Synthese und Antitumoraktivität neuer Porphyrin‐Platin(II)‐Komplexe mit an den Porphyrin‐Seitenketten gebundenem cytostatischen Platin‐Rest

Abstract

Fifteen ligands of the porphyrin type, all derived from natural porphyrins, and their platinum(I1) complexes, in which the Pt fragment is attached to the porphyrin side chains, were synthesized and characterized. Two different kinds of ligands were prepared: eight compounds with propionic acid substituents in the positions 6 and 7 of the porphyrin skeleton and seven ligands with 3-aminopropyl side chains in the same positions. The ligands were transformed into eight diammine(dicarboxylato)platinum(II) complexes and into seven diaminedichloroplatinum(I1) complexes. One of the water-inso-Synthese der Liganden und Komplexe Zur Synthese des Hamatoporphyrin-Derivats (HPD) geht man vom Hamatoporphyrin aus, das rnit Eisessig und Schwefelsaure zum Diacetat 1 umgesetzt wird. Die Hydrolyse von 1 erfolgt rnit waDriger NaOH-Losung, und nach Neutralisation erhalt man HPD[''-ls]. Das Rohprodukt enthalt neben Monomeren auch Oligomere, die bis zu Hexameren reichenI'1 und die iiber Ester-oder Ether-Funktionen verkniipft sind. Die Reinigung des HPD-Rohprodukts erfolgt iiber Gelfiltrati~n['~]. Zur Gelchromatographie verwendet man hydroxypropyliertes Dextran-Gel[20]. Die drei isolierten Fraktionen entsprechen den Verbindungen 2-4[211. Als Edukt fur die Synthese von 5-7 dient Hamin. Nach Umsetzung rnit HBr in Eisessig erhalt man das Markownikoff-HBr-Addukt des Protoporphyrins. Die Bromid-Ionen werden durch die entsprechenden Alkoholate (Phenolat, Cyclohexanolat und Monomethyletherdiethylenglycolat)

Synthesis, structural investigations on organotin(IV) chlorin-e6 complexes, their effect on sea urchin embryonic development and induced apoptosis

“…Meso-tetra(4-carboxyphenyl)porphine, [H 6 TPPC], and meso-tetra(4-sulfo natophenyl)porphine, [H 6 TPPS], interactions with diorgano and tri-organotin(IV) moieties have been investigated and the results evidenced the formation of complexes with formula (R 2 Sn) 2 H 2 -TPPC, (R 3 Sn) 4 H 2 TPPC, (R 2 Sn) 2 H 2 TPPS and (R 3 Sn) 4 -H 2 TPPS (R = Me, n-Bu, Ph), respectively. Their solid state and solution configurations were reported, together with their in vivo cytotoxic activity [6,7].…”

“…Fifteen side-chain platinum(II)-porphyrin complexes were synthesized, chemically characterized and their antitumor activity in vivo towards MDA-MB 231 mammary carcinoma cell line tested [4].…”

Synthesis and Characterization of Uncharged Water-Soluble Star Polymers Containing a Porphyrin Core

“…[3,4] Since, up to now, uncharged water-soluble porphyrins have not been easily available, almost all the compounds tested have ionic structures. [5 -7] Although their affinity to DNA seems to be little affected by electrical charges, the interaction with cell membranes could be different from that of nonionic compounds.…”

Synthesis and spectroscopic properties of new phthalocyanine complexes with potentially combined photodynamic activity and cytotoxicity for photodynamic therapy

“…The relative fluorescence intensity is lowered if the heavy metal ion-containing fragments are linked to Pcs by direct C(Pc)-C (Hetaryl) bonds [12], while it does not diminish for p-conjugated macrocycles when the heavy metal ioncontaining fragments are linked via alkyl or heteroatomlinked chains [8,9]. Since carboxy, alkylamino or heterocyclic amino groups are required for the coordination of platinum-containing fragments to the periphery of the Pc core, zinc tetrakis(3-pyridyloxy)phthalocyanine(1) was chosen as the starting material for the preparation of platinum-containing heteropolynuclear Pcs (Scheme 1).…”

“…Thus the combination of the photodynamic activity of different photosensitizers and the high cytotoxicity of platinum-based complexes should lead to the development of new highly effective antitumor drugs. Using this concept, some platinum-containing complexes of tetraphenylporphyrin (TPP) and naturally occurring porphyrins have recently been synthesized which, as expected, show high antitumor activity, reflecting the combined effect of the photodynamic activity of the porphyrin core and the cytotoxicity of the platinum-containing fragments [8,9]. However, there is no report on the preparation of this kind of drug using secondgeneration photosensitizers such as Pcs.…”