Design and synthesis of manganese porphyrins with tailored lipophilicity: Investigation of redox properties and superoxide dismutase activity

Bioorganic and Medicinal Chemistry

Volumn 15, Issue 22, 2007, Pages 7066-7086

  Lahaye, Dorothée ^a   Muthukumaran, Kannan ^a   Hung, Chen Hsiung ^a   Gryko, Dorota ^a   Rebouças, Júlio S ^b   Spasojević, Ivan ^b   Batinić Haberle, Ines ^b   Lindsey, Jonathan S ^a  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

^b DUKE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Amphipathic; Cyclic voltammetry; Lipophilic; Manganese; Porphodimethene; Porphyrin; Superoxide dismutase

Indexed keywords

10 NITRO 5,15 DI N PENTYLPORPHINATOMANGANESE CHLORIDE; 5 BENZOYL 10,15,20 TRIS(4 METHYLPHENYL)PORPHINATOMANGANESE CHLORIDE; 5 TRIFLUOROMETHYLPORPHINATOZINC; 5,15 BIS(2,3,5,6 TETRAFLUORO 4 DIMETHYLAMINOPHENYL) 10,20 DIOXOPORPHODIMETHENATOMANGANESE CHLORIDE; 5,15 BIS(2,3,5,6 TETRAFLUORO 4 DIMETHYLAMINOPHENYL)PORPHINATOMANGANESE CHLORIDE; 5,15 DI N PENTYLPORPHINATOMANGANESE CHLORIDE; 5,15 DIBENZOYL 10,20 BIS(TRIFLUOROMETHYL)PORPHINATOMANGANESE CHLORIDE; 5,15 DIISOPROPYL 10 NITRO 20(TRIFLUOROMETHYL)PORPHINATOMANGANESE CHLORIDE; 5,15 DIISOPROPYL 10(N MORPHOLINOMETHYL) 20 (TRIFLUOROMETHYL)PORPHINATOMANGANESE CHLORIDE; 5,15 DIISOPROPYL 10(TRIFLUOROMETHYL)PORPHINATOMANGANESE CHLORIDE; 5,15 DINITRO 10(TRIFLUOROMETHYL)PORPHINATOMANGANESE CHLORIDE; 5,15 DINITRO 10,20 DI N PENTYLPORPHINATOMANGANESE CHLORIDE; 5,15 DIOXO 10,20 DIPHENYLPORPHODIMETHENATOMANGANESE CHLORIDE; 5,15 DIPHENYL 10,20 BIS(TRIFLUOROMETHYL)PORPHINATOMANGANESE CHLORIDE; 5,5,15,15 TETRAMETHYL 10,20 DIPHENYLPORPHODIMETHENATOMANGANESE CHLORIDE; MANGANESE DERIVATIVE; MESO TETRABENZOYLPORPHINATOMANGANESE CHLORIDE; PORPHYRIN DERIVATIVE; SUPEROXIDE DISMUTASE; UNCLASSIFIED DRUG;

ARTICLE; BLOOD BRAIN BARRIER; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME KINETICS; LIPID BILAYER; LIPOPHILICITY; OXIDATION REDUCTION REACTION; REDUCTION KINETICS;

CATALYSIS; CYTOCHROMES C; DRUG DESIGN; ELECTROCHEMISTRY; ELECTRON TRANSPORT; ENZYME ACTIVATION; LIPID BILAYERS; MANGANESE; METALLOPORPHYRINS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; SOLUBILITY; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; SUPEROXIDE DISMUTASE; SUPEROXIDES;

EID: 34548837750     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.07.015     Document Type: Article

References (115)

1. Halliwell B., and Gutteridge J.M.C. Free Radicals in Biology and Medicine. third ed. (1999), Oxford University Press
2. Gutteridge J.M.C. Free Rad. Res. Comm 19 (1993) 141-158
3. Halliwell B. Biochem. J. 401 (2007) 1-11
4. Halliwell B. Plant Physiol. 141 (2006) 312-322
5. Fridovich I. Ann. Rev. Biochem. 64 (1995) 97-112
6. Dworakowski R., Anilkumar N., Zhang M., and Shah A.M. Biochem. Soc. Trans. 34 (2006) 960-964
7. Infanger D.W., Sharma R.V., and Davisson R.L. Antioxid. Redox Signal. 8 (2006) 1583-1596
8. Cuzzocrea S. Pharmacol. Res. 52 (2005) 72-82
9. Muravchick S., and Levy R.J. Anesthesiology 105 (2006) 819-836
10. Jones D.P. Antioxid. Redox Signal. 8 (2006) 1865-1879
11. World C.J., Yamawaki H., and Berk B.C. J. Mol. Med. 84 (2006) 997-1003
12. Sasaki Y. J. Gastroenterol. 41 (2006) 1135-1148
13. Szeto H.H. AAPS J. 8 (2006) E521-E531
14. Browne S.E., and Beal M.F. Antioxid. Redox Signal. 8 (2006) 2061-2073
15. Lin M.T., and Beal M.F. Nature 443 (2006) 787-795
16. Valko M., Leibfritz D., Moncol J., Cronin M.T.D., Mazur M., and Telser J. Int. J. Biochem. Cell Biol. 39 (2007) 44-84
17. Madamanchi N.R., and Runge M.S. Circ. Res. 100 (2007) 460-473
18. Trushina E., and McMurray C.T. Neurosci. 145 (2007) 1233-1248
19. Whitton P.S. Br. J. Pharmacol. 150 (2007) 963-976
20. Denicola A., and Radi R. Toxicol. 208 (2005) 273-288
21. Lancaster Jr. J.R. Chem. Res. Toxicol. 19 (2006) 1160-1174
22. Pacher P., Beckman J.S., and Liaudet L. Physiol. Rev. 87 (2007) 315-424
23. Demicheli V., Quijano C., Alvarez B., and Radi R. Free Radic. Biol. Med. 42 (2007) 1359-1368
24. Wood P.M. Biochem. J. 253 (1988) 287-289
25. Vance C.K., and Miller A.-F. J. Am. Chem. Soc. 120 (1998) 461-467
26. Ellerby L.M., Cabelli D.E., Graden J.A., and Valentine J.S. J. Am. Chem. Soc. 118 (1996) 6556-6561
27. Michel E., Nauser T., Sutter B., Bounds P.L., and Koppenol W.H. Arch. Biochem. Biophys. 439 (2005) 234-240
28. Goldstein S., Fridovich I., and Czapski G. Free Radical Biol. Med. 41 (2006) 937-941
29. Spasojevic I., Batinic-Haberle I., Reboucas J.S., Idemori Y.M., and Fridovich I. J. Biol. Chem 278 (2003) 6831-6837
30. Pardridge W.M. In: Pardridge W.M. (Ed). Introduction to the Blood-Brain Barrier (1998), Cambridge University Press, Cambride, UK 1-8
31. Imlay J.A. Mol. Microbiol. 59 (2006) 1073-1082
32. Pasternack R.F., and Halliwell B. J. Am. Chem. Soc. 101 (1979) 1026-1031
33. Pasternack R.F., and Skowronek Jr. W.R. J. Inorg. Biochem. 11 (1979) 261-267
34. Batinic-Haberle I., Benov L., Spasojevic I., and Fridovich I. J. Biol. Chem. 273 (1998) 24521-24528
35. Lee J., Hunt J.A., and Groves J.T. J. Am. Chem. Soc. 120 (1998) 6053-6061
36. Ferrer-Sueta G., Batinic-Haberle I., Spasojevic I., Fridovich I., and Radi R. Chem. Res. Toxicol. 12 (1999) 442-449
37. Batinic-Haberle I., Spasojevic I., Hambright P., Benov L., Crumbliss A.L., and Fridovich I.T. Inorg. Chem. 38 (1999) 4011-4022
38. Batinic-Haberle I. Methods Enzymol. 349 (2002) 223-233
39. Batinic-Haberle I., Spasojevic I., Stevens R.D., Hambright P., and Fridovich I. J. Chem. Soc., Dalton Trans. (2002) 2689-2696
40. Ferrer-Sueta G., Vitturi D., Batinic-Haberle I., Fridovich I., Goldstein S., Czapski G., and Radi R. J. Biol. Chem. 278 (2003) 27432-27438
41. Batinic-Haberle I., Spasojevic I., Stevens R.D., Hambright P., Neta P., Okado-Matsumoto A., and Fridovich I. Dalton Trans. (2004) 1696-1702
42. Batinic-Haberle I., Spasojevic I., Stevens R.D., Bondurant B., Okado-Matsumoto A., Fridovich I., Vujaskovic Z., and Dewhirst M.W. Dalton Trans. (2006) 617-624
43. Ferrer-Sueta G., Hannibal L., Batinic-Haberle I., and Radi R. Free Radic. Biol. Med. 41 (2006) 503-512
44. Saba H., Batinic-Haberle I., Munusamy S., Mitchell T., Lichti C., Megyesi J., and MacMillan-Crow L.A. Free Radic. Biol. Med. 42 (2007) 1571-1578
45. Spasojevic I., Chen Y., Noel T.J., Yu Y., Cole M.P., Zhang L., Zhao Y., Clair D.K.St., and Batinic-Haberle I. Free Radical Biol. Med. 42 (2007) 1193-1200
46. Lee J., Hunt J.A., and Groves J.T. J. Am. Chem. Soc 120 (1998) 7493-7501
47. Shimanovich R., and Groves J.T. Arch. Biochem. Biophys. 387 (2001) 307-317
48. Obrosova I.G., Mabley J.G., Zsengeller Z., Charniauskaya T., Abatan O.I., Groves J.T., and Szabo C. FASEB J. 19 (2005) 401-403
49. Soule B.P., Hyodo F., Matsumoto K.-I., Simone N.L., Cook J.A., Krishna M.C., and Mitchell J.B. Free Radical Biol. Med. 42 (2007) 1632-1650
50. Riley D.P. Adv. Supramol. Chem. 6 (2000) 217-244
51. Salvemini D., Riley D.P., and Cuzzocrea S. Nat. Rev. Drug Disc. 1 (2002) 367-374
52. Olcott A.P., Tocco G., Tian J., Zekzer D., Fukuto J., Ignarro L., and Kaufman D.L. Diabetes 53 (2004) 2574-2580
53. Morten K.J., Ackrell B.A.C., and Melov S. J. Biol. Chem. 281 (2006) 3354-3359
54. James A.M., Cocheme H.M., Smith R.A.J., and Murphy M.P. J. Biol. Chem. 280 (2005) 21295-21312
55. Dhanasekaran A., Kotamraju S., Karunakaran C., Kalivendi S.V., Thomas S., Joseph J., and Kalyanaraman B. Free Radical Biol. Med. 39 (2005) 567-583
56. Asayama S., Kawamura E., Nagaoka S., and Kawakami H. Mol. Pharm. 3 (2006) 468-470
57. Warner D.S., Sheng H., and Batinic-Haberle I. J. Exp. Biol. 207 (2004) 3221-3231
58. Tse H.M., Milton M.J., and Piganelli J.D. Free Radical Biol. Med. 36 (2004) 233-247
59. Moeller B.J., Cao Y., Li C.Y., and Dewhirst M.W. Cancer Cell 5 (2004) 429-441
60. Zhao Y., Chaiswing L., Oberley T.D., Batinic-Haberle I., Clair W.St., Epstein C.J., and St. Clair D. Cancer Res. 65 (2005) 1401-1405
61. Spasojevic, I.; Zhang, L.; Chen, Y.; Noel, T. J.; Cole, M. P.; Zhao Y.; Reboucas, J. S.; St. Clair, D. K.; Batinic-Haberle, I. Int. Conf. Rad. Res. San Francisco 2007.
62. Okado-Matsumoto A., Batinic-Haberle I., and Fridovich I. Free Radical Biol. Med. 37 (2004) 401-410
63. Giraudeau A., Callot H.J., Jordan J., Ezhar I., and Gross M. J. Am. Chem. Soc. 101 (1979) 3857-3862
64. Worthington P., Hambright P., Williams R.F.X., Feldman M.R., Smith K.M., and Langry K.C. Inorg. Nucl. Chem. Lett. 16 (1980) 441-447
65. Worthington P., Hambright P., Williams R.F.X., Reid J., Burnham C., Shamim A., Turay J., Bell D.M., Kirkland R., Little R.G., Datta-Gupta N., and Eisner U. J. Inorg. Biochem. 12 (1980) 281-291
66. Gong L.-C., and Dolphin D. Can. J. Chem. 63 (1985) 401-405
67. Rao S., and Krishnan V. J. Mol. Struct. 327 (1994) 279-285
68. Ghosh A. J. Am. Chem. Soc. 117 (1995) 4691-4699
69. Rivkin A., Biswas K., Chou T.-C., and Danishefsky S.J. Org. Lett. 4 (2002) 4081-4084
70. Wilson R.M., and Danishefsky S.J. J. Org. Chem. 71 (2006) 8329-8351
71. Ojima I., Inoue T., and Chakravarty S. J. Fluorine Chem. 97 (1999) 3-10
72. Gryshuk A., Chen Y., Goswami L.N., Pandey S., Missert J.R., Ohulchanskyy T., Potter W., Prasad P.N., Oseroff A., and Pandey R.K. J. Med. Chem. 50 (2007) 1754-1767
73. Littler B.J., Ciringh Y., and Lindsey J.S. J. Org. Chem. 64 (1999) 2864-2872
74. Rao P.D., Dhanalekshmi S., Littler B.J., and Lindsey J.S. J. Org. Chem. 65 (2000) 7323-7344
75. Brown W.H., and French W.N. Can. J. Chem. 36 (1958) 371-377
76. Littler B.J., Miller M.A., Hung C.-H., Wagner R.W., O'Shea D.F., Boyle P.D., and Lindsey J.S. J. Org. Chem. 64 (1999) 1391-1396
77. Nishino N., Wagner R.W., and Lindsey J.S. J. Org. Chem. 61 (1996) 7534-7544
78. Borovkov V.V., Lintuluoto J.M., and Inoue Y. Synlett (1999) 61-62
79. Adler A.D., Longo F.R., Kampas F., and Kim J. J. Inorg. Nucl. Chem. 32 (1970) 2443-2445
80. Lindsey J.S., Prathapan S., Johnson T.E., and Wagner R.W. Tetrahedron 50 (1994) 8941-8968
81. Benech J.-M., Bonomo L., Solari E., Scopelliti R., and Floriani C. Angew. Chem. Int. Ed. 38 (1999) 1957-1959
82. Kral V., Sessler J.L., Zimmerman R.S., Seidel D., Lynch V., and Andrioletti B. Angew. Chem. Int. Ed. 39 (2000) 1055-1058
83. Bucher C., Seidel D., Lynch V., Kral V., and Sessler J.L. Org. Lett. 2 (2000) 3103-3106
84. Bischoff I., Feng X., and Senge M.O. Tetrahedron 57 (2001) 5573-5583
85. Hong S.-J., Ka J.-W., Won D.-H., and Lee C.-H. Bull. Korean Chem. Soc. 24 (2003) 661-663
86. Sharada D.S., Muresan A.Z., Muthukumaran K., and Lindsey J.S. J. Org. Chem. 70 (2005) 3500-3510
87. Manka J.S., and Lawrence D.S. Tetrahedron Lett. 30 (1989) 6989-6992
88. Barnett G.H., Hudson M.F., McCombie S.W., and Smith K.M. J. Chem. Soc., Perkin Trans. I (1973) 691-696
89. Fuhrhop J.-H., Baumgartner E., and Bauer H. J. Am. Chem. Soc. 103 (1981) 5854-5861
90. Lindsey J.S., and Wagner R.W. J. Org. Chem. 54 (1989) 828-836
91. Kadish K.M., Han B.C., Franzen M.M., and Araullo-McAdams C. J. Am. Chem. Soc. 112 (1990) 8364-8368
92. La T., Richards R., and Miskelly G.M. Inorg. Chem. 33 (1994) 3159-3163
93. Wiehe A., Shaker Y.M., Brandt J.C., Mebs S., and Senge M.O. Tetrahedron 61 (2005) 5535-5564
94. Bonnett R., and Stephenson G.F. J. Org. Chem. 30 (1965) 2791-2798
95. Laszlo P., and Pennetreau P. J. Org. Chem. 52 (1987) 2407-2410
96. Wickramasinghe A., Jaquinod L., Nurco D.J., and Smith K.M. Tetrahedron 57 (2001) 4261-4269
97. Fan D., Taniguchi M., Yao Z., Dhanalekshmi S., and Lindsey J.S. Tetrahedron 61 (2005) 10291-10302
98. Fischer H., Gottschlich R., and Seelig A. J. Membrane Biol. 165 (1998) 201-211
99. Xiong Y., Peterson P.L., Muizellaar J.P., and Lee C.P. J. Neurotrauma 14 (1997) 907-917
100. Brenner E., Baldwin R.M., and Tamagnan G. Org. Lett. 7 (2005) 937-939
101. Brockmann Jr. V.H., Bliesener K.-M., and Inhoffen H.H. Liebigs Ann. Chem 718 (1968) 148-161
102. Ley S.V., Bolli M.H., Hinzen B., Gervois A.-G., and Hall B.J. J. Chem. Soc. Perkin Trans. 1 (1998) 2239-2242
103. Hoffmann P., Robert A., and Meunier B. Bull. Soc. Chim. Fr. 129 (1992) 85-97
104. Tsuchiya S., and Seno M. Chem. Lett. (1989) 263-266
105. Spasojevic I., and Batinic-Haberle I. Inorg. Chim. Acta 317 (2001) 230-242
106. Spasojevic I., Batinic-Haberle I., Stevens R.D., Hambright P., Thorpe A.N., Grodkowski J., Neta P., and Fridovich I. Inorg. Chem. 40 (2001) 726-739
107. Gong L., and Yang X. Acta Chim. Sinica 43 (1985) 302-305
108. Sen A., and Krishnan V. J. Chem. Soc., Faraday Trans. 93 (1997) 4281-4288
109. Ozette K., Battioni P., Leduc P., Bartoli J.-F., and Mansuy D. Inorg. Chim. Acta 272 (1998) 4-6
110. Halliwell B. Cardiovasc. Res. 73 (2007) 341-347
111. Guzman M.L., Rossi R.M., Karnischky L., Li X., Peterson D.R., Howard D.S., and Jordan C.T. Blood 105 (2005) 4163-4169
112. Hashemy S.I., Ungerstedt J.S., Avval F.Z., and Holmgren A. J. Biol. Chem. 281 (2006) 10691-10697
113. Rosenberg A., and Knox S. Int. J. Rad. Oncol. Biol. Phys. 64 (2006) 343-354
114. Aslan M., Ryan T.M., Adler B., Townes T.M., Parks D.A., Thompson J.A., Tousson A., Gladwin M.T., Patel R.P., Tarpey M.M., Batinic-Haberle I., White C.R., and Freeman B.A. Proc. Natl. Acad. Sci. U.S.A. 98 (2001) 15215-15220
115. McCord J.M., and Fridovich I. J. Biol. Chem. 244 (1969) 6049-6055