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Synthesis of curcumin

Anjali M Prabhat, M Lakshmi Kuppusamy, Balázs Bognár, Tamás Kálai, Kálmán Hideg, Periannan Kuppusamy
The synthesis and antiproliferative effect of a novel curcumin analog, 4,4'-disulfonyldiarylidenyl piperidone, are reported. The design of the molecule is based on the fusion of an antiproliferative segment, namely diarylidenyl piperidone (DAP), with N-hyroxypyrroline, which is known to metabolically convert to nitroxide and protect healthy cells. Cellular uptake, metabolic conversion, cytotoxicity and antiproliferative effect of the DAP derivative against HCT-116 human colon cancer cells have been determined...
December 14, 2018: Cell Biochemistry and Biophysics
Miri Lee, Hyunju Choi, Kyoung-Sook Kim, Dong-Hyun Kim, Cheorl-Ho Kim, Young-Choon Lee
Our recent report showed that curcumin, polyphenolic compound isolated from the herb Curcuma longa , upregulated the gene expression of human GD3 synthase (hST8Sia I) responsible for ganglioside GD3 synthesis with autophagy induction in human lung adenocarcinoma A549 cells. In this study, on the contrary to this finding, we demonstrated that curcumin downregulated the gene expression of human GM3 synthase (hST3Gal V) catalyzing ganglioside GM3 synthesis with autophagy induction in human colon carcinoma HCT116 cells...
2018: Evidence-based Complementary and Alternative Medicine: ECAM
Ahmed M Abdellah, Mahmoud A Sliem, Mona Bakr, Rehab M Amin
AIM: There is an urgent need to develop alternative antimicrobial agents and, one of which is via the use of nanotechnology. Green synthetic routes are recently being replaced for nanoparticles preparation. Methods results: Silver-curcumin nanoconjugates (Ag-CurNCs) were prepared in an eco-friendly method. The prepared nanomaterials were characterized and the photostability was studied under the influence of UV irradiation. Results showed that, the conjugation between curcumin and silver in the nanoform improve the photostability of curcumin...
November 2018: Future Medicinal Chemistry
Xinlong Huo, Yongqiang Zhang, Xinchun Jin, Yongang Li, Li Zhang
The main factors of Alzheimer's disease (AD) are the cerebral accumulation and the formation of extracellular amyloid plaques. The Aβ peptides are highly able to accumulative and produce fibrils that are placed to form these plaques in the AD. The biological action and drug delivery properties of curcumin (Cur) nanoformulation in the Alzheimer's disease therapeutics can be developed by the altering surface of the Poly-lactide-co-glycolide (PLGA) polymer and encapsulation of selenium nanoparticles (Se NPs)...
November 15, 2018: Journal of Photochemistry and Photobiology. B, Biology
Andrii Bazylevich, Helena Tuchinsky, Eti Zigman-Hoffman, Ran Weissman, Ofer Shpilberg, Oshrat Hershkovitz-Rokah, Leonid Patsenker, Gary Gellerman
BACKGROUND: Scientists have extensively investigated curcumin, yielding many publications on treatments of cancer. Numerous derivatives of curcumin were synthesized, evaluated for their anti-oxidant and free-radical scavenging, SAR, ADME properties and tested in anticancer applications. OBJECTIVE: We decided to exploit curcumin as a bioactive core platform for carrying anticancer drugs, which likely possesses a carboxyl moiety for potential linkage to the carrier for drug delivery...
December 2, 2018: Medicinal Chemistry
Yurngdong Jahng, Jae Gyu Park
Diarylheptanoids are a family of plant secondary metabolites with a 7 carbon skeleton possessing two phenyl rings at the 1- and 7-positions. They can be subdivided into acyclic and cyclic diarylheptanoids where the latter are further divided into meta , meta -bridged biphenyls ([7.0]metacyclophanes) and meta , para -bridged diphenyl ether heptanoids (oxa[7.1]metapara-cyclophanes). Since the isolation of curcumin from the rhizomes of turmeric ( Curcuma longa ) in 1815 which was named curcumin, a variety of diarylheptanoids have been isolated from a number of plant families such as Aceraceae, Actinidiaceae, Betulaceae, Burseraceae, Casuarinaceae, Juglandaceae, Leguminosae, Myricaceae, and Zingiberaceae...
November 27, 2018: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Silvia Ravalli, Marta Anna Szychlinska, Rosalia Maria Leonardi, Giuseppe Musumeci
Osteoarthritis (OA) is a chronic degenerative disease of articular cartilage with limited treatment options. This reality encourages clinicians to suggest preventive measures to delay and contain the outbreak of the pathological conditions. Articular cartilage and synovium suffering from OA are characterised by an inflammatory state and by significant oxidative stress, responsible for pain, swelling and loss of mobility in the advanced stages. This review will focus on the ability of olive oil to exert positive effects on the entire joint to reduce pro-inflammatory cytokine release and increase lubricin synthesis, olive leaf extract, since it maintains lubrication by stimulating high molecular weight hyaluronan synthesis in synovial cells, curcumin, which delays the start of pathological cartilage breakdown, sanguinarine, which downregulates catabolic proteases, vitamin D for its capacity to influence the oxidative and pro-inflammatory environment, and carnosic acid as an inducer of heme oxygenase-1, which helps preserve cartilage degeneration...
November 18, 2018: World Journal of Orthopedics
E Halevas, T A Papadopoulos, C H Swanson, G C Smith, A Hatzidimitriou, G Katsipis, A Pantazaki, I Sanakis, G Mitrikas, K Ypsilantis, G Litsardakis, A Salifoglou
Curcumin is a natural product with a broad spectrum of beneficial properties relating to pharmaceutical applications, extending from traditional remedies to modern cosmetics. The biological activity of such pigments, however, is limited by their solubility and bioavailability, thereby necessitating new ways of achieving optimal tissue cellular response and efficacy as drugs. Metal ion complexation provides a significant route toward improvement of curcumin stability and biological activity, with vanadium being a representative such metal ion, amply encountered in biological systems and exhibiting exogenous bioactivity through potential pharmaceuticals...
November 6, 2018: Journal of Inorganic Biochemistry
Neelam Malik, Priyanka Dhiman, Anurag Khatkar
BACKGROUND: Curcumin is a well-known pharmacophore and some of its derivatives are shown to target xanthine oxidase (XO) to alleviate disorders caused by the excess production of uric acid. OBJECTIVE: Curcumin based derivatives were designed, synthesized and evaluated for their antioxidant and xanthine oxidase inhibitory potential. METHOD: In this report, we designed and synthesized two series of curcumin derivatives modified by inserting pyrazole and pyrimidine ring to central keto group...
November 21, 2018: Current Drug Targets
Satyendra Mishra, Sejal Patel, Chandni G Halpani
Curcumin is a admired, plant-derived compound that has been extensively investigated for diverse range of biological activities, but the use of this polyphenol is limited due to its instability. Chemical modifications in curcumin is reported to seize this limitation, such efforts are intensively performed to discover molecules with similar but improved stability and better properties. Focal point of these review are synthesis of stable pyrazole and isoxazole analogs of curcumin and application in various biological systems...
November 20, 2018: Chemistry & Biodiversity
Lijun You, Xiaocui Liu, Zhexiang Fang, Qianhui Xu, Qiqing Zhang
A new folic acid (FA)-conjugated poly (lactic-co-glycolicacid) (PLGA)-polyethylene glycol (PEG) nano-noisome was prepared. The noisome was employed as a drug delivery system to load curcumin (Cur) as a model drug and fluorescent probe for cervical cancer therapy and cell imaging. The Fe3 O4 @PLGA-PEG@FA noisomes were prepared through facile emulsion solvent evaporation and conjugation chemistry method, possessing the properties of high rapid magnetic separation and targeting character. X-ray photoelectron spectroscopy (XRD), Fourier transform infrared spectroscopy (FTIR), dynamic light scattering (DLS), thermogravimetric analysis (TGA), and vibrating sample magnetometer (VSM) were adopted to characterize the chemical structure and properties of these niosomes...
January 1, 2019: Materials Science & Engineering. C, Materials for Biological Applications
Moumita Khamrai, Sovan Lal Banerjee, Saikat Paul, Sarthik Samanta, Patit Paban Kundu
In this context, we have prepared a biocompatible gelatin based polyelectrolyte hydrogel patch that has an inherent ability to self-heal in the presence of physiological pH (pH = 7.4). The gelatin-based hydrogel patch consists of the ionically modified self-assembled bacterial cellulose (iBC), extracted from Glucanoacetobacter xylinus (MTCC7795) bacterial strain. Presence of the iBC provides a sturdy cage to the gelatin matrix and also participates into the self-healing activity via formation of the ionic interlocking system in the presence of buffer solution having a pH of 7...
October 29, 2018: International Journal of Biological Macromolecules
Dina Sadeq Al-Namil, Digambara Patra
Curcumin mediated rhamnolipids stabilized Ag Nanoparticles (NPs) have been successfully synthesized in a green solid-state procedure and in a solvent free environment. Depending on growth time, the synthesis process offers Ag NPs of different sizes and spherical shapes as reflected in the scanning electron microscope (SEM) images. The absorbance of rhamnolipids stabilized Ag NPs consistently increases with increase in growth time in rhamnolipids medium reconfirming growth in size of the particles. Even after 7 days of growth time in the rhamnolipids medium, the size slightly increases but the shapes remain spherical unlike the case observed in ethanolic environment...
October 19, 2018: Colloids and Surfaces. B, Biointerfaces
Giordano Lesma, Andrea Luraghi, Teodora Bavaro, Roberta Bortolozzi, Giulia Rainoldi, Gabriella Roda, Giampietro Viola, Daniela Ubiali, Alessandra Silvani
Fifteen new multifunctional conjugates were designed and synthesized by chemically linking the steroidal framework of natural occurring γ-oryzanol and γ-oryzanol-derived phytosterols to a wide range of bioactive natural compounds (fatty acids, phenolic acids, amino acids, lipoic acid, retinoic acid, curcumin, and resveratrol). Starting from γ-oryzanol, which is the main component of rice bran oil, this study was aimed at assessing if the conjugation strategy might enhance some γ-oryzanol bioactivities. The antioxidant activity was evaluated through three different mechanisms, namely, DPPH-scavenging activity, metal-chelating activity, and β-carotene-bleaching inhibition...
October 26, 2018: Journal of Natural Products
Rajpreet Kaur, Poonam Khullar, Aabroo Mahal, Anita Gupta, Narpinder Singh, Gurinder Kaur Ahluwalia, Mandeep Singh Bakshi
In order to provide a solution for the poor aqueous solubility and poor bioavailability of curcumin, we present the synthesis and characteristic features of water-soluble curcumin hydrated nanoparticles (CNPs). They are stable and nearly monodisperse in the aqueous phase where the keto form of curcumin self-assembles into spherical CNPs, which are highly sensitive to temperature and pH variations. The CNPs are quite stable up to 40 °C and at neutral pH. A higher temperature range reduces their hydration and makes them unstable, thereby disintegrating them into smaller aggregates...
November 14, 2018: Journal of Agricultural and Food Chemistry
Taki Sato, Mayumi Hotsumi, Koki Makabe, Hiroyuki Konno
Amyloid β fibrillation is an early event in Alzheimer's disease, so its detection is important to understand its roles in Alzheimer's disease. Curcumin, which has poor water solubility, has been reported to have many pharmacological activities including potent anti-amyloid β fibril activity in Alzheimer's disease. In this study, we found that curcumin analogues with the fluorescence property instead of non-inhibition of amyloid β fibrils. The development of new curcumin analogue, Me-CUR (9), as fluorescent switchable probe to detect amyloid β fibrils is described...
October 3, 2018: Bioorganic & Medicinal Chemistry Letters
Amirah Adlia, Ilham Tomagola, Sophi Damayanti, Ardyanto Mulya, Heni Rachmawati
Conjugation of curcumin and gold with green chemistry is an approach to improve the effectiveness of curcumin as anti-fibrosis. In this work, curcumin and gold were conjugated to deliver curcumin to the liver. Curcumin-gold nanoparticles (cAuNPs) were prepared by varying curcumin pH and concentration. The successful of cAuNPs formation were identified by using UV-visible and FTIR spectrophotometers. The particle size and morphology were analyzed using particle size analyzer and cryo-TEM respectively. In vitro antioxidant assay was performed to determine the curcumin activity after conjugation...
September 21, 2018: Scientia Pharmaceutica
Yuzhen Hu, Miao Li, Mengmeng Zhang, Yiguang Jin
Idiopathic pulmonary fibrosis (IPF) is a progressive interstitial lung disease with high mortality and poor prognosis. Curcumin shows anti-inflammatory effect by suppressing pro-inflammatory cytokines and inhibiting NF-κB mediated inflammation. Here, we developed inhalable curcumin-loaded poly(lactic-co-glycolic)acid (PLGA) large porous microparticles (LPMPs) for the treatment of IPF. Curcumin LPMPs were rough and loose particles with many pores on the surfaces and channels in the inner spaces. The mean geometric diameter of them was larger than 10 µm while the aerodynamic diameter was only 3...
November 15, 2018: International Journal of Pharmaceutics
Marta Rui, Giacomo Rossino, Stefania Coniglio, Stefania Monteleone, Arianna Scuteri, Alessio Malacrida, Daniela Rossi, Laura Catenacci, Milena Sorrenti, Mayra Paolillo, Daniela Curti, Letizia Venturini, Dirk Schepmann, Bernhard Wünsch, Klaus R Liedl, Guido Cavaletti, Vittorio Pace, Ernst Urban, Simona Collina
In this manuscript we report on the design, synthesis and evaluation of dual Sigma 1 Receptor (S1R) modulators/Acetylcholinesterase (AChE) inhibitors endowed with antioxidant and neurotrophic properties, potentially able to counteract neurodegeneration. The compounds based on arylalkylaminoketone scaffold integrate the pharmacophoric elements of RRC-33, a S1R modulator developed by us, donepezil, a well-known AChE inhibitor, and curcumin, a natural antioxidant compound with neuroprotective properties. A small library of compounds was synthesized and preliminary in vitro screening performed...
October 5, 2018: European Journal of Medicinal Chemistry
Cihui Tian, Sajid Asghar, Yurui Xu, Zhipeng Chen, Jingwei Zhang, Qineng Ping, Yanyu Xiao
Redox-sensitive micelles based onhydrophilic hyaluronic acid-ss-hydrophobic curcumin conjugate were designed as a novel delivery system for gliomas targeting. Furthermore, the obtained micelles were further functionalized with Tween 80 (CUR-THSC) for better brain penetration. Dynamic light scattering experiment and in vitro release study showed that the synthetic disulfide-linked conjugate possessed redox-sensitivity under high glutathione conditions. Spherical micelles with a mean particle size of 74.2 nm, negative zeta potential (-30...
December 2018: International Journal of Biological Macromolecules
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