Interactions with Aromatic Rings in Chemical and Biological Recognition

Abstract

Intermolecular interactions involving aromatic rings are key processes in both chemical and biological recognition. Their understanding is essential for rational drug design and lead optimization in medicinal chemistry. Different approaches-biological studies, molecular recognition studies with artificial receptors, crystallographic database mining, gas-phase studies, and theoretical calculations-are pursued to generate a profound understanding of the structural and energetic parameters of individual recognition modes involving aromatic rings. This review attempts to combine and summarize the knowledge gained from these investigations. The review focuses mainly on examples with biological relevance since one of its aims it to enhance the knowledge of molecular recognition forces that is essential for drug development.

Structure–activity relationships for organometallic osmium arene phenylazopyridine complexes with potent anticancer activity

“…24,40 Introducing biphenyl as the arene instead of pcymene not only provides a potential DNA intercalator but also increases the hydrophobicity for interaction with proteins which may contribute to the increased activity. 5,50 Consideration of the substituents on the pyridine ring shows that changing from chloride at R 3 to fluoride causes the cellular accumulation of osmium to increase dramatically and is accompanied by an improvement in anticancer activity. The difference in the extent of cellular accumulation within this family may contribute to the observed variations in anticancer activity, as may interactions with targets (which may be proteins) .…”

“…The difference in the extent of cellular accumulation within this family may contribute to the observed variations in anticancer activity, as may interactions with targets (which may be proteins) . 50 To investigate whether there is a link between lipophilicity and anticancer activity for these complexes. The log P values were determined; they cover a broad range from -1.446 to 0.1330 (Table S3).…”

Photoionization-induced large-amplitude pendular motion in phenol+–Kr

“…[1][2][3] These intermolecular forces are often classified as electrostatic and dispersion interactions. In this simple scheme, hydrogen bonds (H-bonds) are based on electrostatic interactions, whereas van der Waals forces (p-stacking) arise from dispersion.…”

Modeling π–π Interactions with the Effective Fragment Potential Method: The Benzene Dimer and Substituents

“…2 Interactions between aromatic rings are largely responsible for DNA base-pair stacking, 3 host-guest complexation, [4][5][6][7] and the tertiary structure of proteins. 8,9 Certain drugs rely on π-π interactions for intercalation into DNA.…”