SGC-CBP30
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MedKoo CAT#: 406442

CAS#: 1613695-14-9

Description: SGC-CBP30 is a potent and selective inhibitor of CREBBP (CBP) and EP300; which are general transcriptional co-activators. CREBBP has also been associated with amyotrophic lateral sclerosis (ALS) or Lou Gehrig’s disease, a neurodegenerative disease with progressive degeneration of motor neurons in the brain and spinal cord, Alzheimer's disease and poly glutamine repeat diseases such as Spinal and Bulbar Muscular Atrophy and Huntington’s disease.

Chemical Structure

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SGC-CBP30
CAS# 1613695-14-9
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 406442
Name: SGC-CBP30
CAS#: 1613695-14-9
Chemical Formula: C28H33ClN4O3
Exact Mass: 508.22
Molecular Weight: 509.040
Elemental Analysis: C, 66.07; H, 6.53; Cl, 6.96; N, 11.01; O, 9.43

Price and Availability

Size Price Availability Quantity
10mg USD 150 Ready to ship
25mg USD 250 Ready to ship
50mg USD 450 Ready to ship
100mg USD 750 Ready to ship
200mg USD 1250 Ready to ship
500mg USD 2850 Ready to ship
1g USD 4450 2 Weeks
2g USD 6950 2 Weeks
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Synonym: SGC-CBP30; SGC-CBP 30; SGC-CBP-30.

IUPAC/Chemical Name: (S)-4-(1-(2-(3-chloro-4-methoxyphenethyl)-5-(3,5-dimethylisoxazol-4-yl)-1H-benzo[d]imidazol-1-yl)propan-2-yl)morpholine

InChi Key: GEPYBHCJBORHCE-SFHVURJKSA-N

InChi Code: InChI=1S/C28H33ClN4O3/c1-18(32-11-13-35-14-12-32)17-33-25-8-7-22(28-19(2)31-36-20(28)3)16-24(25)30-27(33)10-6-21-5-9-26(34-4)23(29)15-21/h5,7-9,15-16,18H,6,10-14,17H2,1-4H3/t18-/m0/s1

SMILES Code: C[C@H](N1CCOCC1)CN2C(CCC3=CC=C(OC)C(Cl)=C3)=NC4=CC(C5=C(C)ON=C5C)=CC=C24

Appearance: white to off-white 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: CREBBP (CBP) and EP300 are involved in many biological processes like maintenance of genomic stability by affecting DNA replication and DNA repair as well as cell growth, transformation and development. They also play and essential role in neuronal plasticity/ memory formation hematopoiesis and energy homeostasis as demonstrated in a variety of mouse models. They possess both acetyl-transferase enzymatic and bromodomain containing regions. Through acetylation of non-histone proteins CREBBP can have a positive or negative effect on transcriptional regulation by affecting protein- protein interactions, protein-DNA interactions, nuclear retention or protein half-life.  (http://www.thesgc.org/chemical-probes/SGC-CBP30).       

Biological target: SGC-CBP30 is a potent and highly selective CBP/p300 bromodomain (Kds of 21 nM and 32 nM for CBP and p300, respectively) inhibitor, displaying 40-fold selectivity over the first bromodomain of BRD4 [BRD4(1)] bound.
In vitro activity: SGC-CBP30 treatment effectively reduced IL6 autocrine secretion in XG1LenRes cells, regardless of the presence of lenalidomide, as demonstrated by decreased IL6 levels in the culture media. Additionally, SGC-CBP30 inhibited STAT3 activation and enhanced sensitivity to lenalidomide in IMiD-sensitive HMCLs. SGC-CBP30's impact on chromatin structure in regulatory regions or its regulation of other genes may contribute to increased sensitivity to IMiD-induced signals. Reference: Blood Cancer J. 2019 Feb; 9(2): 19. https://pubmed.ncbi.nlm.nih.gov/30741931/
In vivo activity: Delayed administration of SGC-CBP30 at 8 hours effectively attenuated lung, liver, and renal injury in septic mice induced by LPS or CLP. SGC-CBP30 reduced histopathological damage, inflammatory cell infiltration, and improved organ architecture, comparable to the positive control DEX-0.5 h. CBP bromodomain inhibitors like SGC-CBP30 may not only suppress the inflammatory response but also ameliorate organ injury in conditions such as LPS-induced endotoxemia and CLP-induced sepsis. Reference: Front Immunol. 2020; 11: 625542. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7884462/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 47.0 92.33
Ethanol 53.0 104.12

Preparing Stock Solutions

The following data is based on the product molecular weight 509.04 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.

Recalculate based on batch purity %
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. Zhu YX, Shi CX, Bruins LA, Wang X, Riggs DL, Porter B, Ahmann JM, de Campos CB, Braggio E, Bergsagel PL, Stewart AK. Identification of lenalidomide resistance pathways in myeloma and targeted resensitization using cereblon replacement, inhibition of STAT3 or targeting of IRF4. Blood Cancer J. 2019 Feb 11;9(2):19. doi: 10.1038/s41408-019-0173-0. PMID: 30741931; PMCID: PMC6370766. 2. Sun J, Zhang W, Tan Z, Zheng C, Tang Y, Ke X, Zhang Y, Liu Y, Li P, Hu Q, Wang H, Mao P, Zheng Z. Zika virus promotes CCN1 expression via the CaMKIIα-CREB pathway in astrocytes. Virulence. 2020 Dec;11(1):113-131. doi: 10.1080/21505594.2020.1715189. PMID: 31957543; PMCID: PMC6984649. 3. Bi X, Jiang B, Zhou J, Fan X, Yan X, Liang J, Luo L, Yin Z. CBP Bromodomain Inhibition Rescues Mice From Lethal Sepsis Through Blocking HMGB1-Mediated Inflammatory Responses. Front Immunol. 2021 Feb 2;11:625542. doi: 10.3389/fimmu.2020.625542. PMID: 33603756; PMCID: PMC7884462. 4. Tao J, Zhang M, Wen Z, Wang B, Zhang L, Ou Y, Tang X, Yu X, Jiang Q. Inhibition of EP300 and DDR1 synergistically alleviates pulmonary fibrosis in vitro and in vivo. Biomed Pharmacother. 2018 Oct;106:1727-1733. doi: 10.1016/j.biopha.2018.07.132. Epub 2018 Jul 30. PMID: 30119248.
In vitro protocol: 1. Zhu YX, Shi CX, Bruins LA, Wang X, Riggs DL, Porter B, Ahmann JM, de Campos CB, Braggio E, Bergsagel PL, Stewart AK. Identification of lenalidomide resistance pathways in myeloma and targeted resensitization using cereblon replacement, inhibition of STAT3 or targeting of IRF4. Blood Cancer J. 2019 Feb 11;9(2):19. doi: 10.1038/s41408-019-0173-0. PMID: 30741931; PMCID: PMC6370766. 2. Sun J, Zhang W, Tan Z, Zheng C, Tang Y, Ke X, Zhang Y, Liu Y, Li P, Hu Q, Wang H, Mao P, Zheng Z. Zika virus promotes CCN1 expression via the CaMKIIα-CREB pathway in astrocytes. Virulence. 2020 Dec;11(1):113-131. doi: 10.1080/21505594.2020.1715189. PMID: 31957543; PMCID: PMC6984649.
In vivo protocol: 1. Bi X, Jiang B, Zhou J, Fan X, Yan X, Liang J, Luo L, Yin Z. CBP Bromodomain Inhibition Rescues Mice From Lethal Sepsis Through Blocking HMGB1-Mediated Inflammatory Responses. Front Immunol. 2021 Feb 2;11:625542. doi: 10.3389/fimmu.2020.625542. PMID: 33603756; PMCID: PMC7884462. 2. Tao J, Zhang M, Wen Z, Wang B, Zhang L, Ou Y, Tang X, Yu X, Jiang Q. Inhibition of EP300 and DDR1 synergistically alleviates pulmonary fibrosis in vitro and in vivo. Biomed Pharmacother. 2018 Oct;106:1727-1733. doi: 10.1016/j.biopha.2018.07.132. Epub 2018 Jul 30. PMID: 30119248.

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