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A. V. Szeghalmi, L. Leopold, S. Pinzaru, V. Chis, I. Silaghi-Dumitrescu, M. Schmitt, J. Popp, W. Kiefer. Adsorption of 6-Mercaptopurine and 6-Mercaptopurine-Riboside on Silver Colloid: A pH Dependent Surface En-hanced Raman Spectros-copy and Density Func-tional Theory Study. Part I. 6-Mercaptopurine. Journal of Molecular Structure, 735-736, pp. 103-113, 2005.

Abstract: Surface enhanced Raman spectroscopy (SERS) on silver colloid has been applied to characterize the interaction of 6-mercaptopurine
(6MP), an active drug used in chemotherapy of acute lymphoblastic leukemia, with a model biological substrate at therapeutical concentrations and as function of the pH value. The adsorption active sites and molecular orientation on the metal surface have been determined on the basis of SERS ‘surface selection rules’ subsequent to a detailed vibrational analysis of the 6MP tautomeric forms.
Therefore, DFT calculations (vibrational wavenumbers, Raman scattering activities, partial atomic charges) of the optimized tautomers and
potential energy distribution calculations have been performed. Around neutral pH value reorientation of the molecule has been observed.
Under basic conditions the 6MP molecule is probably adsorbed on the silver colloid through the N1 atom of the purine ring and possibly the S
atom, and adopts a tilted orientation to the surface. A reduction in the number of adsorbed molecules under basic conditions is proposed,
since the SERS spectrum recorded at 10K6 M concentration at neutral pH value resembles the SERS spectra obtained under basic conditions
at 10K5 M concentration. At acidic pH values a stronger interaction through the N9 and N3 atoms is suggested with an end-on orientation.
q 2004 Elsevier B.V. All rights reserved.

Keywords: Adsorption; 6-Mercaptopurine; Raman and SERS spectroscopy; DFT calculations

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