Abstract
Two diastereomeric tetraphenylporphyrinyl-ω-hypericinyl-ethylenes were prepared and their properties investigated. The (Z)-diastereomer displayed an even higher photosensitization of singlet oxygen and/or reactive oxygen species than hypericin, whereas the (E)-configured derivative showed a somewhat weaker effect. Accordingly, hybridization of hypericin and porphyrin chromophores seems to be a promising target for the development of novel sensitizers for photodynamic therapy.
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H Falk (1999) Angew Chem 111 3306 Occurrence Handle10.1002/(SICI)1521-3757(19991102)111:21<3306::AID-ANGE3306>3.0.CO;2-E
H Falk (1999) Angew Chem Int Ed Engl 38 3116 Occurrence Handle10.1002/(SICI)1521-3773(19991102)38:21<3116::AID-ANIE3116>3.0.CO;2-S
M Waser H Falk (2007) Curr Org Chem 11 547 Occurrence Handle10.2174/138527207780368229 Occurrence Handle1:CAS:528:DC%2BD2sXkt1Ojsrg%3D
Bonnett R (1995) Chem Soc Rev 10
ED Sternberg D Dolphin (1998) Tetrahedron 54 4151 Occurrence Handle10.1016/S0040-4020(98)00015-5 Occurrence Handle1:CAS:528:DyaK1cXisFGlt7c%3D
H Brunner KM Schellerer (2002) Monatsh Chem 133 679 Occurrence Handle10.1007/s007060200041 Occurrence Handle1:CAS:528:DC%2BD38XkvFOlsb4%3D
D Bonifaz G Accorsi N Armaroli F Song A Palkar L Echegoyen M Scholl P Seiler B Jaun F Diederich (2005) Helv Chim Acta 88 1839 Occurrence Handle10.1002/hlca.200590144
DA Drain C Michael (2004) Biochem 43 10918 Occurrence Handle10.1021/bi049272v Occurrence Handle1:CAS:528:DC%2BD2cXmtVSntLc%3D
J Osterloh MGH Vicente (2002) J Porphyrins Phthalocyanines 6 305 Occurrence Handle1:CAS:528:DC%2BD3sXhtVOnuw%3D%3D Occurrence Handle10.1142/S1088424602000373
R Luguya J Laurent FR Fronczek MCH Vicente KM Smith (2004) Tetrahedron 60 2757 Occurrence Handle10.1016/j.tet.2004.01.080 Occurrence Handle1:CAS:528:DC%2BD2cXhslWlsbs%3D
O Wennerström H Ericssin I Raston S Svennson W Pimlott (1989) Tetrahedron Lett 30 1229 Occurrence Handle10.1016/S0040-4039(01)80378-6
H Falk TNH Tran (1996) Monatsh Chem 127 717 Occurrence Handle10.1007/BF00817262 Occurrence Handle1:CAS:528:DyaK28XmvVCqsbw%3D
TA Salama B Lackner H Falk (2003) Monatsh Chem 134 1113 Occurrence Handle1:CAS:528:DC%2BD3sXlsFKmsb8%3D
AD Adler FR Longo JD Finarelli F Goldmacher J Assauer L Korsakoff (1967) J Org Chem 32 467 Occurrence Handle10.1021/jo01288a053
Aigner S, Falk H (2008) Monatsh Chem, in print, doi: 10.1007/s00706-008-0876-6
RA Obermüller K Hohenthanner H Falk (2001) Photochem Photobiol 74 211 Occurrence Handle10.1562/0031-8655(2001)074<0211:THDPPT>2.0.CO;2
RA Obermüller H Falk (2001) Monatsh Chem 132 1519 Occurrence Handle10.1007/s007060170009
B Lackner C Etzlstorfer H Falk (2004) Monatsh Chem 135 1157 Occurrence Handle1:CAS:528:DC%2BD2cXntVegsb4%3D
K Hagenbuchner H Falk (1999) Monatsh Chem 130 1075 Occurrence Handle1:CAS:528:DyaK1MXmtlKls70%3D
ATR Williams SA Winfield JN Miller (1983) Analyst 108 1067 Occurrence Handle10.1039/an9830801067 Occurrence Handle1:CAS:528:DyaL2cXislKquw%3D%3D
H Falk J Meyer M Oberreiter (1993) Monatsh Chem 124 339 Occurrence Handle10.1007/BF00810594 Occurrence Handle1:CAS:528:DyaK3sXltlyqtLw%3D
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Correspondence: Heinz Falk, Department of Organic Chemistry, Johannes Kepler University Linz, 4040 Linz, Austria, Europe.
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Aigner, S., Falk, H. On synthesis and properties of hypericin-porphyrin hybrids. Monatsh Chem 139, 1513–1518 (2008). https://doi.org/10.1007/s00706-008-0940-2
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DOI: https://doi.org/10.1007/s00706-008-0940-2