Synthesis, characterization and cytotoxicity studies of palladium(II)-proflavine complexes.
An investigation of the reaction of Pd(II) complexes with proflavine (3,6-diaminoacridine) resulted in the isolation of the compounds [Pd(terpy)(proflavine)](NO(3))(HSO(4))*3H(2)O, 1, (terpy = 2,2':6',2″-terpyridine), [Pd(en)(proflavineH))](NO(3))(SO(4)), 2, (en = ethylenediamine), and [Pd(proflavineH)Cl(2)](SO(4))(0.5)*H(2)O, 3. They have been isolated and characterized by NMR, IR, and electro-spray ionization mass spectrometry techniques and by elemental analyses. The proflavine was bonded to the Pd(II) through the endocyclic nitrogen in 1, but through the proflavine NH(2) in 2. Compound 3 appeared to be polymeric in the solid state with a 1:1 mole ratio of Pd(II):proflavine. Upon solution of 3 in DMSO, two unique species were formed. In one species the Pd(II) was bonded to two proflavines through the endocyclic nitrogen (1:2 mole ratio) and in the other species, a Pd(II) was bonded to each NH(2) group of a single proflavine (2:1 mole ratio). Molecular modeling of the equilibrium geometry by Spartan 8 produced structures which were consistent with the experimental data on the solutions of the three compounds. In vitro cytotoxicity testing against two breast cancer cell lines and one ovarian cancer cell line showed that compounds 1 and 3 had significant activity.
Polyanskaya
Tatyana V
TV
Department of Chemistry, The University of Texas at San Antonio, One UTSA Circle, San Antonio, TX 78249, United States.
Kazhdan
Irene
I
Motley
D Michelle
DM
Walmsley
Judith A
JA
D001665:Binding Sites; D001943:Breast Neoplasms / Q000188:drug therapy / Q000473:pathology; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D005260:Female; D006801:Humans; D020128:Inhibitory Concentration 50; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D010051:Ovarian Neoplasms / Q000188:drug therapy / Q000473:pathology; D010165:Palladium / Q000737:chemistry* / Q000494:pharmacology*; D011370:Proflavine / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D012996:Solutions; D021241:Spectrometry, Mass, Electrospray Ionization
D012996:Solutions; D010165:Palladium; D011370:Proflavine