Synthesis and photophysical characterization of quasi push–pull dicyanodibenzodioxins and their anti-tumor activity against glioma cell line C6

Banerjee, Subhadeep; Chattopadhyay, Asis Kumar; Banerjee, Arundhati; Haridas, Meera; Saini, Praveen; Das, Mitali; Majik, Mahesh S.; Maurya, Yogesh Kumar

doi:10.1016/j.bmcl.2015.01.006

Cited by 13 publications

(41 citation statements)

References 18 publications

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“…This could be due to their better biocompatibility and solubility in polar solvents compared to probes based on naphthalene and anthracene. In this context dibenzodioxin compounds (Figure 1, 4 and 5) 11,12 are examples of an important class of heteroaromatic molecules that could be further modified with donor-π-acceptor architecture as probes for long wavelength applications. Dibenzodioxins have exhibited in vitro and in vivo antitumor activity against a range of different cell lines.…”

Section: Letter Syn Lettmentioning

confidence: 99%

“…Dibenzodioxins have exhibited in vitro and in vivo antitumor activity against a range of different cell lines. [12][13][14] We recently published a simple synthesis of 2,3-dicyanodibenzodioxin (5, and other examples), utilizing a double S N Ar reaction between catechols and an activated ortho-difluorobenzene. Theoretical studies on their photophysical properties and antitumor activity against glioma cell line C6 were also reported.…”

Section: Letter Syn Lettmentioning

confidence: 99%

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Synthesis and Optical Properties of 1,4- and 1,2-Dicyanodibenzodioxins Possessing Donor–π-Acceptor Architecture

Banerjee

Chattopadhyay

Saini

2015

Synlett

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The synthesis and photophysical characterization of isomeric 1,4-and 1,2-dicyanodibenzodioxins is reported. The molecules exhibit optical spectra in the visible region and possess large (ca. 100 nm) Stokes shifts. The synthetic protocol is simple and high-yielding and the presence of replaceable fluorine atoms on the activated dibenzodioxin moiety provides the opportunity for further transformation towards molecules bearing push-pull architecture.

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Section: Letter Syn Lettmentioning

confidence: 99%

Section: Letter Syn Lettmentioning

confidence: 99%

Synthesis and Optical Properties of 1,4- and 1,2-Dicyanodibenzodioxins Possessing Donor–π-Acceptor Architecture

Banerjee

Chattopadhyay

Saini

2015

Synlett

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“…In course of our research into design and synthesis of novel fluorescent organic molecules, we have developed several push‐pull type dibenzodioxins and phenazines, some of which have shown moderate to good emission capacity, while some others are non‐emissive . These molecules have proven their potential in (1) medicinal chemistry as anti‐tumor agents in vitro ,, (2) as fluorescent imaging agents in microscopy and as (3) pH sensitive probes . These functions were attributed to the extensive charge delocalization possible in the molecules, through the push and pull groups connected by an anthracene‐like heteroaromatic (dibenzodioxin/phenazine) moiety.…”

Section: Introductionmentioning

confidence: 99%

“…The symmetric nature of the groups in the benzonitrile ring of 1 a and proximity of the push and pull groups was responsible for the charge delocalization and observed optical properties . In contrast, the first generation dibenzodioxins with nitrile groups, where the electron withdrawing groups were further away from the dioxin moiety were mostly non‐fluorescent . Further developments were made towards substituted dibenzodioxins by inclusion of electron withdrawing carboxy methyl ester groups in the previously unsubstituted benzene ring of 1 a to yield 1 b and 1 c .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Green Emitting Multi‐substituted Dibenzodioxins and Related Heteroacenes and Computational Investigation of Substituent Effects on Emission Spectra

et al. 2020

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Push‐pull dibenzodioxins with electron withdrawing and donating groups were prepared in good yields through a short and simple synthesis. Strong green emission above 500 nm occurs in those derivatives where there is maximum charge transfer to the most electron deficit terephthalonitrile ring, from proximal cyclic amino donor groups. Theoretical calculations support experimental findings through evaluation of excited state properties. In molecules with a nitro group, the excited state localizes electron density exclusively onto it and twisted nitro geometry was also found. In effect, electronic charge cannot relocate into the molecular plane, rendering them non‐fluorescent. Also, studies on the fluorescent derivatives show that best emission would occur when the donor moiety contains a saturated cyclic amino ring and the amines are 2°. Overall, our study establishes structure‐property guidelines and limits on dibenzodioxin functionalization towards preparing fluorescent derivatives of the same.

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“…Hence, structural analogues of PAHs could be used as platforms for designing small molecular drugs. We have focused our research on design and synthesis of push-pull dibenzodioxins and phenazines as attractive options due to their planar ‘anthracene-like’ structures and well established bioactivity [ 3 , 4 ]. We previously synthesised push-pull dibenzodioxin molecules ( Fig.…”

Section: Introductionmentioning

confidence: 99%

Spectroscopic and viscometric determination of DNA-binding modes of some bioactive dibenzodioxins and phenazines

Phadte

Banerjee

Mate

et al. 2019

Biochemistry and Biophysics Reports

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Push-pull dibenzodioxins and phenazines having ‘anthracene-like’ planar structures and good charge transfer character had been previously synthesised in our laboratory. The dibenzodioxins had earlier proven their anti-proliferative nature against HeLa tumor cell lines. Since phenazines are structural analogues of the former, these molecules were evaluated in course of the current study for their cytotoxic action against HeLa cell lines and they exhibited strong anti-tumor activity. This behavior could be related to their good DNA binding property. The DNA binding modes of molecules 1 – 4 (Fig. 1) were evaluated using various experimental techniques and they interacted with DNA in a non-covalently by both intercalative as well as groove binding mechanisms. Molecule 1 follows predominantly intercalative binding mode whereas molecules 2 and 3 have nearly equal and opposite preferences for both groove binding and intercalative modes. For molecule 4 , groove binding is preferred mode of binding to DNA. A rationale for such differential binding behaviour is provided based on the subtle structural differences in our synthesised dibenzodioxins and phenazines. Elucidation of the mode of a molecule-DNA-binding event is relevant for understanding the mechanism of action of these molecules and will help promote further research into designing better DNA targeting small molecules.

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Synthesis and photophysical characterization of quasi push–pull dicyanodibenzodioxins and their anti-tumor activity against glioma cell line C6

Cited by 13 publications

References 18 publications

Synthesis and Optical Properties of 1,4- and 1,2-Dicyanodibenzodioxins Possessing Donor–π-Acceptor Architecture

Synthesis and Optical Properties of 1,4- and 1,2-Dicyanodibenzodioxins Possessing Donor–π-Acceptor Architecture

Synthesis of Green Emitting Multi‐substituted Dibenzodioxins and Related Heteroacenes and Computational Investigation of Substituent Effects on Emission Spectra

Spectroscopic and viscometric determination of DNA-binding modes of some bioactive dibenzodioxins and phenazines

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