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Balsalazide

CAS# 80573-04-2

Balsalazide

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Chemical structure

Balsalazide

3D structure

Chemical Properties of Balsalazide

Cas No. 80573-04-2 SDF Download SDF
PubChem ID 6335412 Appearance Powder
Formula C17H15N3O6 M.Wt 357.32
Type of Compound N/A Storage Desiccate at -20°C
Solubility DMSO : ≥ 41 mg/mL (114.74 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name (3Z)-3-[[4-(2-carboxyethylcarbamoyl)phenyl]hydrazinylidene]-6-oxocyclohexa-1,4-diene-1-carboxylic acid
SMILES C1=CC(=CC=C1C(=O)NCCC(=O)O)NN=C2C=CC(=O)C(=C2)C(=O)O
Standard InChIKey KONZVQJABTUMFX-NDENLUEZSA-N
Standard InChI InChI=1S/C17H15N3O6/c21-14-6-5-12(9-13(14)17(25)26)20-19-11-3-1-10(2-4-11)16(24)18-8-7-15(22)23/h1-6,9,19H,7-8H2,(H,18,24)(H,22,23)(H,25,26)/b20-12-
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Balsalazide Dilution Calculator

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Balsalazide Molarity Calculator

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Preparing Stock Solutions of Balsalazide

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.7986 mL 13.9931 mL 27.9861 mL 55.9722 mL 69.9653 mL
5 mM 0.5597 mL 2.7986 mL 5.5972 mL 11.1944 mL 13.9931 mL
10 mM 0.2799 mL 1.3993 mL 2.7986 mL 5.5972 mL 6.9965 mL
50 mM 0.056 mL 0.2799 mL 0.5597 mL 1.1194 mL 1.3993 mL
100 mM 0.028 mL 0.1399 mL 0.2799 mL 0.5597 mL 0.6997 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Balsalazide

Balsalazide is an anti-inflammatory compound used in the treatment of Inflammatory Bowel Disease. IC50: Target: Others Balsalazide is a new 5-aminosalicylic acid (5-ASA) containing prodrug. High dose balsalazide (3.0 g twice daily) was superior in maintaining remission in patients with ulcerative colitis compared with a low dose (1.5 g twice daily) or a standard dose of mesalazine (0.5 g three times daily). All three treatments were safe and well tolerated [1]. Balsalazide is approved for the treatment of mild-to-moderate active UC. It is efficacious for the induction of remission in mild to moderate UC and has a favorable safety profile, with the added advantages of greater efficacy of remission induction and rapidity of onset [2].

References:
[1]. Kruis W, et al. Low dose balsalazide (1.5 g twice daily) and mesalazine (0.5 g three times daily) maintained remission of ulcerative colitis but high dose balsalazide (3.0 g twice daily) was superior in preventing relapses. Gut, 2001. 49(6): p. 783-789. [2]. Wiggins JB, et al. Balsalazide: a novel 5-aminosalicylate prodrug for the treatment of active ulcerative colitis. Expert Opin Drug Metab Toxicol, 2009. 5(10): p. 1279-1284.

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References on Balsalazide

Balsalazide Potentiates Parthenolide-Mediated Inhibition of Nuclear Factor-kappaB Signaling in HCT116 Human Colorectal Cancer Cells.[Pubmed:26130998]

Intest Res. 2015 Jul;13(3):233-41.

BACKGROUND/AIMS: Balsalazide is an anti-inflammatory drug used in the treatment of inflammatory bowel disease. Balsalazide can reduce inflammatory responses via several mechanisms, including inhibition of nuclear factor-kappaB (NF-kappaB) activity. Parthenolide (PT) inhibits NF-kappaB and exerts promising anticancer effects by promoting apoptosis. The present investigated the antitumor effects of Balsalazide, combined with PT, on NF-kappaB in a representative human colorectal carcinoma cell line, HCT116. METHODS: We counted cells and conducted annexin-V assays and cell cycle analysis to measure apoptotic cell death. Western blotting was used investigate the levels of proteins involved in apoptosis. RESULTS: PT and Balsalazide produced synergistic anti-proliferative effects and induced apoptotic cell death. The combination of Balsalazide and PT markedly suppressed nuclear translocation of the NF-kappaB p65 subunit and the phosphorylation of inhibitor of NF-kappaB. Moreover, PT and Balsalazide dramatically enhanced NF-kappaB p65 phosphorylation. Apoptosis, through the mitochondrial pathway, was confirmed by detecting effects on Bcl-2 family members, cytochrome c release, and activation of caspase-3 and -8. CONCLUSIONS: Combination treatment with PT and Balsalazide may offer an effective strategy for the induction of apoptosis in HCT116 cells.

Sustainable Synthesis of Balsalazide and Sulfasalazine Based on Diazotization with Low Concentrations of Nitrogen Dioxide in Air.[Pubmed:28054726]

Chemistry. 2017 Mar 23;23(17):4042-4045.

Low concentrations of nitrogen dioxide, which arises as a side product from a range of industrial processes, can effectively be recycled through the diazotization of anilines. The studies reported herein now demonstrate that the removal of nitrogen dioxide from gas streams is even more effective when hydrophilic anilines are used as starting materials. The diazonium salts, which are obtained in this way in up to quantitative yields, can directly be employed in azo coupling reactions, thus opening up an attractive route to the industrially important group of azo compounds.

Combined Parthenolide and Balsalazide Have Enhanced Antitumor Efficacy Through Blockade of NF-kappaB Activation.[Pubmed:28108625]

Mol Cancer Res. 2017 Feb;15(2):141-151.

Balsalazide is a colon-specific prodrug of 5-aminosalicylate that is associated with a reduced risk of colon cancer in patients with ulcerative colitis. Parthenolide, a strong NF-kappaB inhibitor, has recently been demonstrated to be a promising therapeutic agent, promoting apoptosis of cancer cells. In the current study, the antitumor effect of Balsalazide combined with parthenolide in human colorectal cancer cells and colitis-associated colon cancers (CAC) was investigated. The results demonstrate that the combination of Balsalazide and parthenolide markedly suppress proliferation, nuclear translocation of NF-kappaB, IkappaB-alpha phosphorylation, NF-kappaB DNA binding, and expression of NF-kappaB targets. Apoptosis via NF-kappaB signaling was confirmed by detecting expression of caspases, p53 and PARP. Moreover, treatment of a CAC murine model with parthenolide and Balsalazide together resulted in significant recovery of body weight and improvement in histologic severity. Administration of parthenolide and Balsalazide to CAC mice also suppressed carcinogenesis as demonstrated by uptake of 18F-fluoro-2-deoxy-D-glucose (FDG) using micro-PET/CT scans. These results demonstrate that parthenolide potentiates the efficacy of Balsalazide through synergistic inhibition of NF-kappaB activation and the combination of dual agents prevents colon carcinogenesis from chronic inflammation. IMPLICATIONS: This study represents the first evidence that combination therapy with Balsalazide and parthenolide could be a new regimen for colorectal cancer treatment. Mol Cancer Res; 15(2); 141-51. (c)2016 AACR.

Suppression of colitis-associated carcinogenesis through modulation of IL-6/STAT3 pathway by balsalazide and VSL#3.[Pubmed:26711554]

J Gastroenterol Hepatol. 2016 Aug;31(8):1453-61.

BACKGROUND AND AIM: Recent studies suggest that the anti-inflammatory agent Balsalazide (BSZ) and probiotic agent VSL#3 have potential therapeutic benefits for the treatment of patients with inflammatory bowel disease. However, their effectiveness in preventing colitis-associated carcinogenesis (CAC) remains uncertain. The aim of the present study was to determine the chemopreventive effects of BSZ and VSL#3 in the murine azoxymethane (AOM)/dextran sodium sulfate (DSS) model. METHODS: C57B/L6J mice were randomly divided into four groups: CAC group, BSZ group, VSL#3 group, and BSZ + VSL#3 group. After 2 weeks, the AOM/DSS model was induced by AOM injection followed by two cycles of 2% DSS. RESULTS: During first and second cycles of DSS, the number of F4/80-positive macrophages was significantly lower in the drug-treated groups compared with the CAC group (P < 0.05). At the endpoint, the total numbers of tumors in the drug-treated groups were significantly low compared with the CAC group (P < 0.05), and the drug-treated groups had significantly lower F4/80-positive macrophages in the tumor stroma (P < 0.01). The protein production of macrophage inflammatory protein 1 beta, monocyte chemoattractant protein-1, interleukin (IL)-6, and IL-10 in the colon tissues decreased in concordance with the plasma concentrations of the cytokines (P < 0.05). The drug-treated groups revealed lower expression of p-STAT3 compared with the CAC group. In addition, BCL2 decreased, and BAX increased markedly in the BSZ + VSL#3 group. CONCLUSIONS: These results revealed that BSZ and VSL#3 have chemopreventive effects against CAC through IL-6/STAT3 suppression. BSZ and VSL#3 could be suitable options for chemoprevention of colorectal cancer.

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Balsalazide could suppress colitis-associated carcinogenesis through modulation of IL-6/STAT3 pathway.

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