1. Raman Optical Activity Spectra and ConformationalElucidation of Chiral Drugs. The Case of the Antiangiogenic Aeroplysinin-1.
- Author
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BeleÌn Nieto-Ortega, Juan Casado, Ewan W. Blanch, Juan T. LoÌpez Navarrete, Ana R. Quesada, and Francisco J. RamiÌrez
- Subjects
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RAMAN effect , *CONFORMATIONAL analysis , *CHIRAL drugs , *VIBRATIONAL circular dichroism , *CANCER treatment , *MOLECULAR shapes - Abstract
We present the determination of the conformational properties ofaeroplysinin-1 in aqueous solution by means of a combined experimentaland theoretical Raman optical activity (ROA) and vibrational circulardichroism (VCD) study. Aeroplysinin-1 is an antiangiogenic drug extractedfrom the sponge Aplysina cavernicolawhich has beenproved to be a valuable candidate for the treatment of cancer andother antiangiogenic diseases. Our study shows that this moleculepossesses the 1S,6Rabsolute configurationin aqueous solution, where only two conformers are present to a significantlevel. We discuss in detail the relationships between the chiro-opticalROA and VCD features, and the structural properties of various energyaccessible conformers are described. The present work is one of thefirst studies in which both ROA and VCD have been used as complementarytools for the determination of absolute configuration and dominantsolution-state conformations of an unknown therapeutically significantmolecule. [ABSTRACT FROM AUTHOR]
- Published
- 2011
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