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Synthesis of curcumin

Natalia Piekuś-Słomka, Renata Mikstacka, Joanna Ronowicz, Stanisław Sobiak
The growing interest in anticancer hybrids in the last few years has resulted in a great number of reports on hybrid design, synthesis and bioevaluation. Many novel multi-target-directed drug candidates were synthesized, and their biological activities were evaluated. For the design of anticancer hybrid compounds, the molecules of stilbenes, aromatic quinones, and heterocycles (benzimidazole, imidazole, pyrimidine, pyridine, pyrazole, quinoline, quinazoline) were applied. A distinct group of hybrids comprises the molecules built with natural compounds: Resveratrol, curcumin, coumarin, and oleanolic acid...
March 14, 2019: International Journal of Molecular Sciences
Renata Novak Kujundžić, Višnja Stepanić, Lidija Milković, Ana Čipak Gašparović, Marko Tomljanović, Koraljka Gall Trošelj
Pleiotropic effects of curcumin have been the subject of intensive research. The interest in this molecule for preventive medicine may further increase because of its potential to modulate inflamm-aging. Although direct data related to its effect on inflamm-aging does not exist, there is a strong possibility that its well-known anti-inflammatory properties may be relevant to this phenomenon. Curcumin's binding to various proteins, which was shown to be dependent on cellular oxidative status, is yet another feature for exploration in depth...
March 8, 2019: International Journal of Molecular Sciences
Shiva Ghadiri, Veronica Spalenza, Luca Dellafiora, Paola Badino, Andrea Barbarossa, Chiara Dall'Asta, Carlo Nebbia, Flavia Girolami
Aflatoxin (AF) B1, a widespread food and feed contaminant, is bioactivated by drug metabolizing enzymes (DME) to cytotoxic and carcinogenic metabolites like AFB1-epoxide and AFM1, a dairy milk contaminant. A number of natural antioxidants have been reported to afford a certain degree of protection against AFB1 (cyto)toxicity. As the mammary gland potentially participates in the generation of AFB1 metabolites, we evaluated the role of selected natural antioxidants (i.e. curcumin, quercetin and resveratrol) in the modulation of AFB1 toxicity and metabolism using a bovine mammary epithelial cell line (BME-UV1)...
March 5, 2019: Toxicology in Vitro: An International Journal Published in Association with BIBRA
Atiruj Theppawong, Tim Van de Walle, Charlotte Grootaert, Kristof Van Hecke, Nathalie Catry, Tom Desmet, John Van Camp, Matthias D'hooghe
Curcumin is known to display pronounced anticancer effects and a variety of other biological activities. However, the low bioavailability and fast metabolism of this molecule present an issue of concern with respect to its medicinal applications. To address this issue, structural modifications of the curcumin scaffold can be envisioned as a strategy to improve both the solubility and stability of this chemical entity, without compromising its biological activities. Previous work in our group targeted the synthesis of symmetrical azaheteroaromatic curcuminoids, which showed better solubility and cytotoxicity profiles compared to curcumin...
February 2019: ChemistryOpen
Martina Barchitta, Andrea Maugeri, Giuliana Favara, Roberta Magnano San Lio, Giuseppe Evola, Antonella Agodi, Guido Basile
Wound healing implicates several biological and molecular events, such as coagulation, inflammation, migration-proliferation, and remodeling. Here, we provide an overview of the effects of malnutrition and specific nutrients on this process, focusing on the beneficial effects of curcumin. We have summarized that protein loss may negatively affect the whole immune process, while adequate intake of carbohydrates is necessary for fibroblast migration during the proliferative phase. Beyond micronutrients, arginine and glutamine, vitamin A, B, C, and D, zinc, and iron are essential for inflammatory process and synthesis of collagen...
March 5, 2019: International Journal of Molecular Sciences
Deepak Kumar, Vinit Raj, Abhishek Verma, Pramendra Kumar, Jyoti Pandey
The study deals with the synthesis and characterization of chitosan-g-Poly (Acrylic acid-co-Acrylamide) [chit-g-Poly (AA-co-Am)] for sustained release of curcumin. The formation of chit-g-Poly (AA-co-Am) was ascertained through various spectral, thermal, microscopic methods and zeta potential. The potential of chit-g-Poly (AA-co-Am) for drug delivery applications were investigated through pH regulated kinetic models, in vitro antibacterial assay and molecular docking studies. The study reveals antibacterial activity of chit-g-Poly (AA-co-Am) against Escherichia coli, Staphylococcus aureus and Pseudomonas aeruginosa along with enhanced binding with bacterial receptors...
March 3, 2019: International Journal of Biological Macromolecules
Yen-Chou Chen, Bing-Chang Chen, Huei-Mei Huang, Shin-Hua Lin, Chien-Huang Lin
In the present study, we investigated the role of PKR-like endoplasmic reticular kinase (PERK), an endoplasmic reticulum (ER) stress kinase, in endothelin 1 (ET-1)- and thrombin-induced pulmonary fibrosis (PF), and the preventive effects of curcumin (CUR). Using the human embryonic WI-38 lung fibroblast cell line, ET-1 and thrombin induced the expression of ER stress-related proteins (CCAAT-enhancer-binding protein homologous protein, PERK, and binding immunoglobulin protein), a profibrogenic factor (cellular communication network factor 2 [CCN2]), and differentiation markers including α-smooth muscle actin (α-SMA), collagen I (Col I), and Col IV...
March 1, 2019: Journal of Cellular Physiology
Shefali Jaiswal, P K Dutta, Santosh Kumar, Joonseok Koh, Shambhavi Pandey
A methyl methacrylate (MMA) modified chitosan (CS) conjugate (CSMMA) has been synthesized by a green method via Michael addition reaction between CS and MMA in ethanol. The synthesized conjugate was characterized by FT-IR, 1 H NMR, X-ray diffraction spectrometry and SEM analysis. The results confirmed that CS was covalently linked to MMA yielding a highly porous framework. The uses of CSMMA were analyzed as a potential gene and drug delivery agent. CSMMA proved to be a reasonably good gene delivery agent based on transfection efficiency studies in mammalian cancer cell lines (A549, HeLa and HepG2)...
May 1, 2019: Carbohydrate Polymers
Monika Chaudhary, Neeraj Kumar, Ashish Baldi, Ramesh Chandra, M Arockia Babu, Jitender Madan
With an endeavor to develop novel curcumin analogues as potential anti-cancer agents, we designed and synthesized a series of Knoevenagel condensates by clubbing pyrazole carbaldehydes at the active methylene carbon atom of the curcumin backbone. Molecular docking studies were carried out to target the proposed derivatives on human kinase β (IKKβ), a potential anti-cancer target. The chloro derivative displayed five hydrogen bond interactions with a docking score of -11.874 kcal/mol higher than curcumin (docking score =-7...
February 20, 2019: Journal of Biomolecular Structure & Dynamics
Muhammad Jamshed Khan, Kamyar Shameli, Awis Qurni Sazili, Jinap Selamat, Suriya Kumari
Green synthesis of silver nanoparticles is desirable practice. It is not only the required technique for industrial and biomedical purposes but also a promising research area. The aim of this study was to synthesize green curcumin silver nanoparticles (C-Ag NPs). The synthesis of C-Ag NPs was achieved by reduction of the silver nitrate (AgNO₃) in an alkaline medium. The characterizations of the prepared samples were conducted by ultraviolet visible (UV-vis) spectroscopy, powder X-ray diffraction (PXRD), field emission scanning electron microscopy (FESEM), high-resolution transmission electron microscopy (HRTEM), selected area electron diffraction (SAED) and zeta potential (ZP) analyses...
February 16, 2019: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Jianchang Qian, Xianxin Chen, Sheng Shu, Wenxin Zhang, Bo Fang, Xiaojing Chen, Yunjie Zhao, Zhiguo Liu, Guang Liang
A novel series of di-carbonyl analogs of curcumin (DACs) were prepared and evaluated for their anti-inflammatory properties. Preliminary results showed that a vast majority of compounds tested in this study could effectively suppress LPS-induced production of tumor necrosis factor (TNF)-α and interleukin (IL)-6. Structure-activity relationships of the compounds were discussed. Compounds 5a27 and 5a28 showed the most potent anti-inflammatory activities and had higher structural stability and orally bioavailability than curcumin in vitro...
February 12, 2019: European Journal of Medicinal Chemistry
Mina Karimpour, Mohammad Ali Hosseinpour Feizi, Majid Mahdavi, Barbara Krammer, Thomas Verwanger, Farhood Najafi, Esmaeil Babaei
BACKGROUND: Curcumin, the polyphenolic constituent of turmeric, has been recognized as an effective anticancer agent in the treatment of breast cancer. However, the poor bioavailability of curcumin triggers finding of new approaches for elevating its therapeutic efficiency. PURPOSE: We aimed to use gemini surfactant nanocarriers for curcumin in order to overcome its limitations. STUDY DESIGN: We investigated the in vitro characterization of gemini surfactant-curcumin (Gemini-Cur) and examined its antiproliferative & apoptotic activities on breast cancer cell lines...
November 15, 2018: Phytomedicine: International Journal of Phytotherapy and Phytopharmacology
Giulia Orteca, Federica Pisaneschi, Sara Rubagotti, Tracy W Liu, Giacomo Biagiotti, David Piwnica-Worms, Michele Iori, Pier Cesare Capponi, Erika Ferrari, Mattia Asti
Colorectal cancer is the third most commonly occurring cancer in men and the second most commonly occurring cancer in women worldwide. We have recently reported that curcuminoid complexes labelled with gallium-68 have demonstrated preferential uptake in HT29 colorectal cancer and K562 lymphoma cell lines compared to normal human lymphocytes. In the present study, we report a new gallium-68-labelled curcumin derivative (68 Ga-DOTA-C21) and its initial validation as marker for early detection of colorectal cancer...
February 12, 2019: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Mehri Bemani Naeini, Amir Abbas Momtazi, Mahmoud Reza Jaafari, Thomas P Johnston, George Barreto, Maciej Banach, Amirhossein Sahebkar
Lipid metabolism plays an important role in cancer development due to the necessities of rapidly dividing cells to increase structural, energetic, and biosynthetic demands for cell proliferation. Basically, obesity, type 2 diabetes, and other related diseases, and cancer are associated with a common hyperactivated "lipogenic state." Recent evidence suggests that metabolic reprogramming and overproduction of enzymes involved in the synthesis of fatty acids are the new hallmarks of cancer, which occur in an early phase of tumorigenesis...
February 11, 2019: Journal of Cellular Physiology
Bongki Park, Sooseong You, William C S Cho, Jun-Yong Choi, Myeong Soo Lee
OBJECTIVE: The aim of this study is to summarize preclinical studies on herbal medicines used to treat cancer cachexia and its underlying mechanisms. METHODS: We searched four representing databases, including PubMed, EMBASE, the Allied and Complementary Medicine Database, and the Web of Science up to December 2016. Randomized animal studies were included if the effects of any herbal medicine were tested on cancer cachexia. The methodological quality was evaluated by the Collaborative Approach to Meta-Analysis and Review of Animal Data from Experimental Studies (CAMARADE) checklist...
2019: Journal of Zhejiang University. Science. B
Maryam Pourhajibagher, Abbas Salehi Vaziri, Nasrin Takzaree, Roghayeh Ghorbanzadeh
BACKGROUND: Potential complications on the crown level during fixed orthodontic procedures are white spot, enamel demineralization and the tooth decay. This study evaluated the antimicrobial properties of an orthodontic adhesive incorporating cationic curcumin doped zinc oxide nanoparticles (cCur/ZnONPs), which can have the highest concentration of cCur/ZnONPs and shear bond strength (SBS) value simultaneously, on the against cariogenic bacteria including Streptococcus mutans, Streptococcus sobrinus, and Lactobacillus acidophilus...
January 3, 2019: Photodiagnosis and Photodynamic Therapy
Kumbam Lingeshwar Reddy, Peeyush Kumar Sharma, Ashutosh Singh, Ajay Kumar, Konathala Ravi Shankar, Yashveer Singh, Neha Garg, Venkata Krishnan
Upconversion nanoparticles (UCNP) with unique multi-photon excitation photo-luminescence properties have been extensively explored as novel contrast agents for low-background biomedical imaging. There is an increasing interest in employing UCNPs as carrier for drug delivery as these offers a unique opportunity to combine therapy and diagnostics in one platform (theranostics). In the present work, we report microwave-assisted synthesis of hexagonal NaYF4 :Yb/Er UCNPs coated with porous silica and functionalized with amine (UCNP@mSiO2 )...
March 2019: Materials Science & Engineering. C, Materials for Biological Applications
Tarana Umar, Shruti Shalini, Md Kausar Raza, Siddharth Gusain, Jitendra Kumar, Waqar Ahmed, Manisha Tiwari, Nasimul Hoda
In the journey towards the development of potent multi-targeted ligands for the treatment of Alzheimer's disease, a series of Aβ aggregation inhibitors having quinoline scaffold were designed utilizing computational biology tools, synthesized and characterized by various spectral techniques including single-crystal X-ray crystallography. Organic syntheses relying upon convergent synthetic routes were employed. Investigations via ThT fluorescence assay, electron microscopy and transmission electron microscopy revealed the synthesized derivatives to exhibit Aβ self-aggregation inhibition...
November 1, 2018: MedChemComm
Ngoc The Nguyen, Ngoc Nhat Thanh Nguyen, Ngo The Nhan Tran, Phung Ngan Le, Thi Bich Tram Nguyen, Ngoc Hoa Nguyen, Long Giang Bach, Vu Nguyen Doan, Ha Le Bao Tran, Van Thu Le, Ngoc Quyen Tran
Nanogel-based systems loaded with single anticancer drugs display miscellaneous effectiveness in tumor remission, gradually circumventing mutation and resistance in chemotherapy. Hence, the existence of dual-drug delivered nano-sized systems has been contemporaneous with drug development and preceded the conventional-dose chemotherapy. Among outstanding synergistic drug nanoplatforms, thermosensitive copolymer heparin-Pluronic F127 (Hep-F127) co-delivering cisplatin (CDDP) and curcumins (Cur) (Hep-F127/CDDP/Cur) has emerged as a notable candidate for temperature-responsive drug delivery...
December 18, 2018: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Manita Das, Archana Solanki, Apeksha Joshi, Ranjitsinh Devkar, Sriram Seshadri, Sonal Thakore
Multifunctional nanoconjugates possessing an assortment of key functionalities such as magnetism, florescence, cell-targeting, pH and thermo-responsive features were developed for dual drug delivery. The novelty lies in careful conjugation of each of the functionality with magnetic Fe3 O4 nanoparticles by virtue of urethane linkages instead of silica in a simple one pot synthesis. Further β-cyclodextrin (CD) was utilized to carry hydrophobic as well as hydrophilic drug. Superlative release of DOX could be obtained under acidic pH conditions and elevated temperature, which coincides with the tumor microenvironment...
February 15, 2019: Carbohydrate Polymers
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