- Effect of solvent on the photophysical properties of isoxazole derivative of curcumin: A combined spectroscopic and theoretical study
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The present work aims to decipher the photophysics of a β-diketo modified curcumin analog named isoxazole derivative of curcumin (IOC). IOC itself happens to be a potential drug molecule possessing numerous biological applications such as; anti-cancer, an
- Sharma, Manisha,Pal, Uttam,Kumari, Mamta,Bagchi, Damayanti,Rani, Swati,Mukherjee, Dipanjan,Bera, Arpan,Pal, Samir Kumar,Saha Dasgupta, Tanusree,Mozumdar, Subho
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- Design, synthesis, biological evaluation and molecular docking of curcumin analogues as antioxidant, cyclooxygenase inhibitory and anti-inflammatory agents
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Curcuminoids were isolated from Curcuma longa and their pyrazole and isoxazole analogues were synthesized and evaluated for antioxidant, COX-1/COX-2 inhibitory and anti-inflammatory activities. The designed analogues significantly enhance COX-2/COX-1 selectivity and possess significant anti-inflammatory activity in carrageenan induced rat paw edema assay. Pyrazole, isoxazole analogues of curcumin (4 and 7) exhibited higher antioxidant activity than trolox. Molecular docking study revealed the binding orientations of curcumin analogues in the active sites of COX and thereby helps to design novel potent inhibitors.
- Selvam,Jachak, Sanjay M.,Thilagavathi, Ramasamy,Chakraborti, Asit. K.
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- In-silico designing, chemical synthesis, characterization and in-vitro assessment of antibacterial properties of some analogues of curcumin
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In the present work two key regulator proteins, monomeric MipZ of Caulobacter vibrioides (similar to Pseudomonas aeruginosa) and Pyruvate kinase of Staphylococcus aureus were docked with curcumin, the wonder molecule from the spice turmeric and structures
- Shrivash, Manoj K.,Mishra, Sonali,UpmaNarain,Pandey, Jyoti,Misra, Krishna
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- Perturbations in the photophysical properties of isoxazole derivative of curcumin up on interaction with different anionic, cationic and non-ionic surfactants
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Surfactants are organized assemblies that are often used as models for biomembranes and they can also act as solubilizing agents for various hydrophobic drug molecules. Isoxazole derivative of curcumin (IOC) is a potential drug molecule whose biological e
- Sharma, Manisha,Rani, Swati,Mozumdar, Subho
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- Synergistic antifungal effects of curcumin derivatives as fungal biofilm inhibitors with fluconazole
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Lack of novel antifungal agents and severe drug resistance has led to high incidence and associated mortality of invasive fungal infections. To tackle the challenges, novel antifungal agents with anti-resistant potency are highly desirable. Thus, derivati
- Dong, Huai-Huai,Wang, Yuan-Hua,Peng, Xue-Mi,Zhou, He-Yang,Zhao, Fei,Jiang, Yuan-Ying,Zhang, Da-Zhi,Jin, Yong-Sheng
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p. 1079 - 1088
(2021/02/11)
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- The inhibitory potency of isoxazole-curcumin analogue for the management of breast cancer: A comparative in vitro and molecular modeling investigation
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Curcumin, a potent phytochemical derived from the spice element turmeric, has been identified as a herbal remedy decades ago and has displayed promise in the field of medicinal chemistry. However, multiple traits associated with curcumin, such as poor bio
- Hari, Gangadhar,Kumar, N. V. Anil,Pai, K. S. R.,Rodrigues, Fiona C.,Thakur, Goutam
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p. 5995 - 6008
(2021/07/26)
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- The inhibitory role of curcumin derivatives on AMPA receptor subunits and their effect on the gating biophysical properties
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Curcumin is a natural polyphenol that has a broad spectrum of therapeutic characters, including neuroprotective actions against various neurological diseases. However, the molecular mechanism behind its neuroprotective properties remains obscure. The curr
- Qneibi, Mohammad,Hamed, Othman,Fares, Oswa,Jaradat, Nidal,Natsheh, Abdel-Razzak,AbuHasan, Qais,Emwas, Nour,Al-Kerm, Rana,Al-Kerm, Rola
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- New histone deacetylase inhibitors and anticancer agents from Curcuma longa
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The aims of this study were to explore histone deacetylase inhibitory and antioxidant activities of curcuminoids as well as derivatives of curcumin. Curcumin (6), demethoxycurcumin (7), dihydrocurcumin (8), bisdemethoxycurcumin (9), and hydroxycurcumin (1
- Kumboonma, Pakit,Senawong, Thanaset,Saenglee, Somprasong,Senawong, Gulsiri,Somsakeesit, La-or,Yenjai, Chavi,Phaosiri, Chanokbhorn
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p. 1773 - 1782
(2019/08/08)
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- Screening of curcumin-derived isoxazole, pyrazoles, and pyrimidines for their anti-inflammatory, antinociceptive, and cyclooxygenase-2 inhibition
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Curcumin has shown pharmacological properties against different phenotypes of various disease models. Different synthetic routes have been employed to develop its numerous derivatives for diverse and improved therapeutic roles. In this study, we have synt
- Ahmed, Mahmood,Qadir, Muhammad Abdul,Hameed, Abdul,Imran, Muhammad,Muddassar, Muhammad
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p. 338 - 343
(2017/12/29)
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- Synthesis of curcuminoids and evaluation of their cytotoxic and antioxidant properties
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Curcumin (1) and ten derivatives (2-11) were synthesized and evaluated as cytotoxic and antioxidant agents. The results of primary screening by Sulforhodamine B assay against five human cancer cell lines (U-251 MG, glioblastoma; PC-3, human prostatic; HCT-15, human colorectal; K562, human chronic myelogenous leukemia; and SKLU-1, non-small cell lung cancer) allowed us to calculate the half maximal inhibitory concentration (IC50) values for the more active compounds against HCT-15 and K562 cell lines. Compounds 2 and 10 were the most active against both cell lines and were more active than curcumin itself. Thiobarbituric acid reactive substances (TBARS) assay showed that 7 has potent activity; even stronger than curcumin, α-tocopherol, and quercetin.
- Lozada-García, María Concepción,Enríquez, Raúl G.,Ramírez-Apán, Teresa O.,Nieto-Camacho, Antonio,Palacios-Espinosa, Juan Francisco,Custodio-Galván, Zeltzin,Soria-Arteche, Olivia,Pérez-Villanueva, Jaime
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- Multispectroscopic analysis and molecular modeling to investigate the binding of beta lactoglobulin with curcumin derivatives
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Bovine beta lactoglobulin (β-lg), the major whey protein, has a great affinity for a wide range of organic compounds like fatty acids, retinol etc. Curcumin, a polyphenolic antioxidant present in turmeric and its isoxazole (IOC) and pyrazole (PY) derivati
- Maity, Sanhita,Pal, Sampa,Sardar, Subrata,Sepay, Nayim,Parvej, Hasan,Chakraborty, Jishnu,Chandra Halder, Umesh
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p. 112175 - 112183
(2016/12/07)
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- Mechanochemical Synthesis and Antioxidant Activity of Curcumin-Templated Azoles
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A solvent-free, mechanochemical method for the synthesis of curcumin (1) derived 3,5-bis(styryl)pyrazoles and 3,5-bis(styryl)isoxazole (2a-g) at room temperature, with very short reaction time, is reported. Such earlier structural modifications of curcumin, at its β-diketone unit by transforming it into an isosteric pyrazole or isoxazole unit, required prolonged heating. The evaluation of the antioxidant activity of these compounds, based on DPPH, FRAP, and β-carotene bleaching assays, showed that several of these azoles are better antioxidants than curcumin, with the isoxazole derivative 2g being overall the best. Typically, the inhibition of 2,2-diphenyl-1-picrylhydrazyl (10-2 mmol), expressed as EC50 values, by curcumin (1), 3,5-bis(4-hydroxy-3-methoxystyryl)pyrazole (2a), and 3,5-bis(4-hydroxy-3-methoxystyryl)isoxazole (2g) are 40 ± 0.06, 14 ± 0.18, and 8 ± 0.11 μmol, respectively. Moreover, the reported method is useful in accessing 3,5-bis(4-hydroxy-3-methoxystyryl)-1-phenylpyrazole (2b), which is important in studies related to neuroprotection and Alzheimer's disease, and 2a and 2g, which are inhibitors of protein kinases involved in neuronal excitotoxicity.
- Sherin, Daisy R.,Rajasekharan, Kallikat N.
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p. 908 - 914
(2015/12/24)
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- Curcumin is an inhibitor of calcium/calmodulin dependent protein kinase II
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Calcium/calmodulin dependent protein kinase II (CaMKII) is involved in the mechanisms underlying higher order brain functions such as learning and memory. CaMKII participates in pathological glutamate signaling also, since it is activated by calcium influx through the N-methyl-d-aspartate type glutamate receptor (NMDAR). In our attempt to identify phytomodulators of CaMKII, we observed that curcumin, a constituent of turmeric and its analogs inhibit the Ca2+-dependent and independent kinase activities of CaMKII. We further report that a heterocyclic analog of curcumin I, (3,5-bis[β-(4- hydroxy-3-methoxyphenyl)ethenyl]pyrazole), named as pyrazole-curcumin, is a more potent inhibitor of CaMKII than curcumin. Microwave assisted, rapid synthesis of curcumin I and its heterocyclic analogues is also reported.
- Mayadevi, M.,Omkumar, R. V.,Sherin, D. R.,Keerthi, V. S.,Rajasekharan, K. N.
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p. 6040 - 6047,8
(2020/08/20)
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- Binding of isoxazole and pyrazole derivatives of curcumin with the activator binding domain of novel protein kinase C
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The protein kinase C (PKC) family of serine/threonine kinases is an attractive drug target because of its involvement in the regulation of various cellular functions, including cell growth, differentiation, metabolism, and apoptosis. The endogenous PKC ac
- Das, Joydip,Pany, Satyabrata,Panchal, Shyam,Majhi, Anjoy,Rahman, Ghazi M.
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experimental part
p. 6196 - 6202
(2011/12/14)
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- Isoxazole analogs of curcuminoids with highly potent multidrug-resistant antimycobacterial activity
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Curcumin (1), demethoxycurcumin (2) and bisdemethoxycurcumin (3), the curcuminoid constituents of the medicinal plant Curcuma longa L., have been structurally modified to 55 analogs and antimycobacterial activity against Mycobacterium tuberculosis has been evaluated. Among the highly active curcuminoids, the isoxazole analogs are the most active group, with mono-O-methylcurcumin isoxazole (53) being the most active compound (MIC 0.09 μg/mL). It was 1131-fold more active than curcumin (1), the parent compound, and was approximately 18 and 2-fold more active than the standard drugs kanamycin and isoniazid, respectively. Compound 53 also exhibited high activity against the multidrug-resistant M. tuberculosis clinical isolates, with the MICs of 0.195-3.125 μg/mL. The structural requirements for a curcuminoid analog to exhibit antimycobacterial activity are the presence of an isoxazole ring and two unsaturated bonds on the heptyl chain. The presence of a suitable para-alkoxyl group on the aromatic ring which is attached in close proximity to the nitrogen function of the isoxazole ring and a free para-hydroxyl group on another aromatic ring enhances the biological activity.
- Changtam, Chatchawan,Hongmanee, Poonpilas,Suksamrarn, Apichart
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experimental part
p. 4446 - 4457
(2010/10/19)
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- Synthesis and evaluation of electron-rich curcumin analogues
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The natural product curcumin has long been recognized for its medicinal properties and is utilized for the treatment of many diseases. However, it remains unknown whether this activity is based on its presumably promiscuous scaffold, or if it results from the Michael acceptor properties of the α,β-unsaturated 1,3-diketone moiety central to its structure. To probe this issue, electron-rich pyrazole and isoxazole analogues were prepared and evaluated against two breast cancer cell lines, which resulted in the identification of several compounds that exhibit low micromolar to mid nanomolar anti-proliferative activity. A conjugate addition study was also performed to compare the relative electrophilicity of the diketone, pyrazole and isoxazole analogues.
- Amolins, Michael W.,Peterson, Laura B.,Blagg, Brian S.J.
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experimental part
p. 360 - 367
(2011/02/26)
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- Antitumor effects of curcumin and structurally β-diketone modified analogs on multidrug resistant cancer cells
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Using concepts of bioisostery a series of curcumin analogs were synthesized: the diketonic system of the compound was elaborated into enaminones, oximes, and the isoxazole heterocycle. The cell growth inhibitory and apoptosis inducing effects of the new analogs were evaluated by in vitro assays in the hepatocellular carcinoma HA22T/VGH cells, as well as in the MCF-7 breast cancer cell line and in its multidrug resistant (MDR) variant MCF-7R. Increased antitumor activity on all cell lines was found with the isoxazole analog and especially with the benzyl oxime derivative; in the HA22T/VGH cell model, the latter compound inhibited constitutive NF-κB activation.
- Simoni, Daniele,Rizzi, Michele,Rondanin, Riccardo,Baruchello, Riccardo,Marchetti, Paolo,Invidiata, Francesco Paolo,Labbozzetta, Manuela,Poma, Paola,Carina, Valeria,Notarbartolo, Monica,Alaimo, Alessandra,D'Alessandro, Natale
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p. 845 - 849
(2008/09/19)
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- Synthesis and exploration of novel curcumin analogues as anti-malarial agents
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Curcumin, a major yellow pigment and active component of turmeric, has been shown to possess anti-inflammatory and anti-cancer activities. Recent studies have indicated that curcumin inhibits chloroquine-sensitive (CQ-S) and chloroquine-resistant (CQ-R) Plasmodium falciparum growth in culture with an IC50 of ~3.25 μM (MIC = 13.2 μM) and IC50 4.21 μM (MIC = 14.4 μM), respectively. In order to expand their potential as anti-malarials a series of novel curcumin derivatives were synthesized and evaluated for their ability to inhibit P. falciparum growth in culture. Several curcumin analogues examined show more effective inhibition of P. falciparumgrowth than curcumin. The most potent curcumin compounds 3, 6, and 11 were inhibitory for CQ-S P. falciparum at IC50 of 0.48, 0.87, 0.92 μM and CQ-R P. falciparum at IC50 of 0.45 μM, 0.89, 0.75 μM, respectively. Pyrazole analogue of curcumin (3) exhibited sevenfold higher anti-malarial potency against CQ-S and ninefold higher anti-malarial potency against CQ-R. Curcumin analogues described here represent a novel class of highly selective P. falciparum inhibitors and promising candidates for the design of novel anti-malarial agents.
- Mishra, Satyendra,Karmodiya, Krishanpal,Surolia, Namita,Surolia, Avadhesha
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p. 2894 - 2902
(2008/09/19)
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