Aromatic-aromatic interaction of amitriptyline: implication of overdosed drug detoxification.
The objectives of this work are to explore the pi-pi complexation of amitriptyline with pi electron-deficient aromatic rings and demonstrate the feasibility of pi-pi complexation for overdosed drug detoxification. Water-soluble oligochitosan was chemically modified with dinitrobenzenesulfonyl groups to induce selective binding toward amitriptyline through pi-pi complexation. NMR studies showed that benzenesulfonyl and dinitrobenzenesulfonyl protons were upfield shifted by the addition of amitriptyline, indicating the formation of pi-pi complexes. The pi-pi complexation of amitriptyline is driven primarily by a desolvation driving force, whereas the magnitude of interaction is dictated by the complementrary electrostatic interaction. Isolated rat heart tests revealed that dinitrobenzenesulfonyl oligochitosan prevented the amitriptyline-induced cardiotoxicity and was itself not cardiotoxic.
Lee
Dong-Won
DW
Department of Materials Science and Engineering, Gainesville, Florida 32611, USA.
Flint
Jason
J
Morey
Timothy
T
Dennis
Donn
D
Partch
Richard
R
Baney
Ronald
R
D000327:Adsorption; D000639:Amitriptyline / Q000737:chemistry / Q000493:pharmacokinetics* / Q000633:toxicity*; D000818:Animals; D001557:Benzenesulfonates / Q000737:chemistry / Q000494:pharmacology; D048271:Chitosan / Q000737:chemistry / Q000494:pharmacology; D004347:Drug Interactions; D062787:Drug Overdose; D005240:Feasibility Studies; D008658:Inactivation, Metabolic; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011522:Protons; D051381:Rats; D012995:Solubility; D014867:Water / Q000737:chemistry
D001557:Benzenesulfonates; D011522:Protons; D014867:Water; C007488:dinitrobenzenesulfonic acid; D000639:Amitriptyline; D048271:Chitosan