CC-885 | CAS#1010100-07-8 | Cereblon Modulator

MedKoo Cat#: 206829 | Name: CC-885

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Description:

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

CC-885 is a potent Cereblon Modulator with potent antitumor activity mediated through the degradation of GSPT1. was demonstrated to mediate antitumor effects through the recruitment and degradation of G1 to S phase transition 1 protein (GSPT1). GSPT1 (also named eRF3a) is a translation termination factor that binds eukaryotic translation termination factor 1 (eFR1) to mediate stop codon recognition and nascent protein release from the ribosome.

Chemical Structure

CC-885

CAS#1010100-07-8

Theoretical Analysis

MedKoo Cat#: 206829

Name: CC-885

CAS#: 1010100-07-8

Chemical Formula: C22H21ClN4O4

Exact Mass: 440.1251

Molecular Weight: 440.88

Elemental Analysis: C, 59.93; H, 4.80; Cl, 8.04; N, 12.71; O, 14.52

Price and Availability

Size	Price	Availability
10mg	USD 90.00	Ready to ship
25mg	USD 150.00	Ready to ship
50mg	USD 250.00	Ready to ship
100mg	USD 450.00	Ready to ship
200mg	USD 750.00	Ready to ship
500mg	USD 1,650.00	Ready to ship
1g	USD 2,950.00	Ready to Ship
2g	USD 5,250.00	Ready to Ship

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Synonym

CC-885, CC 885, CC885.

IUPAC/Chemical Name

N-(3-chloro-4-methylphenyl)-N'-[[2-(2,6-dioxo-3-piperidinyl)-2,3-dihydro-1-oxo-1H-isoindol-5-yl]methyl]-urea

InChi Key

DOEVCIHTTTYVCC-UHFFFAOYSA-N

InChi Code

InChI=1S/C22H21ClN4O4/c1-12-2-4-15(9-17(12)23)25-22(31)24-10-13-3-5-16-14(8-13)11-27(21(16)30)18-6-7-19(28)26-20(18)29/h2-5,8-9,18H,6-7,10-11H2,1H3,(H2,24,25,31)(H,26,28,29)

SMILES Code

O=C(NCC1=CC2=C(C(N(C(CC3)C(NC3=O)=O)C2)=O)C=C1)NC4=CC=C(C)C(Cl)=C4

Appearance

Off white to light purple 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

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#YXM90130

QC Data

View QC data: current batch, Lot#YXM90130

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

CC-885 is a cereblon (CRBN) modulator.

In vitro activity:

Proteomic data suggested that 19 proteins, such as BNIP3L, UBE2S, and UBE2C, were downregulated in the CRBN+/+ cells but not in the CRBN−/− cells after treatment with CC-885. Western blotting data also confirmed that CC-885 treatment could decrease these exogenously expressed proteins in the CRBN+/+ cells (Supplementary Fig. S5), which represented the high-confidence neosubstrates of CC-885. Given the critical role of BNIP3L in the regulation of mitophagy, this study then selected BNIP3L for further investigation and proved that BNIP3L is a bona fide neosubstrate of CC-885. First, consistent with the MS data, CC-885 induced rapid BNIP3L destruction in both a time- and dose-dependent manner. Second, CC-885 failed to decrease the BNIP3L protein level when CRBN was depleted, indicating that CRBN is required for CC-885-induced BNIP3L degradation. Third, CC-885 bridges the interaction between BNIP3L and CRBN. Reference: Acta Pharmacol Sin. 2020 Sep; 41(9): 1246–1254. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7608331/

In vivo activity:

Next, this study assessed the therapeutic efficacy of this combination in vivo by using nude mice bearing tumors. While volasertib and CC-885 alone inhibited tumor growth, the combination of both small molecular drugs markedly inhibited tumor growth and reduced tumor weights (Figures 1I and IJ). Taken together, these data clearly show that CC-885 synergizes with volasertib against NSCLC cells both in vitro and in vivo. Reference: Mol Ther Oncolytics. 2020 Sep 25; 18: 215–225. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7369516/

	Solvent	mg/mL	mM
Solubility
	DMSO	40.0	90.72
	DMSO:PBS (pH 7.2) (1:4)	0.2	0.45
	DMF	12.5	28.35

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 440.88 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:

1. Li L, Xue W, Shen Z, Liu J, Hu M, Cheng Z, Wang Y, Chen Y, Chang H, Liu Y, Liu B, Zhao J. A Cereblon Modulator CC-885 Induces CRBN- and p97-Dependent PLK1 Degradation and Synergizes with Volasertib to Suppress Lung Cancer. Mol Ther Oncolytics. 2020 Jun 23;18:215-225. doi: 10.1016/j.omto.2020.06.013. PMID: 32728610; PMCID: PMC7369516. 2. Hao BB, Li XJ, Jia XL, Wang YX, Zhai LH, Li DZ, Liu J, Zhang D, Chen YL, Xu YH, Lee SK, Xu GF, Chen XH, Dang YJ, Liu B, Tan MJ. The novel cereblon modulator CC-885 inhibits mitophagy via selective degradation of BNIP3L. Acta Pharmacol Sin. 2020 Sep;41(9):1246-1254. doi: 10.1038/s41401-020-0367-9. Epub 2020 Mar 24. PMID: 32210356; PMCID: PMC7608331. 3. Li L, Xue W, Shen Z, Liu J, Hu M, Cheng Z, Wang Y, Chen Y, Chang H, Liu Y, Liu B, Zhao J. A Cereblon Modulator CC-885 Induces CRBN- and p97-Dependent PLK1 Degradation and Synergizes with Volasertib to Suppress Lung Cancer. Mol Ther Oncolytics. 2020 Jun 23;18:215-225. doi: 10.1016/j.omto.2020.06.013. PMID: 32728610; PMCID: PMC7369516.

In vitro protocol:

In vivo protocol:

1: Bobowski-Gerard M, Boulet C, Zummo FP, Dubois-Chevalier J, Gheeraert C, Bou Saleh M, Strub JM, Farce A, Ploton M, Guille L, Vandel J, Bongiovanni A, Very N, Woitrain E, Deprince A, Lalloyer F, Bauge E, Ferri L, Ntandja-Wandji LC, Cotte AK, Grangette C, Vallez E, Cianférani S, Raverdy V, Caiazzo R, Gnemmi V, Leteurtre E, Pourcet B, Paumelle R, Ravnskjaer K, Lassailly G, Haas JT, Mathurin P, Pattou F, Dubuquoy L, Staels B, Lefebvre P, Eeckhoute J. Functional genomics uncovers the transcription factor BNC2 as required for myofibroblastic activation in fibrosis. Nat Commun. 2022 Sep 10;13(1):5324. doi: 10.1038/s41467-022-33063-9. PMID: 36088459; PMCID: PMC9464213. 2: Fuchs O. Targeting cereblon in hematologic malignancies. Blood Rev. 2023 Jan;57:100994. doi: 10.1016/j.blre.2022.100994. Epub 2022 Jul 31. PMID: 35933246. 3: Baradaran-Heravi A, Balgi AD, Hosseini-Farahabadi S, Choi K, Has C, Roberge M. Effect of small molecule eRF3 degraders on premature termination codon readthrough. Nucleic Acids Res. 2021 Apr 19;49(7):3692-3708. doi: 10.1093/nar/gkab194. PMID: 33764477; PMCID: PMC8053119. 4: Zhao M, Hu M, Chen Y, Liu H, Chen Y, Liu B, Fang B. Cereblon modulator CC-885 induces CRBN-dependent ubiquitination and degradation of CDK4 in multiple myeloma. Biochem Biophys Res Commun. 2021 Apr 16;549:150-156. doi: 10.1016/j.bbrc.2021.02.110. Epub 2021 Mar 3. PMID: 33676183. 5: Li L, Xue W, Shen Z, Liu J, Hu M, Cheng Z, Wang Y, Chen Y, Chang H, Liu Y, Liu B, Zhao J. A Cereblon Modulator CC-885 Induces CRBN- and p97-Dependent PLK1 Degradation and Synergizes with Volasertib to Suppress Lung Cancer. Mol Ther Oncolytics. 2020 Jun 23;18:215-225. doi: 10.1016/j.omto.2020.06.013. PMID: 32728610; PMCID: PMC7369516. 6: Hao BB, Li XJ, Jia XL, Wang YX, Zhai LH, Li DZ, Liu J, Zhang D, Chen YL, Xu YH, Lee SK, Xu GF, Chen XH, Dang YJ, Liu B, Tan MJ. The novel cereblon modulator CC-885 inhibits mitophagy via selective degradation of BNIP3L. Acta Pharmacol Sin. 2020 Sep;41(9):1246-1254. doi: 10.1038/s41401-020-0367-9. Epub 2020 Mar 24. PMID: 32210356; PMCID: PMC7608331. 7: Tateno S, Iida M, Fujii S, Suwa T, Katayama M, Tokuyama H, Yamamoto J, Ito T, Sakamoto S, Handa H, Yamaguchi Y. Genome-wide screening reveals a role for subcellular localization of CRBN in the anti-myeloma activity of pomalidomide. Sci Rep. 2020 Mar 4;10(1):4012. doi: 10.1038/s41598-020-61027-w. PMID: 32132601; PMCID: PMC7055313. 8: Gao S, Wang S, Song Y. Novel immunomodulatory drugs and neo-substrates. Biomark Res. 2020 Jan 9;8:2. doi: 10.1186/s40364-020-0182-y. PMID: 31938543; PMCID: PMC6953231. 9: Chung CI, Zhang Q, Shu X. Dynamic Imaging of Small Molecule Induced Protein- Protein Interactions in Living Cells with a Fluorophore Phase Transition Based Approach. Anal Chem. 2018 Dec 18;90(24):14287-14293. doi: 10.1021/acs.analchem.8b03476. Epub 2018 Nov 30. PMID: 30431263; PMCID: PMC6298840. 10: Fuchs O. Treatment of Lymphoid and Myeloid Malignancies by Immunomodulatory Drugs. Cardiovasc Hematol Disord Drug Targets. 2019;19(1):51-78. doi: 10.2174/1871529X18666180522073855. PMID: 29788898. 11: Ito T, Handa H. [Recent topics in IMiDs and cereblon]. Rinsho Ketsueki. 2017;58(10):2067-2073. Japanese. doi: 10.11406/rinketsu.58.2067. PMID: 28978850. 12: Hansen JD, Condroski K, Correa M, Muller G, Man HW, Ruchelman A, Zhang W, Vocanson F, Crea T, Liu W, Lu G, Baculi F, LeBrun L, Mahmoudi A, Carmel G, Hickman M, Lu CC. Protein Degradation via CRL4CRBN Ubiquitin Ligase: Discovery and Structure-Activity Relationships of Novel Glutarimide Analogs That Promote Degradation of Aiolos and/or GSPT1. J Med Chem. 2018 Jan 25;61(2):492-503. doi: 10.1021/acs.jmedchem.6b01911. Epub 2017 Apr 13. PMID: 28358507. 13: Matyskiela ME, Lu G, Ito T, Pagarigan B, Lu CC, Miller K, Fang W, Wang NY, Nguyen D, Houston J, Carmel G, Tran T, Riley M, Nosaka L, Lander GC, Gaidarova S, Xu S, Ruchelman AL, Handa H, Carmichael J, Daniel TO, Cathers BE, Lopez- Girona A, Chamberlain PP. A novel cereblon modulator recruits GSPT1 to the CRL4(CRBN) ubiquitin ligase. Nature. 2016 Jul 14;535(7611):252-7. doi: 10.1038/nature18611. Epub 2016 Jun 22. PMID: 27338790.