Structure of Curcumin
CAS No.: 458-37-7
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Curcumin (Diferuloylmethane) is a natural phenolic compound that specifically inhibits p300/CREB-binding protein acetyltransferase, inhibiting acetylation of histones/non-histones and histone acetyltransferase-dependent chromatin transcription. Curcumin inhibits NF-κB and MAPKs and has anti-inflammatory, antioxidant, antiproliferative, and antiangiogenic pharmacological effects.
Synonyms: Diferuloylmethane; Natural Yellow 3; UNIIIT942ZTH98.
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Arylnitro monocarbonyl curcumin analogues: Synthesis and in vitro antitubercular evaluation
du Preez, Charne ; Legoabe, Lesetja J. ; Jordaan, Audrey ; Jesumoroti, Omobolanle J. ; Warner, Digby F. ; Beteck, Richard M.
Abstract: Curcumin is a natural product that has been reported to exhibit myriad pharmacol. properties, one of which is antitubercular activity. It demonstrates antitubercular activity by directly inhibiting Mycobacterium tuberculosis (M.tb) and also enhances immune responses that ultimately lead to the elimination of M.tb by macrophages. This natural product is, however, unstable, and several analogs, noticeably monocarbonyl analogs, have been synthesized to overcome this challenge. Curcumin and its monocarbonyl analogs reported so far exhibit moderate antitubercular activity in the range of 7 to 16 μM. Herein, we report a straightforward synthesis of novel monocarbonyl curcumin analogs, their antitubercular activity, and the structure-activity relationship. The hit compound from this study, 3a, exhibits potent MIC90 values in the range of 0.2 to 0.9 μM in both ADC and CAS media.
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Keywords: analogues ; aryl nitro ; curcumin ; synthesis ; tuberculosis
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Purchased from AmBeed: 552-89-6 ; 458-37-7 ; 698-63-5 ; 99-61-6 ; 30626-03-0 ; 30625-98-0 ; 1675220-86-6 ; 30625-99-1
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Impregnação assistida por fluido supercrítico de curcumina em micropartículas de quitosana
Porto Alegre ;
Abstract: Curcumin, a polyphenol extracted from turmeric, has many therapeutic properties. Those benefits make this compound a promissing alternative in medicine that can be used in the treatment of diseases such as arthritis, metabolic syndrome, liver disease, obesity, neurodegenerative illness and multiple types of câncer. Colon cancer is high occurrence disease and it’s the second most letal type of cancer. As chemotherapy has too many side effects, new natural products are widely researched as alternative drugs to treat all kinds of cancer. Curcumin is being researched as a replacement for the traditional chemotherapy drugs, however, it’s instability when ingested makes it unable to reach the colon with treatment potential. Incorporating the compound in a biopolymer is a common strategy to by-pass this problem and allow the drug to reach the desired location. Chitosan is an example of biopolymer which suits this characteristics and can be used to transport the curcumin through the digestive tract. Supercritical impregnation was the technique chosen to incorporate the curcumin into the chitosan, which is a method that utilizes a supercritical fluid technology to achieve this objective. The goal of this work was to impregnate the chitosan particles with curcumin using carbon dioxide expanded in ethanol and evaluate its delivery capacity as well as making the mathematical modeling of the process. SEM and FTIR were used to characterize the particles before and after the impregnation. The pressure of 200 bar resulted in highest percent and amount of curcumin impregnated (15,8% and 3,16 mg) in the particles and there was no significant difference between the quantities of ethanol evaluated. The first order model was the one that best described the curcumin liberation in PBS (pH 7,4).
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Keywords: colon cancer ; drug delivery ; CO2 ; mathematical modeling
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CAS No. : | 458-37-7 |
Formula : | C21H20O6 |
M.W : | 368.38 |
SMILES Code : | O=C(CC(/C=C/C1=CC=C(O)C(OC)=C1)=O)/C=C/C2=CC=C(O)C(OC)=C2 |
Synonyms : |
Diferuloylmethane; Natural Yellow 3; UNIIIT942ZTH98.
|
MDL No. : | MFCD00008365 |
InChI Key : | VFLDPWHFBUODDF-FCXRPNKRSA-N |
Pubchem ID : | 969516 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362+P364-P403+P233-P501 |
Target |
|
In Vitro:
Cell Line
|
Concentration | Treated Time | Description | References |
CHO cells | 10 µM | 24 h | Curcumin significantly reduced the secretion of Aβ40 and Aβ42 | Cells. 2020 Feb 3;9(2):349. |
SH-SY5Y cells | 10 µM | 24 h | Curcuminsignificantly reduced the secretion of Aβ40 | Cells. 2020 Feb 3;9(2):349. |
ARPE-19 cells | 0.01 mM | 24 h | To evaluate the effect of curcumin on cell proliferation, results showed that 0.01 mM curcumin significantly increased cell proliferation. | Int J Mol Sci. 2022 Nov 25;23(23):14771. |
ARPE-19 cells | 0.05 mM | 24 h | To evaluate the effect of curcumin on cell proliferation, results showed that 0.05 mM curcumin significantly decreased cell viability and triggered S-phase cell cycle arrest. | Int J Mol Sci. 2022 Nov 25;23(23):14771. |
ARPE-19 cells | 0.1 mM | 24 h | To evaluate the effect of curcumin on cell proliferation, results showed that 0.1 mM curcumin significantly decreased cell viability and triggered S-phase cell cycle arrest. | Int J Mol Sci. 2022 Nov 25;23(23):14771. |
Human cervical cancer cells (HeLa) | 5–50 μM | 72 h | To compare the cytotoxicity of free curcumin and FA-CLAP nanocurcumin on HeLa cells. Results showed that FA-CLAP nanocurcumin exhibited higher cytotoxicity at doses of 15 μM, 25 μM, and 50 μM. | J Nanobiotechnology. 2014 Jul 15;12:25. |
Human cervical cancer cells (HeLa) | 25 μM | 2 h | To study the cellular uptake of FA-CLAP nanocurcumin. Results showed that FA-CLAP nanocurcumin exhibited better cellular uptake than free curcumin. | J Nanobiotechnology. 2014 Jul 15;12:25. |
4T1 breast cancer cells | 6 µg/mL | 1, 2, and 4 h | To evaluate the cellular uptake of CUR/IR780@SMEDDS, results showed that the uptake of CUR/IR780@SMEDDS in 4T1 cells increased over time and further increased with NIR laser irradiation. | Int J Nanomedicine. 2019 May 7;14:3311-3330. |
Lewis Lung Carcinoma cells | 10, 20, 50, 100 µM | 24 and 48 h | To evaluate the effect of curcumin on tumor cell proliferation, results showed that curcumin significantly reduced tumor cell proliferation | Br J Cancer. 2012 Sep 25;107(7):1083-92. |
BZR human lung epithelial tumour cells | 10, 20, 50 µM | 48 h | To evaluate the effect of curcumin on tumor cell proliferation, results showed that curcumin significantly reduced tumor cell proliferation | Br J Cancer. 2012 Sep 25;107(7):1083-92. |
IEC-6 cells | 17.4 µg/ml | 24 h | To evaluate the cytotoxicity of Curcumin on IEC-6 cells, the results showed that SP@Curcumin had significantly lower cytotoxicity than free Curcumin. | Sci Adv. 2021 Nov 26;7(48):eabi9265. |
CT26 cells | 17.4 µg/ml | 4 h | To evaluate the antitumor effect of SP@Curcumin on CT26 cells, the results showed that SP@Curcumin combined with X-ray significantly enhanced the tumor cell killing effect. | Sci Adv. 2021 Nov 26;7(48):eabi9265. |
Microglia | 4 μM | 24 h | To assess the cytotoxicity of curcumin on microglia and hUC-MSC to determine the optimal concentration. | J Neuroinflammation. 2023 Feb 24;20(1):49. |
In Vivo:
Species
|
Animal Model
|
Administration | Dosage | Frequency | Description | References |
Rats | Sprague Dawley rats | Oral | 75 mg/kg | Single dose | To evaluate the oral bioavailability of CUR/IR780@SMEDDS in rats, results showed that CUR/IR780@SMEDDS significantly improved the oral absorption of curcumin and IR780, with relative bioavailability of 743.7% and 307.0%, respectively. | Int J Nanomedicine. 2019 May 7;14:3311-3330. |
C57Bl/6 mice | Lung tumor model | Oral | 3 mg/kg | 5 days per week, until the end of the experiment | To evaluate the effect of curcumin on lung tumor growth, results showed that curcumin significantly reduced the size of lung tumors | Br J Cancer. 2012 Sep 25;107(7):1083-92. |
C57BL/6 mice | Cisplatin-induced acute kidney injury model | Gavage | 100 mg/kg | Once daily for 3 days | To observe the protective effect of curcumin on cisplatin-induced acute kidney injury, results showed that curcumin significantly reduced serum creatinine and BUN levels, and decreased tubular cell necrosis and inflammation. | J Cell Mol Med. 2021 Sep;25(18):8775-8788. |
Balb/c mice | Colon cancer model | Oral | 1.2 mg/ml | Every 3 days for 15 days | To evaluate the chemoradiotherapeutic effect of SP@Curcumin in a colon cancer model, the results showed that SP@Curcumin significantly inhibited tumor growth and improved the survival rate of mice. | Sci Adv. 2021 Nov 26;7(48):eabi9265. |
Mice | MCAO model | Intraperitoneal injection | 100 mg/kg | Once every 24 hours for 3 days | To evaluate the functional recovery and neuroprotective effects of combined curcumin and hUC-MSC therapy in MCAO mice. | J Neuroinflammation. 2023 Feb 24;20(1):49. |
Clinical Trial:
NCT Number | Conditions | Phases | Recruitment | Completion Date | Locations |
NCT02978339 | Primary Sclerosing Cholangitis | PHASE1|PHASE2 | COMPLETED | 2019-01-08 | Mayo Clinic, Rochester, Minnes... More >>ota, 55905-0001, United States Less << |
NCT01543386 | Healthy Volunteers (Middle-age... More >>d Smokers) Less << | PHASE1|PHASE2 | COMPLETED | 2025-04-12 | CHU Clermont-Ferrand, Clermont... More >>-Ferrand, 63003, France Less << |
NCT02255370 | Crohn's Disease | PHASE3 | COMPLETED | 2025-06-18 | CHU de Clermont-Ferrand, Clerm... More >>ont-Ferrand, 63003, France Less << |
NCT04971382 | Horizontal Alveolar Bone Loss | PHASE4 | NOT_YET_RECRUITING | 2025-03-01 | faculty of dentistry Ain shams... More >> university, Cairo, 11566, Egypt Less << |
NCT01052025 | Type 2 Diabetes|Pre-diabetes|I... More >>nsulin Resistance|Cardiovascular Risk Less << | PHASE4 | UNKNOWN | 2025-04-10 | HRH Princess Maha Chakri Sirin... More >>dhorn Medical Center, Ongkarak, Nakornnayok, 26120, Thailand Less << |
NCT00094445 | Pancreatic Neoplasms|Adenocarc... More >>inoma Less << | PHASE2 | COMPLETED | 2025-04-14 | UT MD Anderson Cancer Center, ... More >>Houston, Texas, 77030, United States Less << |
NCT01831193 | Proteinuria | PHASE3 | COMPLETED | 2025-04-14 | Instituto Nacional de Cardiolo... More >>gia Ignacio Chavez, Mexico city, DF, 14080, Mexico Less << |
NCT02554344 | Cervical Intraepithelial Neopl... More >>asia Less << | EARLY_PHASE1 | UNKNOWN | 2025-01-17 | Baylor Charles A. Sammons Canc... More >>er Center, Dallas, Texas, 75246, United States Less << |
NCT06626230 | Anal High Grade Squamous Intra... More >>epithelial Lesion Less << | PHASE1 | NOT_YET_RECRUITING | 2025-03-25 | Grady Memorial Hospital, Atlan... More >>ta, Georgia, 30303, United States|Grady Hospital - Ponce De Leon Clinic, Atlanta, Georgia, 30308, United States Less << |
NCT00889161 | Inflammatory Bowel Disease|Ulc... More >>erative Colitis|Crohn's Disease Less << | PHASE1 | COMPLETED | 2025-06-10 | Seattle Children's Hosptial, S... More >>eattle, Washington, 98105, United States Less << |
NCT00181662 | Healthy | COMPLETED | 2007-10-17 | Massachusetts General Hospital... More >>, Boston, Massachusetts, 02114, United States Less << | |
NCT01928043 | Bipolar Disorder | PHASE2 | TERMINATED | 2017-03-03 | Sunnybrook Health Sciences Cen... More >>tre, Toronto, Ontario, M4N 3M5, Canada Less << |
NCT01344291 | Hyperprolactinoma | PHASE1 | UNKNOWN | 2025-08-12 | Mashad University of Medical S... More >>ciences, Mashad, Khorasan Razavi, Iran, Islamic Republic of Less << |
NCT03980509 | Breast Cancer | PHASE1 | COMPLETED | 2023-03-24 | Medical University of South Ca... More >>rolina, Charleston, South Carolina, 29425, United States Less << |
Tags: Curcumin | Diferuloylmethane | Natural Yellow 3 | Turmeric yellow | Natural Yellow3 | Natural Yellow 3 | Natural Yellow-3 | Histone Acetyltransferase | NF-κB | MAPK | Wnt/β-catenin | COX-2 | LOX | 458-37-7
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