Studies on Intramolecular Charge Transfer Fluorescence Probe and DNA Binding Characteristics

Yang, Xin; Shen, Guo‐Li; Yu, Ru‐Qin

doi:10.1006/mchj.1999.1747

Cited by 28 publications

(11 citation statements)

References 21 publications

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“…Hence, main emphasis was given to the absorption band occurring at 210 nm. The hypochromicity is due to the interaction of electronic states of the intercalating chromophore with stacked base pairs of DNA, due to which the probability of π–π * transitions reduces to much lesser extent, whereas bathochromic shifts can be described by the lowering in π–π* transition energy of Sul and organotin(IV) complexes due to their ordered stacking between the DNA base pairs after intercalation . The intrinsic binding constants ( K b ) have been determined from plots of [DNA]/( ε a − ε f ) versus [DNA] and values were found to be in the range 7.9 × 10 3 –3.69 × 10 4 M −1 , which is very much less in comparison to those of classical DNA intercalators where binding constant was reported to be of the order of 10 7 .…”

Section: Resultsmentioning

confidence: 99%

Tri‐ and diorganotin(IV) derivatives of non‐steroidal anti‐inflammatory drug sulindac: Characterization, electronic structures (DFT), DNA binding and plasmid cleavage studies

Kumari

Nath

2017

Applied Organom Chemis

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Tri‐ and diorganotin(IV) derivatives of non‐steroidal anti‐inflammatory drug sulindac (Sul), coordinated with carboxylate oxygen, namely C23H25FO3SSn (1), C38H31FO3SSn (2), C32H43FO3SSn (3), C52H42F2O6S2Sn (4), C44H44S2Cl2O6F2Sn2 (5), C48H50F2O6S2Sn (6) and C56H66F2O6S2Sn (7), have been synthesized and characterized using analytical and spectroscopic (IR, 1H NMR, 13C NMR, 119Sn NMR and ESI‐MS) techniques. Optimized geometry and electronic structures of the complexes obtained from density functional theory calculations indicate that complexes 1, 2, 3 and 7 are tetra‐coordinated with monodentate carboxylates, 4 and 6 are hexa‐coordinated with highly distorted octahedral geometry, whereas 5 is penta‐coordinated with distorted trigonal bipyramidal geometry. Probable mode of DNA binding with ligand (Sul) and complexes 1–7 has been revealed via various biophysical techniques (UV–visible spectroscopy, fluorometry and circular dichroism). Intrinsic binding constants (Kb) obtained from UV–visible spectroscopy for Sul and complexes 1–7 are 3.69 × 104, and 7.3 × 103, 1.14 × 104, 1.47 × 104, 1.55 × 104, 1.49 × 104, 2.02 × 104, 1.17 × 104 M−1, respectively. The quenching constants (Ksv) using fluorometric titrations, calculated from competitive binding of ethidium bromide versus Sul/complexes with calf thymus DNA, also correspond to the above results. Circular dichroism spectral patterns of calf thymus DNA with Sul and complexes 1–7 have also been investigated. All the results reveal that the complexes bind with DNA through partial intercalative mode. pBr322 plasmid fragmentation has also been studied using gel electrophoresis, which shows the fragmentation of circular DNA by an increase in nicked form and also by the appearance of linear form with increasing concentration of drug or complexes.

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Section: Resultsmentioning

confidence: 99%

Tri‐ and diorganotin(IV) derivatives of non‐steroidal anti‐inflammatory drug sulindac: Characterization, electronic structures (DFT), DNA binding and plasmid cleavage studies

Kumari

Nath

2017

Applied Organom Chemis

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“…Further, the importance of such systems with the carbonyl substituents is known in many applications, such as optoelectron-ics [6][7][8][9] and as vibrational probe [10]. Moreover, the carbonyl C=O chromophore is recognized as an important spectroscopic probe in studying intermolecular interactions by means of theoretical methods [11], transient optical [12], solid state 17 O NMR [13], UV [14], and IR spectroscopic techniques [10]. In medicinal chemistry, where the C=O is common in many biological structures, it is understood that the oxygen acting as a hydrogen bond acceptor can interact with a binding site.…”

Section: Introductionmentioning

confidence: 99%

“…This interaction is possible by two means: i) through dipole-dipole interaction, due to C=O polarization, or ii) via hydrogen bonding (H-bonding) that involves the two lone-pair electrons of the oxygen sp 2 hybridized orbital [15]. Moreover, recent studies based on fluorescence spectroscopy showed that cycloalkanones bind to BSA protein and DNA and the outcome of this interaction depends on their concentration [16,17].…”

Section: Introductionmentioning

confidence: 99%

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The electronic origin of the ground state spectral features and excited state deactivation in cycloalkanones: the role of intermolecular H-bonding in neat and binary mixtures of solvents

Al‐Ansari

2019

J Mol Model

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In this study, a D-A cycloalkanone (K1) has been investigated by steady state absorption and fluorescence in neat solvents and in three binary mixtures of nonpolar aprotic/polar protic, polar aprotic/polar protic, and polar protic/polar protic solvents. The experimental findings were complemented by density functional theory (DFT), time-dependent density functional theory (TD-DFT), and NBO quantum-mechanical calculations. Experimentally, effective changes in absorption and fluorescence were observed by solute-solvent interaction. The binary K1-solvent 1-solv 2 configuration, modeled at the B3LYP-DFT level, confirms involvement of inter-molecular H-bonding with the carbonyl C=O in the fluorescence deactivation process (quenching). This is supported by considerable electron delocalization from C=O to the solvent's hydroxyl (n O → σ* H-O). This type of hyperconjugation was found to be the main driver for solute-solvent stabilization.

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“…Yu et al. showed that 4‐(dimethylamino)‐4‐amino chalcone can interact into base pair and created a new method to determine trace amount of DNA …”

Section: Introductionmentioning

confidence: 99%

3‐Aminomethyl pyridine chalcone derivatives: Design, synthesis, DNA binding and cytotoxic studies

et al. 2018

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Herein we report design, synthesis, and anticancer activity of compounds 6a-h and 11a-j. Compounds 6a-f were designed based on 3-aminomethyl pyridine attached to different acetamide derivatives and in compounds 6g-h it was attached to coumarin moiety. Coumarin containing compounds 6g-h showed very poor anticancer activity against both A549 (Lungs cancer cell line), and MCF-7 (Breast cancer cell line) cell lines in MTT assay. Compounds 11a-j were designed as derivatives of 3-aminomethyl pyridine and 4-amino chalcones. A series of chalcone derivatives of 3-aminomethyl pyridine 11a-j have been synthesized and screened for their in vitro anticancer activity and DNA binding affinity. Most of the compounds showed very good antimitotic activity against A549 cell line as compared to fluorouracil. Compounds 11g and 11i were selected for DNA-binding studies as they showed excellent activity against cancer cell lines in MTT assay. CT-DNA binding affinity of compounds 11g and 11i have been investigated by UV based DNA titration and fluorescence emission study against DNA-EtBr complex. Interestingly, compound 11i has displayed excellent antiproliferative activity, with IC 0.0067 ± 0.0002 μm, against MCF-7 cell line. Compound 11i has been studied for its cytotoxicity using MTT, LDH, as well as EtBr/AO assay and was found to induce apoptosis in the cancerous cell line.

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Studies on Intramolecular Charge Transfer Fluorescence Probe and DNA Binding Characteristics

Cited by 28 publications

References 21 publications

Tri‐ and diorganotin(IV) derivatives of non‐steroidal anti‐inflammatory drug sulindac: Characterization, electronic structures (DFT), DNA binding and plasmid cleavage studies

Tri‐ and diorganotin(IV) derivatives of non‐steroidal anti‐inflammatory drug sulindac: Characterization, electronic structures (DFT), DNA binding and plasmid cleavage studies

The electronic origin of the ground state spectral features and excited state deactivation in cycloalkanones: the role of intermolecular H-bonding in neat and binary mixtures of solvents

3‐Aminomethyl pyridine chalcone derivatives: Design, synthesis, DNA binding and cytotoxic studies

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