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)
Twelve new diamine ligands are synthesized and characterized in which a benzyl group and another vicinal substituent or a benzyl group, a 4‐Cl‐benzyl group, and a 4‐MeO‐benzyl group, respectively, and two other geminal substituents are attached to the 1,2‐diaminoethane skeleton. The diamine ligands are transformed into the dichloroplatinum(II) complexes. The chloride ligands of four complexes are replaced by the lactate anion, α‐Cyclodextrin and polyvinylpyrrolidone are used to increase the water solubility of the Pt(II) complexes. The antitumor activity of the Pt(II) complexes is tested towards the P388 leukemia. The compounds with small alkyl substituents show antitumor activities which are much higher than the antitumor activity of cis‐platinum. Compared to the insoluble dichloro complexes, the lactate complexes and the formulations with α‐cyclodextrin and polyvinylpyrrolidone exhibit good water solubility, and no decrease of the antitumor activity is observed.
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