Chemistry, chemical biology and photophysics of certain new chromene–triazole–coumarin triads as fluorescent inhibitors of CDK2 and CDK4 induced cancers

Shankar, E. P. Shyam; Bahulayan, D.

doi:10.1039/c9nj02924a

Cited by 6 publications

(4 citation statements)

References 38 publications

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“…In addition to two carbon atoms with sp 2 hybridization on the triazole ring, it is thought that three nitrogen atoms can make the system electron rich. Thus, it can be stated that electron transfer through triazole and coumarin rings is enabled and increases the absorption capacity of coumarin . This situation can be clearly seen in Table and Figures and .…”

Section: Resultsmentioning

confidence: 82%

“…Thus, it can be stated that electron transfer through triazole and coumarin rings is enabled and increases the absorption capacity of coumarin. [41] This situation can be clearly seen in Table 3 and Figures 7 and 8. Table 3 demonstrates that the molar absorption coefficient of the coumarin backbone before binding to triazole is lower.…”

Section: Triazole Effect On Absorption and Fluorescence Spectra Of Ctdmentioning

confidence: 82%

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Synthesis and solvent‐dependent photophysics of a novel fluorescent triazole‐coumarin‐based dye

Kaya

Menteşe

2020

Journal of Heterocyclic Chem

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Synthesis of a new coumarin‐triazole‐based dye and its photophysical parameters such as absorption, fluorescence emission, and fluorescence quantum yield were investigated. Studies have shown that the present dye has symmetry with a mirror image, especially in the ethanol solvent, with respect to the absorption and fluorescence spectra. As a result of the UV‐vis and fluorescence spectroscopy techniques used, it was determined that absorption and emission spectra were shifted to the red with increasing solvent polarity. In addition, the spectral data of the synthesized compound exhibited that the stokes shifts are small, usually less than 50 nm, and the quantum yields are significantly high. In accordance with the results obtained, it can be stated that this novel dye synthesized here can offer an insight into application in sensor applications as analytical or biosensors, optoelectronic devices, and medicine industry.

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Section: Resultsmentioning

confidence: 82%

Section: Triazole Effect On Absorption and Fluorescence Spectra Of Ctdmentioning

confidence: 82%

Synthesis and solvent‐dependent photophysics of a novel fluorescent triazole‐coumarin‐based dye

Kaya

Menteşe

2020

Journal of Heterocyclic Chem

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“…Moreover, being widely used in drug discovery [ 15 , 16 ], CuAAC has been applied in other areas, including bioimaging [ 17 , 18 ], biological [ 19 ], and biomedical [ 20 ] applications, synthesis of polymers [ 21 , 22 ] and dendrimers [ 23 , 24 ], and preparation of chemosensors [ 25 ], among others.…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in Bioactive Flavonoid Hybrids Linked by 1,2,3-Triazole Ring Obtained by Click Chemistry

et al. 2021

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As a result of the biological activities of natural flavonoids, several synthetic strategies aiming to obtain analogues with improved potency and/or pharmacokinetic profile have been developed. Since the triazole ring has been associated with several biological activities and metabolic stability, hybridization with a 1,2,3-triazole ring has been increasingly reported over the last years. The feasible synthesis through copper (I) catalyzed azide-alkyne cycloaddition (CuAAC) has allowed the accomplishment of several hybrids. Since 2017, almost 700 flavonoid hybrids conjugated with 1,2,3-triazole, including chalcones, flavones, flavanones and flavonols, among others, with antitumor, antimicrobial, antidiabetic, neuroprotective, anti-inflammatory, antioxidant, and antifouling activity have been reported. This review compiles the biological activities recently described for these hybrids, highlighting the mechanism of action and structure–activity relationship (SAR) studies.

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“…This supported them to be encapsulated into the hydrophobic pockets of CDK2 and CDK4. Furthermore, there is also a possibility of hydrogen bonding and π–cation interactions between the inhibitor molecules and CDK4 enhancing the binding affinities [ 37 ]. A recent study showed that the newly synthesized 4-flourophenylacetamide-acetyl coumarin (4-FPAC) IV produced cytotoxic effect and arrested metastasis in A549 as well as cell cycle progression at the G0/G1 by modulating p21, CDK2, and CDK4 expression [ 38 ] ( Figure 2 ).…”

Section: Introductionmentioning

confidence: 99%

Discovery of New Coumarin-Based Lead with Potential Anticancer, CDK4 Inhibition and Selective Radiotheranostic Effect: Synthesis, 2D & 3D QSAR, Molecular Dynamics, In Vitro Cytotoxicity, Radioiodination, and Biodistribution Studies

et al. 2021

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Novel 6-bromo-coumarin-ethylidene-hydrazonyl-thiazolyl and 6-bromo-coumarin-thiazolyl-based derivatives were synthesized. A quantitative structure activity relationship (QSAR) model with high predictive power r2 = 0.92, and RMSE = 0.44 predicted five compounds; 2b, 3b, 5a, 9a and 9i to have potential anticancer activities. Compound 2b achieved the best ΔG of –15.34 kcal/mol with an affinity of 40.05 pki. In a molecular dynamic study 2b showed an equilibrium at 0.8 Å after 3.5 ns, while flavopiridol did so at 0.5 Å after the same time (3.5 ns). 2b showed an IC50 of 0.0136 µM, 0.015 µM, and 0.054 µM against MCF-7, A-549, and CHO-K1 cell lines, respectively. The CDK4 enzyme assay revealed the significant CDK4 inhibitory activity of compound 2b with IC50 of 0.036 µM. The selectivity of the newly discovered lead compound 2b toward localization in tumor cells was confirmed by a radioiodination biological assay that was done via electrophilic substitution reaction utilizing the oxidative effect of chloramine-t. 131I-2b showed good in vitro stability up to 4 h. In solid tumor bearing mice, the values of tumor uptake reached a height of 5.97 ± 0.82%ID/g at 60 min p.i. 131I-2b can be considered as a selective radiotheranostic agent for solid tumors with promising anticancer activity.

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Chemistry, chemical biology and photophysics of certain new chromene–triazole–coumarin triads as fluorescent inhibitors of CDK2 and CDK4 induced cancers

Abstract: The chromene–triazole–coumarin triads synthesized through the MCR-Click strategy possess intense solution state fluorescence, intense solid-state fluorescence and CDK2/CDK4 targeted cytotoxic activity against human cervical cancer cells (HeLa).

Cited by 6 publications

References 38 publications

Synthesis and solvent‐dependent photophysics of a novel fluorescent triazole‐coumarin‐based dye

Synthesis and solvent‐dependent photophysics of a novel fluorescent triazole‐coumarin‐based dye

Recent Advances in Bioactive Flavonoid Hybrids Linked by 1,2,3-Triazole Ring Obtained by Click Chemistry

Discovery of New Coumarin-Based Lead with Potential Anticancer, CDK4 Inhibition and Selective Radiotheranostic Effect: Synthesis, 2D & 3D QSAR, Molecular Dynamics, In Vitro Cytotoxicity, Radioiodination, and Biodistribution Studies

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