title: Boron-containing chlorins and tetraazaporphyrins: synthesis and cell uptake of boronated pyropheophorbide a derivatives.
abstract: 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.
authors.affiliation: Department of Chemistry, University of Bremen, PO Box 330440, D-28334 Bremen, Germany.
authors.forename: Michal
authors.initials: M
authors.lastname: Ratajski
authors.forename: Jens
authors.initials: J
authors.lastname: Osterloh
authors.forename: Detlef
authors.initials: D
authors.lastname: Gabel
mesh_terms: 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
chemical_list: D000970:Antineoplastic Agents; D001896:Boron Compounds; D007211:Indoles; D054833:Isoindoles; D011166:Porphyrins; D011719:Pyrazines; D002734:Chlorophyll; C040298:pyropheophorbide a; C013647:phthalocyanine