Complexation of Mg-tetrabenzoporphyrin with pyridine enhances singlet oxygen generation and affects its partitioning into apolar microenvironments

Journal of Photochemistry and Photobiology A: Chemistry

Volumn 203, Issue 1, 2009, Pages 7-12

  Weitman, Hana ^a   Shatz, Smadar ^a   Ehrenberg, Benjamin ^a  

^a BAR ILAN UNIVERSITY   (Israel)

Author keywords

Complexation; Ligand; Liposomes; Micelles; Photosensitization; Principal component analysis; Pyridine

Indexed keywords

EID: 60549086077     PISSN: 10106030     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jphotochem.2008.11.026     Document Type: Article

References (32)

1. Kadish K.M., Smith K.M., and Guilard R. The Porphyrin Handbook (1999), Academic Press, Burlington, MA
2. Milgrom L.R. The Colours of Life: An Introduction to the Chemistry of Porphyrins and Related Compounds (1997), Oxford University Press, New York
3. Smith K.M. Porphyrins and Metalloporphyrins (1975), Elsevier, Amsterdam
4. Scheer H. Chlorophylls (1991), CRC Press, Boca Raton, FL
5. Barrett R.P., Linstead R.P., Rundall F.G., and Tuey G.A.D. Phtalocyanines and related compounds. XIX. Tetrabenzoporphyrin, tetrabenzmonazaporphyrin and their metallic derivatives. J. Chem. Soc. 92 (1940) 1097-1092
6. Linstead P. Discoveries among conjugated macrocyclic compounds. J. Chem. Soc. 105 (1953) 2873-2884
7. Ehrenberg B., Malik Z., Nitzan Y., Ladan H., Johnson F.M., and Sessler J.L. The binding and photosensitization of tetrabenzoporphyrins and texaphyrin in bacterial and leukemic cells. Lasers Med. Sci. 8 (1993) 197-203
8. 2 TBP. Spectrochim. Acta 46A 10 (1990) 1521-1532
9. Lee M.R., Liou S.T., and Cheng R.J. Study of adduct ions of meso-phenyl-substituted tetrabenzoporphyrins by fast-atom bombardment mass spectrometry. J. Am. Soc. Mass. Spectrom. 8 (1997) 62-67
10. Matsuzawa Y., Ichimura K., and Kudo K. Preperation of soluble tetrabenzoporphyrins with substituents at the peripheral positions. Inorg. Chim. Acta 277 (1997) 151-156
11. Stiel H., Volkmer A., Ruckmann I., Zeug A., Ehrenberg B., and Röder B. Non-linear and transient absorption spectroscopy of magnesium (II)-tetrabenzoporphyrin in solution. Opt. Commun. 155 (1998) 135-143
12. Buchler J.W. Static coordination chemistry of metalloporphyrins. In: Smith K.M. (Ed). Porphyrins and Metalloporphyrins (1975), Elsevier, Amsterdam 157-231
13. Scheer H., and Katz J.J. Nuclear magnetic resonance spectroscopy of porphyrins and metalloporphyrins. In: Smith K.M. (Ed). Porphyrins and Metalloporphyrins (1975), Elsevier, Amsterdam 399-452
14. Hambright P. Dynamic coordination chemistry of metalloporphyrins. In: Smith K.M. (Ed). Porphyrins and Metalloporphyrins (1975), Elsevier, Amsterdam 233-278
15. Cromer S., Hambright P., Grodkowski J., and Neta P. Tetrabenzoporphyrins: metal incorporation and exchange kinetics, ligational equilibria and pulse radiolysis studies. J. Porphyr. Phthal. 1 (1997) 45-54
16. 25Mg NMR, X-ray crystallographic, and quantum mechanical study of bis(pyridine)-(5,10,15,20-tetraphenylporphyrinato) magnesium(II). Can. J. Chem. 81 (2003) 275-283
17. Malinowski E.R. Factor Analysis in Chemistry (1991), Wiley-Interscience Publication, New York
18. 2(1.DELTA. g) bimolecular processes. Solvent and compartmentalization effects. Bol. Soc. Chil. Quim. 93 (1993) 699-723
19. Weitman H., Schatz S., Gottlieb H.E., Kobayashi N., and Ehrenberg B. Spectroscopic probing of the acid-base properties and photosensitization of afluorinated phthalocyanine in organic solutions and liposomes. Photochem. Photobiol. 73 (2001) 473-481
20. Wilkinson F., Helman W.P., and Ross A.B. Quantum yields for the photosensitized formation of the lowest electronically excited singlet state of molecular oxygen in solution. J. Phys. Chem. Ref. Data 22 (1993) 113-262
21. Bevington P.R. Data Reduction and Error Analysis for the Physical Sciences (1969), McGraw-Hill, New York
22. Gouterman M. Optical spectra and electronic structure of porphyrins and related rings. In: Dolphin D. (Ed). The Porphyrins vol. III (1978), Academic Press 1-165
23. Gouterman M. Spectra of porphyrins. J. Mol. Spectrosc. 6 (1961) 138-163
24. Irish D.E., and Ozeki T. Raman spectroscopy of inorganic species in solution. In: Grasselli J.G., and Bulkin B.J. (Eds). Analytical Raman spectroscopy (1991), Wiley, New York 59-106
25. Reichardt C. Solvents and Solvents Effects in Organic Chemistry. second ed. (1990), VCH, Weinheim
26. Linnanto J., and Korppi-Tommola J. Semiempirical PM5 molecular orbital study on chlorophylls and bacteriochlorophylls: comparison of semiempirical, ab initio, and density functional results. J. Comput. Chem. 25 (2003) 123-137
27. Miller J.R., and Dorough G.D. Pyridinatedcomplexes of some metallo-derivatives of tetraphenylporphine and tetraphenylchlorin. J. Am. Chem. Soc. 74 (1952) 3977-3981
28. Yamauchi S., Suzuki Y., Ueda T., Akiyama K., Ohba Y., and Iwaizumi M. Fluorescence studies on the photoinduced ligation in the excited singlet-state of magnesium tetraphenylporphine. Chem. Phys. Lett. 232 (1995) 121-126
29. Satake A., and Kobuke Y. Dynamic supramolecular porphyrin systems. Tetrahedron 61 (2005) 13-41
30. Lebedeva N.S., Yakubov S.P., Vyugin A.I., and Parfenyuk E.V. Termodynamics of complex formation of natural iron(III)porphyrins with neutral ligands. Thermochim. Acta 404 (2003) 19-24
31. Missel P.J., Mazer N.A., Benedek G.B., Young C.Y., and Carey M. Thermodynamic analysis of the growth of sodium dodecyl sulfate micelles. J. Phys. Chem. 84 (1980) 1044-1057
32. Helenius A., McCaslin D.R., Fries E., and Tanford C. Properties of detergents. Meth. Enzymol. 56 (1979) 734-749