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Dimethoxycurcumin

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https://www.readbyqxmd.com/read/29621898/curcumin-and-its-synthetic-analogue-dimethoxycurcumin-differentially-modulates-antioxidant-status-of-normal-human-peripheral-blood-mononuclear-cells
#1
Emmanuel Simon, P Aswini, V B Sameer Kumar, Gokuldas Mankadath
Curcumin is a polyphenol derived from the herb Curcuma longa, which has been extensively studied in terms of its antitumour, antioxidant, and chemopreventive activity as well as various other effects. In the present work we compared curcumin with its synthetic analogue dimethoxycurcumin (dimc) in terms of its antioxidant enzyme-modulating effects in human peripheral blood mononuclear cells (PBMC). We found that these compounds modulate antioxidant enzymes differentially. Both curcumin and dimethoxycurcumin effected a decrease in lipid peroxidation status in PBMC, however, curcumin had better activity in this regard...
May 2018: Free Radical Research
https://www.readbyqxmd.com/read/29124231/curcumin-bisdemethoxycurcumin-and-dimethoxycurcumin-complexed-with-cyclodextrins-have-structure-specific-effect-on-the-paracellular-integrity-of-lung-epithelia-in-vitro
#2
Berglind Eva Benediktsdottir, Olafur Baldursson, Thorarinn Gudjonsson, Hanne Hjorth Tønnesen, Mar Masson
The phytochemical curcumin may improve translocation of the cystic fibrosis transmembrane regulatory (CFTR) protein in lung epithelium and therefore be helpful in the treatment of cystic fibrosis (CF) symptoms. However, previous studies often use commercial curcumin that is a combination of curcumin, demethoxycurcumin and bisdemethoxycurcumin which could affect the investigated cells differently. In the present study, we investigated the potential difference between curcumin, bisdemethoxycurcumin and dimethoxycurcumin on the epithelial tight junction complex, in the bronchial epithelial cell line VA10, by measuring transepithelial electrical resistance (TER), immunofluorescence and western blotting of tight junction proteins...
December 2015: Biochemistry and Biophysics Reports
https://www.readbyqxmd.com/read/28573788/in-vitro-additive-antitumor-effects-of-dimethoxycurcumin-and-5-fluorouracil-in-colon-cancer-cells
#3
Huiying Zhao, Qingchun Liu, Saisai Wang, Fang Dai, Xiaofei Cheng, Xiaobin Cheng, Wenbin Chen, Min Zhang, Dong Chen
Dimethoxycurcumin (DMC) is a lipophilic analog of curcumin, an effective treatment for colon cancer, which has greater chemical and metabolic stability. Chemotherapy treatments, such as 5-fluorouracil (5-Fu), play a key role in the current management of colon cancer. In this study, we investigated the antitumor efficacy of DMC in combination with 5-Fu in SW480 and SW620 colon cancer cells. CCK-8 assay was used to evaluate the inhibitory effect of DMC and 5-Fu on cancer cells proliferation, and the combination index was calculated...
July 2017: Cancer Medicine
https://www.readbyqxmd.com/read/27996095/biological-and-pharmacological-evaluation-of-dimethoxycurcumin-a-metabolically-stable-curcumin-analogue-with-a-promising-therapeutic-potential
#4
REVIEW
Manouchehr Teymouri, Nastaran Barati, Matteo Pirro, Amirhosein Sahebkar
Dimethoxycurcumin (DiMC) is a synthetic analog of curcumin with superior inter-related pro-oxidant and anti-cancer activity, and metabolic stability. Numerous studies have shown that DiMC reserves the biologically beneficial features, including anti-inflammatory, anti-carcinogenic, and cytoprotective properties, almost to the same extent as curcumin exhibits. DiMC lacks the phenolic-OH groups as opposed to curcumin, dimethoxycurcumin, and bis-demethoxycurcumin that all vary in the number of methoxy groups per molecule, and has drawn the attentions of researchers who attempted to discover the structure-activity relationship (SAR) of curcumin...
January 2018: Journal of Cellular Physiology
https://www.readbyqxmd.com/read/27588609/the-combination-of-dimethoxycurcumin-with-dna-methylation-inhibitor-enhances-gene-re-expression-of-promoter-methylated-genes-and-antagonizes-their-cytotoxic-effect
#5
Hazem E Hassan, Jean-Arnaud Keita, Lawrence Narayan, Sean M Brady, Richard Frederick, Samuel Carlson, Karen C Glass, Senthil Natesan, Thomm Buttolph, Tamer E Fandy
Curcumin and its analogs exhibited antileukemic activity either as single agent or in combination therapy. Dimethoxycurcumin (DMC) is a more metabolically stable curcumin analog that was shown to induce the expression of promoter-methylated genes without reversing DNA methylation. Accordingly, co-treatment with DMC and DNA methyltransferase (DNMT) inhibitors could hypothetically enhance the re-expression of promoter-methylated tumor suppressor genes. In this study, we investigated the cytotoxic effects and epigenetic changes associated with the combination of DMC and the DNMT inhibitor decitabine (DAC) in primary leukemia samples and cell lines...
September 2, 2016: Epigenetics: Official Journal of the DNA Methylation Society
https://www.readbyqxmd.com/read/27550987/bmi1-is-downregulated-by-the-natural-compound-curcumin-but-not-by-bisdemethoxycurcumin-and-dimethoxycurcumin
#6
Temitope A Adeyeni, Natasha Khatwani, KayKay San, Uthayashanker R Ezekiel
The B-cell-specific Moloney murine leukemia virus integration site 1 (BMI1) locus encodes a 37-kD protein that is a key regulatory component of the polycomb regulatory complex 1 (PRC1). When overexpressed in various cancer types, the BMI1 protein induces cell growth and promotes tumor growth in vitro and in vivo. Curcumin, a major phytochemical in turmeric (Curcuma longa), inhibits the proliferation and survival of many types of cancer cells, both in vitro and in vivo, and has been reported to reduce BMI1 expression in breast cancer cells...
August 2016: Physiological Reports
https://www.readbyqxmd.com/read/27461789/amyloid-binding-properties-of-curcumin-analogues-in-alzheimer-s-disease-postmortem-brain-tissue
#7
Emma R Veldman, Zhisheng Jia, Christer Halldin, Marie M Svedberg
The presence of β-amyloid (Aβ) containing plaques in the brain is a hallmark of Alzheimer's disease (AD) and serves as a biomarker for confirmation of diagnosis postmortem. Early diagnosis is of great importance for optimal treatment and for monitoring disease progression in the brain. Highly specific and sensitive biomarkers are thus greatly needed to assess therapeutic efficacy, not only clinically, but also in terms of clearance of histopathological lesions and decelerated neurodegeneration. The objective of the present study was to give more insight into the binding of curcumin analogues, curcuminoids, to Aβ containing plaques in postmortem tissue from AD patients...
September 6, 2016: Neuroscience Letters
https://www.readbyqxmd.com/read/27381867/dimethoxycurcumin-a-metabolically-stable-analogue-of-curcumin-enhances-the-radiosensitivity-of-cancer-cells-possible-involvement-of-ros-and-thioredoxin-reductase
#8
Sundarraj Jayakumar, R S Patwardhan, Debojyoti Pal, Deepak Sharma, Santosh K Sandur
Dimethoxycurcumin (DIMC), a structural analogue of curcumin, has been shown to have more stability, bioavailability, and effectiveness than its parent molecule curcumin. In this paper the radiosensitizing effect of DIMC has been investigated in A549 lung cancer cells. As compared to its parent molecule curcumin, DIMC showed a very potent radiosensitizing effect as seen by clonogenic survival assay. DIMC in combination with radiation significantly increased the apoptosis and mitotic death in A549 cells. This combinatorial treatment also lead to effective elimination of cancer stem cells...
September 9, 2016: Biochemical and Biophysical Research Communications
https://www.readbyqxmd.com/read/26504386/preparation-characterization-in-vivo-pharmacokinetics-and-biodistribution-of-polymeric-micellar-dimethoxycurcumin-for-tumor-targeting
#9
Hui Liu, Hui Xu, Yunxia Jiang, Shengyuan Hao, Feirong Gong, Hongjie Mu, Ke Liu
Dimethoxycurcumin (DMC) is an analog of curcumin with superior efficacy in various disease models. Currently, drug delivery system research on DMC is very limited, and it has become a huge challenge to realize further developments and clinical applications. In the present study, a kind of amphiphilic block copolymer, N-t-butoxycarbonyl-phenylalanine terminated monomethoxyl poly (ethylene glycol)-b-poly (ε-caprolactone), or mPEG-PCL-Phe(Boc), was prepared from monomethoxyl poly (ethylene glycol)-b-poly (ε-caprolactone) (mPEG-PCL) with its hydroxyl terminal chemically converted into N-t-butoxycarbonyl-phenylalanine (Boc-Phe)...
2015: International Journal of Nanomedicine
https://www.readbyqxmd.com/read/26393568/selected-phytochemicals-and-culinary-plant-extracts-inhibit-fructose-uptake-in-caco-2-cells
#10
Yurim Lee, Yeni Lim, Oran Kwon
This study compared the ability of nine culinary plant extracts containing a wide array of phytochemicals to inhibit fructose uptake and then explored the involvement of intestinal fructose transporters and phytochemicals for selected samples. The chemical signature was characterized by high performance liquid chromatography with mass spectrometry. Inhibition of [(14)C]-fructose uptake was tested by using human intestinal Caco-2 cells. Then, the relative contribution of the two apical-facing intestinal fructose transporters, GLUT2 and GLUT5, and the signature components for fructose uptake inhibition was confirmed in naive, phloretin-treated and forskolin-treated Caco-2 cells...
September 18, 2015: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://www.readbyqxmd.com/read/25753330/novel-curcumin-analogs-to-overcome-egfr-tki-lung-adenocarcinoma-drug-resistance-and-reduce-egfr-tki-induced-gi-adverse-effects
#11
Koji Wada, Jen-Yi Lee, Hsin-Yi Hung, Qian Shi, Li Lin, Yu Zhao, Masuo Goto, Pan-Chyr Yang, Sheng-Chu Kuo, Hui-Wen Chen, Kuo-Hsiung Lee
Curcumin (1) down-regulates the expression as well as phosphorylation of epidermal growth factor receptor (EGFR) in lung adenocarcinoma cells expressing gefitinib-resistant EGFR. Thirty-seven newly synthesized curcumin analogues including dimethoxycurcumin (2, DMC) were evaluated for their effects on EGFR expression as well as phosphorylation in two gefitinib-resistant lung adenocarcinoma cell lines, CL1-5 (EGFR(wt)) and H1975 (EGFR(L858R+T790M)). Based on the identified structure-activity relationships, methoxy substitution at C-3', C-4', or both positions favored inhibitory activity (compounds 1, 2, 5, 8-15, 17, 36), while compounds with more polar substituents were generally less active in both cell lines...
April 1, 2015: Bioorganic & Medicinal Chemistry
https://www.readbyqxmd.com/read/25186441/curcumin-and-dimethoxycurcumin-induced-epigenetic-changes-in-leukemia-cells
#12
Hazem E Hassan, Samuel Carlson, Inas Abdallah, Thomm Buttolph, Karen C Glass, Tamer E Fandy
PURPOSE: Curcumin is an ideal chemopreventive and antitumor agent characterized by poor bioavailability and low stability. The development of synthetic structural analogues like dimethoxycurcumin (DMC) could overcome these drawbacks. In this study we compared the cytotoxicity, metabolism and the epigenetic changes induced by both drugs in leukemia cells. METHODS: Apoptosis and cell cycle analysis were analyzed by flow cytometry. Real-time PCR was used for gene expression analysis...
March 2015: Pharmaceutical Research
https://www.readbyqxmd.com/read/24625971/stronger-proteasomal-inhibition-and-higher-chop-induction-are-responsible-for-more-effective-induction-of-paraptosis-by-dimethoxycurcumin-than-curcumin
#13
COMPARATIVE STUDY
M J Yoon, Y J Kang, J A Lee, I Y Kim, M A Kim, Y S Lee, J H Park, B Y Lee, I A Kim, H S Kim, S-A Kim, A-R Yoon, C-O Yun, E-Y Kim, K Lee, K S Choi
Although curcumin suppresses the growth of a variety of cancer cells, its poor absorption and low systemic bioavailability have limited its translation into clinics as an anticancer agent. In this study, we show that dimethoxycurcumin (DMC), a methylated, more stable analog of curcumin, is significantly more potent than curcumin in inducing cell death and reducing the clonogenicity of malignant breast cancer cells. Furthermore, DMC reduces the tumor growth of xenografted MDA-MB 435S cells more strongly than curcumin...
2014: Cell Death & Disease
https://www.readbyqxmd.com/read/23934646/neuroprotection-by-monocarbonyl-dimethoxycurcumin-c-ameliorating-the-toxicity-of-mutant-tdp-43-via-ho-1
#14
Weisong Duan, Yansu Guo, Jian Xiao, Xiaoyu Chen, Zhongyao Li, Huihui Han, Chunyan Li
Mutation of TAR DNA-binding protein-43 (TDP-43) was detected in familiar and sporadic amyotrophic lateral sclerosis, and pathological TDP-43 was identified in the frontotemporal lobar degeneration. The neuroprotective functions of curcumin derivatives were assessed in motor neurons transfected with mutant TDP-43. We found that curcumin derivatives reduced the levels of TDP-43 fragments. Furthermore, we evaluated these compounds on the cellular model that the cells were transfected with TDP-25. We found that the expression level and aggregate formation of TDP-25 were significantly reduced by monocarbonyl dimethoxycurcumin C (Compound C)...
February 2014: Molecular Neurobiology
https://www.readbyqxmd.com/read/23294394/incorporation-of-dimethoxycurcumin-into-charged-liposomes-and-the-formation-kinetics-of-fractal-aggregates-of-uncharged-vectors
#15
Marilena Hadjidemetriou, Natassa Pippa, Stergios Pispas, Costas Demetzos
Dimethoxycurcumin (DMC) is a lipophilic analog of curcumin found in Curcuma longa Linn., which is known to possess significant activity against various cancer cell lines. The purpose of this study was to develop suitable liposomal formulations in order to overcome DMC's poor water solubility and to study the aggregation kinetic profile using the fractal analysis. DMC was incorporated into liposomal formulations composed of DPPC, DPPC:DPPG:chol (9:1:1 molar ratio) and DPPC:DODAP:chol (9:1:1 molar ratio) liposomes...
June 2013: Journal of Liposome Research
https://www.readbyqxmd.com/read/22849714/trapping-of-methylglyoxal-by-curcumin-in-cell-free-systems-and-in-human-umbilical-vein-endothelial-cells
#16
Te-Yu Hu, Cheng-Ling Liu, Charng-Cherng Chyau, Miao-Lin Hu
Curcumin, the most active compound of curcuminoids, has been shown to inhibit formation of advanced glycation end products (AGEs) in streptozotocin-induced diabetic rats. However, little is known on whether curcumin may trap methylglyoxal (MGO), a major reactive dicarbonyl compound, to inhibit AGE formation. We found that one molecule of curcumin effectively trapped one molecule of MGO at a 1:3 ratio at 24 h of incubation under physiological conditions (pH 7.4, 37 °C). Curcumin decreased N(ε)-(carboxymethyl)lysine (CML) expression in human umbilical vein endothelial cells...
August 22, 2012: Journal of Agricultural and Food Chemistry
https://www.readbyqxmd.com/read/22119759/dimethoxycurcumin-induced-cell-death-in-human-breast-carcinoma-mcf7-cells-evidence-for-pro-oxidant-activity-mitochondrial-dysfunction-and-apoptosis
#17
A Kunwar, S Jayakumar, A K Srivastava, K I Priyadarsini
The factors responsible for the induction of cell death by dimethoxycurcumin (Dimc), a synthetic analog of curcumin, were assessed in human breast carcinoma MCF7 cells. Initial cytotoxic studies with both curcumin and Dimc using MTT assay indicated their comparable effects. Further, the mechanism of action was explored in terms of oxidative stress, mitochondrial dysfunction, and modulation in the expression of proteins involved in cell cycle regulation and apoptosis. Dimc (5-50 μM) caused generation of reactive oxygen species, reduction in glutathione level, and induction of DNA damage...
April 2012: Archives of Toxicology
https://www.readbyqxmd.com/read/22037833/studies-on-curcumin-and-curcuminoids-xlvi-photophysical-properties-of-dimethoxycurcumin-and-bis-dehydroxycurcumin
#18
L Nardo, A Andreoni, M Bondani, M Másson, T Haukvik, H H Tønnesen
The steady-state absorption and fluorescence, as well as the time-resolved fluorescence properties of dimethoxycurcumin and bis-dehydroxycurcumin dissolved in several solvents differing in polarity and H-bonding capability are presented. The singlet oxygen generation efficiency of the two compounds relative to curcumin is estimated. The photodegradation quantum yield of the former compound in acetonitrile and methanol is determined. The dimethoxycurcumin and bis-dehydroxycurcumin decay mechanisms from the S (1) state are discussed and compared with those of curcumin, dicinnamoylmethane and bis-demethoxycurcumin...
March 2012: Journal of Fluorescence
https://www.readbyqxmd.com/read/21726543/dimethoxycurcumin-a-metabolically-stable-analogue-of-curcumin-exhibits-anti-inflammatory-activities-in-murine-and-human-lymphocytes
#19
Raghavendra S Patwardhan, Rahul Checker, Deepak Sharma, Vineet Kohli, K I Priyadarsini, Santosh K Sandur
The aim of this study was to investigate whether dimethoxycurcumin (DiMC), a synthetic curcumin analogue having higher metabolic stability over curcumin, could exhibit anti-inflammatory activity in murine and human lymphocytes. Both curcumin and DiMC suppressed mitogen as well as antigen driven proliferation of murine splenic lymphocytes. Further, mitogen and antigen-stimulated cytokine (IL-2, IL-4, IL-6 and IFN-γ) secretion by T cells was also abrogated by curcumin and DiMC. Interestingly, curcumin and DiMC suppressed B cell proliferation induced by lipopolysaccharide...
September 15, 2011: Biochemical Pharmacology
https://www.readbyqxmd.com/read/21615275/differential-antioxidant-pro-oxidant-activity-of-dimethoxycurcumin-a-synthetic-analogue-of-curcumin
#20
REVIEW
Amit Kunwar, Atanu Barik, Santosh K Sandur, K Indira Priyadarsini
Dimethoxycurcumin (Dimc), a metabolically stable analogue of curcumin, is under investigation as an anti-tumour agent. Recently a number of studies have been performed on Dimc in this laboratory and also by others. In the present article, all these results have been summarized and wherever possible compared with those of curcumin. Rate constant for reactions of Dimc with superoxide radicals was comparable with that of curcumin, while its reaction with peroxyl radicals was much slower. These results were further supported by the observations on the scavenging of basal ROS levels in lymphocytes and evaluation of antioxidant activities...
August 2011: Free Radical Research
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