BAZ2-ICR
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MedKoo CAT#: 406642

CAS#: 1665195-94-7

Description: BAZ2-ICR is an excellent chemical probe for functional studies of the BAZ2 bromodomains in vitro and in vivo. The bromodomain containing proteins BAZ2A/B play essential roles in chromatin remodeling and regulation of noncoding RNAs. BAZ2-ICR has IC50 (BAZ2A) = 130 nM; IC50(BAZ2B) = 180 nM; logD = 1.05; solubility 25 mM (D2O) and F = 70%.

Chemical Structure

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BAZ2-ICR
CAS# 1665195-94-7
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 406642
Name: BAZ2-ICR
CAS#: 1665195-94-7
Chemical Formula: C20H19N7
Exact Mass: 357.17
Molecular Weight: 357.410
Elemental Analysis: C, 67.21; H, 5.36; N, 27.43

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 650 Ready to ship
200mg USD 950 Ready to ship
500mg USD 2250 Ready to ship
1g USD 3150 Ready to ship
2g USD 5450 Ready to ship
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Synonym: BAZ2-ICR; BAZ2ICR; BAZ2 ICR.

IUPAC/Chemical Name: 4-(4-(1-methyl-1H-pyrazol-4-yl)-1-(2-(1-methyl-1H-pyrazol-4-yl)ethyl)-1H-imidazol-5-yl)benzonitrile

InChi Key: RRZVGDGTWNQAPW-UHFFFAOYSA-N

InChi Code: InChI=1S/C20H19N7/c1-25-12-16(10-23-25)7-8-27-14-22-19(18-11-24-26(2)13-18)20(27)17-5-3-15(9-21)4-6-17/h3-6,10-14H,7-8H2,1-2H3

SMILES Code: CN(N=C1)C=C1C2=C(C3=CC=C(C#N)C=C3)N(CCC4=CN(C)N=C4)C=N2

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:         

Biological target: BAZ2-ICR is a BAZ2A/B bromodomains inhibitor with IC50s of 130 nM and 180 nM, and Kds of 109 nM and 170 nM, respectively.
In vitro activity: To investigate whether 13 (BAZ2-ICR) can displace BAZ2 bromodomains from chromatin in living cells, this study performed a fluorescence recovery after photobleaching (FRAP) assay utilizing GFP-tagged BAZ2A full length protein transfected into human osteosarcoma cells (U2OS). As a control this study used a mutant (N1873F) that does not bind KAc containing peptides and therefore mirrors the behavior of inhibitor bound BAZ2A. In addition, this study used the histone deacetylase (HDAC) inhibitor SAHA to increase overall levels of histone acetylation, resulting in a sufficient window measuring differences in recovery time and demonstrating the acetylation dependence of the FRAP experiments (Figure 6). Importantly, 1 μM 13 reduced the recovery time of the wild-type (wt) construct to a level similar to the dominant negative mutant, confirming that 13 inhibits BAZ2A in cells. Reference: J Med Chem. 2015 Mar 12; 58(5): 2553–2559. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4441536/
In vivo activity: Compound 13 (BAZ2-ICR) showed very high solubility (25 mM in D2O), a measured log D of 1.05, high stability in mouse microsomes, and permeation in the CaCo-2 model (see SI) and thus a suitable profile for oral and intravenous gavage. This study therefore performed a full mouse pharmacokinetic experiment. In agreement with the in vitro data, 13 showed 70% bioavailability and moderate clearance (∼50% of mouse liver blood flow) and volume of distribution (see SI). This set of data therefore suggested that 13 is suitable for modulating BAZ2A and BAZ2B in vivo. Reference: J Med Chem. 2015 Mar 12; 58(5): 2553–2559. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4441536/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 18.6 51.99
DMF 20.0 55.96
DMF:PBS (pH 7.2) (1:1) 0.5 1.40
Ethanol 13.4 37.41

Preparing Stock Solutions

The following data is based on the product molecular weight 357.41 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. Drouin L, McGrath S, Vidler LR, Chaikuad A, Monteiro O, Tallant C, Philpott M, Rogers C, Fedorov O, Liu M, Akhtar W, Hayes A, Raynaud F, Müller S, Knapp S, Hoelder S. Structure enabled design of BAZ2-ICR, a chemical probe targeting the bromodomains of BAZ2A and BAZ2B. J Med Chem. 2015 Mar 12;58(5):2553-9. doi: 10.1021/jm501963e. Epub 2015 Feb 26. PMID: 25719566; PMCID: PMC4441536.
In vitro protocol: 1. Drouin L, McGrath S, Vidler LR, Chaikuad A, Monteiro O, Tallant C, Philpott M, Rogers C, Fedorov O, Liu M, Akhtar W, Hayes A, Raynaud F, Müller S, Knapp S, Hoelder S. Structure enabled design of BAZ2-ICR, a chemical probe targeting the bromodomains of BAZ2A and BAZ2B. J Med Chem. 2015 Mar 12;58(5):2553-9. doi: 10.1021/jm501963e. Epub 2015 Feb 26. PMID: 25719566; PMCID: PMC4441536.
In vivo protocol: 1. Drouin L, McGrath S, Vidler LR, Chaikuad A, Monteiro O, Tallant C, Philpott M, Rogers C, Fedorov O, Liu M, Akhtar W, Hayes A, Raynaud F, Müller S, Knapp S, Hoelder S. Structure enabled design of BAZ2-ICR, a chemical probe targeting the bromodomains of BAZ2A and BAZ2B. J Med Chem. 2015 Mar 12;58(5):2553-9. doi: 10.1021/jm501963e. Epub 2015 Feb 26. PMID: 25719566; PMCID: PMC4441536.

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1: Drouin L, McGrath S, Vidler LR, Chaikuad A, Monteiro O, Tallant C, Philpott M, Rogers C, Fedorov O, Liu M, Akhtar W, Hayes A, Raynaud F, Müller S, Knapp S, Hoelder S. Structure Enabled Design of BAZ2-ICR, A Chemical Probe Targeting the Bromodomains of BAZ2A and BAZ2B. J Med Chem. 2015 Mar 12;58(5):2553-9. doi: 10.1021/jm501963e. Epub 2015 Feb 26. PubMed PMID: 25719566.