Drug delivery with a calixpyrrole--trans-Pt(II) complex.
A meso-p-nitroaniline-calix[4]pyrrole derivative trans-coordinated to a Pt(II) center was synthesized and its structure solved by X-ray analysis. Adenosine monophosphate (AMP) was used as a model compound to evaluate the potential for the assisted delivery of the metal to the DNA nucleobases via the phosphate anion-binding properties of the calix[4]pyrrole unit. An NMR investigation of the kinetics of AMP complexation in the absence of an H-bonding competing solvent (dry CD(3)CN) was consistent with this hypothesis, but we could not detect the interaction of the calix[4]pyrrole with phosphate in the presence of water. However, in vitro tests of the new trans-calixpyrrole-Pt(II) complex on different cancer cell lines indicate a cytotoxic activity that is unquestionably derived from the coexistence of both the trans-Pt(II) fragment and the calix[4]pyrrole unit.
Dipartimento di Scienze Chimiche, Università di Messina, viale F. Stagno D'Alcontres 31, 98166 Messina, Italy.
Grazia
G
Cafeo
Grazia
G
Carbotti
Angela
A
Cuzzola
Marina
M
Fabbi
Silvano
S
Ferrini
Franz H
FH
Kohnke
Georgia
G
Papanikolaou
Maria Rosaria
MR
Plutino
Camillo
C
Rosano
Andrew J P
AJ
White
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D047250:Calixarenes / Q000737:chemistry*; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D056831:Coordination Complexes / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D016503:Drug Delivery Systems; D005434:Flow Cytometry; D006801:Humans; D020128:Inhibitory Concentration 50; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D010984:Platinum / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry*
D000970:Antineoplastic Agents; D056831:Coordination Complexes; D011758:Pyrroles; D047250:Calixarenes; D010984:Platinum