Girard's reagent P derivative of β-Apo-8′-carotenal: A potent photoprotective agent

Photochemistry and Photobiology

Volumn 73, Issue 4, 2001, Pages 349-358

  Kanofsky, Jeffrey R ^a,b,d   Sima, Paul D ^c  

^a Medical Service   (United States)

^b LOYOLA UNIVERSITY CHICAGO   (United States)

^c Research Service   (United States)

^d HINES VA HOSPITAL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA CAROTENE; BIS(4 SULFONATOPHENYL)DIPHENYLPORPHINE; CAROTENAL; CAROTENOID; CHEMICAL COMPOUND; CROCETIN; DETERGENT; HYPERICIN; PHOTOSENSITIZING AGENT; PROTOPORPHYRIN; SINGLET OXYGEN; UNCLASSIFIED DRUG;

ARTICLE; CELL DAMAGE; CELLULAR DISTRIBUTION; CONTROLLED STUDY; FLUORESCENCE; HUMAN; HUMAN CELL; LEUKEMIA CELL; MICELLE; PHOTOSENSITIZATION; RADIATION PROTECTION; SYNTHESIS;

CAROTENOIDS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HUMANS; K562 CELLS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; OXYGEN; PERYLENE; PHOTOCHEMISTRY; PHOTOSENSITIZING AGENTS; PORPHYRINS; PROTOPORPHYRINS; SINGLET OXYGEN; TUMOR CELLS, CULTURED;

EID: 0035324283     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1562/0031-8655(2001)073<0349:GSRPDO>2.0.CO;2     Document Type: Article

References (48)

1. Matheson, I. B. C., R. D. Etheridge, N. R. Kratowich and J. Lee (1975) The quenching of singlet oxygen by amino acids and proteins. Photochem. Photobiol. 21, 165-171.
2. Moan, J. and K. Berg (1991) The photodegradation of porphyrins in cells can be used to estimate the lifetime of singlet oxygen. Photochem. Photobiol. 53, 549-553.
3. Baker, A. and J. R. Kanofsky (1992) Quenching of singlet oxygen by biomolecules from L1210 leukemia cells. Photochem. Photobiol. 55, 523-528.
4. Deadwyler, G., P. D. Sima, Y. Fu and J. R. Kanofsky (1997) Singlet-oxygen mediated inactivation of acetylcholinesterase: a comparison of purified enzyme in solution and enzyme bound to K562 leukemia cells. Photochem. Photobiol. 65, 884-894.
5. Kanofsky, J. R., A. Baker and P. D. Sima (1995) Singlet-oxygen diffusion and quenching in studies of photooxidative damage to intact cells and to cell membranes. In The Oxygen Paradox (Edited by K. J. A. Davies and F. Ursini), pp. 539-549. CLEUP University Press, Padova.
6. Chaloupka, R., P. X. Petit, N. Israel and F. Sureau (1999) Overexpression of Bcl-2 does not protect cells from hypericin photoinduced mitochondrial membrane depolarization, but delays subsequent events in the apoptotic pathway. FEBS Lett. 462, 295-301.
7. Johnson, S. A. S., A. E. Dalton and R. S. Pardini (1998) Time-course of hypericin phototoxicity and effect on mitochondrial energies in EMT6 mouse mammary carcinoma cells. Free Radic. Biol. Med. 25. 144-152.
8. Iinuma, S., S. S. Farshi, B. Ortel and T. Hasan (1994) A mechanistic study of cellular photodestruction with 5-aminolaevulinic acid-induced porphyrin. Br. J. Cancer 70, 21-28.
9. Sandberg, S., I. Romslo, G. Hovding and T. Bjorndal (1982) Porphyrin-induced photodamage as related to the subcellular localization of the porphyrins. Acta Dermato-Venereol. Suppl. (Stockh.) 100, 75-80.
10. Berg, K. and J. Moan (1997) Lysosomes and microtubules as targets for photochemotherapy of cancer. Photochem. Photobiol. 65, 403-409.
11. Berg, K. and J. Moan (1994) Lysosomes as photochemical targets. Int. J. Cancer 59, 814-822.
12. Berg, K., A. Western, J. C. Bommer and J. Moan (1990) Intracellular localization of sulfonated meso-tetraphenylporphines in a human carcinoma cell line. Photochem. Photobiol. 52, 481-487.
13. Kanofsky, J. R. and P. D. Sima (2000) Preferential cytotoxicity for multidrug-resistant K562 cells using the combination of a photosensitizer and a cyanine dye. J. Photochem. Photobiol. B: Biol. 54, 136-144.
14. Sima, P. D. and J. R. Kanofsky (2000) Cyanine dyes as protectors of K562 ceils from photosensitized cell damage. Photochem. Photobiol. 71, 413-421.
15. Foote, C. S. and R. W. Denny (1968) Chemistry of singlet oxygen. VII. Quenching by β-carotene. J. Am. Chem. Soc. 90, 6233-6235.
16. Foote, C. S., R. W. Denny, L. Weaver, Y. Chang and J. Peters (1970) Quenching of singlet oxygen. Ann. New York Acad. Sci. 171, 139-145.
17. Edge, R., D. J. McGarvey and T. G. Truscott (1997) The carotenoids as anti-oxidants - a review. J. Photochem. Photobiol. B: Biol. 41, 189-200.
18. Wilkinson, F. and W.-T. Ho (1978) Electronic energy transfer from singlet oxygen to carotenoids. Spectrosc. Lett. 11, 455-463.
19. Jung, M. Y. and D. B. Min (1991) Effects of quenching mechanisms of carotenoids on the photosensitized oxidation of soybean oil. J. Am. Oil Chem. Soc. 68, 653-658.
20. Matheson, I. B. C. and M. A. J. Rodgers (1982) Crocetin, a water soluble carotenoid monitor for singlet oxygen. Photochem. Photobiol. 36, 1-4.
21. Chen, L. B. (1988) Mitochondrial potential in living cells. Ann. Rev. Cell Biol. 4, 155-181.
22. March, J. (1992) Advanced Organic Chemistry. Wiley, New York.
23. Kanofsky, J. R. and P. D. Sima (2000) Structural and environmental requirements for quenching of singlet oxygen by cyanine dyes. Photochem. Photobiol. 71, 361-368.
24. Kanofsky, J. R. (1990) Quenching of singlet oxygen by human plasma. Photochem. Photobiol. 51, 299-303.
25. Parker, J. G. and W. D. Stanbro (1984) Dependence of photosensitized singlet oxygen production on porphyrin structure and solvent. In Porphyrin Localization and Treatment of Tumors, Vol. 170, Progress in Clinical and Biological Research Series (Edited by D. R. Doiron and C. J. Gomer), pp. 259-284. Alan R. Liss, New York.
26. Klein, E., H. Ben-Bassat, H. Neumann, P. Ralph, J. Zeuthen, A. Polliack and F. Vánky (1976) Properties of the K562 cell line, derived from a patient with chronic myeloid leukemia. Int. J. Cancer 18, 421-431.
27. Bertram, J. S., A. Pang, M. Churley, T. J. Kappock IV, L. R. Wilkins and R. V. Cooney (1991) Diverse carotenoids protect against chemically induced neoplastic transformation. Carcinogenesis 12, 671-678.
28. Netzel, T. L., K. Nafisi, M. Zhao, J. R. Lenhard and I. Johnson (1995) Base-content dependence of emission enhancements, quantum yields, and lifetimes for cyanine dyes bound to double-strand DNA: photophysical properties of monomeric and hichromophoric DNA stains. J. Phys. Chem. 99, 17 936-17 947.
29. Becker, B., J. Clapper, K. R. Harkins and J. A. Olson (1994) In situ screening assay for cell viability using a dimeric cyanine nucleic acid stain. Anal. Biochem. 221, 78-84.
30. Mathews-Roth, M. M., T. Wilson, E. Fujimori and N. I. Krinsky (1974) Carotenoid chromophore length and protection against photosensitization. Photochem. Photobiol. 19, 217-222.
31. Englert, G. (1995) NMR spectroscopy. In Carotenoids, Vol. 1B: Spectroscopy (Edited by G. Britton, S. Liaaen-Jensen and H. Pfander), pp. 147-260. Birkhäuser Verlag, Basel.
32. Foote, C. S., Y. C. Chang and R. W. Denny (1970) Chemistry of singlet oxygen. X. Carotenoid quenching parallels biological protection. J. Am. Chem. Soc. 92, 5216-5218.
33. Lowe, G. M., L. A. Booth, A. J. Young and R. F. Bilton (1999) Lycopene and β-carotene protect against oxidative damage in HT29 cells at low concentrations but rapidly lose this capacity at higher doses. Free Radic. Res. 30, 141-151.
34. Lindig, B. A. and M. A. J. Rodgers (1981) Rate parameters for the quenching of singlet oxygen by water-soluble and lipid-soluble substrates in aqueous and micellar systems. Photoehem. Photobiol. 33, 627-634.
35. Oliveros, E., P. Murasecco-Suardi, A. M. Braun and H.-J. Hansen (1992) Efficiency of singlet oxygen quenching by carotenoids measured by near-infrared steady-state luminescence. In Methods in Enzymology, Vol. 213 (Edited by L. Packer), pp. 420-429. Academic Press, San Diego.
36. Zang, L.-Y., O. Sommerburg and F. J. G. M. van Kuijk (1997) Absorbance changes of carotenoids in different solvents. Free Radic. Biol. Med. 23, 1086-1089.
37. Britton, G. (1995) UV/visible spectroscopy. In Carotenoids, Vol. 1B: spectroscopy (Edited by G. Britton, S. Liaaen-Jensen and H. Pfander), pp. 13-62. Birkhäuser Verlag, Basel.
38. Strauss, W. S. L., R. Sailer, M. H. Gschwend, H. Emmert, R. Steiner and H. Schneckenburger (1998) Selective examination of plasma membrane-associated photosensitizers using total internal reflection fluorescence spectroscopy: correlation between photobleaching and photodynamic efficacy of protoporphyrin IX. Photochem. Photobiol. 67, 363-369.
39. Selvin, P. R. (1995) Fluorescence resonance energy transfer. In Methods in Enzymology, Vol. 246 (Edited by K. Sauer), pp. 300-334. Academic Press, San Diego.
40. Fischkoff, S. and J. M. Vanderkooi (1975) Oxygen diffusion in biological and artificial membranes determined by the fluorochrome pyrene. J. Gen. Physiol. 65, 663-676.
41. O'Loughlin, M. A., D. W. Whillans and J. W. Hunt (1980) A fluorescence approach to testing the diffusion of oxygen into mammalian cells. Radiat. Res. 84, 477-495.
42. St-Denis, C. E. and C. J. D. Fell (1971) Diffusivity of oxygen in water. Can. J. Chem. Eng. 49, 885.
43. Fuchs, J. (1998) Potentials and limitations of the natural antioxidants RRR-alpha-tocopherol, L-ascorbic acid and β-carotene in cutaneous photoprotection. Free Radic. Biol. Med. 25, 848-873.
44. Kanofsky, J. R. (1991) Quenching of singlet oxygen by human red cell ghosts. Photochem. Photobiol. 53, 93-99.
45. Fu, Y. and J. R. Kanofsky (1995) Singlet oxygen generation from liposomes: a comparison of time-resolved 1270 nm emission with singlet-oxygen kinetics calculated from a one-dimensional model of singlet-oxygen diffusion and quenching. Photochem. Photobiol. 62, 692-702.
46. Fu, Y., P. D. Sima and J. R. Kanofsky (1996) Singlet-oxygen generation from liposomes: a comparison of 6β-cholesterol hydroperoxide formation with predictions from a one-dimensional model of singlet-oxygen diffusion and quenching. Photochem. Photobiol. 63, 468-476.
47. Palozza, P. and N. I. Krinsky (1992) Antioxidant effects of carotenoids in vivo and in vitro: an overview. In Methods in Enzymology, Vol. 213 (Edited by L. Packer), pp. 403-420. Academic Press, San Diego.
48. Gardiner, W. C. Jr. (1969) Rates and Mechanisms of Chemical Reactions. W. A. Benjamin, New York.