Interaction of cationic meso-porphyrins with liposomes, mitochondria and erythrocytes
Tóm tắt
Two series of cationic porphyrins meso-(3N-methylpyridinium)phenylporphyrin (3P1, 3P2c, 3P2t, 3P3 and 3P4) and meso-(4N-methylpyridinium)phenylporphyrin (4P1, 4P2c, 4P2t, 4P3 and 4P4) were studied to obtain a comprehensive understanding of factors that influence the binding of cationic porphyrins to liposomes and mitochondria, as well as their photodynamic efficiencies in erythrocytes. Binding and photodynamic efficiency were found to be inversely proportional to the number of positively charged groups and directly proportional to n-octanol/water partition coefficients (log POW), except for the cis molecules 3P2c and 4P2c. In the cis molecules, binding and photodynamic efficiency were much higher than expected, indicating that specific interactions not accounted by log POW enhance photodynamic efficiency. The effect of mitochondrial transmembrane electrochemical potentials on cationic porphyrin binding constants was estimated to be as large as 15%, and may be useful to selectively target this organelle when promoting photodynamic therapy to induce apoptosis.
Tài liệu tham khảo
Angeli NG, Lagorio MG, SanRomán EA, et al (2000) Photochem Photobiol 72:49–56
Barber DC, VanDerMeid KR, Gibson SL, et al (1991) Cancer Res 51:1836–1845
Ben Amor T, Jori G (2000) Photochem Photobiol 71:124–128
Ben-Dror S, Bronshtein I, Wiehe A, et al (2006) Photochem Photobiol 82:695–701
Bronshtein I, Afri M, Weitman H (2004) Biophys J 87:1155–1164
Casteel MJ, Jayaraj K, Gold A, et al (2004) Photochem Photobiol 80:294–300
Cernay T, Zimmermann HW (1996) J Photochem Photobiol B: Biol 34:191–196
Chen LB (1988) Annu Rev Cell Biol 48:155–181
Collander R (1951) Acta Chem Scand 5:774–780
Csik G, Balog E, Voszka I, et al (1998) J Photochem Photobiol B: Biol 44:216–224
Dixon DW, Steullet V (1998) J Inorg Biochem 69:25–32
Dougherty TJ, Gomer CJ, Henderson BW, et al (1998) J Natl Cancer I 90:889–905
Ehrenberg B, Anderson JL, Foote CS (1998) Photochem Photobiol 68:135–140
Eltayar N, Tsai RS, Testa B, et al (1991) J Pharm Sci 80:590–598
Engelmann FM, Losco P, Winnischofer H, et al (2002) J. Porphyrins Phthalocyanines 6:33–42
Engelmann FM, Rocha SVO, Araki K, et al (2007) Int J Pharm 329:12–18
Gabrielli D, Belisle E, Severino D, et al (2004) Photochem Photobiol 79:227–232
Henderson BW, Dougherty TJ (1992) Photochem Photobiol 55:145–157
Hidalgo AA, Tabak M, Oliveira ON (2005) Chem Phys Lipids 134:97–108
Junqueira HC, Severino D, Dias LG, et al (2002) Phys Chem Chem Phys 4:2320–2328
Kano K, Fukuda K, Wakami H, et al. (2000) J Am Chem Soc 122:7494–7502
Kepczynski M, Pandian RP, Smith KM, et al (2002) Photochem Photobiol 76:127–134
Kessel D, Luo Y (1998) J Photochem Photobiol B: Biol 42:89–95
Kessel D, Luo Y (1999) Cell Death and Differentiation 6:28–35
Khalili M, Grossweiner LI (1997) J Photochem Photobiol B: Biol 37:236–244
Kramer-Marek G, Serpa C, Szurko A (2006) J Photochem Photobiol B:Biol 84:1–14
Lambrechts SAG, Aalders MCG, Langeveld-Klerks DH (2004) Photochem Photobiol 79:297–302
Lambrechts SAG, Aalders MCG, Van Marle J (2005) Antimicrob Agents Chemother 49:2026–2034
Lavi A, Weitman H, Holmes RT, et al (2002) Biophys J 82:2101–2110
Lawrence DS, Gibson SL, Nguyen ML, et al (1995) Photochem Photobiol 61:90–98
Lemasters JJ (1999). Am J Physiol-Gastroint Liver Physiol 276:G1–G6
Lissi EA, Encinas MV, Lemp E, et al (1993) Chem Rev 93:699–723
Meng GG, James BR, Skov KA, et al (1994). Canadian J Chemistry-Revue Canadienne De Chimie 72:2447–2457
Merchat M, Spikes JD, Bertoloni G, et al (1996) J Photochem Photobiol B: Biol 35:149–157
Morgan J, Oseroff AR (2001) Advanced Drug Delivery Reviews 49:71–86
Netto LE, Kowaltowski AJ, Castilho RF, et al (2002) Methods Enzymol 260–270
Ochsner M (1997) J. Photochem Photobiol B: Biol 39:1–18
Parkash J, Robblee JH, Agnew J, et al (1998) Biophys J 74: 2089–2099
Reddi E, Ceccon M, Valduga G, et al (2002) Photochem Photobiol 75:462–470
Redmond RW, Gamlin JN (1999) Photochem Photobiol 70:391–475
Ricchelli F, Franchi L, Miotto G (2005) Int J Biochem 37:306–319
Rouser G, Fleische S, Yamamoto A (1970) Lipids 5:494
Schneckenburger H, Gschwend MH, Sailer R, Ruck A, and Strauss WSL (1995) J Photochem Photobiol B: Biol 27:251–255
Seiler P (1974) Eur J Med Chem 9:473–479
Severino D, Junqueira HC, Gabrielli DS, et al (2003) Photochem Photobiol 77:459–468
Silva EMP, Giuntini F, Faustino MAF, et al (2005) Bioorg Med Chem Lett 15:3333–3337
Smijs TGM, Schuitmaker HJ (2003) Photochem Photobiol 77:556–560
Spesia MB, Lazzeri D, Pascual L, et al (2005) FEMS Immunol Med Microbiol 44:289–295
Strauss WSL, Gschwend MH, Sailer R, et al (1995) J Photochem Photobiol B: Biol 28:155–161
Stromhaug PE, Berg TO, Berg K, et al (1997) Biochem J 321:217–225
Woodburn KW, Stylli S, Hill JS, et al (1992) Br J Cancer 65:321–328
Villanueva A, Jori G (1993) Cancer Lett 73:59–64
Voszka I, Galantai R, Maillard P, et al (1999) J Photochem Photobiol B: Biol 52:92–98
Zeitouni NC, Oseroff AR, Shieh S (2003) Mol Immunol 39:1133–1136