Core Electron Binding Energy (CEBE) as Descriptors in Quantitative Structure-Activity Relationship (QSAR) Analysis of Cytotoxicities of a Series of Simple Phenols

Author(s)

Takahata‚ Y. ; Arakawa‚ M. ; Funatsu‚ K. ; Costa‚ M.C.A. ; Segala‚ M.

• Document type: Journal article
• Source: QSAR & COMBINATORIAL SCIENCE; v. 26, n. 3, p. 378-384, 2007.

Abstract

Core Electron Binding Energies (CEBEs) of ring carbon atoms in 4-X-phenols were calculated using density-functional theory with the scheme Delta E-KS (PW86-PW91)/TZP//HF/ 6-31G*. The phenols show toxicity to fast growing cells. Using CEBEs of four distinguished carbon atoms in the phenyl ring and oxygen atom in -OH of the phenols, the compounds were well separated and grouped by Principal Component Analysis (PCA). Using three out of the five CEBEs, together with sigma(+) and log P of the phenols as descriptor, we established a QSAR model with Partial Least Squares (PLS) regression which resulted in Q(2)=0.914. CEBE values when used together with traditionally used descriptors such as log P and sigma(+) turned out to be useful descriptors in modeling the activity (QSAR) of the compounds with PLS. (AU)

• FAPESP's process: 03/00075-9 - Development of an alternative mehod to calculate core electron binding energies (CEBEs) of molecules, and evaluation of its applicability in drug design
• Grantee: Yuji Takahata
• Support Opportunities: Research Projects - Thematic Grants