Study of photoinduced energy and electron transfer in tv-terthienyl-bovine serum albumin conjugates: A laser flash photolysis study

Photochemistry and Photobiology

Volumn 64, Issue 1, 1996, Pages 92-99

  Boch, R ^a   Mohtat, N ^a   Lear, Y ^a   Arnason, J T ^a   Durst, T ^a   Scaianof, J C ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BOVINE SERUM ALBUMIN; PHOTOSENSITIZING AGENT; TERTHIENYL; THIOPHENE DERIVATIVE;

ANIMAL; ARTICLE; CATTLE; CHEMISTRY; ELECTRON TRANSPORT; ENERGY TRANSFER; IN VITRO STUDY; PHOTOLYSIS; RADIATION EXPOSURE;

ANIMALS; CATTLE; ELECTRON TRANSPORT; ENERGY TRANSFER; PHOTOLYSIS; PHOTOSENSITIZING AGENTS; SERUM ALBUMIN, BOVINE; THIOPHENES;

ANIMALIA; BOS TAURUS; BOVINAE;

EID: 0030198728     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1751-1097.1996.tb02426.x     Document Type: Article

References (38)

1. Murray, C, M. Quaglia, J. T. Arnason and C. E. Morris (1994) Putative nicotine pump at the metabolic blood brain barrier of the tobacco hornworm. J. Neiirobiol..25, 23-34.
2. Weir, D., J. C. Scaiano, J. T. Arnason and C. Evans (1985) Photochemistry of the phototoxic polyacetylene phenylheptatriyne. Pholochem. Pliotobiol. 42, 223-230.
3. Arnason, J. T., B. J. R. Philogene, P. Morand, K. Imrie, S. lyengar, F. Duval, C. Soucy-Breau, J. C. Scaiano, N. H. Werstiuk, B. Hasspieler and A. E. R. Downe (1989) Insecticides of plant origin. In Naturally Occurring and Synthetic Thiophenes as Photoactivated Insecticides. ACS Symposium Series 387, Washington.
4. Scaiano, J. C., A. MacEachern, J. T. Arnason, P. Morand and D. Weir (1987) Singlet oxygen generating efficiency of a-terthienyl and some of its synthetic analogues. Pholochem. Pliotobiol. 46, 193-199.
5. Scaiano, J. C., R. W. Redmond, B. Mehta and J. T. Arnason (1990) Efficiency of the photoprocesses leading to singlet oxygen generation by alpha-terthienyl: optical absorption, optoacoustic calorimetry and infrared luminescence studies. Photochem. Pliotobiol. 52, 655-659.
6. Evans, C., D. Weir, J. C. Scaiano, A. MacEachern, J. T. Arnason, P. Morand, B. Hollebone, L. C. Leitch and B. J. R. Philogene (1986) Photochemistry of the botanical phototoxin ot-terthienyl and some related compounds. Photochem. Pliotobiol. 44, 441-451.
7. Evans, C. and J. C. Scaiano (1990) Photochemical generation of radical cations from alpha-terthienyl and related thiophenes: kinetic behavior and magnetic field effects on radical-ion pairs in micellar solution. J. Am. Chem. Soc. 112, 2694-2701.
8. Scaiano, J. C., C. Evans and J. T. Arnason (1989) Characterization of the a-terthienyl radical cation: evidence against electron transfer to oxygen in vitro. J. Photochem. Photobiol. B Biol. 3,411-418.
9. Boch, R., B. Mehta, T. Connolly, T. Durst, J. T. Amason, R. W. Redmond and J. C. Scaiano (1995) Singlet oxygen photosensitizing properties of bithiophene and terthiophene derivatives. J. Photochem. Photobiol. A Chem. 93, 39-47.
10. Devanathan, S., T. A. Dahl, W. R. Midden and D. C. Neckers (1990) Readily available fluorescein isothiocyanate-conjugated antibodies can be easily converted into targeted phototoxic agents for antibacterial, antiviral, and anticancer therapy. Proc. Nail. Acad. Sci. USA 87, 2980-2984.
11. Rakestraw, S. L., R. G. Tompkins and M. L. Yarmush (1990) Antibody-targeted photolysis: in vitro studies with Sn(IV) chlorin e6 covalently bound to monoclonal antibodies using a modified dextran carrier. Proc. Natl. Acad. Sci. USA 87, 4217-4221.
12. Vilaseca, L. A., K. Rose, R. Werten, A. Meunier, R. E. Offord, C. L. Nichols and W. L. Scott (1993) Protein conjugates of defined structure: synthesis and use of a new carrier molecule. Bioconj. Chem. 4, 515-520.
13. Morgan, J., H. Lottman, C. C. Abbou and D. K. Chopin (1994) A comparison of direct and liposomal antibody conjugates of sulfonated aluminum phthalocyanines for selective photoimmunotherapy of human bladder carcinoma. Photochem. Photobiol. 60, 486-496.
14. Rakestraw, S. L., W. E. Ford, R. G. Tompkins, M. A. J. Rodgers, W. P. Thorpe and M. L. Yarmush (1992) Antibody-targeted photolysis: in vitro immunological, photophysical, and cytotoxic properties of monoclonal antibody-dextran-Sn(IV) chlorin e6 immunoconjugates. Biotechnol. Prog. 8, 30-39.
15. Philogene, B. J. R., J. T. Arnason, C. Berg, F. Duval, D. Champagne, R. G. Taylor, L. Leitch and P. Morand (1984) Synthesis and evaluation of the naturally occurring phototoxin a-terthienyl as a control agent for larvae of Aedes spp. and Simulium verecimdum. J. Econ. Entomol. 78, 121-126.
16. MacEachern, A., C. Soucy, L. C. Leitch, J. T. Arnason and P. Morand (1988) Synthesis and characterization of alkyl-, haloand hetero-substituted derivatives of the potent phototoxin a-terthienyl. Tetrahedron 44, 2403-2412.
17. Erlanger, B. F. (1980) The preparation of antigenic hapten-carrier conjugates: a survey. Methods Enzymol. 70, 85-107.
18. Kagan, J., S. K. Arora and A. Ustunol (1983) 2,2′:5′,2″-Terthiophene-5-carboxylic acid and 2,2′:5′,2″-terthiophene-5,5″-dicarboxlic acid. J. Org. Chem. 48, 4076-4078.
19. Houba-Herin, N., C. M. Calberg-Bacq, J. Piette and A. Van De Vorst (1982) Mechanisms for dye-mediated photodynamic action: singlet oxygen production, deoxyguanosine oxidation and phage inactivating efficiencies. Photochem. Photobiol. 36, 297306.
20. Soucy-Breau, C., A. MacEachern, L. C. Leitch, T. Arnason and P. Morand (1991) Synthesis and characterization of alkyl-, alkenyl-, acyl- and nitrogen-substituted derivatives of the potent phototoxin a-terthiophene. J. Heterocycl. Chem. 28, 411-416.
21. Scaiano, J. C. (1980) Solvent effects in the photochemistry of xanthone. J. Am. Chem. Soc. 102, 7747-7753.
22. Scaiano, J. C., M. Tanner and D. Weir (1985) Exploratory study of the intermolecular reactivity of excited diphenylmethyl radicals. J. Am. Chem. Soc. 107, 4396-4403.
23. Rodgers, M. A. J. and P. T. Snowden (1982) Lifetime of singlet oxygen in liquid water as determined by time-resolved infrared luminescence measurements. J. Am. Chem. Soc. 104, 55415543.
24. Keene, J. P., D. Kessel, E. J. Land, R. W. Redmond and T. G. Truscott (1986) Direct detection of singlet oxygen sensitized by haematoporphyrin and related compounds. Photochem. Photobiol. 43, 117-120.
25. Kosower, E. M. and J. L. Cotter (1964) Stable free radicals. II. The reduction of l-methyI-4-cyanopyridinium ion to methylviologen cation radical. J. Am. Chem. Soc. 86, 5524-5527.
26. Scaiano, J. C., E. B. Abuin and L. C. Stewart (1982) Photo-chemistry of benzophenone in micelles. Formation and decay of radical pairs. J. Am. Chem. Soc. 104, 5673-7679.
27. Hurst, J. R. and G. B. Schuster (1983) Nonradiative relaxation of singlet oxygen in solution. J. Am. Chem. Soc. 105, 57565760.
28. Parker, J. G. and W. D. Stanbro (1982) Optical determination of the collisional lifetime of singlet molecular oxygen in acetone and deuterated acetone. J. Am. Chem. Soc. 104, 2067-2069.
29. Ogilby, P. R. and C. S. Foote (1982) Chemistry of singlet oxygen. 36. Singlet molecular oxygen luminescence in solution following pulsed laser excitation. Solvent deuterium isotope effects on the lifetime of singlet oxygen. J. Am. Chem. Soc. 104, 2069-2070.
30. Braun, C. L. and S. N. Smirnov (1993) Why is water blue? J. Chem. Educ. 70, 612-614.
31. Redmond, R. W. (1991) Enhancement of the sensitivity of radiative and non-radiative detection techniques in the study of photosensitization by water soluable sensitizers using a reverse micelle system. Photochem. Photobiol. 54, 547-556.
32. Gandin, E., Y. Lion and A. Van de Vorst (1983) Quantum yield of singlet oxygen production by xanthene derivatives. Pholochem. Photobiol. 37, 271-278.
33. Aveline, B. M., T. Hasan and R. W. Redmond (1995) The effects of aggregation, protein binding and cellular incorporation on the photophysical properties of benzoporphyrin derivative monoacid ring A (BPDMA). J. Photochem. Photobiol. B Biol. 30, 161-169.
34. Davila, J. and A. Harriman (1990) Photoreactions of macrocyclic dyes bound to human serum albumin. Photochem. Photobiol. 51, 9-19.
35. Abuin, E. B. and E. A. Lissi (1991) Diffusion and concentration of oxygen in microheterogeneous systems. Evaluation from luminescence quenching data. Prog. Reaction Kinetics 16, 1-33.
36. Gorman, A. A. and M. A. J. Rodgers (1989) Singlet oxygen. In Handbook of Organic Photochemistry. J. C. Scaiano, ed. CRC Press, Boca Raton, FL.
37. Rodgers, M. A. J. (1983) Solvent-induced deactivation of singlet oxygen: additivity relationships in nonaromatic solvents. J. Am. Chem. Soc. 105, 6201-6205.
38. Michaeli, A. and J. Feitelson (1995) Reactivity of singlet oxygen toward large peptides. Photochem. Photobiol. 61, 255-260.