TY - JOUR
T1 - PHTHALOCYANINE‐INDUCED PHOTOHEMOLYSIS
T2 - STRUCTURE‐ACTIVITY RELATIONSHIP AND THE EFFECT OF FLUORIDE
AU - Ben‐Hur, E.
AU - Malik, Z.
AU - Dubbelman, T. M.A.R.
AU - Margakon, P.
AU - Ali, H.
AU - van Lier, J. E.
PY - 1993/9
Y1 - 1993/9
N2 - Abstract— Phthalocyanine (Pc) containing AI, Ga or Zn as central metal ligand and substituted with a varying number of sulfonic acid residues as well as additional benzene rings were synthesized and their photodynamic activity was assayed using photohemolysis of human erythrocytes as an endpoint. The Pc derivatives vaned > 300‐fold in their photodynamic activity. Activity corrclated with binding of the dye to the cell, with the exception of some of the amphiphilic dyes where cell uptake was an order of magnitude higher than expected from the observed activity. Fluoride was shown to inhibit AIPcSn‐induccd photohemolysis. This effect occurred also with other AlPc and GaPc derivatives, but the concentration of F required to slow photohemolysis by a factor of two (Ki) varied between 4 μM and 10 mM. Fluorescence spectral studies indicated complex formation between F− and the dye, which was stronger for AlPc than GaPc derivatives. Ultrastructural studies using scanning electron microscopy showed that the photosensitized cells were converted to spherocytes and that F− prevented this to a large extent.
AB - Abstract— Phthalocyanine (Pc) containing AI, Ga or Zn as central metal ligand and substituted with a varying number of sulfonic acid residues as well as additional benzene rings were synthesized and their photodynamic activity was assayed using photohemolysis of human erythrocytes as an endpoint. The Pc derivatives vaned > 300‐fold in their photodynamic activity. Activity corrclated with binding of the dye to the cell, with the exception of some of the amphiphilic dyes where cell uptake was an order of magnitude higher than expected from the observed activity. Fluoride was shown to inhibit AIPcSn‐induccd photohemolysis. This effect occurred also with other AlPc and GaPc derivatives, but the concentration of F required to slow photohemolysis by a factor of two (Ki) varied between 4 μM and 10 mM. Fluorescence spectral studies indicated complex formation between F− and the dye, which was stronger for AlPc than GaPc derivatives. Ultrastructural studies using scanning electron microscopy showed that the photosensitized cells were converted to spherocytes and that F− prevented this to a large extent.
UR - http://www.scopus.com/inward/record.url?scp=0027670077&partnerID=8YFLogxK
U2 - 10.1111/j.1751-1097.1993.tb09573.x
DO - 10.1111/j.1751-1097.1993.tb09573.x
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C2 - 8234468
AN - SCOPUS:0027670077
SN - 0031-8655
VL - 58
SP - 351
EP - 355
JO - Photochemistry and Photobiology
JF - Photochemistry and Photobiology
IS - 3
ER -