Fluorescence of curcumin in alkaline dimethyl sulfoxide and the effects of alkali metal cations on it

Tsaplev, Yu. B.; Lapina, V. A.; Trofimov, Aleksei V.

doi:10.1016/j.jphotochem.2020.112967

Cited by 8 publications

(8 citation statements)

References 27 publications

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“…Cancer cells express more AQPs in their cytoplasmic membrane than normal cells; thus, combination therapy of CAP and CUR has more effect on B16-F10 when compared to the L929 cell line. Previous studies reported the solvent can affect the physicochemical properties of CUR [66][67][68]. Therefore, DMSO and culture medium may have a role in the interactions between CUR and AQP channels.…”

Section: Discussionmentioning

confidence: 99%

Combined Effect of Cold Atmospheric Plasma and Curcumin in Melanoma Cancer

Yazdani

Mehrabanjoubani

Rafiei

et al. 2021

BioMed Research International

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Curcumin (CUR) has interesting properties to cure cancer. Cold atmospheric plasma (CAP) is also an emerging biomedical technique that has great potential for cancer treatment. Therefore, the combined effect of CAP and CUR on inducing cytotoxicity and apoptosis of melanoma cancer cells might be promising. Here, we investigated the combined effects of CAP and CUR on cytotoxicity and apoptosis in B16-F10 melanoma cancer cells compared to L929 normal cells using MTT method, acridine orange/ethidium bromide fluorescence microscopic assay, and Annexin V/PI flow cytometry. In addition, the activation of apoptosis pathways was evaluated using BCL2, BAX, and Caspase-3 (CASP3) gene expression and ratio of BAX to BCL2 (BAX/BCL2). Finally, in silico study was performed to suggest the molecular mechanism of this combination therapy on melanoma cancer. Results showed that although combination therapy with CUR and CAP has cytotoxic and apoptotic effects on cancer cells, it did not improve apoptosis rate in melanoma B16-F10 cancer cells compared to monotherapy with CAP or CUR. In addition, evaluation of gene expression in cancer cell line confirmed that CUR and CAP concomitant treatment did not enhance the expression of apoptotic genes. In silico analysis of docked model suggested that CUR blocks aquaporin- (AQP-) 1 channel and prevents penetration of CAP-induced ROS into the cells. In conclusion, combination therapy with CAP and CUR does not improve the anticancer effect of each alone.

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Section: Discussionmentioning

confidence: 99%

Combined Effect of Cold Atmospheric Plasma and Curcumin in Melanoma Cancer

Yazdani

Mehrabanjoubani

Rafiei

et al. 2021

BioMed Research International

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“…Tsaplev et al suggested that Cur À 3 exists as metal coordinated [CurM] 2À where M is an alkali metal to explain the stability and higher fluorescence quantum yield of Cur À 3 . [23] Our time-resolved experiments suggested that the excited state lifetime of Cur À 3 is higher than that of CurH 3 (Figure 3a, Table 1). While, formation of a metal complex may be one of the factors responsible for higher excited state lifetime, it is definitely not the only one.…”

Section: Chemphyschemmentioning

confidence: 79%

“…[20,21] Recently, Tsaplev et al reported the unusual stability of CurH 3 in alkaline dimethyl sulfoxide (DMSO) which they attributed to the complex formation between CurH 3 β-diketone oxygens and a metal cation. [22,23] [2,2'-Bipyridyl]-3,3'-diol is a another well studied molecule because of its unique excited state double proton transfer phenomenon. [24,25] Photophysical studies have also been performed on other anticancer drug molecules doxorubicin, ellipticine, and topotecan, to study their behavior in confined media and interaction with lipid bilayers, proteins and DNA.…”

Section: Introductionmentioning

confidence: 99%

Excited State Photophysics of Curcumin and its Modulation in Alkaline Non‐Aqueous Medium

Ghosh,

Parida,

Khatoon

et al. 2023

ChemPhysChem

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Curcumin, a well‐known medicinal pigment, has seen limited applications in biology despite having great potential as a therapeutic drug. Deprotonation is one of the possible ways to enhance solubility of curcumin in polar solvent. Here, we have explored the effect of deprotonation on the ultrafast dynamics of this biomolecule with the help of the time‐resolved fluorescence spectroscopic measurements using the femtosecond fluorescence upconversion technique. The excited state photophysics of fully deprotonated curcumin significantly differs from that of neutral curcumin. We have observed that the completely deprotonated curcumin not only has higher quantum yield, but also higher excited state lifetime and slower solvation dynamics in comparison to neutral curcumin. We propose solvation dynamics and intramolecular charge transfer as the excited state processes associated with the radiative decay of the completely deprotonated molecule, while ruling out the possibility of excited state proton exchange or proton transfer. Our results are well supported by time‐dependent density‐functional theory calculations. Lastly, we have also demonstrated the possibility of modulating the ultrafast dynamics of fully deprotonated curcumin using non‐aqueous alkaline binary solvent mixtures. We believe our results will provide significant physical insight towards unveiling the excited state dynamics of this molecule.

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“…The planarity of HCur molecules can be distorted when their R-substituents are incorporated into the hydrophobic layer of the vesicles, which may blue-shift the emission bands. The deprotonation of the enolic form of curcumine and curcuminoide derivatives is another reason for the changes in their emissive properties [ 65 ]. The phase transitions in the mixed bilayers should also be mentioned as the factor triggering a translocation of the dye molecules from the hydrophobic core of the PhL bilayers to their polar periphery, typically manifested by the changes in the dye spectra [ 66 , 67 ].…”

Section: Resultsmentioning

confidence: 99%

“…The enolic forms of HCur molecules can undergo dissociation in specific pH conditions, followed by the enhancement of the lower energy emission [ 65 ]. The lack of detectable changes in the ratios of the intensities of the lower and higher energy transitions of HCur -PDA or HCur -PC(PS) vesicles under the acidification of their aqueous dispersions to pH values below 7.5 ( Figure S5a–c ) indicates the insignificant deprotonation of HCur molecules in the aforesaid conditions.…”

Section: Resultsmentioning

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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Fluorescence of curcumin in alkaline dimethyl sulfoxide and the effects of alkali metal cations on it

Cited by 8 publications

References 27 publications

Combined Effect of Cold Atmospheric Plasma and Curcumin in Melanoma Cancer

Combined Effect of Cold Atmospheric Plasma and Curcumin in Melanoma Cancer

Excited State Photophysics of Curcumin and its Modulation in Alkaline Non‐Aqueous Medium

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

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