High-Affinity Binding of Quinine to Iron(III) Porphyrins: Novel Formation of Alkoxide Complexes from Alcohols and Amines

Journal of the American Chemical Society

Volumn 106, Issue 17, 1984, Pages 4945-4950

  Behere, D V ^a   Goff, Harold M ^a  

^a UNIVERSITY OF IOWA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS;

DRUG PRODUCTS;

HEMIN; QUININE;

NONHUMAN; THEORETICAL STUDY;

EID: 0021473147     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00329a053     Document Type: Article

References (29)

1. Chou, A. C.; Cheuli, R.; Fitch, C. D. Biochemistry 1980, 19, 1543–1549.
2. Warhurst, D. C. Biochem. Pharmacol. 1981, 30, 3323–3327.
3. Cohen, S. N.; Phifer, K. O.; Yielding, K. L. Nature (London) 1964, 202, 805–806.
4. Blauer, G.; Ginsburg, H. Biochem. Int. 1982, 5, 519–523.
5. Blauer, G. Biochem. Int. 1983, 6, 777–782.
6. Morishima, I.; Kitagawa, S.; Matsuki, E.; Inubushi, T. J. Am. Chem. Soc. 1980, 102, 2429–2437.
7. Boersma, A. D.; Goff, H. M. Inorg. Chem. 1982, 21, 581–586.
8. O’Keeffe, D. H.; Barlow, C. H.; Smythe, G. A.; Fuchsman, W. H.; Moss, T. H.; Lilienthal, H. R.; Caughey, W. S. Bioinorg. Chem. 1975, 5, 125–147.
9. Hickman, D. L.; Goff, H. M. J. Am. Chem. Soc., in press.
10. Smith, K. M.; Langry, K. C.; DeRopp, J. S. J. Chem. Soc., Chem. Commun. 1979, 1001–1003.
11. Evans, D. F. J. Chem. Soc. 1959, 2003–2005.
12. Eaton, S. S.; Eaton, G. R. Inorg. Chem. 1980, 19, 1095–1096.
13. Adams, P. A.; Baldwin, D. A.; Hepner, C. E.; Pratt, J. M. Bioinorg. Chem. 1978, 9, 479–94.
14. Dunford, H. B.; Stillman, J. S. Coord. Chem. Rev. 1976, 19, 187–251.
15. Alben, J. O.; Fuchsman, W. H.; Beaudreau, C. A.; Caughey, W. S. Biochemistry 1968, 7, 624–635.
16. Fleischer, E. B.; Palmer, J. M.; Srivastava, T. S.; Chatterjee, A. J. Am. Chem. Soc. 1971, 93, 3162–3167.
17. Walker, F. A.; Lo, M.-W.; Ree, M. T. J. Am. Chem. Soc. 1976, 98, 5552–5560.
18. Kobayashi, H.; Higuchi, T.; Kaizu, Y.; Osada, H.; Aoki, M. Bull. Chem. Soc. Jpn. 1975, 48, 3137–3141.
19. Cheng, R.-J.; Latos-Grazynski, L.; Balch, A. L. Inorg. Chem. 1982, 21, 2412–2418.
20. Bottomley, L. A.; Kadish, K. M. Inorg. Chem. 1981, 20, 1348–1357.
21. La Mar, G. N.; Walker, F. A. “The Porphyrins”; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. 4, pp 61–157.
22. Goff, H. M., “Iron Porphyrins—Part I”; Lever, A. B. P., Gray, H. B., Eds.; Addison-Wesley: Reading, MA, 1982; pp 237–281.
23. La Mar, G. N.; Eaton, G. R.; Holm, R. H.; Walker, F. A. J. Am. Chem. Soc. 1973, 95, 63–75.
24. Behere, D. V.; Birdy, R.; Mitra, S. Inorg. Chem. 1982, 21, 386–390.
25. Goff, H. M., Shimomura, E. T., Phillippi, M. A. Inorg. Chem. 1983, 22, 66–71.
26. Caughey, W. S.; Johnson, L. F. Chem. Commun. 1969, 1362–1363.
27. Moreland, C. G.; Philip, A.; Carroll, F. I. J. Org. Chem. 1974, 39, 2413–2416.
28. Kurland, R. J.; Little, R. G.; Davis, D. G.; Ho, C. Biochemistry 1971, 12, 2237–2246.
29. Budd, D. L.; La Mar, G. N.; Langry, K. C.; Smith, K. M.; Nayyir-Mazhir, R. J. Am. Chem. Soc. 1979, 101, 6091–6096.