The Deprotonation and Protonation Equilibria of a Hypericin Derivative in Aqueous Solution

Monatshefte fur Chemie

Volumn 128, Issue 6-7, 1997, Pages 571-583

  Altmann, R ^a   Falk, H ^a  

^a JOHANNES KEPLER UNIVERSITY LINZ   (Austria)

Author keywords

Electrophoresis; Hypericin; P a values; Spectrophotometric titrations; , Polyethylene glycol appended hypericin

Indexed keywords

EID: 0001491912     PISSN: 00269247     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF00807587     Document Type: Article

References (37)

1. Song PS, Häder DP, Poff K (1980) Photochem Photobiol 32: 781; Giese AC, (1981) Photochem Photobiol Rev 6: 139; Meruelo D, Lavie G, Lavie D (1988) Proc Natl Acad Sci USA 85: 5230; Lavie G, Valentine F, Levin B, Mazur Y, Gallo G, Lavie D, Weiner D, Meruelo D (1989) Proc Natl Acad USA 86: 5963; Tang J, Calacino JM, Larsen SH, Spitzer W (1990) Antiviral Research 13: 313; Kim I, Rhee J, Huh JW, Florell S, Faure B, Lee KW, Kahsai T, Song PS, Tamai N, Yamazaki T, Yamazaki I (1990) Biochim Biophys Acta 1040: 43; Lopez-Bazzocchi I, Hudson JB, Towers HN (1991) Photochem Photobiol 54: 95; Carenter S, Kraus GA (1991) Photochem Photobiol 53: 169; Tao N, Orlando M, Hyon J, Grass M, Song PS (1993) J Amer Chem Soc 115: 2526; Wynn JL, Kim JH, Tao N, Dai R, Song PS, Cotton TM (1995) J Phys Chem 99: 2208; Agostinis P, Donella-Deana A, Cuveele J, Vandenbogaerde A, Sarno S, Merlevede W, de Witte P (1996) Biochem Biophys Res Commun 220: 613; Sureau F, Miskovsky P, Chinsky L, Turpin PY (1996) J Chem Soc 118: 9484; Kubin A, Alth G, Jindra RH, Jessner G, Ebermann R (1996) J Photochem Photobiol B 36: 103; Koren H, Schenk GM, Jindra RH, Alth G, Ebermann R, Kubin A, Koderhold G, Kreitner M (1996) J Photochem Photobiol B 36: 113
2. Song PS, Häder DP, Poff K (1980) Photochem Photobiol 32: 781; Giese AC, (1981) Photochem Photobiol Rev 6: 139; Meruelo D, Lavie G, Lavie D (1988) Proc Natl Acad Sci USA 85: 5230; Lavie G, Valentine F, Levin B, Mazur Y, Gallo G, Lavie D, Weiner D, Meruelo D (1989) Proc Natl Acad USA 86: 5963; Tang J, Calacino JM, Larsen SH, Spitzer W (1990) Antiviral Research 13: 313; Kim I, Rhee J, Huh JW, Florell S, Faure B, Lee KW, Kahsai T, Song PS, Tamai N, Yamazaki T, Yamazaki I (1990) Biochim Biophys Acta 1040: 43; Lopez-Bazzocchi I, Hudson JB, Towers HN (1991) Photochem Photobiol 54: 95; Carenter S, Kraus GA (1991) Photochem Photobiol 53: 169; Tao N, Orlando M, Hyon J, Grass M, Song PS (1993) J Amer Chem Soc 115: 2526; Wynn JL, Kim JH, Tao N, Dai R, Song PS, Cotton TM (1995) J Phys Chem 99: 2208; Agostinis P, Donella-Deana A, Cuveele J, Vandenbogaerde A, Sarno S, Merlevede W, de Witte P (1996) Biochem Biophys Res Commun 220: 613; Sureau F, Miskovsky P, Chinsky L, Turpin PY (1996) J Chem Soc 118: 9484; Kubin A, Alth G, Jindra RH, Jessner G, Ebermann R (1996) J Photochem Photobiol B 36: 103; Koren H, Schenk GM, Jindra RH, Alth G, Ebermann R, Kubin A, Koderhold G, Kreitner M (1996) J Photochem Photobiol B 36: 113
3. Song PS, Häder DP, Poff K (1980) Photochem Photobiol 32: 781; Giese AC, (1981) Photochem Photobiol Rev 6: 139; Meruelo D, Lavie G, Lavie D (1988) Proc Natl Acad Sci USA 85: 5230; Lavie G, Valentine F, Levin B, Mazur Y, Gallo G, Lavie D, Weiner D, Meruelo D (1989) Proc Natl Acad USA 86: 5963; Tang J, Calacino JM, Larsen SH, Spitzer W (1990) Antiviral Research 13: 313; Kim I, Rhee J, Huh JW, Florell S, Faure B, Lee KW, Kahsai T, Song PS, Tamai N, Yamazaki T, Yamazaki I (1990) Biochim Biophys Acta 1040: 43; Lopez-Bazzocchi I, Hudson JB, Towers HN (1991) Photochem Photobiol 54: 95; Carenter S, Kraus GA (1991) Photochem Photobiol 53: 169; Tao N, Orlando M, Hyon J, Grass M, Song PS (1993) J Amer Chem Soc 115: 2526; Wynn JL, Kim JH, Tao N, Dai R, Song PS, Cotton TM (1995) J Phys Chem 99: 2208; Agostinis P, Donella-Deana A, Cuveele J, Vandenbogaerde A, Sarno S, Merlevede W, de Witte P (1996) Biochem Biophys Res Commun 220: 613; Sureau F, Miskovsky P, Chinsky L, Turpin PY (1996) J Chem Soc 118: 9484; Kubin A, Alth G, Jindra RH, Jessner G, Ebermann R (1996) J Photochem Photobiol B 36: 103; Koren H, Schenk GM, Jindra RH, Alth G, Ebermann R, Kubin A, Koderhold G, Kreitner M (1996) J Photochem Photobiol B 36: 113
4. Song PS, Häder DP, Poff K (1980) Photochem Photobiol 32: 781; Giese AC, (1981) Photochem Photobiol Rev 6: 139; Meruelo D, Lavie G, Lavie D (1988) Proc Natl Acad Sci USA 85: 5230; Lavie G, Valentine F, Levin B, Mazur Y, Gallo G, Lavie D, Weiner D, Meruelo D (1989) Proc Natl Acad USA 86: 5963; Tang J, Calacino JM, Larsen SH, Spitzer W (1990) Antiviral Research 13: 313; Kim I, Rhee J, Huh JW, Florell S, Faure B, Lee KW, Kahsai T, Song PS, Tamai N, Yamazaki T, Yamazaki I (1990) Biochim Biophys Acta 1040: 43; Lopez-Bazzocchi I, Hudson JB, Towers HN (1991) Photochem Photobiol 54: 95; Carenter S, Kraus GA (1991) Photochem Photobiol 53: 169; Tao N, Orlando M, Hyon J, Grass M, Song PS (1993) J Amer Chem Soc 115: 2526; Wynn JL, Kim JH, Tao N, Dai R, Song PS, Cotton TM (1995) J Phys Chem 99: 2208; Agostinis P, Donella-Deana A, Cuveele J, Vandenbogaerde A, Sarno S, Merlevede W, de Witte P (1996) Biochem Biophys Res Commun 220: 613; Sureau F, Miskovsky P, Chinsky L, Turpin PY (1996) J Chem Soc 118: 9484; Kubin A, Alth G, Jindra RH, Jessner G, Ebermann R (1996) J Photochem Photobiol B 36: 103; Koren H, Schenk GM, Jindra RH, Alth G, Ebermann R, Kubin A, Koderhold G, Kreitner M (1996) J Photochem Photobiol B 36: 113
5. Song PS, Häder DP, Poff K (1980) Photochem Photobiol 32: 781; Giese AC, (1981) Photochem Photobiol Rev 6: 139; Meruelo D, Lavie G, Lavie D (1988) Proc Natl Acad Sci USA 85: 5230; Lavie G, Valentine F, Levin B, Mazur Y, Gallo G, Lavie D, Weiner D, Meruelo D (1989) Proc Natl Acad USA 86: 5963; Tang J, Calacino JM, Larsen SH, Spitzer W (1990) Antiviral Research 13: 313; Kim I, Rhee J, Huh JW, Florell S, Faure B, Lee KW, Kahsai T, Song PS, Tamai N, Yamazaki T, Yamazaki I (1990) Biochim Biophys Acta 1040: 43; Lopez-Bazzocchi I, Hudson JB, Towers HN (1991) Photochem Photobiol 54: 95; Carenter S, Kraus GA (1991) Photochem Photobiol 53: 169; Tao N, Orlando M, Hyon J, Grass M, Song PS (1993) J Amer Chem Soc 115: 2526; Wynn JL, Kim JH, Tao N, Dai R, Song PS, Cotton TM (1995) J Phys Chem 99: 2208; Agostinis P, Donella-Deana A, Cuveele J, Vandenbogaerde A, Sarno S, Merlevede W, de Witte P (1996) Biochem Biophys Res Commun 220: 613; Sureau F, Miskovsky P, Chinsky L, Turpin PY (1996) J Chem Soc 118: 9484; Kubin A, Alth G, Jindra RH, Jessner G, Ebermann R (1996) J Photochem Photobiol B 36: 103; Koren H, Schenk GM, Jindra RH, Alth G, Ebermann R, Kubin A, Koderhold G, Kreitner M (1996) J Photochem Photobiol B 36: 113
6. Song PS, Häder DP, Poff K (1980) Photochem Photobiol 32: 781; Giese AC, (1981) Photochem Photobiol Rev 6: 139; Meruelo D, Lavie G, Lavie D (1988) Proc Natl Acad Sci USA 85: 5230; Lavie G, Valentine F, Levin B, Mazur Y, Gallo G, Lavie D, Weiner D, Meruelo D (1989) Proc Natl Acad USA 86: 5963; Tang J, Calacino JM, Larsen SH, Spitzer W (1990) Antiviral Research 13: 313; Kim I, Rhee J, Huh JW, Florell S, Faure B, Lee KW, Kahsai T, Song PS, Tamai N, Yamazaki T, Yamazaki I (1990) Biochim Biophys Acta 1040: 43; Lopez-Bazzocchi I, Hudson JB, Towers HN (1991) Photochem Photobiol 54: 95; Carenter S, Kraus GA (1991) Photochem Photobiol 53: 169; Tao N, Orlando M, Hyon J, Grass M, Song PS (1993) J Amer Chem Soc 115: 2526; Wynn JL, Kim JH, Tao N, Dai R, Song PS, Cotton TM (1995) J Phys Chem 99: 2208; Agostinis P, Donella-Deana A, Cuveele J, Vandenbogaerde A, Sarno S, Merlevede W, de Witte P (1996) Biochem Biophys Res Commun 220: 613; Sureau F, Miskovsky P, Chinsky L, Turpin PY (1996) J Chem Soc 118: 9484; Kubin A, Alth G, Jindra RH, Jessner G, Ebermann R (1996) J Photochem Photobiol B 36: 103; Koren H, Schenk GM, Jindra RH, Alth G, Ebermann R, Kubin A, Koderhold G, Kreitner M (1996) J Photochem Photobiol B 36: 113
7. Song PS, Häder DP, Poff K (1980) Photochem Photobiol 32: 781; Giese AC, (1981) Photochem Photobiol Rev 6: 139; Meruelo D, Lavie G, Lavie D (1988) Proc Natl Acad Sci USA 85: 5230; Lavie G, Valentine F, Levin B, Mazur Y, Gallo G, Lavie D, Weiner D, Meruelo D (1989) Proc Natl Acad USA 86: 5963; Tang J, Calacino JM, Larsen SH, Spitzer W (1990) Antiviral Research 13: 313; Kim I, Rhee J, Huh JW, Florell S, Faure B, Lee KW, Kahsai T, Song PS, Tamai N, Yamazaki T, Yamazaki I (1990) Biochim Biophys Acta 1040: 43; Lopez-Bazzocchi I, Hudson JB, Towers HN (1991) Photochem Photobiol 54: 95; Carenter S, Kraus GA (1991) Photochem Photobiol 53: 169; Tao N, Orlando M, Hyon J, Grass M, Song PS (1993) J Amer Chem Soc 115: 2526; Wynn JL, Kim JH, Tao N, Dai R, Song PS, Cotton TM (1995) J Phys Chem 99: 2208; Agostinis P, Donella-Deana A, Cuveele J, Vandenbogaerde A, Sarno S, Merlevede W, de Witte P (1996) Biochem Biophys Res Commun 220: 613; Sureau F, Miskovsky P, Chinsky L, Turpin PY (1996) J Chem Soc 118: 9484; Kubin A, Alth G, Jindra RH, Jessner G, Ebermann R (1996) J Photochem Photobiol B 36: 103; Koren H, Schenk GM, Jindra RH, Alth G, Ebermann R, Kubin A, Koderhold G, Kreitner M (1996) J Photochem Photobiol B 36: 113
8. Song PS, Häder DP, Poff K (1980) Photochem Photobiol 32: 781; Giese AC, (1981) Photochem Photobiol Rev 6: 139; Meruelo D, Lavie G, Lavie D (1988) Proc Natl Acad Sci USA 85: 5230; Lavie G, Valentine F, Levin B, Mazur Y, Gallo G, Lavie D, Weiner D, Meruelo D (1989) Proc Natl Acad USA 86: 5963; Tang J, Calacino JM, Larsen SH, Spitzer W (1990) Antiviral Research 13: 313; Kim I, Rhee J, Huh JW, Florell S, Faure B, Lee KW, Kahsai T, Song PS, Tamai N, Yamazaki T, Yamazaki I (1990) Biochim Biophys Acta 1040: 43; Lopez-Bazzocchi I, Hudson JB, Towers HN (1991) Photochem Photobiol 54: 95; Carenter S, Kraus GA (1991) Photochem Photobiol 53: 169; Tao N, Orlando M, Hyon J, Grass M, Song PS (1993) J Amer Chem Soc 115: 2526; Wynn JL, Kim JH, Tao N, Dai R, Song PS, Cotton TM (1995) J Phys Chem 99: 2208; Agostinis P, Donella-Deana A, Cuveele J, Vandenbogaerde A, Sarno S, Merlevede W, de Witte P (1996) Biochem Biophys Res Commun 220: 613; Sureau F, Miskovsky P, Chinsky L, Turpin PY (1996) J Chem Soc 118: 9484; Kubin A, Alth G, Jindra RH, Jessner G, Ebermann R (1996) J Photochem Photobiol B 36: 103; Koren H, Schenk GM, Jindra RH, Alth G, Ebermann R, Kubin A, Koderhold G, Kreitner M (1996) J Photochem Photobiol B 36: 113
9. Song PS, Häder DP, Poff K (1980) Photochem Photobiol 32: 781; Giese AC, (1981) Photochem Photobiol Rev 6: 139; Meruelo D, Lavie G, Lavie D (1988) Proc Natl Acad Sci USA 85: 5230; Lavie G, Valentine F, Levin B, Mazur Y, Gallo G, Lavie D, Weiner D, Meruelo D (1989) Proc Natl Acad USA 86: 5963; Tang J, Calacino JM, Larsen SH, Spitzer W (1990) Antiviral Research 13: 313; Kim I, Rhee J, Huh JW, Florell S, Faure B, Lee KW, Kahsai T, Song PS, Tamai N, Yamazaki T, Yamazaki I (1990) Biochim Biophys Acta 1040: 43; Lopez-Bazzocchi I, Hudson JB, Towers HN (1991) Photochem Photobiol 54: 95; Carenter S, Kraus GA (1991) Photochem Photobiol 53: 169; Tao N, Orlando M, Hyon J, Grass M, Song PS (1993) J Amer Chem Soc 115: 2526; Wynn JL, Kim JH, Tao N, Dai R, Song PS, Cotton TM (1995) J Phys Chem 99: 2208; Agostinis P, Donella-Deana A, Cuveele J, Vandenbogaerde A, Sarno S, Merlevede W, de Witte P (1996) Biochem Biophys Res Commun 220: 613; Sureau F, Miskovsky P, Chinsky L, Turpin PY (1996) J Chem Soc 118: 9484; Kubin A, Alth G, Jindra RH, Jessner G, Ebermann R (1996) J Photochem Photobiol B 36: 103; Koren H, Schenk GM, Jindra RH, Alth G, Ebermann R, Kubin A, Koderhold G, Kreitner M (1996) J Photochem Photobiol B 36: 113
10. Song PS, Häder DP, Poff K (1980) Photochem Photobiol 32: 781; Giese AC, (1981) Photochem Photobiol Rev 6: 139; Meruelo D, Lavie G, Lavie D (1988) Proc Natl Acad Sci USA 85: 5230; Lavie G, Valentine F, Levin B, Mazur Y, Gallo G, Lavie D, Weiner D, Meruelo D (1989) Proc Natl Acad USA 86: 5963; Tang J, Calacino JM, Larsen SH, Spitzer W (1990) Antiviral Research 13: 313; Kim I, Rhee J, Huh JW, Florell S, Faure B, Lee KW, Kahsai T, Song PS, Tamai N, Yamazaki T, Yamazaki I (1990) Biochim Biophys Acta 1040: 43; Lopez-Bazzocchi I, Hudson JB, Towers HN (1991) Photochem Photobiol 54: 95; Carenter S, Kraus GA (1991) Photochem Photobiol 53: 169; Tao N, Orlando M, Hyon J, Grass M, Song PS (1993) J Amer Chem Soc 115: 2526; Wynn JL, Kim JH, Tao N, Dai R, Song PS, Cotton TM (1995) J Phys Chem 99: 2208; Agostinis P, Donella-Deana A, Cuveele J, Vandenbogaerde A, Sarno S, Merlevede W, de Witte P (1996) Biochem Biophys Res Commun 220: 613; Sureau F, Miskovsky P, Chinsky L, Turpin PY (1996) J Chem Soc 118: 9484; Kubin A, Alth G, Jindra RH, Jessner G, Ebermann R (1996) J Photochem Photobiol B 36: 103; Koren H, Schenk GM, Jindra RH, Alth G, Ebermann R, Kubin A, Koderhold G, Kreitner M (1996) J Photochem Photobiol B 36: 113
11. Song PS, Häder DP, Poff K (1980) Photochem Photobiol 32: 781; Giese AC, (1981) Photochem Photobiol Rev 6: 139; Meruelo D, Lavie G, Lavie D (1988) Proc Natl Acad Sci USA 85: 5230; Lavie G, Valentine F, Levin B, Mazur Y, Gallo G, Lavie D, Weiner D, Meruelo D (1989) Proc Natl Acad USA 86: 5963; Tang J, Calacino JM, Larsen SH, Spitzer W (1990) Antiviral Research 13: 313; Kim I, Rhee J, Huh JW, Florell S, Faure B, Lee KW, Kahsai T, Song PS, Tamai N, Yamazaki T, Yamazaki I (1990) Biochim Biophys Acta 1040: 43; Lopez-Bazzocchi I, Hudson JB, Towers HN (1991) Photochem Photobiol 54: 95; Carenter S, Kraus GA (1991) Photochem Photobiol 53: 169; Tao N, Orlando M, Hyon J, Grass M, Song PS (1993) J Amer Chem Soc 115: 2526; Wynn JL, Kim JH, Tao N, Dai R, Song PS, Cotton TM (1995) J Phys Chem 99: 2208; Agostinis P, Donella-Deana A, Cuveele J, Vandenbogaerde A, Sarno S, Merlevede W, de Witte P (1996) Biochem Biophys Res Commun 220: 613; Sureau F, Miskovsky P, Chinsky L, Turpin PY (1996) J Chem Soc 118: 9484; Kubin A, Alth G, Jindra RH, Jessner G, Ebermann R (1996) J Photochem Photobiol B 36: 103; Koren H, Schenk GM, Jindra RH, Alth G, Ebermann R, Kubin A, Koderhold G, Kreitner M (1996) J Photochem Photobiol B 36: 113
12. Song PS, Häder DP, Poff K (1980) Photochem Photobiol 32: 781; Giese AC, (1981) Photochem Photobiol Rev 6: 139; Meruelo D, Lavie G, Lavie D (1988) Proc Natl Acad Sci USA 85: 5230; Lavie G, Valentine F, Levin B, Mazur Y, Gallo G, Lavie D, Weiner D, Meruelo D (1989) Proc Natl Acad USA 86: 5963; Tang J, Calacino JM, Larsen SH, Spitzer W (1990) Antiviral Research 13: 313; Kim I, Rhee J, Huh JW, Florell S, Faure B, Lee KW, Kahsai T, Song PS, Tamai N, Yamazaki T, Yamazaki I (1990) Biochim Biophys Acta 1040: 43; Lopez-Bazzocchi I, Hudson JB, Towers HN (1991) Photochem Photobiol 54: 95; Carenter S, Kraus GA (1991) Photochem Photobiol 53: 169; Tao N, Orlando M, Hyon J, Grass M, Song PS (1993) J Amer Chem Soc 115: 2526; Wynn JL, Kim JH, Tao N, Dai R, Song PS, Cotton TM (1995) J Phys Chem 99: 2208; Agostinis P, Donella-Deana A, Cuveele J, Vandenbogaerde A, Sarno S, Merlevede W, de Witte P (1996) Biochem Biophys Res Commun 220: 613; Sureau F, Miskovsky P, Chinsky L, Turpin PY (1996) J Chem Soc 118: 9484; Kubin A, Alth G, Jindra RH, Jessner G, Ebermann R (1996) J Photochem Photobiol B 36: 103; Koren H, Schenk GM, Jindra RH, Alth G, Ebermann R, Kubin A, Koderhold G, Kreitner M (1996) J Photochem Photobiol B 36: 113
13. Song PS, Häder DP, Poff K (1980) Photochem Photobiol 32: 781; Giese AC, (1981) Photochem Photobiol Rev 6: 139; Meruelo D, Lavie G, Lavie D (1988) Proc Natl Acad Sci USA 85: 5230; Lavie G, Valentine F, Levin B, Mazur Y, Gallo G, Lavie D, Weiner D, Meruelo D (1989) Proc Natl Acad USA 86: 5963; Tang J, Calacino JM, Larsen SH, Spitzer W (1990) Antiviral Research 13: 313; Kim I, Rhee J, Huh JW, Florell S, Faure B, Lee KW, Kahsai T, Song PS, Tamai N, Yamazaki T, Yamazaki I (1990) Biochim Biophys Acta 1040: 43; Lopez-Bazzocchi I, Hudson JB, Towers HN (1991) Photochem Photobiol 54: 95; Carenter S, Kraus GA (1991) Photochem Photobiol 53: 169; Tao N, Orlando M, Hyon J, Grass M, Song PS (1993) J Amer Chem Soc 115: 2526; Wynn JL, Kim JH, Tao N, Dai R, Song PS, Cotton TM (1995) J Phys Chem 99: 2208; Agostinis P, Donella-Deana A, Cuveele J, Vandenbogaerde A, Sarno S, Merlevede W, de Witte P (1996) Biochem Biophys Res Commun 220: 613; Sureau F, Miskovsky P, Chinsky L, Turpin PY (1996) J Chem Soc 118: 9484; Kubin A, Alth G, Jindra RH, Jessner G, Ebermann R (1996) J Photochem Photobiol B 36: 103; Koren H, Schenk GM, Jindra RH, Alth G, Ebermann R, Kubin A, Koderhold G, Kreitner M (1996) J Photochem Photobiol B 36: 113
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