Synthesis of a novel 4H-pyran analog as minor groove binder to DNA using ethidium bromide as fluorescence probe

Ramana, M. M. V.; Betkar, Rahul R.; Nimkar, Amey; Ranade, Prasanna; Mundhe, Balaji; Pardeshi, Sachin D.

doi:10.1016/j.saa.2015.07.037

Cited by 47 publications

(19 citation statements)

References 46 publications

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“…DNA binding studies of the final products have been performed by viscosity measurements, circular dichroism, UV-visible absorption and fluorescence spectroscopy. These studies allow to conclude that the synthesized 4H-pyrans bind to DNA through the minor groove rather than to major groove or by intercalation, with a higher K b than those previously reported for a 4H-pyran 78,79 . This work represents one of the scarce studies carried out with pyrans and their DNA binding interactions, thus opening the door for the future development of these scaffolds as promising drugs.…”

Section: Resultsmentioning

confidence: 52%

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Ultrasound-assisted multicomponent synthesis of 4H-pyrans in water and DNA binding studies

Auria‐Luna

Fernández‐Moreira

Marqués‐López

et al. 2020

Sci Rep

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A simple approach to synthesize new highly substituted 4H-pyran derivatives is described. Efficient et 3 n acts as a readily accessible catalyst of this process performed in pure water and with only a 20 mol% of catalyst loading. The extremely simple operational methodology, short reaction times, clean procedure and excellent product yields render this new approach extremely appealing for the synthesis of 4H-pyrans, as potentially biological scaffolds. Additionally, DNA interaction analysis reveals that 4H-pyran derivatives behave preferably as minor groove binders over major groove or intercalators. Therefore, this is one of the scarce examples where pyrans have resulted to be interesting DnA binders with high binding constants (K b ranges from 1.53 × 10 4 M −1 to 2.05 × 10 6 M −1).

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Section: Resultsmentioning

confidence: 52%

“…Based on our own experience in this field 76 , 77 , the plausible DNA interactions of 4 H -pyrans synthesized in this work have been studied because of their wide range of biological properties 78 , 79 . Thus, the interaction effect of 4 H -pyrans 3 , 6–9 towards calf thymus DNA (ctDNA) was investigated.…”

Section: Resultsmentioning

confidence: 99%

Ultrasound-assisted multicomponent synthesis of 4H-pyrans in water and DNA binding studies

Auria‐Luna

Fernández‐Moreira

Marqués‐López

et al. 2020

Sci Rep

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“…Fluorescence intensity of EB increases upon interaction with DNA due to the intercalation of the planar phenenthridinium ring between adjacent base pairs on the double helix. [ 29–31 ] Incremental additions of ZnS NPs (2 to 20 μM) to the EB–CT DNA complex, caused a reduction in the fluorescence intensity, without altering the peak position (Figure 4a). The extent of decrease in the fluorescence intensity (quenching), without any changes in the wavelength of maximum emission, may be due to the following possible reasons: (i) ZnS NPs may bind to EB, causing fluorescence quenching; (ii) ZnS NPs might replace EB from EB–CT DNA complex, decreasing the EB concentration; and (iii) the formation of a new complex (ZnS NP–CT DNA–EB) due to interaction of ZnS NPs with the CT DNA–EB system.…”

Section: Resultsmentioning

confidence: 99%

“…The extent of decrease in the fluorescence intensity (quenching), without any changes in the wavelength of maximum emission, may be due to the following possible reasons: (i) ZnS NPs may bind to EB, causing fluorescence quenching; (ii) ZnS NPs might replace EB from EB–CT DNA complex, decreasing the EB concentration; and (iii) the formation of a new complex (ZnS NP–CT DNA–EB) due to interaction of ZnS NPs with the CT DNA–EB system. [ 30,32 ]…”

Section: Resultsmentioning

confidence: 99%

Molecular interaction studies of zinc sulphide nanoparticles with DNA and its consequence: a multitechnique approach

2020

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Molecular interaction studies between nanoparticles (NPs) and biomolecules are of great importance in the field of nanomedicine as they affect many physiological processes. Therefore, the interaction of zinc sulphide nanoparticles (ZnS NPs) with calf thymus deoxyribonucleic acid (CT DNA) and its significance was analyzed using ultraviolet (UV)–visible light, fluorescence, circular dichroism (CD), zeta potential, viscometry, electrochemical, and polymerase chain reaction methods. Fluorescence quenching analysis revealed that the fluorescence of ZnS NPs was quenched using CT DNA through a static quenching mechanism. The negative values of thermodynamic parameters (ΔG, ΔH, and ΔS) showed that the binding process was spontaneous, exothermic, and van der Waals or hydrogen bonding plays an important role in the interaction of ZnS NPs with CT DNA. Thermal melting (Tm) studies indicated a decrease in the Tm of CT DNA, suggesting the destabilization of CT DNA upon interaction with ZnS NPs. In addition, the results obtained from competitive binding, zeta potential, CD, and viscometry measurements showed that the interaction of ZnS NPs with CT DNA is through groove binding. Electrochemical analysis further confirmed the observed results from various spectroscopic and other related studies, in which decrease in the redox peak current along with changes in peak potential (CV) and increase in the electrical resistance (EIS) indicated the interaction between ZnS NPs and CT DNA. Furthermore, PCR analysis using DNA polymerase revealed the potential of ZnS NPs to inhibit DNA replication in vitro. ZnS NP–CT DNA interaction studies can be explored to define new horizons in biomedical applications of ZnS NPs.

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“…This can also be attributed to the formation of the ground-state DNA-complex adduct due to the cationic metal complexes binding with the negatively charged oxygen of the phosphodiester of DNA, where the contraction of DNA drives a few EB molecules out of the DNA base pairs. 28 DNA binding parameters by electrochemical analysis. Cyclic voltammetry is an essential tool to investigate the electrontransfer reactions of complexes.…”

Section: Dna/bsa Interaction Studiesmentioning

confidence: 99%

Spectro-electrochemical assessments of DNA/BSA interactions, cytotoxicity, radical scavenging and pharmacological implications of biosensitive and biologically active morpholine-based metal(ii) complexes: a combined experimental and computational investigation

Sakthikumar¹,

Solomon²,

Raja

2019

RSC Adv.

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Synthesis of a novel 4H-pyran analog as minor groove binder to DNA using ethidium bromide as fluorescence probe

Cited by 47 publications

References 46 publications

Ultrasound-assisted multicomponent synthesis of 4H-pyrans in water and DNA binding studies

Ultrasound-assisted multicomponent synthesis of 4H-pyrans in water and DNA binding studies

Molecular interaction studies of zinc sulphide nanoparticles with DNA and its consequence: a multitechnique approach

Spectro-electrochemical assessments of DNA/BSA interactions, cytotoxicity, radical scavenging and pharmacological implications of biosensitive and biologically active morpholine-based metal(ii) complexes: a combined experimental and computational investigation

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