Photodynamic DNA Strand Breaking Activities of Acridine Compounds
Induction of single strand breaks in DNA was assessed by the conversion of supercoiled closed circular plasmid DNA into the open circular form. Euflavine produced single-strand breaks following irradiation but not in the control maintained in the dark. The single strand breaking activity of photoact...
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| Published in | Biological & pharmaceutical bulletin Vol. 16; no. 12; pp. 1244 - 1247 |
|---|---|
| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Tokyo
The Pharmaceutical Society of Japan
1993
Maruzen Japan Science and Technology Agency |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0918-6158 1347-5215 |
| DOI | 10.1248/bpb.16.1244 |
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| Abstract | Induction of single strand breaks in DNA was assessed by the conversion of supercoiled closed circular plasmid DNA into the open circular form. Euflavine produced single-strand breaks following irradiation but not in the control maintained in the dark. The single strand breaking activity of photoactivated euflavine was found to be dose-dependent. The effective dose convertion 50% (ED50) of the closed circular DNA to the open circular form was 0.53 μM. A comparison of 8 acridine compounds revealed that the ED50 of diaminoacridines such as euflavine, proflavine and acridine yellow or the 3, 6-dimethylamino-derivative (acridine orange) was less than 1 μM while the ED50 values of the other acridines were greater than 80 μM. Euflavine was markedly inhibited by singlet oxygen scavengers such as NaN3, histidine, α-tocopherol or β-carotene and partly inhibited by superoxide dismutase, mannitol or catalase. These results suggest that enflavine induces single strand breaks in DNA mainly by a type II photodynamic mechanism. Photodynamic single strand breaking activities appeared related to their mutagenic activities on yeast.This experimental system described here is useful for the quantitative assessment of the single strand breaking activities of various photosensitizers in vitro and for the determination of active oxygen species involved in those processes. |
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| AbstractList | Induction of single strand breaks in DNA was assessed by the conversion of supercoiled closed circular plasmid DNA into the open circular form. Euflavine produced single-strand breaks following irradiation but not in the control maintained in the dark. The single strand breaking activity of photoactivated euflavine was found to be dose-dependent. The effective dose convertion 50% (ED50) of the closed circular DNA to the open circular form was 0.53 μM. A comparison of 8 acridine compounds revealed that the ED50 of diaminoacridines such as euflavine, proflavine and acridine yellow or the 3, 6-dimethylamino-derivative (acridine orange) was less than 1 μM while the ED50 values of the other acridines were greater than 80 μM. Euflavine was markedly inhibited by singlet oxygen scavengers such as NaN3, histidine, α-tocopherol or β-carotene and partly inhibited by superoxide dismutase, mannitol or catalase. These results suggest that enflavine induces single strand breaks in DNA mainly by a type II photodynamic mechanism. Photodynamic single strand breaking activities appeared related to their mutagenic activities on yeast.This experimental system described here is useful for the quantitative assessment of the single strand breaking activities of various photosensitizers in vitro and for the determination of active oxygen species involved in those processes. Induction of single strand breaks in DNA was assessed by the conversion of supercoiled closed circular plasmid DNA into the open circular form. Euflavine produced single-strand breaks following irradiation but not in the control maintained in the dark. The single strand breaking activity of photoactivated euflavine was found to be dose-dependent. The effective dose conversion 50% (ED50) of the closed circular DNA to the open circular form was 0.53 microM. A comparison of 8 acridine compounds revealed that the ED50 of diaminoacridines such as euflavine, proflavine and acridine yellow or the 3,6-dimethylamino-derivative (acridine orange) was less than 1 microM while the ED50 values of the other acridines were greater than 80 microM. Euflavine was markedly inhibited by singlet oxygen scavengers such as NaN3, histidine, alpha-tocopherol or beta-carotene and partly inhibited by superoxide dismutase, mannitol or catalase. These results suggest that enflavine induces single strand breaks in DNA mainly by a type II photodynamic mechanism. Photodynamic single strand breaking activities appeared related to their mutagenic activities on yeast. This experimental system described here is useful for the quantitative assessment of the single strand breaking activities of various photosensitizers in vitro and for the determination of active oxygen species involved in those processes.Induction of single strand breaks in DNA was assessed by the conversion of supercoiled closed circular plasmid DNA into the open circular form. Euflavine produced single-strand breaks following irradiation but not in the control maintained in the dark. The single strand breaking activity of photoactivated euflavine was found to be dose-dependent. The effective dose conversion 50% (ED50) of the closed circular DNA to the open circular form was 0.53 microM. A comparison of 8 acridine compounds revealed that the ED50 of diaminoacridines such as euflavine, proflavine and acridine yellow or the 3,6-dimethylamino-derivative (acridine orange) was less than 1 microM while the ED50 values of the other acridines were greater than 80 microM. Euflavine was markedly inhibited by singlet oxygen scavengers such as NaN3, histidine, alpha-tocopherol or beta-carotene and partly inhibited by superoxide dismutase, mannitol or catalase. These results suggest that enflavine induces single strand breaks in DNA mainly by a type II photodynamic mechanism. Photodynamic single strand breaking activities appeared related to their mutagenic activities on yeast. This experimental system described here is useful for the quantitative assessment of the single strand breaking activities of various photosensitizers in vitro and for the determination of active oxygen species involved in those processes. Induction of single strand breaks in DNA was assessed by the conversion of supercoiled closed circular plasmid DNA into the open circular form. Euflavine produced single-strand breaks following irradiation but not in the control maintained in the dark. The single strand breaking activity of photoactivated euflavine was found to be dose-dependent. The effective dose conversion 50% (ED50) of the closed circular DNA to the open circular form was 0.53 microM. A comparison of 8 acridine compounds revealed that the ED50 of diaminoacridines such as euflavine, proflavine and acridine yellow or the 3,6-dimethylamino-derivative (acridine orange) was less than 1 microM while the ED50 values of the other acridines were greater than 80 microM. Euflavine was markedly inhibited by singlet oxygen scavengers such as NaN3, histidine, alpha-tocopherol or beta-carotene and partly inhibited by superoxide dismutase, mannitol or catalase. These results suggest that enflavine induces single strand breaks in DNA mainly by a type II photodynamic mechanism. Photodynamic single strand breaking activities appeared related to their mutagenic activities on yeast. This experimental system described here is useful for the quantitative assessment of the single strand breaking activities of various photosensitizers in vitro and for the determination of active oxygen species involved in those processes. |
| Author | MASUZAWA, Toshiyuki MORITA, Tamotsu SHIMIZU, Tadayori YASUDA, Kyoko IWAMOTO, Yoshihisa YANAGIHARA, Yasutake ITOYAMA, Toshio |
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| Keywords | Single strand break Mutagenesis Acridine derivatives DNA Lesion Mechanism of action In vitro Photosensitizer |
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| References | 33) H. Kasai, S. Nishimura, Nucleic Acids Res., 12, 2137 (1984). 8) Y. Iwamoto, I. Mifuchi, K.L. Yielding, Mutat. Res., 158, 169 (1985). 12) M. Tsuchiya, Y. Iwamoto, T. Masuzawa, T. Shimizu, T. Morita, Y. Yanagihara, Photochem. Photobiol., 48, 545 (1988). 6) Y. Iwamoto, I. Mifuchi, L.W. Yielding, W.J. Firth III, K.L. Yielding, Mutat. Res., 125, 213 (1984). 37) J. Morita, T. Komano, Agric. Biol. Chem., 47, 11 (1983). 14) J. Piette, Calberg-Bacq, A.V.D. Vorst, Photochem. Photobiol., 30, 369 (1979). 25) T. Artuso, J. Bernadou, B. Meunier, J. Piette, N. Paillous, Photochem. Photobiol., 54, 205 (1991). 4) T. Ito, Photochem. Photobiol. Rev., 7, 141 (1983). 32) H.J. Rhaese, E. Freese, Biochim. Biophys. Acta, 155, 491 (1968). 15) J. Piette, M. Lopez, Calsberg-Bacq, A.V.D. Vorst, Int. Radiat. Biol., 40, 427 (1981). 13) H. Triebel, H. Baer, H.E. Jacob, E. Sarfert, H. Berg, Photochem. Photobiol., 28, 331 (1978). 31) H.J. Rhaese, E. Freese, Biochim. Biophys. Acta, 155, 476 (1968). 21) J. Decuyper, J. Piette, M.P. Merville, A.V.D. Vorst, Biochem. Pharmacol., 35, 1345 (1986). 22) J. Decuyper, A.V.D. Vorst, "Oxygen Radicals in Chemistry and Biology," H. Sies, Academic Press Inc., New York, 1985, pp. 11-36. W. Bors, M. Saran, D. Tait, Walter de Gruyter & Co., Berlin-New York, 1984, pp. 555-558. 2) J.P. Pooler, Med. Phys., 8, 614 (1981). 23) A. Aboul-Enein, P. Schulter-Frohlinde, Photochem. Photobiol., 48, 27 (1988). 7) Y. Iwamoto, I. Mifuchi, Chem. Pharm. Bull., 32, 2759 (1984). 36) E.M. Nelson, K.M. Tewey, L.F. Liu, Proc. Natl. Acad. Sci. U.S.A., 81, 1361 (1984). 3) M.A. Pathak, J. Natl. Cancer Inst., 69, 163 (1982). 5) J.H. Epstein, B.U. Wintroub, Drugs, 30, 42 (1985). 17) A.A. Schothorst, D. Suurmond, R. Schouten, Photochem. Photobiol., 38, 659 (1983). 16) B.S. Rosenstein, J.M. Ducore, S.W. Cummings, Mutat. Res., 112, 397 (1983). 24) J. Piette, J. Decuyper, A.V.D. Vorst, J. Invest. Dermatol., 86, 653 (1986). 26) V.S. Gupta, S.C. Kraft, J.S. Samuelson, J. Chromatogr., 26, 158 (1967). 34) H. Kasai, S. Nishimura, "Oxidative Stress, Oxidants and Antioxidants," 9) Y. Iwamoto, H. Yoshioka, Y. Yanagihara, I. Mifuchi, Chem. Pharm. Bull., 33, 5529 (1985). 38) T.A. Ciulla, J.R. Van Camp, E. Rosenfeld, I.E. Kochevar, Photochem. Photobiol., 49, 293 (1989). 30) D.S. Frohlinde, C.V. Sonntag, "Oxidative Stress," 27) T. Maniatis, E.F. Fritsch, J. Sambrook, "Molecular Cloning, a Laboratory Manual," Cold Spring Harbor Laboratory, New York, 1982, pp. 86-96. 35) T.C. Rowe, G.L. Chen, Y.H. Hsiang, L.F. Liu, Cancer Res., 46, 2021 (1986). 29) M. Rosenberg-Arska, B.S.V. Asbeck, T.J. Martens, J. Verhoef, J. Gen. Microbiol., 131, 3325 (1985). 1) J. Amagasa, Photochem. Photobiol., 33, 947 (1981). 11) Y. Iwamoto, C. Tominaga, Y. Yanagihara, Chem. Pharm. Bull., 37, 1632 (1989). H. Sies, Academic Press Inc., New York, 1991, pp. 99-116. 19) H. Fujita, I. Matsuo, Chem.-Biol. Interact., 66, 27 (1988). 39) Y. Iwamoto, T. Itoyama, K. Yasuda, T. Uzuhashi, H. Tanizawa, Y. Takino, T. Oku, H. Hashizume, Y. Yanagihara, Chem. Pharm. Bull., 40, 1868 (1992). 10) Y. Iwamoto, H. Yoshioka, Y. Yanagihara, Chem. Pharm. Bull., 35, 2478 (1987). 18) H. Fujita, Mutat. Res., 158, 135 (1985). 20) J. Decuyper, J. Piette, M. Lopez, M.P. Merville, A.V.D. Vorst, Biochem. Pharmacol., 33, 4025 (1984). 28) R. Radloff, W. Bauer, J. Vinograd, Proc. Natl. Acad. Sci. U.S.A., 57, 1514 (1967). |
| References_xml | – reference: 24) J. Piette, J. Decuyper, A.V.D. Vorst, J. Invest. Dermatol., 86, 653 (1986). – reference: 35) T.C. Rowe, G.L. Chen, Y.H. Hsiang, L.F. Liu, Cancer Res., 46, 2021 (1986). – reference: 12) M. Tsuchiya, Y. Iwamoto, T. Masuzawa, T. Shimizu, T. Morita, Y. Yanagihara, Photochem. Photobiol., 48, 545 (1988). – reference: 32) H.J. Rhaese, E. Freese, Biochim. Biophys. Acta, 155, 491 (1968). – reference: 21) J. Decuyper, J. Piette, M.P. Merville, A.V.D. Vorst, Biochem. Pharmacol., 35, 1345 (1986). – reference: 15) J. Piette, M. Lopez, Calsberg-Bacq, A.V.D. Vorst, Int. Radiat. Biol., 40, 427 (1981). – reference: 2) J.P. Pooler, Med. Phys., 8, 614 (1981). – reference: 18) H. Fujita, Mutat. Res., 158, 135 (1985). – reference: 39) Y. Iwamoto, T. Itoyama, K. Yasuda, T. Uzuhashi, H. Tanizawa, Y. Takino, T. Oku, H. Hashizume, Y. Yanagihara, Chem. Pharm. Bull., 40, 1868 (1992). – reference: 6) Y. Iwamoto, I. Mifuchi, L.W. Yielding, W.J. Firth III, K.L. Yielding, Mutat. Res., 125, 213 (1984). – reference: 23) A. Aboul-Enein, P. Schulter-Frohlinde, Photochem. Photobiol., 48, 27 (1988). – reference: 36) E.M. Nelson, K.M. Tewey, L.F. Liu, Proc. Natl. Acad. Sci. U.S.A., 81, 1361 (1984). – reference: 29) M. Rosenberg-Arska, B.S.V. Asbeck, T.J. Martens, J. Verhoef, J. Gen. Microbiol., 131, 3325 (1985). – reference: 16) B.S. Rosenstein, J.M. Ducore, S.W. Cummings, Mutat. Res., 112, 397 (1983). – reference: 4) T. Ito, Photochem. Photobiol. Rev., 7, 141 (1983). – reference: 7) Y. Iwamoto, I. Mifuchi, Chem. Pharm. Bull., 32, 2759 (1984). – reference: 11) Y. Iwamoto, C. Tominaga, Y. Yanagihara, Chem. Pharm. Bull., 37, 1632 (1989). – reference: 13) H. Triebel, H. Baer, H.E. Jacob, E. Sarfert, H. Berg, Photochem. Photobiol., 28, 331 (1978). – reference: 5) J.H. Epstein, B.U. Wintroub, Drugs, 30, 42 (1985). – reference: 30) D.S. Frohlinde, C.V. Sonntag, "Oxidative Stress," – reference: 25) T. Artuso, J. Bernadou, B. Meunier, J. Piette, N. Paillous, Photochem. Photobiol., 54, 205 (1991). – reference: H. Sies, Academic Press Inc., New York, 1991, pp. 99-116. – reference: 28) R. Radloff, W. Bauer, J. Vinograd, Proc. Natl. Acad. Sci. U.S.A., 57, 1514 (1967). – reference: H. Sies, Academic Press Inc., New York, 1985, pp. 11-36. – reference: 20) J. Decuyper, J. Piette, M. Lopez, M.P. Merville, A.V.D. Vorst, Biochem. Pharmacol., 33, 4025 (1984). – reference: 22) J. Decuyper, A.V.D. Vorst, "Oxygen Radicals in Chemistry and Biology," – reference: 34) H. Kasai, S. Nishimura, "Oxidative Stress, Oxidants and Antioxidants," – reference: 10) Y. Iwamoto, H. Yoshioka, Y. Yanagihara, Chem. Pharm. Bull., 35, 2478 (1987). – reference: 19) H. Fujita, I. Matsuo, Chem.-Biol. Interact., 66, 27 (1988). – reference: 31) H.J. Rhaese, E. Freese, Biochim. Biophys. Acta, 155, 476 (1968). – reference: 27) T. Maniatis, E.F. Fritsch, J. Sambrook, "Molecular Cloning, a Laboratory Manual," Cold Spring Harbor Laboratory, New York, 1982, pp. 86-96. – reference: 26) V.S. Gupta, S.C. Kraft, J.S. Samuelson, J. Chromatogr., 26, 158 (1967). – reference: 33) H. Kasai, S. Nishimura, Nucleic Acids Res., 12, 2137 (1984). – reference: 3) M.A. Pathak, J. Natl. Cancer Inst., 69, 163 (1982). – reference: 38) T.A. Ciulla, J.R. Van Camp, E. Rosenfeld, I.E. Kochevar, Photochem. Photobiol., 49, 293 (1989). – reference: 9) Y. Iwamoto, H. Yoshioka, Y. Yanagihara, I. Mifuchi, Chem. Pharm. Bull., 33, 5529 (1985). – reference: 14) J. Piette, Calberg-Bacq, A.V.D. Vorst, Photochem. Photobiol., 30, 369 (1979). – reference: 1) J. Amagasa, Photochem. Photobiol., 33, 947 (1981). – reference: 17) A.A. Schothorst, D. Suurmond, R. Schouten, Photochem. Photobiol., 38, 659 (1983). – reference: 37) J. Morita, T. Komano, Agric. Biol. Chem., 47, 11 (1983). – reference: 8) Y. Iwamoto, I. Mifuchi, K.L. Yielding, Mutat. Res., 158, 169 (1985). – reference: W. Bors, M. Saran, D. Tait, Walter de Gruyter & Co., Berlin-New York, 1984, pp. 555-558. |
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| SubjectTerms | acridine compound Acriflavine - toxicity active oxygen scavenger Biological and medical sciences Biological effects of radiation DNA - drug effects DNA - radiation effects DNA Damage DNA strand break ED50 Free Radical Scavengers Fundamental and applied biological sciences. Psychology Light Oxygen photodynamic Radiosensitizing agents. Photosensitizing agents. Thermosensitizing agents Singlet Oxygen singlet oxygen production Tissues, organs and organisms biophysics |
| Title | Photodynamic DNA Strand Breaking Activities of Acridine Compounds |
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| ispartofPNX | Biological and Pharmaceutical Bulletin, 1993/12/15, Vol.16(12), pp.1244-1247 |
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