Boron-containing chlorins and tetraazaporphyrins: synthesis and cell uptake of boronated pyropheophorbide a derivatives.
The literature on the synthesis and the biological properties of boron-containing chlorins and phthalocyanines is reviewed. A series of homologous derivatives of pyropheophorbide A is described. The compounds contain the B(12)H(11)SH(2-) cluster attached to the single carboxyl group and vary in the length of the alkyl chain (methyl, propyl, pentyl, heptyl and nonyl) attached via an ether linkage to the former vinyl group. Cellular uptake was found for all derivatives except the nonyl sidechain. The compounds were moderately cell-toxic. Localization in lysosomes could be excluded; the compounds localized probably in the mitochondria.
Ratajski
Michal
M
Department of Chemistry, University of Bremen, PO Box 330440, D-28334 Bremen, Germany.
Osterloh
Jens
J
Gabel
Detlef
D
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis; D001896:Boron Compounds / Q000138:chemical synthesis* / Q000378:metabolism*; D016754:Boron Neutron Capture Therapy / Q000379:methods; D002734:Chlorophyll / Q000031:analogs & derivatives / Q000138:chemical synthesis; D007211:Indoles / Q000138:chemical synthesis; D054833:Isoindoles; D011166:Porphyrins / Q000138:chemical synthesis* / Q000378:metabolism*; D011719:Pyrazines / Q000138:chemical synthesis
D000970:Antineoplastic Agents; D001896:Boron Compounds; D007211:Indoles; D054833:Isoindoles; D011166:Porphyrins; D011719:Pyrazines; D002734:Chlorophyll; C040298:pyropheophorbide a; C013647:phthalocyanine