Meso tetrakis ortho-, meta-, and para-n-alkylpyridinioporphyrins: Kinetics of copper(II) and zinc(II) incorporation and zinc porphyrin demetalation

Journal of Porphyrins and Phthalocyanines

Volumn 7, Issue 3, 2003, Pages 139-146

  Hambright, Peter ^a   Batinić Haberle, Ines ^b   Spasojević, Ivan ^b  

^a HOWARD UNIVERSITY   (United States)

^b DUKE UNIVERSITY MEDICAL CENTER   (United States)

Author keywords

Effective porphyrin charge; Metalation kinetics; N alkylpyridinio porphyrins

Indexed keywords

CATION; COPPER; HYDROCHLORIC ACID; PORPHYRIN DERIVATIVE; UNCLASSIFIED DRUG; ZINC; ZINC PORPHYRIN;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; CHEMOREACTIVITY; DEMETALATION; ELECTRICITY; IONIC STRENGTH; ISOMER; LIPOPHILICITY; METAL BINDING; METALATION;

EID: 0038170547     PISSN: 10884246     EISSN: None     Source Type: Journal    
DOI: 10.1142/S1088424603000197     Document Type: Article

References (49)

1. Hambright P. In The Porphyrin Handbook, Vol. 3, Kadish KM, Smith KM, Guilard R. (Eds.) Academic Press: New York, 2000; p 129.
2. Hambright P and Fleisher EB. Inorg. Chem. 1970; 9: 1757-1761.
3. Hambright P, Gore T and Burton M. Inorg. Chem. 1976; 15: 2314-2315.
4. Pasternack RF and Gibbs EJ. In Metal ions in biological systems: biological properties of metal alkyl derivatives, Vol. 33, Siegel H. (Ed.) Marcel Dekker Inc.: New York, 1986; p 367.
5. Trommel JS and Marzilli LG. Inorg. Chem. 2001; 40: 4374-4383.
6. Mosseri S, Nahor GS, Neta P and Hambright P. J. Chem. Soc. Faraday Trans. 1991; 87: 2567-2572.
7. Batinic-Haberle I, Spasojevic I, Hambright P, Benov L, Crumbliss AL and Fridovich I. Inorg. Chem. 1999; 38: 4011-4022.
8. Spasojevic I and Batinic Haberle I. Inorg. Chim. Acta 2001; 317: 230-242.
9. Batinic-Haberle I, Spasojevic I, Stevens RD, Hambright P and Fridovich I. J. Chem. Soc. Faraday Trans. 2002: 2689-2696.
10. Welcher F. The analytical uses of ethylenediamine tetraacetic acid; Van Nostrand: New York, 1958; pp 149, 241, 230.
11. Benov L, Batinic-Haberle I, Spasojevic I and Fridovich I. Arch. Biochem. Biophys. 2002; 402: 159-165.
12. Herrmann O, Mehdi SH and Corsini A. Can. J. Chem. 1978; 56: 1084-1087.
13. Baker H, Hambright P and Wagner L. J. Am. Chem. Soc. 1973; 95: 5942-5946.
14. Reid JB and Hambright P. Inorg. Chem. 1977; 16: 968-969.
15. Espenson JH. Chemical kinetics and reaction mechanisms; McGraw-Hill Companies: New York, 1981; p 176.
16. Baes Jr. CF and Mesmer RE. The hydrolysis of cations; Kreiger Publishing Company: Malabar, Florida, 1986; p 512.
17. Kaufmann T, Shamsai B, Lu RS, Bau R and Miskelly GM. Inorg. Chem. 1995; 34: 5073-5079.
18. Batinic-Haberle I, Stevens RD and Fridovich I. J. Porphyrins Phthalocyanines 2000; 4: 217-227.
19. Inamo M, Tomita A, Inagaki Y, Asano N, Suenaga K, Tabata M and Funahashi S. Inorg. Chim. Acta 1997; 256: 77-85.
20. Nwaeme J and Hambright P. Inorg. Chem. 1984; 23: 1990-1992.
21. Spasojevic I, Batinic Haberle I, Reboucas JS, Idemori YM and Fridovich I. J. Biol. Chem. 2003; 278: 6831-6837.
22. Dixon DW and Steullet V. J. Inorg. Biochem. 1998; 69: 25-32.
23. Krishnamurthy M and Sutter JR. Inorg. Chem. 1985; 24: 1943-1946.
24. Steinfeld JI, Francisco JS and Hase WL. Chemical kinetics and dynamics; Prentice Hall: Englewood Cliffs, New Jersey, 1989; p 168.
25. Hambright P and Chock PB. J. Am. Chem. Soc. 1974; 96: 3123-3131.
26. Inada Y, Sugimoto Y, Nakano Y, Itoh Y and Funahashi S. Inorg. Chem. 1998; 37: 5519-5526.
27. Margerum DW, Cayley GR, Weatherburn DC and Pagenkopf GK. In Coordination chemistry, Vol. 2: Washington, 1978; p 9.
28. Tobe ML and Burgess J. Inorganic reaction mechanisms; Addison Wesley Longman: New York, 1999; p 278.
29. Sutter TPG and Hambright P. J. Coord. Chem. 1993; 30: 317-326.
30. Wilkins RG. Kinetics and mechanisms of transition metal complexes; 2nd ed.; VCH: New York, 1991; p 202.
31. Tabata M and Ishimi H. Bull. Chem. Soc. Jpn. 1997; 70: 1353-1359.
32. Hambright P. Inorg. Chem. 1977; 16: 2987-2988.
33. Bailey SL and Hambright P. Inorg. React. Mech. (Amsterdam, Neth.) 2001; 3: 51-61.
34. Pasternack RF, Gibbs EJ, Santucci R, Schaertel S, Ellinas P and Mah SC. J. Chem. Soc., Chem. Commun. 1987: 1771-1774.
35. Shamim A and Hambright P. Inorg. Chem. 1980; 19: 564-566.
36. Haye SE and Hambright P. Inorg. Chem. 1984; 23: 4777-4779.
37. Robinson LR and Hambright P. Inorg. Chim. Acta 1991; 185: 17-24.
38. Shah B and Hambright P. J. Inorg. Nucl. Chem. 1970; 32: 3420-3422.
39. Davila J, Harriman A, Richoux MC and Milgrom LR. J. Chem. Soc., Chem. Commun. 1987: 525-527.
40. Kano K, Fukuda K, Wakami H, Nishiyabu R and Pasternack RF. J. Am. Chem. Soc. 2000; 122: 7494-7502.
41. Batinic-Haberle I. Methods Enzymol. 2002; 349: 223-233.
42. Pasternack RF and Halliwell B. J. Am. Chem. Soc. 1979; 101: 1026-1031.
43. Spasojevic I, Batinic-Haberle I and Fridovich I. Nitric Oxide-Biol. Chem. 2000; 4: 526-533.
44. Ferrer-Sueta G, Batinic-Haberle I, Spasojevic I, Fridovich I and Radi R. Chem. Res. Toxicol. 1999; 12: 442-449.
45. Lee J, Hunt JA and Groves JT. J. Am. Chem. Soc. 1998; 120: 6053-6061.
46. Szabo C, Mabley JG, Moeller SM, Shimanovich R, Pacher P, Virag L, Soriano FG, Van Duzer JH, Williams W, Salzman AL and Groves JT. Mol. Med. 2002; 8: 571-580.
47. Vzorov AN, Dixon DW, Trommel JS, Marzilli LG and Compans RW. Antimicrob. Agents Chemother. 2002; 46: 3917-3925.
48. Shi DF, Wheelhouse RT, Sun DY and Hurley LH. J. Med. Chem. 2001; 44: 4509-4523.
49. Ferrer-Sueta G, Vitturi D, Batinic-Haberle I, Fridovich I, Goldstein S, Czapski G and Radi R. J. Biol. Chem. 2003: in press.