Cd. Selassie et al., On the toxicity of phenols to fast growing cells. A QSAR model for a radical-based toxicity, J CHEM S P2, (12), 1999, pp. 2729-2733
Citations number
27
Categorie Soggetti
Physical Chemistry/Chemical Physics
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2
The cytotoxicities of a series of simple phenols as well as estrogenic phen
ols such as octyl and nonyl phenols, Bisphenol A, diethylstilbestrol, estra
diol, estriol, equilin and equilenin were studied in a fast growing murine
leukemia cell line. The use of calculated homolytic bond dissociation energ
ies (BDE) as the electronic parameter led to the development of a Quantitat
ive Structure-Activity Relationship model with superior results; one which
established the importance of relatively low BDE values in enhancing toxici
ty to rapidly multiplying cells. The correlation equation that emerged is a
s follows: log 1/ C = -0.19BDE + 0.21 log P + 3.11. It suggests that toxici
ty is closely related to mostly homolytic cleavage of the phenolic O-H bond
and overall hydrophobicity of the phenol.