Cytosporone B | CAS#321661-62-5 | Nur77 agonist

MedKoo Cat#: 523121 | Name: Cytosporone B

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Cytosporone B is the first naturally occurring agonist for nuclear orphan receptor Nur77. The molecule binds with high affinity (IC50=0.278 nM) to the ligand-binding domain of Nur77 and stimulates Nur77-dependent activities. Nur77 is also involved in glucose homeostasis, where it induces genes involved in gluconeogenesis. Csn-B physically binds to Nur77 and activates its transactivational activity and translocation to mitochondria to induce apoptosis. It inhibits cancer cell proliferation and tumor growth.

Chemical Structure

Cytosporone B

CAS#321661-62-5

Theoretical Analysis

MedKoo Cat#: 523121

Name: Cytosporone B

CAS#: 321661-62-5

Chemical Formula: C18H26O5

Exact Mass: 322.1780

Molecular Weight: 322.40

Elemental Analysis: C, 67.06; H, 8.13; O, 24.81

Price and Availability

Size	Price	Availability
25mg	USD 190.00	Ready to ship
50mg	USD 350.00	Ready to ship
100mg	USD 650.00	Ready to ship
200mg	USD 1,050.00	Ready to ship
500mg	USD 1,950.00	Ready to ship
1g	USD 2,950.00	Ready to ship
2g	USD 4,950.00	Ready to ship
5g	USD 7,650.00	2 weeks

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Synonym

Cytosporone B; Cytosporone-B; Csn-B; Dothiorelone G; Dothiorelone-G

IUPAC/Chemical Name

Ethyl 3,5-dihydroxy-2-(1-oxooctyl)-benzeneacetate

InChi Key

UVVWQQKSNZLUQA-UHFFFAOYSA-N

InChi Code

InChI=1S/C18H26O5/c1-3-5-6-7-8-9-15(20)18-13(11-17(22)23-4-2)10-14(19)12-16(18)21/h10,12,19,21H,3-9,11H2,1-2H3

SMILES Code

O=C(OCC)CC1=CC(O)=CC(O)=C1C(CCCCCCC)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#A9T06K26

QC Data

View QC data: current batch, Lot#A9T06K26

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Cytosporone B is a naturally occurring agonist for nuclear orphan receptor Nur77(NR4A1) with an EC50 of 0.278nM.

In vitro activity:

Human VF fibroblasts were exposed to TGF-β1+/-Csn-B. Expression of genes related to fibrosis were quantified. In addition, contraction was assayed as a surrogate for the fibrotic phenotype in our cell line. Six hours of Csn-B exposure had no effect on SMAD2, SMAD3, or SMAD7. Csn-B significantly downregulated TGF-β1-mediated upregulation of these genes (P = .009, P = .03, respectively). Csn-B had no effect on genes related to TGF-β/Smad signaling. Csn-B also decreased the TGF-β1-mediated contractile phenotype in our cells (P = .004). Reference: Laryngoscope. 2018 Dec;128(12):E425-E428. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/30325029/

In vivo activity:

To analyze the biological function of Csn-B in Nur77-mediated regulation of glucose levels, the levels of blood glucose in wild-type and Nr4a1 / mice were tested. Csn-B signicantly (P o0.01) changed blood glucose levels in fasting wild-type mice (Fig. 5a). In wild-type mice, after fasting for 16 h, the basal levels of blood glucose declined to 3.2 mM. However, Csn-B treatment signicantly increased glucose levels from 3.2 to 11.4 mM (P o 0.01) within the rst 30 min, and thereafter blood glucose gradually decreased before reaching the initial level after 300 min (Fig. 5a). By contrast, in Nr4a1 / mice CsnB induced a diminished increase in glucose levels within the rst 30 min (from 3.7 to 5.8 mM) as compared with the wild type, which was close to the effect of control injections (Supplementary Fig. 5a online). Reference: Nat Chem Biol. 2008 Sep;4(9):548-56. https://doi.org/10.1038/nchembio.106

	Solvent	mg/mL	mM
Solubility
	DMSO	64.0	198.51
	Ethanol	64.0	198.51

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 322.40 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

In vitro protocol:

1. Zhan Y, Du X, Chen H, Liu J, Zhao B, Huang D, Li G, Xu Q, Zhang M, Weimer BC, Chen D, Cheng Z, Zhang L, Li Q, Li S, Zheng Z, Song S, Huang Y, Ye Z, Su W, Lin SC, Shen Y, Wu Q. Cytosporone B is an agonist for nuclear orphan receptor Nur77. Nat Chem Biol. 2008 Sep;4(9):548-56. doi: 10.1038/nchembio.106. PMID: 18690216. 2. Hiwatashi N, Mukudai S, Bing R, Branski RC. The effects of cytosporone-B, a novel antifibrotic agent, on vocal fold fibroblasts. Laryngoscope. 2018 Dec;128(12):E425-E428. doi: 10.1002/lary.27361. Epub 2018 Oct 16. PMID: 30325029; PMCID: PMC6309723.

In vivo protocol:

1: Zhan Y, Du X, Chen H, Liu J, Zhao B, Huang D, Li G, Xu Q, Zhang M, Weimer BC, Chen D, Cheng Z, Zhang L, Li Q, Li S, Zheng Z, Song S, Huang Y, Ye Z, Su W, Lin SC, Shen Y, Wu Q. Cytosporone B is an agonist for nuclear orphan receptor Nur77. Nat Chem Biol. 2008 Sep;4(9):548-56. doi: 10.1038/nchembio.106. PMID: 18690216. 2: Ding X, Le S, Wang K, Su Y, Chen S, Wu C, Chen J, Chen S, Zhang A, Xia J. Cytosporone B (Csn-B), an NR4A1 agonist, attenuates acute cardiac allograft rejection by inducing differential apoptosis of CD4+T cells. Int Immunopharmacol. 2022 Mar;104:108521. doi: 10.1016/j.intimp.2022.108521. Epub 2022 Jan 10. PMID: 35026656. 3: Yin C, Liu H, Shan Y, Gupta VK, Jiang Y, Zhang W, Tan H, Gong L. Cytosporone B as a Biological Preservative: Purification, Fungicidal Activity and Mechanism of Action against Geotrichum citri-aurantii. Biomolecules. 2019 Mar 29;9(4):125. doi: 10.3390/biom9040125. PMID: 30934892; PMCID: PMC6523523. 4: Yu HZ, Zhu BQ, Zhu L, Li S, Wang LM. NR4A1 agonist cytosporone B attenuates neuroinflammation in a mouse model of multiple sclerosis. Neural Regen Res. 2022 Dec;17(12):2765-2770. doi: 10.4103/1673-5374.339492. PMID: 35662227; PMCID: PMC9165396. 5: Li J, Lv C, Sun W, Li Z, Han X, Li Y, Shen Y. Cytosporone B, an inhibitor of the type III secretion system of Salmonella enterica serovar Typhimurium. Antimicrob Agents Chemother. 2013 May;57(5):2191-8. doi: 10.1128/AAC.02421-12. Epub 2013 Mar 4. PMID: 23459474; PMCID: PMC3632957. 6: Patiño-Martínez E, Solís-Barbosa MA, Santana E, González-Domínguez E, Segovia-Gamboa NC, Meraz-Ríos MA, Córdova EJ, Valdés J, Corbí ÁL, Sánchez-Torres C. The Nurr7 agonist Cytosporone B differentially regulates inflammatory responses in human polarized macrophages. Immunobiology. 2022 Nov;227(6):152299. doi: 10.1016/j.imbio.2022.152299. Epub 2022 Nov 2. PMID: 36370518. 7: Ismaiel M, Murphy B, Aldhafiri S, Giffney HE, Thornton K, Mukhopadhya A, Keogh CE, Fattah S, Mohan HM, Cummins EP, Murphy EP, Winter DC, Crean D. The NR4A agonist, Cytosporone B, attenuates pro-inflammatory mediators in human colorectal cancer tissue ex vivo. Biochem Biophys Res Commun. 2021 May 21;554:179-185. doi: 10.1016/j.bbrc.2021.03.110. Epub 2021 Mar 30. PMID: 33798945. 8: Yang PB, Hou PP, Liu FY, Hong WB, Chen HZ, Sun XY, Li P, Zhang Y, Ju CY, Luo LJ, Wu SF, Zhou JX, Wang ZJ, He JP, Li L, Zhao TJ, Deng X, Lin T, Wu Q. Blocking PPARγ interaction facilitates Nur77 interdiction of fatty acid uptake and suppresses breast cancer progression. Proc Natl Acad Sci U S A. 2020 Nov 3;117(44):27412-27422. doi: 10.1073/pnas.2002997117. Epub 2020 Oct 21. PMID: 33087562; PMCID: PMC7959534. 9: Hiwatashi N, Mukudai S, Bing R, Branski RC. The effects of cytosporone-B, a novel antifibrotic agent, on vocal fold fibroblasts. Laryngoscope. 2018 Dec;128(12):E425-E428. doi: 10.1002/lary.27361. Epub 2018 Oct 16. PMID: 30325029; PMCID: PMC6309723. 10: Safe S, Shrestha R, Mohankumar K. Orphan nuclear receptor 4A1 (NR4A1) and novel ligands. Essays Biochem. 2021 Dec 17;65(6):877-886. doi: 10.1042/EBC20200164. PMID: 34096590. 11: Egarnes B, Blanchet MR, Gosselin J. Treatment with the NR4A1 agonist cytosporone B controls influenza virus infection and improves pulmonary function in infected mice. PLoS One. 2017 Oct 20;12(10):e0186639. doi: 10.1371/journal.pone.0186639. PMID: 29053748; PMCID: PMC5650162. 12: Pulakazhi Venu VK, Alston L, Iftinca M, Tsai YC, Stephens M, Warriyar K V V, Rehal S, Hudson G, Szczepanski H, von der Weid PY, Altier C, Hirota SA. Nr4A1 modulates inflammation-associated intestinal fibrosis and dampens fibrogenic signaling in myofibroblasts. Am J Physiol Gastrointest Liver Physiol. 2021 Sep 1;321(3):G280-G297. doi: 10.1152/ajpgi.00338.2019. Epub 2021 Jul 21. PMID: 34288735. 13: Xia Z, Cao X, Rico-Bautista E, Yu J, Chen L, Chen J, Bobkov A, Wolf DA, Zhang XK, Dawson MI. Relative impact of 3- and 5-hydroxyl groups of cytosporone B on cancer cell viability. Medchemcomm. 2013 Feb 1;4(2):332-339. doi: 10.1039/C2MD20243C. Epub 2012 Nov 7. PMID: 24795803; PMCID: PMC4005383. 14: Li Q, Li Y, Huang W, Wang X, Liu Z, Chen J, Fan Y, Peng T, Sadayappan S, Wang Y, Fan GC. Loss of Lipocalin 10 Exacerbates Diabetes-Induced Cardiomyopathy via Disruption of Nr4a1-Mediated Anti-Inflammatory Response in Macrophages. Front Immunol. 2022 Jun 10;13:930397. doi: 10.3389/fimmu.2022.930397. PMID: 35757735; PMCID: PMC9226549. 15: Arifi S, Zaienne D, Heering J, Wein T, Zhubi R, Chaikuad A, Knapp S, Marschner JA, Merk D. Fragment-based discovery of orphan nuclear receptor Nur77/NGFI-B ligands. Bioorg Chem. 2022 Dec;129:106164. doi: 10.1016/j.bioorg.2022.106164. Epub 2022 Sep 17. PMID: 36162288. 16: Finsterwalder R, Ganesan MK, Leb H, Habertheuer A, Basílio J, Lang I, Krunic M, Wiedemann D, Petzelbauer P. Hypoxia/reperfusion predisposes to atherosclerosis. PLoS One. 2018 Oct 5;13(10):e0205067. doi: 10.1371/journal.pone.0205067. PMID: 30289932; PMCID: PMC6173417. 17: Yan J, Huang J, Wu J, Fan H, Liu A, Qiao L, Shen M, Lai X. Nur77 attenuates inflammatory responses and oxidative stress by inhibiting phosphorylated IκB-α in Parkinson's disease cell model. Aging (Albany NY). 2020 May 13;12(9):8107-8119. doi: 10.18632/aging.103128. Epub 2020 May 13. PMID: 32401747; PMCID: PMC7244064. 18: Xiong Y, Ran J, Xu L, Tong Z, Adel Abdo MS, Ma C, Xu K, He Y, Wu Z, Chen Z, Hu P, Jiang L, Bao J, Chen W, Wu L. Reactivation of NR4A1 Restrains Chondrocyte Inflammation and Ameliorates Osteoarthritis in Rats. Front Cell Dev Biol. 2020 Mar 17;8:158. doi: 10.3389/fcell.2020.00158. PMID: 32258036; PMCID: PMC7090231. 19: Luan J, Zhang D, Hao L, Qi L, Liu X, Guo H, Li C, Guo Y, Li T, Zhang Q, Zhai G. Preparation, characterization and pharmacokinetics of Amoitone B-loaded long circulating nanostructured lipid carriers. Colloids Surf B Biointerfaces. 2014 Feb 1;114:255-60. doi: 10.1016/j.colsurfb.2013.10.018. Epub 2013 Oct 19. PMID: 24211416. 20: Wu L, Chen L. Characteristics of Nur77 and its ligands as potential anticancer compounds (Review). Mol Med Rep. 2018 Dec;18(6):4793-4801. doi: 10.3892/mmr.2018.9515. Epub 2018 Sep 27. PMID: 30272297; PMCID: PMC6236262.