Development of a fluorescent chalcone library and its application in the discovery of a mouse embryonic stem cell probe

Lee, Sung-Chan; Kang, Nam‐Young; Park, Sung-Jin; Yun, Seong‐Wook; Chandran, Yogeswari; Chang, Young‐Tae

doi:10.1039/c2cc31662e

Cited by 58 publications

(34 citation statements)

References 31 publications

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“…54,79 For example, Lee et al designed a novel library of 160 fluorescent chalcone amide compounds. 70 Two amides were introduced into these chalcones on each side of the scaffold to enhance the fluorescence emission intensity. Interestingly, CDg4 ( 5 ) was applied as a novel green fluorescent probe for detecting mouse embryonic stem cells (mESCs), where its molecular binding target was identified as the glycogen of the stem cell colony surface.…”

Section: Fluorescent Properties Of Chalconesmentioning

confidence: 99%

Chalcone: A Privileged Structure in Medicinal Chemistry

et al. 2017

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Privileged structures have been widely used as an effective template in medicinal chemistry for drug discovery. Chalcone is a common simple scaffold found in many naturally occurring compounds. Many chalcone derivatives have also been prepared due to their convenient synthesis. These natural products and synthetic compounds have shown numerous interesting biological activities with clinical potentials against various diseases. This review aims to highlight the recent evidence of chalcone as a privileged scaffold in medicinal chemistry. Multiple aspects of chalcone will be summarized herein, including the isolation of novel chalcone derivatives, the development of new synthetic methodologies, the evaluation of their biological properties, and the exploration of the mechanisms of action as well as target identification. This review is expected to be a comprehensive, authoritative, and critical review of the chalcone template to the chemistry community.

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Section: Fluorescent Properties Of Chalconesmentioning

confidence: 99%

Chalcone: A Privileged Structure in Medicinal Chemistry

et al. 2017

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“…In addition to therapeutic molecules, chalcones have also been investigated as imaging probes, including positron emission tomography (PET) radiotracers targeting beta-amyloid plaques in Alzheimer's disease (Ono et al 2010;Chauhan et al 2014;Ono et al 2009). The highly conjugated systems can be modified to include electron push-pull pairs to produce fluorescent compounds (Zhuang et al 2017;Lee et al 2012). Lee et al (2012) developed a fluorescent probe based around the chalcone pharmacophore for in vitro imaging of mouse embryonic stem cells (Lee et al 2012).…”

Section: Introductionmentioning

confidence: 99%

“…The highly conjugated systems can be modified to include electron push-pull pairs to produce fluorescent compounds (Zhuang et al 2017;Lee et al 2012). Lee et al (2012) developed a fluorescent probe based around the chalcone pharmacophore for in vitro imaging of mouse embryonic stem cells (Lee et al 2012). The lead molecule (CDg4) was identified and hypothesised to bind to the unique secondary structure of glycogen α(1 ➔ 6) in embryonic stem cell colonies.…”

Section: Introductionmentioning

confidence: 99%

Development of a fluorine-18 radiolabelled fluorescent chalcone: evaluated for detecting glycogen

Allott

Bričkutė

Chen

et al. 2020

EJNMMI radiopharm. chem.

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Background: Glycogen is a multibranched polysaccharide of glucose produced by cells to store energy and plays a key role in cancer. A previously reported fluorescent probe (CDg4) was shown to selectively bind glycogen in mouse embryonic stem cells, however the molecule was not evaluated in cancer cells. We report the synthesis and biological evaluation of a dual-modality imaging probe based on CDg4, for positron emission tomography (PET) and fluorescence microscopy. Results: A fluorine-18 radiolabelled derivative of CDg4, ([ 18 F]5) for in vivo quantification of total glycogen levels in cancer cells was developed and synthesised in 170 min with a non-decay corrected radiochemical yield (RCY n.d.c) of 5.1 ± 0.9% (n = 4) in > 98% radiochemical purity. Compound 5 and [ 18 F]5 were evaluated in vitro for their potential to bind glycogen, but only 5 showed accumulation by fluorescence microscopy. The accumulation of 5 was determined to be specific as fluorescent signal diminished upon the digestion of carbohydrate polymers with αamylase. PET imaging in non-tumour bearing mice highlighted rapid hepato-biliaryintestinal elimination of [ 18 F]5 and almost complete metabolic degradation after 60 min in the liver, plasma and urine, confirmed by radioactive metabolite analysis. Conclusions: Fluorescent compound 5 selectively accumulated in glycogen containing cancer cells, identified by fluorescence microscopy; however, rapid in vivo metabolic degradation precludes further investigation of [ 18 F]5 as a PET radiopharmaceutical.

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“…Chalcone and its derivatives are widely used as fluorescent probes [20,21], materials with significant nonlinear responses [22] and typical chromophore components for photochemical sensors [23]. Charge transfer character of the low-lying ππ ⁎ transition from the phenyl ring to the polyene chain allows one to vary the energy of the intense transition introducing substituents in the phenyl ring [9].…”

Section: Introductionmentioning

confidence: 99%