Synthesis, characterization, and biological activity of cis-diammineplatinum(II) complexes of the DNA intercalators 9-aminoacridine and chloroquine

• Published in: Journal of the American Chemical Society Vol. 112; no. 4; pp. 1590 - 1596
• Main Authors: Sundquist, Wesley I, Bancroft, Daniel P, Lippard, Stephen J
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 01.02.1990
• Subjects: Bioinorganic chemistry; Chemistry; Exact sciences and technology; Inorganic chemistry and origins of life; Antineoplastic agent; Cationic complex; Divalent metal Complexes; Molecular structure; Nitrogen heterocycle; Organic ligand; Ammino complex; Transition metal Complexes; Tricyclic compound; Experimental study; X ray diffraction; Cis stereoisomer; Amine; Bicyclic compound; Chloro complex; Platinoid Complexes; Platinum II Complexes; Crystalline structure
• ISSN: 0002-7863; 1520-5126
• DOI: 10.1021/ja00160a044

The anticancer drug cis-diamminedichloroplatinum (II) reacts with the DNA intercalators 9-aminoacridine (9-AA) and chloroquine (CQ) to form the novel complexes cis-(Pt(NH sub(3)) sub(2)(N9-9-AA)Cl)(NO sub(3)), cis-(Pt(NH sub(3)) sub(2)(N9-9-AA) sub(2))(NO sub(3)) sub(2), and cis-(Pt(NH sub(3)) sub(2)(Nl-HCQ)Cl)(NO sub(3)) sub(2). Complexes of the general formula cis-(Pt(NH sub(3)) sub(2)(INT)Cl) super(n+), where INT is a DNA intercalator such as 9-AA or CQ, have the potential to bind both covalently and intercalatively to DNA and, consequently, are potential antitumor agents. Complexes were determined to be extremely toxic in animal screens, however, precluding their use as drugs.