Studies on the inclusion behavior of 9-Aminoacridine into cyclodextrins: spectroscopic and theoretical evidences.

C Manivannan, R Vijay Solomon, P Venuvanalingam, R Renganathan

School of Chemistry, Bharathidasan University, Tiruchirappalli 620 024, India.

Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 2013 Feb 15

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9-Aminoacridine (9-AA) is an important attractive pharmaceutical drug employed as chemotheraptic agent for wound dressings. However, 9-AA possesses limited solubility and rapid metabolic decomposition renders this potential drug to limit its applications. Here we propose cyclodextrins (CDs) as a drug carrier to improve the bioavailability, solubility of 9-AA. The interaction between 9-AA and CDs (α-CD and β-CD) has been studied using UV-Vis absorption, steady state time resolved fluorescence, (1)H NMR and FT-IR spectroscopy techniques. The spectroscopic measurements show that 9-AA does not form stable complex with α-CD and also confirmed by DFT calculations. On the other hand, 9-AA forms inclusion complex with β-CD in a 1:1 stoichiometry ratio. Our DFT results suggest that 9-AA stabilizes inside the CD environment through hydrogen bonding that has unambiguously confirmed by AIM analysis. Thus our studies provide a useful insights in the development of Aminoacridine based drugs & its delivery through a suitable carrier like CDs. Copyright © 2012 Elsevier B.V. All rights reserved.

Citation

C Manivannan, R Vijay Solomon, P Venuvanalingam, R Renganathan. Studies on the inclusion behavior of 9-Aminoacridine into cyclodextrins: spectroscopic and theoretical evidences. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2013 Feb 15;103:18-24