/tx970129v

Fazal, 1990, Carcinogenesis, 11, 2005, 10.1093/carcin/11.11.2005

Ahmed, 1994, Carcinogenesis, 15, 1627, 10.1093/carcin/15.8.1627

Sahu, 1994, Cancer Lett., 85, 159, 10.1016/0304-3835(94)90269-0

Li, 1993, Carcinogenesis, 14, 1303, 10.1093/carcin/14.7.1303

Li, 1994, Cancer Res. (Suppl.), 54, 1895s

Li, 1994, Carcinogenesis, 15, 1421, 10.1093/carcin/15.7.1421

Yamanaka, 1997, FEBS Lett., 405, 186, 10.1016/S0014-5793(97)00185-3

Yamanaka, 1997, FEBS Lett., 401, 230, 10.1016/S0014-5793(96)01455-X

Markides, 1998, Arch. Biochem. Biophys., 360, 105, 10.1006/abbi.1998.0934

DeFelippis, 1989, Biochemistry, 28, 4847, 10.1021/bi00437a049

Kagawa, 1991, J. Biol. Chem., 266, 20175, 10.1016/S0021-9258(18)54906-1

Davies, M. J, and, Dean, R. T. 1997, Radical-Mediated Protein Oxidation. From Chemistry to Medicine, Oxford Univ. Press, Oxford.

Marx, 1986, Biochem. J., 236, 397, 10.1042/bj2360397

Ozawa, 1993, Biochem. Mol. Biol. Int., 29, 247

Patterson, 1998, FEBS Lett., 434, 317, 10.1016/S0014-5793(98)01002-3

Uchida, 1986, Biochem. Biophys. Res. Commun., 138, 659, 10.1016/S0006-291X(86)80547-2

Bedwell, 1989, Biochem. J., 262, 707, 10.1042/bj2620707

Graham, 1998, Free Rad. Res., 28, 611, 10.3109/10715769809065817

Heinecke, 1987, J. Biol. Chem., 262, 10098, 10.1016/S0021-9258(18)61082-8

Sparrow, 1993, J. Lipid Res., 34, 1219, 10.1016/S0022-2275(20)37709-9

Heinecke, 1993, J. ipid Res., 34, 2051

Graham, 1996, Free Rad. Res., 25, 181, 10.3109/10715769609149923

Lynch, 1997, Biochim. Biophys. Acta, 1345, 215, 10.1016/S0005-2760(96)00182-8

Asmus, 1990, Methods Enzymol., 186, 168, 10.1016/0076-6879(90)86107-7

Schoneich, 1992, Arch. Biochem. Biophys., 292, 456, 10.1016/0003-9861(92)90016-P

Kachur, 1998, Free Rad. Res., 28, 259, 10.3109/10715769809069278

Searle, 1982, J. Inorg. Biochem., 17, 161, 10.1016/S0162-0134(00)80085-9

Gilbert, 1975, J. Chem. Soc. Perkin Trans., 2, 892, 10.1039/P29750000892

Gilbert, 1977, J. Chem. Soc. Perkin Trans., 2, 497, 10.1039/p29770000497

Hanna, 1992, Arch. Biochem. Biophys., 295, 205, 10.1016/0003-9861(92)90507-S

Gilbert, 1999, J. Chem. Soc. Perkin Trans., 2, 1891, 10.1039/a903403j

Milne, 1993, Arch. Biochem. Biophys., 304, 102, 10.1006/abbi.1993.1327

Gilbert, 1988, J. Chem. Soc. Perkin Trans., II, 1867, 10.1039/P29880001867

Burkitt, 1994, Methods Enzymol., 234, 66, 10.1016/0076-6879(94)34078-1

Tsang, S. Y. 1996, Ph.D. Thesis, Department of Chemistry Aberdeen, Aberdeen, UK.

Santanam, 1995, J. Lipid Res., 36, 2203, 10.1016/S0022-2275(20)39204-X

Rydén, 1984, 37

Fox, 1995, Life Sci., 56, 1749, 10.1016/0024-3205(95)00146-W

Fox, 2000, Free Rad. Biol. Med., 28, 1735, 10.1016/S0891-5849(00)00231-8

Van Eden, 2000, Arch. Biochem. Biophys., 381, 119, 10.1006/abbi.2000.1952

Evans, 1994, Methods Enzymol., 233, 82, 10.1016/S0076-6879(94)33010-7

Burkitt, 2001, Clin. Sci., 100, 239, 10.1042/CS20000237

Lamb, 1994, FEBS Lett., 338, 122, 10.1016/0014-5793(94)80348-X

Ehrenwald, 1996, J. Clin. Invest., 97, 884, 10.1172/JCI118491

Leake, 1997, Atherosclerosis, 129, 149, 10.1016/S0021-9150(96)06035-2

Mukhopadhyay, 1997, Proc. Natl. Acad. Sci. USA, 94, 11546, 10.1073/pnas.94.21.11546

Chisolm, 1999, J. Biol. Chem., 274, 25959, 10.1074/jbc.274.37.25959

Wang, 1992, J. Am. Chem. Soc., 114, 248, 10.1021/ja00027a032

Wood, 1995, FEBS Lett., 366, 75, 10.1016/0014-5793(95)00494-T

Jessup, 1993, Atherosclerosis, 99, 107, 10.1016/0021-9150(93)90056-Z

Buxton, 1988, J. Phys. Chem. Ref. Data, 17, 513, 10.1063/1.555805