메뉴 건너뛰기




Volumn 82, Issue 3, 2006, Pages 695-701

On the correlation between hydrophobicity, liposome binding and cellular uptake of porphyrin sensitizers

Author keywords

[No Author keywords available]

Indexed keywords

LIPOSOME; PHOTOSENSITIZING AGENT; PORPHYRIN;

EID: 33745843675     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1562/2005-09-01-RA-669     Document Type: Article
Times cited : (73)

References (41)
  • 2
    • 0028567108 scopus 로고
    • The use of photodynamic therapy in bone marrow purging
    • Mulroney, C. M., S. Gluck and A. D. Ho (1994) The use of photodynamic therapy in bone marrow purging. Semin. Oncol. 21, 24-27.
    • (1994) Semin. Oncol. , vol.21 , pp. 24-27
    • Mulroney, C.M.1    Gluck, S.2    Ho, A.D.3
  • 3
    • 0028606789 scopus 로고
    • Current status of photodynamic therapy in oncology
    • Van Hillegersberg, R., W. J. Kort and J. H. P. Wilson (1994) Current status of photodynamic therapy in oncology. Drugs 48, 510-527.
    • (1994) Drugs , vol.48 , pp. 510-527
    • Van Hillegersberg, R.1    Kort, W.J.2    Wilson, J.H.P.3
  • 4
    • 0029363458 scopus 로고
    • Advances in photochemical approaches for blood sterilization
    • Ben-Hur, E. and B. Horowitz (1995) Advances in photochemical approaches for blood sterilization. Photochem. Photobiol. 62, 383-388.
    • (1995) Photochem. Photobiol. , vol.62 , pp. 383-388
    • Ben-Hur, E.1    Horowitz, B.2
  • 5
    • 0022051346 scopus 로고
    • Fluorescent spectral changes of hematoporphyrin derivative upon binding to lipid vesicles, S. aureus and E. coli cells
    • Ehrenberg, B., Z. Malik and Y. Nitzan (1985) Fluorescent spectral changes of hematoporphyrin derivative upon binding to lipid vesicles, S. aureus and E. coli cells. Photochem. Photobiol. 41, 429-435.
    • (1985) Photochem. Photobiol. , vol.41 , pp. 429-435
    • Ehrenberg, B.1    Malik, Z.2    Nitzan, Y.3
  • 7
    • 0024000509 scopus 로고
    • Octanol water partition-coefficients of polychlorinated biphenyl congeners
    • Hawker, D. W. and D. W. Connell (1988) Octanol water partition- coefficients of polychlorinated biphenyl congeners. Environ. Sci. Technol. 22, 382-387.
    • (1988) Environ. Sci. Technol. , vol.22 , pp. 382-387
    • Hawker, D.W.1    Connell, D.W.2
  • 8
    • 0000544123 scopus 로고
    • Correlation of octanol water solubility ratios and partition-coefficients
    • Pinsuwan, S., A. Li and S. H. Yalkowsky (1995) Correlation of octanol water solubility ratios and partition-coefficients. J. Chem. Eng. Data 40, 623-626.
    • (1995) J. Chem. Eng. Data , vol.40 , pp. 623-626
    • Pinsuwan, S.1    Li, A.2    Yalkowsky, S.H.3
  • 9
    • 0030636196 scopus 로고    scopus 로고
    • Partition coefficients of indoles and betacarbolines
    • Guardado, P., M. Balon and C. Carmona. (1997) Partition coefficients of indoles and betacarbolines. J. Pharm. Sci. 86, 106-109.
    • (1997) J. Pharm. Sci. , vol.86 , pp. 106-109
    • Guardado, P.1    Balon, M.2    Carmona, C.3
  • 10
    • 0030640969 scopus 로고    scopus 로고
    • Introduction of solvent-accessible surface area in the calculation of the hydrophobicity parameter log P from an atomistic approach
    • Masuda, T., T. Jikihara, K. Nakamura, A. Kimura, T. Takagi and H. Fujiwara (1997) Introduction of solvent-accessible surface area in the calculation of the hydrophobicity parameter log P from an atomistic approach. J. Pharm. Sci. 86, 57-63.
    • (1997) J. Pharm. Sci. , vol.86 , pp. 57-63
    • Masuda, T.1    Jikihara, T.2    Nakamura, K.3    Kimura, A.4    Takagi, T.5    Fujiwara, H.6
  • 11
    • 0028646260 scopus 로고
    • Porphyrin chemistry pertaining to the design of anti-cancer drugs. 2. The synthesis and in vitro tests of water-soluble porphyrins containing, in the meso positions, the functional groups: 4-methylpyridinium, or 4-sulfonatophenyl, in combination with phenyl, 4-pyridyl, 4-nitrophenyl, or 4-aminophenyl
    • Meng, G. G., B. R. James, K. A. Skov and M. Korbelik (1994) Porphyrin chemistry pertaining to the design of anti-cancer drugs. 2. The synthesis and in vitro tests of water-soluble porphyrins containing, in the meso positions, the functional groups: 4-methylpyridinium, or 4-sulfonatophenyl, in combination with phenyl, 4-pyridyl, 4-nitrophenyl, or 4-aminophenyl. Can. J. Chem. 72, 2447-2457.
    • (1994) Can. J. Chem. , vol.72 , pp. 2447-2457
    • Meng, G.G.1    James, B.R.2    Skov, K.A.3    Korbelik, M.4
  • 12
    • 0022486757 scopus 로고
    • Spectrofluorimetric study of porphyrin incorporation into membrane models - Evidence for pH effects
    • Brault, D., C. Vever-Bizet and T. Le Doan (1986) Spectrofluorimetric study of porphyrin incorporation into membrane models - evidence for pH effects. Biochim. Biophys. Acta 857, 238-250.
    • (1986) Biochim. Biophys. Acta , vol.857 , pp. 238-250
    • Brault, D.1    Vever-Bizet, C.2    Le Doan, T.3
  • 14
    • 0034143187 scopus 로고    scopus 로고
    • Porphyrins and related compounds as photoactivatable insecticides. 3. Laboratory and field studies
    • Ben Amor, T., L. Bortolotto and G. Jori (2000) Porphyrins and related compounds as photoactivatable insecticides. 3. Laboratory and field studies. Photochem. Photobiol. 71, 124-128.
    • (2000) Photochem. Photobiol. , vol.71 , pp. 124-128
    • Ben Amor, T.1    Bortolotto, L.2    Jori, G.3
  • 15
    • 0024097922 scopus 로고
    • Accumulation of porphyrins in cells: Influence of hydrophobicity aggregation and protein binding
    • Oenbrink, G., P. Jurgenlimke and D. Gabel (1988) Accumulation of porphyrins in cells: influence of hydrophobicity aggregation and protein binding. Photochem. Photobiol. 48, 451-456.
    • (1988) Photochem. Photobiol. , vol.48 , pp. 451-456
    • Oenbrink, G.1    Jurgenlimke, P.2    Gabel, D.3
  • 17
    • 0026132598 scopus 로고
    • Sulfonated phthalimidomethyl aluminum phthalocyanine: The effect of hydrophobic substituents on the in vitro phototoxicity of phthalocyanines
    • Paquette, B., R. W. Boyle, H. Ali, A. H. Maclennan, T. G. Truscott and J. E. van Lier (1991) Sulfonated phthalimidomethyl aluminum phthalocyanine: the effect of hydrophobic substituents on the in vitro phototoxicity of phthalocyanines. Photochem. Photobiol. 53, 323-327.
    • (1991) Photochem. Photobiol. , vol.53 , pp. 323-327
    • Paquette, B.1    Boyle, R.W.2    Ali, H.3    Maclennan, A.H.4    Truscott, T.G.5    Van Lier, J.E.6
  • 18
    • 0029338998 scopus 로고
    • Sulfophthalocyanines for photodynamic inactivation of viruses in blood products: Effect of structural modifications
    • Allen, C. M., J. M. Weber and J. E. van Lier (1995) Sulfophthalocyanines for photodynamic inactivation of viruses in blood products: effect of structural modifications. Photochem. Photobiol. 62, 184-189.
    • (1995) Photochem. Photobiol. , vol.62 , pp. 184-189
    • Allen, C.M.1    Weber, J.M.2    Van Lier, J.E.3
  • 19
    • 0030075578 scopus 로고    scopus 로고
    • Structure-photodynamic activity relationships of a series of 4-substituted zinc phthalocyanines
    • Margaron, P., M.-J. Grégoire, V. Ščasnár, H. Ali and J. E. van Lier (1996) Structure-photodynamic activity relationships of a series of 4-substituted zinc phthalocyanines. Photochem. Photobiol. 63, 217-223.
    • (1996) Photochem. Photobiol. , vol.63 , pp. 217-223
    • Margaron, P.1    Grégoire, M.-J.2    Ščasnár, V.3    Ali, H.4    Van Lier, J.E.5
  • 21
    • 0030774313 scopus 로고    scopus 로고
    • An in vivo quantitative structure-activity relationship for a congeneric series of pyropheophorbide derivatives as photosensitizers for photodynamic therapy
    • Henderson, B. W., D. A. Bellnier, W. R. Greco, A. Sharma, R. K. Pandey, L. A. Vaughan, K. R. Weishaupt and T. J. Dougherty (1997) An in vivo quantitative structure-activity relationship for a congeneric series of pyropheophorbide derivatives as photosensitizers for photodynamic therapy. Cancer Res. 57, 4000-4007.
    • (1997) Cancer Res. , vol.57 , pp. 4000-4007
    • Henderson, B.W.1    Bellnier, D.A.2    Greco, W.R.3    Sharma, A.4    Pandey, R.K.5    Vaughan, L.A.6    Weishaupt, K.R.7    Dougherty, T.J.8
  • 22
    • 0029037093 scopus 로고
    • The importance of liposomes as models and tools in the understanding of photosensitization mechanisms
    • Hoebeke, M. (1995) The importance of liposomes as models and tools in the understanding of photosensitization mechanisms. J. Photochem. Photobiol. B: Biol. 28, 189-196.
    • (1995) J. Photochem. Photobiol. B: Biol. , vol.28 , pp. 189-196
    • Hoebeke, M.1
  • 23
    • 0026726673 scopus 로고
    • Assessment of the partitioning of probes to membranes by spectroscopic titration
    • Ehrenberg, B. (1992) Assessment of the partitioning of probes to membranes by spectroscopic titration. J. Photochem. Photobiol. B: Biol. 14, 383-386.
    • (1992) J. Photochem. Photobiol. B: Biol. , vol.14 , pp. 383-386
    • Ehrenberg, B.1
  • 25
    • 0033674146 scopus 로고    scopus 로고
    • Liposome binding constants and singlet oxygen quantum yields of hypericin, tetrahydroxy heliathrone and their derivatives: Studies in organic solutions and in liposomes
    • Roslaniec, M., H. Weitman, D. Freeman, Y. Mazur and B. Ehrenberg (2000) Liposome binding constants and singlet oxygen quantum yields of hypericin, tetrahydroxy heliathrone and their derivatives: studies in organic solutions and in liposomes. J. Photochem. Photobiol. B: Biol. 57, 149-158.
    • (2000) J. Photochem. Photobiol. B: Biol. , vol.57 , pp. 149-158
    • Roslaniec, M.1    Weitman, H.2    Freeman, D.3    Mazur, Y.4    Ehrenberg, B.5
  • 26
    • 0000855713 scopus 로고
    • A study of the oxidation of organic compounds by externally generated singlet oxygen molecules
    • Corey, E. J. and W. T. Taylor (1964) A study of the oxidation of organic compounds by externally generated singlet oxygen molecules. J. Am. Chem. Soc. 86, 3881-3882.
    • (1964) J. Am. Chem. Soc. , vol.86 , pp. 3881-3882
    • Corey, E.J.1    Taylor, W.T.2
  • 27
    • 85090883277 scopus 로고
    • Determination of quantum yield of singlet oxygen formation by photosensitization
    • Usui, Y. (1973) Determination of quantum yield of singlet oxygen formation by photosensitization. Chem. Lett. 743-744.
    • (1973) Chem. Lett. , pp. 743-744
    • Usui, Y.1
  • 28
    • 84914911299 scopus 로고
    • Rate constants for the decay and reactions of the lowest electronically excited singlet state of molecular oxygen in solution
    • Wilkinson, F. and J. Brummer (1981) Rate constants for the decay and reactions of the lowest electronically excited singlet state of molecular oxygen in solution. J. Phys. Chem. Ref. Data 10, 809-999.
    • (1981) J. Phys. Chem. Ref. Data , vol.10 , pp. 809-999
    • Wilkinson, F.1    Brummer, J.2
  • 29
    • 84889533712 scopus 로고
    • Rate constants for the decay and reactions of the lowest electronically excited singlet state of molecular oxygen in solution. An expanded and revised compilation
    • Wilkinson, F., W. P. Helman and A. B. Ross (1995) Rate constants for the decay and reactions of the lowest electronically excited singlet state of molecular oxygen in solution. An expanded and revised compilation. J. Phys. Chem. Ref. Data 24, 663-1021.
    • (1995) J. Phys. Chem. Ref. Data , vol.24 , pp. 663-1021
    • Wilkinson, F.1    Helman, W.P.2    Ross, A.B.3
  • 30
    • 0027604077 scopus 로고
    • Singlet oxygen generation by porphyrins and the kinetics of 9,10-dimethylanthracene photosensitization in liposomes
    • Gross, E., B. Ehrenberg and F. M. Johnson (1993) Singlet oxygen generation by porphyrins and the kinetics of 9,10-dimethylanthracene photosensitization in liposomes. Photochem. Photobiol. 57, 808-813.
    • (1993) Photochem. Photobiol. , vol.57 , pp. 808-813
    • Gross, E.1    Ehrenberg, B.2    Johnson, F.M.3
  • 31
    • 84875963900 scopus 로고
    • Quantum yields for the photosensitized formation of the lowest electronically excited singlet state of molecular oxygen in solution. An expanded and revised compilation
    • Wilkinson, F., W. P. Helman and A. B. Ross (1995) Quantum yields for the photosensitized formation of the lowest electronically excited singlet state of molecular oxygen in solution. An expanded and revised compilation. J. Phys. Chem. Ref. Data 22, 113-262.
    • (1995) J. Phys. Chem. Ref. Data , vol.22 , pp. 113-262
    • Wilkinson, F.1    Helman, W.P.2    Ross, A.B.3
  • 32
    • 0031731920 scopus 로고
    • What does photodynamic therapy have to offer radiation oncologists (or their cancer patients)?
    • Stewart, F., P. Baas and W. Star (1988) What does photodynamic therapy have to offer radiation oncologists (or their cancer patients)? Radiotherapy Oncol. 48, 233-248.
    • (1988) Radiotherapy Oncol. , vol.48 , pp. 233-248
    • Stewart, F.1    Baas, P.2    Star, W.3
  • 33
    • 0002956871 scopus 로고    scopus 로고
    • Photophysical properties of 5,10,15,20-tetrakis(m-hydroxyphenyl) porphyrin-(m-THPP), 5,10,15,20-tetrakis (m-hydroxyphenyl)chlorin (m-THPC) and 5,10,15,20-tetrakis(m-hydroxyphenyl)bacteriochlorin (m-THPBC): A comparative study
    • Bonnett, R., P. Charlesworth, B. D. Djelal, S. Foley, D. J. McGarvey and T. G. Truscott (1999) Photophysical properties of 5,10,15,20-tetrakis(m- hydroxyphenyl)porphyrin-(m-THPP), 5,10,15,20-tetrakis (m-hydroxyphenyl)chlorin (m-THPC) and 5,10,15,20-tetrakis(m-hydroxyphenyl)bacteriochlorin (m-THPBC): a comparative study. J. Chem. Soc. Perkin Trans. 2, 325-328.
    • (1999) J. Chem. Soc. Perkin Trans. , vol.2 , pp. 325-328
    • Bonnett, R.1    Charlesworth, P.2    Djelal, B.D.3    Foley, S.4    McGarvey, D.J.5    Truscott, T.G.6
  • 34
    • 0034785206 scopus 로고    scopus 로고
    • Hydrophilicity vs hydrophobicity-varying the amphiphilic structure of porphyrins related to the photosensitizer m-THPC
    • Wiehe, A., E. J. Simonenko, M. O. Senge and B. Roder (2001) Hydrophilicity vs hydrophobicity-varying the amphiphilic structure of porphyrins related to the photosensitizer m-THPC. J. Porphyrins Phtalocyanines 5, 758-761.
    • (2001) J. Porphyrins Phtalocyanines , vol.5 , pp. 758-761
    • Wiehe, A.1    Simonenko, E.J.2    Senge, M.O.3    Roder, B.4
  • 35
    • 17044443180 scopus 로고    scopus 로고
    • Are calculated log P values for some guanine derivatives by different computer programs reliable?
    • Kristl, A., S. Pečar and V. Kmetec (1999) Are calculated log P values for some guanine derivatives by different computer programs reliable? J. Pharm. 181, 219-226.
    • (1999) J. Pharm. , vol.181 , pp. 219-226
    • Kristl, A.1    Pečar, S.2    Kmetec, V.3
  • 36
    • 0028915184 scopus 로고
    • The prediction of the lipophilicity of peptidomimetics. A comparison between experimental and theoretical lipophilicity values of renin inhibitors and their building blocks
    • Karajiannis, H. and H. van de Waterbeemd (1995) The prediction of the lipophilicity of peptidomimetics. A comparison between experimental and theoretical lipophilicity values of renin inhibitors and their building blocks. Pharm. Acta Helv. 70, 67-77.
    • (1995) Pharm. Acta Helv. , vol.70 , pp. 67-77
    • Karajiannis, H.1    Van De Waterbeemd, H.2
  • 37
    • 0029845112 scopus 로고    scopus 로고
    • Calculation procedures for molecular lipophilicity: A comparative study
    • Mannhold, R. and K. Dross (1996) Calculation procedures for molecular lipophilicity: A comparative study. Quant. Struct. Activ. Relationships 15, 403-409.
    • (1996) Quant. Struct. Activ. Relationships , vol.15 , pp. 403-409
    • Mannhold, R.1    Dross, K.2
  • 38
    • 0031024171 scopus 로고    scopus 로고
    • Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings
    • Lipinski, C. A., L. Franco, B. W. Dominy and P. J. Feeney (1997) Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Deliv. Rev. 23, 3-25.
    • (1997) Adv. Drug Deliv. Rev. , vol.23 , pp. 3-25
    • Lipinski, C.A.1    Franco, L.2    Dominy, B.W.3    Feeney, P.J.4
  • 39
    • 0036675906 scopus 로고    scopus 로고
    • Do liposome-binding constants of porphyrins correlate with their measured and predicted partitioning between octanol and water?
    • Kȩpczyński, M., R. P. Pandian, K. M. Smith and B. Ehrenberg (2002) Do liposome-binding constants of porphyrins correlate with their measured and predicted partitioning between octanol and water? Photochem. Photobiol. 76, 127-134.
    • (2002) Photochem. Photobiol. , vol.76 , pp. 127-134
    • Kȩpczyński, M.1    Pandian, R.P.2    Smith, K.M.3    Ehrenberg, B.4
  • 40
    • 0033037957 scopus 로고    scopus 로고
    • Improved method for estimating bioconcentration/bioaccumulation factor from octanol/water partition coefficient
    • Meylan, W. M., P. H. Howard, R. S. Boethling, D. Aronson, H. Printup and S. Gouchie (1999) Improved method for estimating bioconcentration/ bioaccumulation factor from octanol/water partition coefficient. Environ. Toxicol. Chem. 18, 664-672.
    • (1999) Environ. Toxicol. Chem. , vol.18 , pp. 664-672
    • Meylan, W.M.1    Howard, P.H.2    Boethling, R.S.3    Aronson, D.4    Printup, H.5    Gouchie, S.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.