Simple and practical, highly sensitive and responsive recognition of cysteine: Design, synthesis and mechanism study of a novel curcumin fluorescent probe

Hu, Jiatang; Wang, Yuling; Shao, Tingyu; Lian, Guangchang; Hu, Kaibo; Liu, Ying; Zhou, Meng; Wang, Xiangpeng; Huang, Lizhuan; Meng, Xinlei; Jin, Guofan

doi:10.1016/j.arabjc.2022.104087

Cited by 11 publications

(6 citation statements)

References 38 publications

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“…In this case, some excellent curcumin-based fluorescent sensors have constructed. 36–38 Therefore, it is promising for the development of a new curcumin-based fluorescent sensor for H 2 O 2 detection.…”

Section: Introductionmentioning

confidence: 99%

A highly effective “naked eye” colorimetric and fluorimetric curcumin-based fluorescent sensor for specific and sensitive detection of H₂O₂in vivo and in vitro

Shen

Liang

et al. 2023

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Section: Introductionmentioning

confidence: 99%

A highly effective “naked eye” colorimetric and fluorimetric curcumin-based fluorescent sensor for specific and sensitive detection of H₂O₂in vivo and in vitro

Shen

Liang

et al. 2023

Analyst

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“…Curcumine and curcuminoid derivatives provide good basis for the development of sensors [ 12 , 13 , 14 , 15 , 16 , 17 ]. Moreover, synthetic modifications of curcuminoids and hemicurcuminoids allow an embedding of different functional groups into their molecules [ 18 , 19 ].…”

Section: Introductionmentioning

confidence: 99%

Supramolecular Optimization of Sensory Function of a Hemicurcuminoid through Its Incorporation into Phospholipid and Polymeric Polydiacetylenic Vesicles: Experimental and Computational Insight

et al. 2023

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This work presents the synthesis of a new representative of hemicurcuminoids with a nonyloxy substituent (HCur) as a fluorescent amphiphilic structural element of vesicular aggregates based on phosphatidylcholine (PC), phosphatidylserine (PS), and 10,12-pentacosadiynoic acid (PCDA). Both X-ray diffraction analysis of the single crystal and 1H NMR spectra of HCur in organic solvents indicate the predominance of the enol-tautomer of HCur. DFT calculations show the predominance of the enol tautomer HCur in supramolecular assemblies with PC, PS, and PCDA molecules. The results of the molecular modeling show that HCur molecules are surrounded by PC and PS with a rather weak exposure to water molecules, while an exposure of HCur molecules to water is enhanced under its supramolecular assembly with PCDA molecules. This is in good agreement with the higher loading of HCur into PC(PS) vesicles compared to PCDA vesicles converted into polydiacetylene (PDA) ones by photopolymerization. HCur molecules incorporated into HCur-PDA vesicles exhibit greater planarity distortion and hydration effect in comparison with HCur-PC(PS) ones. HCur-PDA is presented as a dual fluorescence-chromatic nanosensor responsive to a change in pH within 7.5–9.5, heavy metal ions and polylysine, and the concentration-dependent fluorescent response is more sensitive than the chromatic one. Thus, the fluorescent response of HCur-PDA allows for the distinguishing between Cd2+ and Pb2+ ions in the concentration range 0–0.01 mM, while the chromatic response allows for the selective sensing of Pb2+ over Cd2+ ions at their concentrations above 0.03 mM.

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“…The important characteristic and active components extracted from the traditional chinese medicine turmeric have good application prospects and clinical therapeutic potential in the diversity of pharmacological actions ( Kocaadam and Sanlier 2017 ; Hosseini and Hosseinzadeh 2018 ; Hay et al, 2019 ; Liu et al, 2022a ). In a number of studies involving cancer and tumor cells, it was found that curcumin may play a good inhibitory role in a variety of different links ( Mortezaee et al, 2019 ; Zendehdel et al, 2019 ), it effectively inhibits the uncontrolled metastasis of cancer cells ( Jia et al, 2019 ), the proliferation of tumor cells, the activity of cancer-inducing chemicals in the stomach and colon ( Porras et al, 2020 ; Naji et al, 2021 ), and inhibits angiogenesis by modulating protease activity ( Binion et al, 2008 ; Liu et al, 2022b ; Hu et al, 2022 ). However, curcumin has some disadvantages such as poor water solubility, low bioavailability and poor gastrointestinal absorption ( Sabet et al, 2021 ; Sohn et al, 2021 ).…”

Section: Introductionmentioning

confidence: 99%

Application study of curcumin fluorescent complex coated with pharmaceutical excipients for cell imaging

et al. 2023

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Taking curcumin as the starting point, β-cyclodextrin was introduced on both sides, and lipid-soluble curcumin was coated by acrylic resin using oil-in-water strategy. Four different types of curcumin fluorescent complexes EPO-Curcumin (EPO-Cur), L100-55-Curcumin (L100-55-Cur), EPO -Curcumin-β-cyclodextrin (EPO-Cur-β-cd) and L100-55-Curcumin-β-cyclodextrin (L100-55-Cur-β-cd) were prepared to solve their own solubility and biocompatibility issues. The prepared curcumin fluorescent complexes were characterized and tested by spectroscopy. The characteristic peaks of 3446 cm−1 (hydroxyl group), 1735cm−1(carbonyl group) and 1455 cm−1 (aromatic group) were determined in the infrared spectrum. In the fluorescence emission spectrum, it was found that the emission intensity of different curcumin fluorescent complexes in polar solvents reached hundreds of times. Through the transmission electron microscopy shows that acrylic resin tightly coats curcumin into rods or clusters. In order to observe their compatibility with tumor cells more directly, live cell fluorescence imaging was carried out, and it was found that all four kinds of curcumin fluorescence complexes had good biocompatibility. In particular, the effect of EPO-Cur-β-cd and L100-55-Cur-β-cd is better than that of EPO-Cur and L100-55-Cur.

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Simple and practical, highly sensitive and responsive recognition of cysteine: Design, synthesis and mechanism study of a novel curcumin fluorescent probe

Cited by 11 publications

References 38 publications

A highly effective “naked eye” colorimetric and fluorimetric curcumin-based fluorescent sensor for specific and sensitive detection of H₂O₂in vivo and in vitro

A highly effective “naked eye” colorimetric and fluorimetric curcumin-based fluorescent sensor for specific and sensitive detection of H₂O₂in vivo and in vitro

Supramolecular Optimization of Sensory Function of a Hemicurcuminoid through Its Incorporation into Phospholipid and Polymeric Polydiacetylenic Vesicles: Experimental and Computational Insight

Application study of curcumin fluorescent complex coated with pharmaceutical excipients for cell imaging

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Simple and practical, highly sensitive and responsive recognition of cysteine: Design, synthesis and mechanism study of a novel curcumin fluorescent probe

Cited by 11 publications

References 38 publications

A highly effective “naked eye” colorimetric and fluorimetric curcumin-based fluorescent sensor for specific and sensitive detection of H2O2in vivo and in vitro

A highly effective “naked eye” colorimetric and fluorimetric curcumin-based fluorescent sensor for specific and sensitive detection of H2O2in vivo and in vitro

Supramolecular Optimization of Sensory Function of a Hemicurcuminoid through Its Incorporation into Phospholipid and Polymeric Polydiacetylenic Vesicles: Experimental and Computational Insight

Application study of curcumin fluorescent complex coated with pharmaceutical excipients for cell imaging

Contact Info

Product

Resources

About

A highly effective “naked eye” colorimetric and fluorimetric curcumin-based fluorescent sensor for specific and sensitive detection of H₂O₂in vivo and in vitro

A highly effective “naked eye” colorimetric and fluorimetric curcumin-based fluorescent sensor for specific and sensitive detection of H₂O₂in vivo and in vitro