Design, synthesis and biological activity of bis-sulfonyl-BODIPY probes for tumor cell imaging

Shao, Chen; Wang, Yuling; Jin, Guofan

doi:10.1016/j.bmcl.2021.128292

Cited by 8 publications

(2 citation statements)

References 29 publications

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“…The current study is directed towards synthesis and investigation of the biological properties of novel 3-spiro-indolin-2-ones prepared through azomethine dipolar cycloaddition to the exocyclic olefinic linkage of 3,5-bis(arylidene)- N -sulfonyl-4-piperidones. Interest in conjugation of the sulfonyl group to the heterocyclic nitrogen of 4-piperidone forming a sulfonamide fragment is due to the distinct physicochemical properties of the oxygen-rich sulfonyl residue that may increase the hydrophilicity of the bio-active agent 29 , 30 . Sulfonamides were flagged as attractive bio-active targets long ago (Gerhard Domagk, 1935) due to their antibacterial properties 31 .…”

Section: Introductionmentioning

confidence: 99%

Development of spiro-3-indolin-2-one containing compounds of antiproliferative and anti-SARS-CoV-2 properties

Fawazy

Panda

Mostafa

et al. 2022

Sci Rep

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A series of 1″-(alkylsulfonyl)-dispiro[indoline-3,2′-pyrrolidine-3′,3″-piperidine]-2,4″-diones 6a‒o has been synthesized through regioselective multi-component azomethine dipolar cycloaddition reaction of 1-(alkylsulfonyl)-3,5-bis(ylidene)-piperidin-4-ones 3a‒h. X-ray diffraction studies (6b‒d,h) confirmed the structures. The majority of the synthesized analogs reveal promising antiproliferation properties against a variety of human cancer cell lines (MCF7, HCT116, A431 and PaCa2) with good selectivity index towards normal cell (RPE1). Some of the synthesized agents exhibit potent inhibitory properties against the tested cell lines with higher efficacies than the standard references (sunitinib and 5-fluorouracil). Compound 6m is the most potent. Multi-targeted inhibitory properties against EGFR and VEGFR-2 have been observed for the synthesized agents. Flow cytometry supports the antiproliferation properties and shows the tested agents as apoptosis and necrosis forming. Vero cell viral infection model demonstrates the anti-SARS-CoV-2 properties of the synthesized agents. Compound 6f is the most promising (about 3.3 and 4.8 times the potency of the standard references, chloroquine and hydroxychloroquine). QSAR models explain and support the observed biological properties.

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Section: Introductionmentioning

confidence: 99%

Development of spiro-3-indolin-2-one containing compounds of antiproliferative and anti-SARS-CoV-2 properties

Fawazy

Panda

Mostafa

et al. 2022

Sci Rep

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“…Inspired by this, at the beginning of the present study, we figured out that the introduction of external active groups could change the biocompatibility of BODIPY and endow the target compound with antitumor activity. Pyrimidine derivatives, an antimetabolite that has been active in clinical practice for more than 60 years, have aroused our interest ( Shao et al, 2021 ; Xu et al, 2021 ). The 2,4,5, and 6 sites of the pyrimidine ring can be substituted, and the existence of multiple modified sites makes pyrimidine occupy an indispensable position in the field of organic synthesis ( De Coen et al, 2016 ; Xu et al, 2020 ; Mittersteiner et al, 2021 ).…”

Section: Introductionmentioning

confidence: 99%

Symmetry dual functional pyrimidine-BODIPY probes for imaging targeting and activity study

Liu²,

Wang³

et al. 2022

Front. Chem.

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Nondestructive diagnosis of tumor has always been the goal of scientists. Fluorescent dyes have become the rising star in the field of cancer diagnosis because of their excellent characteristics. Therefore, in this work, fluorescence probes d-Y-B and dO-Y-B with anti-tumor activity were constructed by introducing pyrimidine groups with high anti-tumor activity using fluorescence dye BODIPY as parent nucleus. The modified BODIPY group in the structure had the advantage of fluorescent dye, ensuring the strong fluorescence and photosensitivity of the target compound. That ethylenediamine acts as a bridge with two -NH- groups to increase molecular hydrogen bonding, and can bind firmly to multiple proteins. Co-localization of the target compounds d-Y-B and dO-Y-B with the hoechst dye for labeling living cells showed that these compounds had high biocompatibility and photostability for localization to HeLa cells. In vivo imaging in mice can realize specific localization and real-time visualization of tumor cells. The results of cytotoxicity experiments in vitro and computer software simulating molecular docking confirmed the potential of the target compounds as an anticancer agents. The bifunctional probe realized visualization of cancer cells in mice, and can kill cancer cells by anti-proliferation, which may provide a direction for future anticancer drug development.

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A Novel Ethylenediamine Bridged Indole-BODIPY Schiff Base Applied for Selective Response to Fe, Cu and Al Detection

Wang,

Feng,

Zhang

et al. 2024

J Fluoresc

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Design, synthesis and biological activity of bis-sulfonyl-BODIPY probes for tumor cell imaging

Cited by 8 publications

References 29 publications

Development of spiro-3-indolin-2-one containing compounds of antiproliferative and anti-SARS-CoV-2 properties

Development of spiro-3-indolin-2-one containing compounds of antiproliferative and anti-SARS-CoV-2 properties

Symmetry dual functional pyrimidine-BODIPY probes for imaging targeting and activity study

A Novel Ethylenediamine Bridged Indole-BODIPY Schiff Base Applied for Selective Response to Fe, Cu and Al Detection

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