Investigation of DNA‐Binding Properties of Organic Molecules Using Quantitative Structure‐Activity Relationship (QSAR) Models

Verma, Rajeshwar P.; Hansch, Corwin

doi:10.1002/jps.21087

Cited by 31 publications

(26 citation statements)

References 40 publications

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“…Furthermore, most published QSARs show the importance of particular physicochemical parameters in describing activity [20]. We observed a correlation between the pharmacological activities and structures in this study.…”

Section: Discussionsupporting

confidence: 72%

Design, Synthesis, and Pharmacological Evaluation of Haloperidol Derivatives as Novel Potent Calcium Channel Blockers with Vasodilator Activity

Chen

Zheng

et al. 2011

PLoS ONE

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Several haloperidol derivatives with a piperidine scaffold that was decorated at the nitrogen atom with different alkyl, benzyl, or substituted benzyl moieties were synthesized at our laboratory to establish a library of compounds with vasodilator activity. Compounds were screened for vasodilatory activity on isolated thoracic aorta rings from rats, and their quantitative structure–activity relationships (QSAR) were examined. Based on the result of QSAR, N-4-tert-butyl benzyl haloperidol chloride (16c) was synthesized and showed the most potent vasodilatory activity of all designed compounds. 16c dose-dependently inhibited the contraction caused by the influx of extracellular Ca2+ in isolated thoracic aorta rings from rats. It concentration-dependently attenuated the calcium channel current and extracellular Ca2+ influx, without affecting the intracellular Ca2+ mobilization, in vascular smooth muscle cells from rats. 16c, possessing the N-4-tert-butyl benzyl piperidine structure, as a novel calcium antagonist, may be effective as a calcium channel blocker in cardiovascular disease.

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Section: Discussionsupporting

confidence: 72%

Design, Synthesis, and Pharmacological Evaluation of Haloperidol Derivatives as Novel Potent Calcium Channel Blockers with Vasodilator Activity

Chen

Zheng

et al. 2011

PLoS ONE

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“…Sandramycin A binds preferably to 5′-AT sequences flanked by CG base pairs [90]. This DNA binding activity has been studied with various chromophore derivatives of these molecules, showing that an increase in the chromophore hydrophobicity (as 3HQA lacking the phenolic hydroxyl group) enhances the DNA binding capability [78,91].…”

Section: Bioactivity Of Bisintercalator Compoundsmentioning

confidence: 99%

Biosynthetic Modularity Rules in the Bisintercalator Family of Antitumor Compounds

et al. 2014

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Diverse actinomycetes produce a family of structurally and biosynthetically related non-ribosomal peptide compounds which belong to the chromodepsipeptide family. These compounds act as bisintercalators into the DNA helix. They give rise to antitumor, antiparasitic, antibacterial and antiviral bioactivities. These compounds show a high degree of conserved modularity (chromophores, number and type of amino acids). This modularity and their high sequence similarities at the genetic level imply a common biosynthetic origin for these pathways. Here, we describe insights about rules governing this modular biosynthesis, taking advantage of the fact that nowadays five of these gene clusters have been made public (thiocoraline, triostin, SW-163 and echinomycin/quinomycin). This modularity has potential application for designing and producing novel genetic engineered derivatives, as well as for developing new chemical synthesis strategies. These would facilitate their clinical development.

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“…Quantitative structure-activity relationships (QSAR) studies attempt to correlate one or two parameters of a molecule to a pharmacological or biological activity including physicochemical properties and structural features of the molecule [1,2]. For example, the use of Hammett electronic parameters r in the QSAR equations shows that electronic effect of the substituent may play an important role in DNA-binding of ligands [3].…”

Section: Introductionmentioning

confidence: 99%

Substituent effects of 1,2-dithiole groups on the electrochemical oxidation of some ferrocenyl-1,2-dithiole compounds

Abasq¹,

Saidi²,

Burgot³

et al. 2009

Journal of Organometallic Chemistry

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Investigation of DNA‐Binding Properties of Organic Molecules Using Quantitative Structure‐Activity Relationship (QSAR) Models

Cited by 31 publications

References 40 publications

Design, Synthesis, and Pharmacological Evaluation of Haloperidol Derivatives as Novel Potent Calcium Channel Blockers with Vasodilator Activity

Design, Synthesis, and Pharmacological Evaluation of Haloperidol Derivatives as Novel Potent Calcium Channel Blockers with Vasodilator Activity

Biosynthetic Modularity Rules in the Bisintercalator Family of Antitumor Compounds

Substituent effects of 1,2-dithiole groups on the electrochemical oxidation of some ferrocenyl-1,2-dithiole compounds

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