Temperature effect of the induced circular dichroism in the heparin-acridine orange complex

Cho, Chong‐Su; Kang, Sung-Woo

doi:10.1007/bf00254858

Cited by 1 publication

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“…It should be noted that accommodation of surfen molecules close to each other along the heparin chain in a chiral array could also give rise to a biphasic CD pattern. In analogy with the GAG association of various planar cationic dyes such as methylene blue and acridine compounds, intermolecular exciton coupling occurs between the aminoquinoline rings of the stacked surfen molecules. In that case, the principal absorption band of the interacting chromophores exhibits a significant intensity reduction (hypochromism) in relation to that of the free form .…”

Section: Resultsmentioning

confidence: 99%

Glycosaminoglycan and DNA Binding Induced Intra‐ and Intermolecular Exciton Coupling of the bis‐4‐Aminoquinoline Surfen

Zsila

2015

Chirality

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Despite the diverse biological activities of the glycosaminoglycan (GAG) antagonist surfen, the molecular details of its interaction with biomacromolecules remain poorly understood. Therefore, heparin and DNA binding properties of surfen were studied by circular dichroism (CD) and UV absorption spectroscopy methods. High-affinity (Ka ~ 10(7) M(-1)) association of surfen to the chiral heparin chain gives rise to a characteristic biphasic CD pattern due to the conformational twist of the aminoquinoline moieties around the central urea bridge. At higher drug loading, intermolecular stacking of surfen molecules alters the induced CD profile and also provokes strong UV hypochromism. In contrast to the right-handed heparin template, binding of surfen to the left-helicity chondroitin sulfate chains produces inverted CD pattern. Large UV hypochromism as well as polyphasic induced ellipticity bands indicate that surfen intercalates between the base pairs of calf-thymus DNA. Extensive CD spectroscopic changes observed at higher drug binding ratios refer to cooperative binding interactions between the intercalated drug molecules. The inherent conformational flexibility of surfen demonstrated here for the first time is important in its binding to distinct macromolecular targets and should be considered for rational drug design of novel GAG antagonists.

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Section: Resultsmentioning

confidence: 99%

Glycosaminoglycan and DNA Binding Induced Intra‐ and Intermolecular Exciton Coupling of the bis‐4‐Aminoquinoline Surfen

Zsila

2015

Chirality

View full text Add to dashboard Cite

show abstract

Temperature effect of the induced circular dichroism in the heparin-acridine orange complex

Cited by 1 publication

References 6 publications

Glycosaminoglycan and DNA Binding Induced Intra‐ and Intermolecular Exciton Coupling of the bis‐4‐Aminoquinoline Surfen

Glycosaminoglycan and DNA Binding Induced Intra‐ and Intermolecular Exciton Coupling of the bis‐4‐Aminoquinoline Surfen

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