Cyclocreatine, an anti-cancer and neuroprotective agent. Spectroscopic, structural and theoretical study

R. PIS-DIEZ; B. S. PARAJÓN-COSTA; C. A. FRANCA; O. E. PIRO; E. E. CASTELLANO; A. C. GONZÁLEZ-BARÓ

JOURNAL OF MOLECULAR STRUCTURE

ELSEVIER SCIENCE BV

Año: 2010 vol. 975 p. 303 - 309

0022-2860

The structural, spectroscopic and theoretical study of Cyclocreatine (1-carboxymethyl-2-iminoimidazolidine, CyCre) has been performed prompted by the biological relevance of the molecule and its potential role as a ligand in biometalic compounds. The crystal structure of CyCre has been determined by X-Ray diffraction methods. The compound crystallizes as a zwitterion in the monoclinic system, space group P21/c. The crystal is further stabilized by a  network of N-H…O bonds. Infrared and Raman spectra of the solid, electronic spectra of aqueous solutions at different pH values and 1H and 13C NMR spectra have been recorded and analyzed. Band assignments were accomplished with the help of theoretical calculations. The optimized molecular geometry and the harmonic vibrational frequencies were calculated using methods based on the Density Functional Theory.