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Chemical Structure| 458-37-7 Chemical Structure| 458-37-7

Structure of Curcumin
CAS No.: 458-37-7

Chemical Structure| 458-37-7

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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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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.

Keywords: analogues ; aryl nitro ; curcumin ; synthesis ; tuberculosis

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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).

Keywords: colon cancer ; drug delivery ; CO2 ; mathematical modeling

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Product Details of Curcumin

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

Safety of Curcumin

GHS Pictogram:
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

Related Pathways of Curcumin

epigenetics

Isoform Comparison

Biological Activity

Target
  • p300/CBP

    p300, IC50:~25 μM

  • HDAC

  • NF-κB

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 <<

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

2.71mL

0.54mL

0.27mL

13.57mL

2.71mL

1.36mL

27.15mL

5.43mL

2.71mL

Dissolving Methods
Please choose the appropriate dissolution scheme according to your animal administration guide.For the following dissolution schemes, clear stock solution should be prepared according to in vitro experiments, and then cosolvent should be added in turn:

in order to ensure the reliability of the experimental results, the clarified stock solution can be properly preserved according to the storage conditions; The working fluid for in vivo experiment is recommended to be prepared now and used on the same day;

The percentage shown in front of the following solvent refers to the volume ratio of the solvent in the final solution; If precipitation or precipitation occurs in the preparation process, it can be assisted by heating and/or ultrasound.
Protocol 1

References

 

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