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)
The complexes [l,2-diam ino-l-(/?-hydroxy)benzyl-l-(methyl, ethyl, and phenyl)]ethane-(dichloro)platinum(II) were synthesized and characterized. The benzylic ^-hydroxy group of the 1,2-diaminoethane ligand leads to good water-solubility o f the complexes. The ligands were synthesized in a Strecker-type reaction, starting from the corresponding /?-methoxybenzylketones. The amino nitriles were reduced to the diamines. Finally, the /?-methoxy groups were converted into hydroxy groups by ether cleavage. For the preparation of the complexes, K 2PtCl4 was added to the ligands. The antitum or activity o f the platinum(II) compounds was tested towards the hum an m am m ary carcinoma cell line M DA-M B 231. The antitum or effect depends on the substituents and increases in the series phenyl, methyl, and ethyl. As a maxi mum, a growth inhibition value of 77% was obtained.
Synthesis and Antitumor Activity of Water-Soluble 2-Benzyl-1,2diaminobutane-α-oxycarboxylatoplatinum(II) Complexes.-The dichloroplatinum(II) complex of the title diamine shows antitumor activity accompanied by low toxicity compared to cis-platinum. However, the solubility in water has to be increased. Therefore, the chloride leaving groups are replaced by the anions of four α-hydroxycarboxylic acids. In each cage the geometrical trans/cis isomers (I) and (II) are obtained, which can be separated in the case of the lactato complexes. Starting with the racemic diamine and its corresponding enantiomers in the case of the lactato-complexes, the optical isomers are also prepared. The compounds possess a high antitumor activity toward the MDA-MB 231 mammary tumor and the P 388 leukemia of the CD2F1 mouse. -(BRUNNER, H.; MAITERTH, F.; TREITTINGER, B.; Inorg. Chim.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.