Photooxygenation, photodegradation and antioxidative activity of platonin, a cyanine photosensitizing dye

In Vivo

Volumn 21, Issue 2, 2007, Pages 163-174

  Ishihara, Mariko ^a   Fujisawa, Seiichiro ^a  

^a MEIKAI UNIVERSITY SCHOOL OF DENTISTRY   (Japan)

Author keywords

Antioxidants; Biological activities; Oxygen uptake; Photodegradation; Platonin; Prooxidant; Review; Visible light

Indexed keywords

(4,4' DIMETHYL 3,3' DI N HEPTYL 8 [2 (4 METHYL 3 N HEPTYHIAZOLE)] 2,2' DICARBOCYANINE DIIODINE; 3 HEPTYL 4 METHYL 2 THIAZOLONE; 3,5 DI (4 METHYL 2 THIAZOLYL) 2,4 PENTADIENIC ACID; 4 METHYL 5 HYDROXYETHYLTHIAZOLE; 5 [2 (3 HEPTYL 4 METHYLTHIAZOLIDINE)] 2 PENTEN 1 ALDEHYDE; ALCOHOL; ANION; ANTIOXIDANT; BENZIMIDAZOLE; CATION; GAMMA (3 HEPTYL 4 METHYL 2 THIAZOLIDENE)CROTONIC ACID; HEPTANE; IMIDAZOLE; LUCIFERIN; PHOTOSENSITIZING AGENT; RIFAMPICIN; SCAVENGER; STEROID; SULFUROL; TESTOSTERONE PROPIONATE; TETRADECANE; TETRADECANE 7 THIOL; THIAZOLE DERIVATIVE; TRAPIDIL; UNCLASSIFIED DRUG; PLATONIN J; SINGLET OXYGEN;

ANTIBACTERIAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; BIOLOGICAL ACTIVITY; BONE GROWTH; BONE MINERALIZATION; CANCER; CELL VIABILITY; COMBINATION CHEMOTHERAPY; DRUG FORMULATION; DYE LASER; LIGHT; LIVER CANCER; LIVER DISEASE; MONOTHERAPY; NONHUMAN; OXYGEN CONSUMPTION; PERIODONTAL DISEASE; PHOTODEGRADATION; PHOTOLYSIS; PHOTOOXIDATION; RECOMMENDED DRUG DOSE; REVIEW; RHEUMATOID ARTHRITIS; ANIMAL; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; HUMAN; KINETICS; LIVER CELL; METABOLISM; PHYSIOLOGY;

ANIMALS; ANTIOXIDANTS; CELL SURVIVAL; HEPATOCYTES; HUMANS; KINETICS; MODELS, MOLECULAR; OXYGEN CONSUMPTION; PHOTOSENSITIZING AGENTS; SINGLET OXYGEN; THIAZOLES;

EID: 34047220621     PISSN: 0258851X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (49)

1. Murofushi T: Fundamental studies on antimicrobial activities of photosensitizing dyes having the characteristic as food-preservatives. Part 1. Studies on antimicrobial activities of 148 sorts of photosensitizing dyes against different sorts of microorganisms and on the relation to the chemical structures. Kankoshikiso 58: 1-25, 1959.
2. Komori T and Yamaoka S: Kanko-so and its antimicrobial action. Koushyokaishi 8: 43-59, 1984.
3. Shima Y, Noguchi K, Wakano Y, Takeuchi H, Kanimori U, Yoshida M and Nakayama G: The effect of platonin on alveolar pyorrhea. Ohosakadaigaku-shigakuzazassi 5: 37-48, 1960.
4. Arakawa N: The relationships of the chemical structural formula of cyanine photosensitive dye and its biological effect. Kankohshikoso 81: 38-44, 1972.
5. Ito K and Kuroda K: Clinical application of photosensitizing dyes on skin disease. (V) Effect of platonin on skin functions as compared with antihistamine. Bull Pharm Res Inst 8: 1, 1955.
6. Mito K: A needle-type immunotherapeutic system incorporating laser light and platonin in combination with ethanol injection in the treatment of cancer growing in deep organs. Front Med Biol Eng 9: 275-284, 1999.
7. Oyanagui Y: Platonin, a photosensitizing cyanine dye, suppresses acute inflammation. Arch Int Pharmacodyn Ther 266: 162-172, 1983.
8. Hsiao G, Lee J, Chou DS, Fong TH, Shen MY, Lin CH and Sheu JR: Platonin, a photosensitizing dye, improves circulatory failure and mortality in rat models of endotoxemia. Biol Pharm Bull 25: 995-999, 2002.
9. Lee JJ, Huang WT, Shao DZ, Liao JF and Lin MT: Platonin a cyanine photosensitizing dye, inhibits pyrogen release and results in antipyresis. J Pharmacol Sci 93: 376-380, 2003.
10. Chen CC, Lee JJ, Tsai PS, Lu YT, Huang CL and Huang CJ: Platonin attenuates LPS-induced CAT-2 and CAT-2B induction in stimulated murine macrophages. Acta Anaesthesiol Scand 50: 604-612, 2006.
11. Ishihara M: Studies on the photodegradation of platonin and the effect of irradiation on the hepatocyte suspension containing the drug. Josai Shika Daigaku Kiyo 16: 68-86, 1987.
12. Foote CS: Mechanisms of photosensitized oxidation. Science 162: 963-969, 1968.
13. Foote CS: Definition of type I and type II photosensitized oxidation. Photochem Photobiol 54: 659, 1991.
14. Gorman AA and Rodgers MAJ: Singlet molecular oxygen. Chem Soc Rev 10: 205-231, 1981.
15. Frimer AA: The reaction of singlet oxygen with olefins: the question of mechanism. Chem Rev 79: 359-387, 1979.
16. Wasserman HH and Ives JL: Singlet oxygen in organic synthesis. Tetrahedron 37: 1825-1852, 1981.
17. Terada H, Nagamune H, Morikawa N and Ikuno M: Uncoupling of oxidative phosphorylation by divalent cationic cyanine dye. Participation of phosphate transporter. Biochim Biophys Acta 807: 168-176, 1985.
18. Shinohara Y, Nagamune H and Terada H: The hydrophobic cationic cyanine dye inhibits oxidative phosphorylation by inhibiting ADP transport, not by electrophoretic transfer, into mitochondria. Biochem Biophys Res Commun 148: 1081-1086, 1987.
19. Kochevar, IE, Bouvier J, Lynch M and Lin CW: Influence of dye and protein location on photosensitization of the plasma membrane. Biochim Biophys Acta 1196: 172-180, 1994.
20. Drahota Z, Krivakova P, Cervinkova Z, Kmonickova E, Lotkova H, Kucera O and Houstek J: Tert-butyl hydroperoxide selectively inhibits mitochondrial respiratory-chain enzymes in isolated rat hepatocytes. Physiol Res 54: 67-72, 2005.
21. Masaki N, Kyle M, Serroni A and Farber JL: Mitochondrial damage as a mechanism of cell injury in the killing of cultured hepatocytes by tert-butyl hydroperoxide. Arch Biochem Biophys 270: 672-680, 1989.
22. Rubin R and Farber JL: Mechanism of the killing of cultured hepatocytes by hydrogen peroxide. Arch Biochem Biophys 228: 450-459, 1984.
23. Atsumi T, Ishihara M, Kadoma Y, Tonosaki K and Fujisawa S: Comparative radical production and cytotoxicity induced by camphorquinone and 9-fluorenone against human pulp fibroblasts. J Oral Rehabil 31: 1155-1164, 2004.
24. Atsumi T, Murakami Y, Shibuya K, Tonosaki K and Fujisawa S: Induction of cytotoxicity and apoptosis and inhibition of cyclooxygenase-2 gene expression, by curcumin and its analog, alpha-diisoeugenol. Anticancer Res 25: 4029-4036, 2005.
25. Lazarova M, Labai J, Eckl P and Slamenova D: Comparative evaluation of DNA damage by genotoxicants in primary rat cells applying the comet assay. Toxicol Lett 164: 54-62, 2006.
26. Kopecky KR, Van der Sande JH and Munford C: Preparation and base-catalyzed reactions of some β-halohydroperoxides. Can J Chem 46: 25-34, 1968.
27. Fukuzumi K and Ikeda N: The effect of sensitizing dyes for photo as antioxidants on the autoxidation of methyl linoleate. J Am Oil Chem Soc 48: 384-386, 1971.
28. Utsumi K and Hasegawa T: Peroxidant reaction on the lipid of biomembranes caused by sulphite and radical interceptor; especially, effect-obstruction by photosensitive dyes. Kankooshikiso 83: 31-35, 1973.
29. 2 supply under normal and pathological conditions. Adv Exp Med Biol 169: 69-80, 1984.
30. Fujisawa S, Kadoma Y and Yokoe I: Radical-scavenging activity of butylated hydroxytoluene (BHT) and its metabolites. Chem Phys Lipids 130: 189-195, 2004.
31. Fujisawa S and Kadoma Y: Kinetic evaluation of polyamines as radical scavengers. Anticancer Res 25: 965-970, 2005.
32. Fujisawa S and Kadoma Y: Comparative study of the alkyl and peroxy radical scavenging activities of polyphenols. Chemosphere 62: 71-79, 2006.
33. Fujisawa S, Kadoma Y, Ishihara M, Shibuya K and Yokoe I: Kinetic radical-scavenging activity of melatonin. In Vivo 20: 215-220, 2006.
34. Fujisawa S and Kadoma Y: Kinetic studies of the radical-scavenging activity of ebselen, a seleno-organic compound. Anticancer Res 25: 3989-3994, 2005.
35. Ishihara M, Kadoma Y and Fujisawa S: Kinetic radical-scavenging activity of platonin, a cyanine photosensitizing dye. In Vivo 20: 845-848, 2006.
36. Hayami M and Nakagawa Y: Study of photodecomposition of NK-19. Nippon Kankooshikiso Institute Okayama Report, 1984.
37. Hatano M, Yamada T, Yoshida A, Miyata K, Okusawa S, Shimizu S, Miura K and Ishihara M: Studies on isolated rat hepatocytes (7). Influence of light irradiation on the activating effect of platonin. Josai Shika Daigaku Kiyo 13: 423-427, 1984.
38. Boiani M and Gonzalez M: Imidazole and benzimidazole derivatives as chemotherapeutic agents. Mini Rev Med Chem 5: 409-424, 2005.
39. Ishihara M: Synthesis of 3-alkyl- and 3-benzyl-2-phenylsulfonylbenzothiazolines: effect of N-substituent on the synthesis. J Arts Sci Meikai Univ 4: 6-11, 1992.
40. Shirai A, Sumitomo T, Yoshida M, Kaimura T, Nagamune H, Maeda T and Kourai H: Synthesis and biological properties of gemini quaternary ammonium compounds, 5,5′-[2,2′-(alpha,omega- polymethylnedicarbonyldioxy) diethyl]bis-(3-alkyl-4-methylthiazolium iodide) and 5,5′-[2,2′- (p-phenylenedicarbonyldioxy)diethyl]bis(3-alkyl-4-methylthiazolium bromide). Chem Pharm Bull (Tokyo) 54: 639-645, 2006.
41. Coburn RA, Clark MT, Evans RT and Genco RJ: Substituted 2-(2-hydroxyphenyl)benzimidazoles as potential agents for the control of periodontal diseases. J Med Chem 30: 205-208, 1987.
42. Bradshaw TD, Trapani V, Vasselin DA and Westwell AD: The aryl hydrocarbon receptor in anticancer drug discovery: friend or foe? Curr Pharm Des 8: 2475-2490, 2002.
43. Motoyoshi F, Kondo N, Ono H and Orii T: The effect of photosensitive dye platonin on juvenile rheumatoid arthritis. Biotherapy 3: 241-244, 1991.
44. Kondo N, Motoyoshi F, Ozawa T and Orii T: A case report of a 9-year-old boy with polyarteritis nodosa in which a combination therapy of corticosteroids and a photosensitive dye platonin was effective. Biotherapy 3: 261-264, 1991.
45. Hatano M, Yamada T, Yoshida A, Miyata K, Okusawa S, Shimizu S, Miura K and Ishihara M: Studies on isolated rat hepatocytes (5). Effects of platonin. (in Japanese). Josai Shika Daigaku Kiyo 12: 459-464, 1983.
46. Nishimura S, Maruyama S, Tajima M, Kim T, Arai T, Mizuno H, Ohhara Y, Hatano M and Sato S: Effect of platonin on bone wound healing in rat calvaria-with special reference to the interaction of platonin and steroid hormones (in Japanese). Nippon Yakugaku Zasshi 89: 285-290, 1987.
47. Ichihashi H and Kondo T: Protection of antibody suppression by photosensitizing dye. Gann/Jpn J Cancer Res 58: 529-539, 1967.
48. Nakagawa Y, Homma S, Yamamoto I, Banno M, Nakazato H, Imanaga H and Yamamoto N: In vivo and in vitro activation of macrophages with a cyanine photosensitizing dye, platonin. Cancer Immunol Immunother 37: 157-162, 1993.
49. Yamamoto I and Morishita K: Development of enzyme immunoassay for platonin (NK 19). J Immunoassay 7: 17-35, 1986.