메뉴 건너뛰기




Volumn 74, Issue 2, 2001, Pages 149-156

Hypericin derivatives: Substituent effects on radical-anion formation

Author keywords

[No Author keywords available]

Indexed keywords

BUFFER; DIMETHYL SULFOXIDE; FORMAMIDE DERIVATIVE; HYDROXYL GROUP; HYPERICIN; N,N' DIMETHYLFORMAMIDE; PHOSPHATE; UNCLASSIFIED DRUG;

EID: 0035437623     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1562/0031-8655(2001)074<0149:HDSEOR>2.0.CO;2     Document Type: Conference Paper
Times cited : (13)

References (47)
  • 1
    • 0033517807 scopus 로고    scopus 로고
    • From the photosensitizer hypericin to the photoreceptor stentorian - The chemistry of phenanthroperylene quinines
    • Falk, H. (1999) From the photosensitizer hypericin to the photoreceptor stentorian - the chemistry of phenanthroperylene quinines. Angew. Chem., Int. Ed. Engl. 38(21), 3117-3136.
    • (1999) Angew. Chem., Int. Ed. Engl. , vol.38 , Issue.21 , pp. 3117-3136
    • Falk, H.1
  • 2
    • 84981383480 scopus 로고
    • Synthese von hypericin
    • Brockmann, H. (1957) Synthese von hypericin. Chem. Ber. 90, 2302.
    • (1957) Chem. Ber. , vol.90 , pp. 2302
    • Brockmann, H.1
  • 5
    • 0032928325 scopus 로고    scopus 로고
    • A photodynamic pathway to apoptosis and necrosis induced by dimethyl tetrahydroxyhelianthrone and hypericin in leukemic cells: Possible relevance to photodynamic therapy
    • Lavie, G., C. Kaplinsky, A. Toren, I. Aizman, D. Meruelo, Y. Mazur and M. Mandel (1999) A photodynamic pathway to apoptosis and necrosis induced by dimethyl tetrahydroxyhelianthrone and hypericin in leukemic cells: possible relevance to photodynamic therapy. Br. J. Cancer 79(3/4), 423-432.
    • (1999) Br. J. Cancer , vol.79 , Issue.3-4 , pp. 423-432
    • Lavie, G.1    Kaplinsky, C.2    Toren, A.3    Aizman, I.4    Meruelo, D.5    Mazur, Y.6    Mandel, M.7
  • 8
    • 0000110320 scopus 로고    scopus 로고
    • Excited-state intramolecular H atom transfer of hypericin and hypocrellin A investigated by fluorescence upconversion
    • Smirnov, A. V., K. Das, D. S. English, Z. Wan, G. A. Kraus and J. W. Petrich (1999) Excited-state intramolecular H atom transfer of hypericin and hypocrellin A investigated by fluorescence upconversion. J. Phys. Chem. A 103(40), 7949-7957.
    • (1999) J. Phys. Chem. A , vol.103 , Issue.40 , pp. 7949-7957
    • Smirnov, A.V.1    Das, K.2    English, D.S.3    Wan, Z.4    Kraus, G.A.5    Petrich, J.W.6
  • 9
    • 0033144512 scopus 로고    scopus 로고
    • Photophysics of hypericin and hypocrellin A in complex with subcellular components: Interactions with human serum albumin
    • Das, K., A. V. Smirnov, J. Wen, P. Miskovsky and J. W. Petrich (1999) Photophysics of hypericin and hypocrellin A in complex with subcellular components: interactions with human serum albumin. Photochem. Photobiol. 69(6), 633-645.
    • (1999) Photochem. Photobiol. , vol.69 , Issue.6 , pp. 633-645
    • Das, K.1    Smirnov, A.V.2    Wen, J.3    Miskovsky, P.4    Petrich, J.W.5
  • 10
    • 0032003630 scopus 로고    scopus 로고
    • Hypericin, hypocrellin, and model compounds: Steady-state and time-resolved fluorescence anisotropies
    • Das, K., E. Dertz, J. Paterson, W. Zhang, G. A. Kraus and J. W. Petrich (1998) Hypericin, hypocrellin, and model compounds: steady-state and time-resolved fluorescence anisotropies. J. Phys. Chem. B 102(8), 1479-1484.
    • (1998) J. Phys. Chem. B , vol.102 , Issue.8 , pp. 1479-1484
    • Das, K.1    Dertz, E.2    Paterson, J.3    Zhang, W.4    Kraus, G.A.5    Petrich, J.W.6
  • 11
    • 0001410290 scopus 로고
    • Role of solvent in excited-state proton transfer in hypericin
    • Gai, F., M. J. Fehr and J. W. Petrich (1994) Role of solvent in excited-state proton transfer in hypericin. J. Phys. Chem. 98(34), 8352-8358.
    • (1994) J. Phys. Chem. , vol.98 , Issue.34 , pp. 8352-8358
    • Gai, F.1    Fehr, M.J.2    Petrich, J.W.3
  • 12
    • 0027988475 scopus 로고
    • Chemiluminescent activation of the antiviral activity of hypericin: A molecular flashlight
    • Carpenter, S., M. J. Fehr, G. A. Kraus and J. W. Petrich (1994) Chemiluminescent activation of the antiviral activity of hypericin: a molecular flashlight. Proc. Natl. Acad. Sci. USA 91(25), 12273-12277.
    • (1994) Proc. Natl. Acad. Sci. USA , vol.91 , Issue.25 , pp. 12273-12277
    • Carpenter, S.1    Fehr, M.J.2    Kraus, G.A.3    Petrich, J.W.4
  • 13
    • 0032573396 scopus 로고    scopus 로고
    • Hypericin-induced photosensitization of HeLa cells leads to apoptosis or necrosis involvement of cytochrome c and procaspase-3 activation in the mechanism of apoptosis
    • Vantieghem, A., Z. Assefa, P. Vandenabeele, W. Declercq, S. Courtois, J. R. Vandenheede, W. Merlevede, P. D. Witte and P. Agostinis (1998) Hypericin-induced photosensitization of HeLa cells leads to apoptosis or necrosis involvement of cytochrome c and procaspase-3 activation in the mechanism of apoptosis. FEBS Lett. 440(1,2), 19-24.
    • (1998) FEBS Lett. , vol.440 , Issue.1-2 , pp. 19-24
    • Vantieghem, A.1    Assefa, Z.2    Vandenabeele, P.3    Declercq, W.4    Courtois, S.5    Vandenheede, J.R.6    Merlevede, W.7    Witte, P.D.8    Agostinis, P.9
  • 15
    • 0028834271 scopus 로고
    • Quantitative analysis of super-oxide anion radicals photosensitized by hypericin in a model membrane using the cytochrome c reduction method
    • Hadjur, C. and P. Jardon (1995) Quantitative analysis of super-oxide anion radicals photosensitized by hypericin in a model membrane using the cytochrome c reduction method. J. Photochem. Photobiol. B: Biol. 29(2-3), 147-156.
    • (1995) J. Photochem. Photobiol. B: Biol. , vol.29 , Issue.2-3 , pp. 147-156
    • Hadjur, C.1    Jardon, P.2
  • 17
    • 0001640920 scopus 로고
    • Formation and reactivity of the singlet oxygen photosensitized by hypericin in the liposomes of dipalmitoylphosphatidylcholine. Evidence of delayed oxidation
    • Bouirig, H., D. Eloy and P. Jardon (1992) Formation and reactivity of the singlet oxygen photosensitized by hypericin in the liposomes of dipalmitoylphosphatidylcholine. Evidence of delayed oxidation. J. Chim. Phys. Phys.-Chim. Biol. 89(6), 1391-1411.
    • (1992) J. Chim. Phys. Phys.-Chim. Biol. , vol.89 , Issue.6 , pp. 1391-1411
    • Bouirig, H.1    Eloy, D.2    Jardon, P.3
  • 18
    • 0001191226 scopus 로고
    • Generation of singlet oxygen 1.DELTA.g photosensitized by hypericin, kinetic study in a nonionic micellar medium
    • Racinet, H., P. Jardon and R. Gautron (1988) Generation of singlet oxygen 1.DELTA.g photosensitized by hypericin, kinetic study in a nonionic micellar medium. J. Chim. Phys. Phys. Chim. Biol. 85(10), 971-977.
    • (1988) J. Chim. Phys. Phys. Chim. Biol. , vol.85 , Issue.10 , pp. 971-977
    • Racinet, H.1    Jardon, P.2    Gautron, R.3
  • 19
    • 0000242074 scopus 로고
    • Formation of singlet oxygen 1.DELTA.g photosensitized by hypericin. Characterization and study of the mechanism by laser spectroscopy
    • Jardon, P., N. Lazortchak and R. Gautron (1987) Formation of singlet oxygen 1.DELTA.g photosensitized by hypericin. Characterization and study of the mechanism by laser spectroscopy. J. Chim. Phys. Phys.-Chim. Biol. 84(10), 1141-1145.
    • (1987) J. Chim. Phys. Phys.-Chim. Biol. , vol.84 , Issue.10 , pp. 1141-1145
    • Jardon, P.1    Lazortchak, N.2    Gautron, R.3
  • 20
    • 0000042617 scopus 로고    scopus 로고
    • Quenching of excited triplet state hypericin with energy acceptors and donors and acceptors of electrons
    • Darmanyan, A. P., W. S. Jenks, D. Eloy and P. Jardon (1999) Quenching of excited triplet state hypericin with energy acceptors and donors and acceptors of electrons. J. Phys. Chem. B 103(17), 3323-3331.
    • (1999) J. Phys. Chem. B , vol.103 , Issue.17 , pp. 3323-3331
    • Darmanyan, A.P.1    Jenks, W.S.2    Eloy, D.3    Jardon, P.4
  • 21
    • 37049084944 scopus 로고
    • EPR studies of hypericin. Photogeneration of free radicals and superoxide
    • Weiner, L. and Y. Mazur (1992) EPR studies of hypericin. Photogeneration of free radicals and superoxide. J. Chem. Soc., Perkin Trans. 2 (9), 1439-1442.
    • (1992) J. Chem. Soc., Perkin Trans. , vol.2 , Issue.9 , pp. 1439-1442
    • Weiner, L.1    Mazur, Y.2
  • 22
    • 0001082253 scopus 로고    scopus 로고
    • A structural proof for the hypericin 1,6-dioxo tautomer
    • Dax, T. G., H. Falk and E. I. Kapinus (1999) A structural proof for the hypericin 1,6-dioxo tautomer. Monatsh. Chem. 130(7), 827-831.
    • (1999) Monatsh. Chem. , vol.130 , Issue.7 , pp. 827-831
    • Dax, T.G.1    Falk, H.2    Kapinus, E.I.3
  • 23
    • 0033461614 scopus 로고    scopus 로고
    • Spectroscopic investigation of the molecular structure of hypericin and its salts
    • Kapinus, E. I., H. Falk and H. T. N. Tran (1999) Spectroscopic investigation of the molecular structure of hypericin and its salts. Monatsh. Chem. 130(5), 623-635.
    • (1999) Monatsh. Chem. , vol.130 , Issue.5 , pp. 623-635
    • Kapinus, E.I.1    Falk, H.2    Tran, H.T.N.3
  • 24
    • 0033536461 scopus 로고    scopus 로고
    • Exploring ground-state heterogeneity of hypericin and hypocrellins A and B: Dynamic and 2D ROESY NMR study
    • Smirnov, A., D. B. Fulton, A. Andreotti and J. W. Petrich (1999) Exploring ground-state heterogeneity of hypericin and hypocrellins A and B: dynamic and 2D ROESY NMR study. J. Am. Chem. Soc. 121(35), 7979-7988.
    • (1999) J. Am. Chem. Soc. , vol.121 , Issue.35 , pp. 7979-7988
    • Smirnov, A.1    Fulton, D.B.2    Andreotti, A.3    Petrich, J.W.4
  • 25
    • 0032002925 scopus 로고    scopus 로고
    • Structure and energetics of ground-state hypericin: Comparison of experiment and theory
    • Petrich, J. W., M. S. Gordon and M. Cagle (1998) Structure and energetics of ground-state hypericin: comparison of experiment and theory. J. Phys. Chem. A 102(9), 1647-1651.
    • (1998) J. Phys. Chem. A , vol.102 , Issue.9 , pp. 1647-1651
    • Petrich, J.W.1    Gordon, M.S.2    Cagle, M.3
  • 26
    • 0040792291 scopus 로고    scopus 로고
    • Hypericin, an intriguing internally heterogenous molecule, forms a covalent intramolecular hydrogen bond
    • Ulicny, J. and A. Laaksonen (2000) Hypericin, an intriguing internally heterogenous molecule, forms a covalent intramolecular hydrogen bond. Chem. Phys. Lett. 319(3-4), 396-402.
    • (2000) Chem. Phys. Lett. , vol.319 , Issue.3-4 , pp. 396-402
    • Ulicny, J.1    Laaksonen, A.2
  • 28
    • 0027389005 scopus 로고
    • Photodynamic inactivation of infectivity of human immunodeficiency virus and other enveloped viruses using hypericin and rose bengal: Inhibition of fusion and syncytia formation
    • Lenard, J., A. Rabson and R. Vanderoef (1993) Photodynamic inactivation of infectivity of human immunodeficiency virus and other enveloped viruses using hypericin and rose bengal: inhibition of fusion and syncytia formation. Proc. Natl. Acad. Sci. USA 90, 158-162.
    • (1993) Proc. Natl. Acad. Sci. USA , vol.90 , pp. 158-162
    • Lenard, J.1    Rabson, A.2    Vanderoef, R.3
  • 29
    • 0033621034 scopus 로고    scopus 로고
    • Targeted cross-linking of a molten globule form of acetylcholinesterase by the virucidal agent hypericin
    • Weiner, L., E. Roth, Y. Mazur and I. Silman (1999) Targeted cross-linking of a molten globule form of acetylcholinesterase by the virucidal agent hypericin. Biochemistry 38(35), 11 401-11 405.
    • (1999) Biochemistry , vol.38 , Issue.35 , pp. 11401-11405
    • Weiner, L.1    Roth, E.2    Mazur, Y.3    Silman, I.4
  • 30
    • 0027391090 scopus 로고
    • Photosensitization with anticancer agents 17. EPR studies of photodynamic action of hypericin: Formation of semiquinone radical and activated oxygen species on illumination
    • Diwu, Z. and J. W. Lown (1993) Photosensitization with anticancer agents 17. EPR studies of photodynamic action of hypericin: formation of semiquinone radical and activated oxygen species on illumination. Free Radic. Biol. Med. 14(2), 209-215.
    • (1993) Free Radic. Biol. Med. , vol.14 , Issue.2 , pp. 209-215
    • Diwu, Z.1    Lown, J.W.2
  • 31
    • 0029584852 scopus 로고
    • Electron-acceptor properties of hypericin and its salts: An ESR/ENDOR and electrochemical study
    • Gerson, F., G. Gescheidt, P. Haering, Y. Mazur, D. Freeman, H. Spreitzer and J. Daub (1995) Electron-acceptor properties of hypericin and its salts: an ESR/ENDOR and electrochemical study. J. Am. Chem. Soc. 117(48), 11 861-11 866.
    • (1995) J. Am. Chem. Soc. , vol.117 , Issue.48 , pp. 11861-11866
    • Gerson, F.1    Gescheidt, G.2    Haering, P.3    Mazur, Y.4    Freeman, D.5    Spreitzer, H.6    Daub, J.7
  • 32
    • 0005421923 scopus 로고
    • The nature of "soluble" hypericin in hypericum species
    • Falk, H. and W. Schmitzberger (1992) The nature of "soluble" hypericin in hypericum species. Monatsh. Chem. 123(8-9), 731-739.
    • (1992) Monatsh. Chem. , vol.123 , Issue.8-9 , pp. 731-739
    • Falk, H.1    Schmitzberger, W.2
  • 33
    • 0001491912 scopus 로고    scopus 로고
    • The deprotonation and protonation equilibria of a hypericin derivative in aqueous solution
    • Altmann, R. and H. Falk (1997) The deprotonation and protonation equilibria of a hypericin derivative in aqueous solution. Monatsh. Chem. 128(6-7), 571-583.
    • (1997) Monatsh. Chem. , vol.128 , Issue.6-7 , pp. 571-583
    • Altmann, R.1    Falk, H.2
  • 34
    • 0001361925 scopus 로고
    • Deprotonation and protonation of hydroxyphenanthroperylenes
    • Falk, H., J. Meyer and M. Oberreiter (1992) Deprotonation and protonation of hydroxyphenanthroperylenes. Monatsh. Chem. 123(3), 277-284.
    • (1992) Monatsh. Chem. , vol.123 , Issue.3 , pp. 277-284
    • Falk, H.1    Meyer, J.2    Oberreiter, M.3
  • 35
    • 0001096893 scopus 로고
    • Pseudohypericin and other phenanthroperylene quinones
    • Cameron, D. W. and W. D. Raverty (1976) Pseudohypericin and other phenanthroperylene quinones. Aust. J. Chem. 29, 1521-1533.
    • (1976) Aust. J. Chem. , vol.29 , pp. 1521-1533
    • Cameron, D.W.1    Raverty, W.D.2
  • 36
    • 0013166270 scopus 로고
    • Zur Konstitution des Fagopyrins
    • Brockmann, H. and H. Lackner (1979) Zur Konstitution des Fagopyrins. Tetrahedron Lett. 18, 1575-1578.
    • (1979) Tetrahedron Lett. , vol.18 , pp. 1575-1578
    • Brockmann, H.1    Lackner, H.2
  • 37
    • 21144459153 scopus 로고
    • On the bromination of hypericin - The gymnochrome chromophores
    • Falk, H. and W. Schmitzberger (1993) On the bromination of hypericin - the gymnochrome chromophores. Monatsh. Chem. 124, 77-81.
    • (1993) Monatsh. Chem. , vol.124 , pp. 77-81
    • Falk, H.1    Schmitzberger, W.2
  • 38
    • 0000109618 scopus 로고
    • A simple experimental setup for the simultaneous measurement of ESR and absorption spectra
    • Gescheidt, G. (1994) A simple experimental setup for the simultaneous measurement of ESR and absorption spectra. Rev. Sci. Instrum. 65(6), 2145-2146.
    • (1994) Rev. Sci. Instrum. , vol.65 , Issue.6 , pp. 2145-2146
    • Gescheidt, G.1
  • 40
    • 0032022669 scopus 로고    scopus 로고
    • An electroreflectance and photoelectrochemicalstudy of hypericin at bare and modified gold electrodes
    • Sagara, T., H. Kawamura, K. Ezoe and N. Nakashima (1998) An electroreflectance and photoelectrochemicalstudy of hypericin at bare and modified gold electrodes. J. Electroanal. Chem. 445, 171-177.
    • (1998) J. Electroanal. Chem. , vol.445 , pp. 171-177
    • Sagara, T.1    Kawamura, H.2    Ezoe, K.3    Nakashima, N.4
  • 41
    • 0027673724 scopus 로고
    • Measurement of formal potentials for hypericin in dimethylsulfoxide
    • Redepenning, J. and N. Tao (1993) Measurement of formal potentials for hypericin in dimethylsulfoxide. Photochem. Photobiol. 58(4), 532-535.
    • (1993) Photochem. Photobiol. , vol.58 , Issue.4 , pp. 532-535
    • Redepenning, J.1    Tao, N.2
  • 43
    • 0013069908 scopus 로고
    • Indirect determination of the half-wave reduction potential of benzene and of [2.2]paracyclophane
    • Gerson, F., H. Ohya-Nishiguchi and C. Wydler (1976) Indirect determination of the half-wave reduction potential of benzene and of [2.2]paracyclophane. Angew. Chem., Int. Ed. Engl. 88(18), 617-618.
    • (1976) Angew. Chem., Int. Ed. Engl. , vol.88 , Issue.18 , pp. 617-618
    • Gerson, F.1    Ohya-Nishiguchi, H.2    Wydler, C.3
  • 44
    • 0033235097 scopus 로고    scopus 로고
    • Electrochemistry of hypericin incorporated into a cationic lipid film on a graphite electrode in an aqueous medium
    • Sagara, T., N. Kaba and N. Nakashima (1999) Electrochemistry of hypericin incorporated into a cationic lipid film on a graphite electrode in an aqueous medium. Chem. Lett. (11), 1201-1202.
    • (1999) Chem. Lett. , Issue.11 , pp. 1201-1202
    • Sagara, T.1    Kaba, N.2    Nakashima, N.3
  • 45
    • 0035437545 scopus 로고    scopus 로고
    • The structure of hypericin in solution. Searching for hypericin 1,6 tautomer
    • in print
    • Freeman, D., L. Konstantinovskii and Y. Mazur (2001) The structure of hypericin in solution. Searching for hypericin 1,6 tautomer Photochem. Photobiol. (in print).
    • (2001) Photochem. Photobiol.
    • Freeman, D.1    Konstantinovskii, L.2    Mazur, Y.3
  • 46
    • 0033550541 scopus 로고    scopus 로고
    • Control of one-versus two-electron reduction of ubiquinone via redox-dependent recognition
    • Greaves, M. D., A. Niemz and V. M. Rotello (1999) Control of one-versus two-electron reduction of ubiquinone via redox-dependent recognition. J. Am. Chem. Soc. 121, 266-267.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 266-267
    • Greaves, M.D.1    Niemz, A.2    Rotello, V.M.3
  • 47
    • 0034731580 scopus 로고    scopus 로고
    • Electrochemically controlled hydrogen bonding, o-Quinones as simple redox-dependent receptors for arylureas
    • Ge, Y., L. Miller, T. Ouimet and D. K. Smith (2000) Electrochemically controlled hydrogen bonding, o-Quinones as simple redox-dependent receptors for arylureas. J. Org. Chem. 65, 8831-8838.
    • (2000) J. Org. Chem. , vol.65 , pp. 8831-8838
    • Ge, Y.1    Miller, L.2    Ouimet, T.3    Smith, D.K.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.