IKK-16 HCl
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MedKoo CAT#: 407298

CAS#: 1186195-62-9 (HCl)

Description: IKK-16 is a potent and slective inhibitor of IκB kinase (IKK) (IC50 values are 40, 70 and 200 nM for IKKβ, IKK complex and IKKα respectively). KK-16 inhibits TNFα-stimulated expression of the adhesion molecules E-selectin, ICAM-1, and VCAM-1 in HUVEC cells.

Chemical Structure

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IKK-16 HCl
CAS# 1186195-62-9 (HCl)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 407298
Name: IKK-16 HCl
CAS#: 1186195-62-9 (HCl)
Chemical Formula: C28H30ClN5OS
Exact Mass: 519.19
Molecular Weight: 520.092
Elemental Analysis: C, 64.66; H, 5.81; Cl, 6.82; N, 13.47; O, 3.08; S, 6.16

Price and Availability

Size Price Availability Quantity
50mg USD 450 2 Weeks
100mg USD 750 2 Weeks
200mg USD 1350 2 Weeks
500mg USD 2950 2 Weeks
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Related CAS #: 873225-46-8 (free base)   1186195-62-9 (HCl)    

Synonym: IKK-16; IKK 16; IKK16; IKK-16 HCl

IUPAC/Chemical Name: (4-((4-(benzo[b]thiophen-2-yl)pyrimidin-2-yl)amino)phenyl)(4-(pyrrolidin-1-yl)piperidin-1-yl)methanone hydrochloride

InChi Key: XFVDIVQCZWDBCW-UHFFFAOYSA-N

InChi Code: InChI=1S/C28H29N5OS.ClH/c34-27(33-17-12-23(13-18-33)32-15-3-4-16-32)20-7-9-22(10-8-20)30-28-29-14-11-24(31-28)26-19-21-5-1-2-6-25(21)35-26;/h1-2,5-11,14,19,23H,3-4,12-13,15-18H2,(H,29,30,31);1H

SMILES Code: O=C(C1=CC=C(NC2=NC=CC(C3=CC4=CC=CC=C4S3)=N2)C=C1)N5CCC(N6CCCC6)CC5.[H]Cl

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: Related CAS# 873225-46-8 ( IKK-16 free base) 1186195-62-9 ( IKK-16 HCl salt).

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: IKK 16 hydrochloride is a selective IκB kinase (IKK) inhibitor for IKK2, IKK complex and IKK1 with IC50s of 40 nM, 70 nM and 200 nM, respectively. IKK16 also inhibits leucine-rich repeat kinase-2 (LRRK2) with an IC50 of 50 nM.
In vitro activity: Phosphorylation of CYLD under basal conditions was inhibited by IKK16. NMDA treatment further promoted phosphorylation of CYLD at the PSD, but IKK16 failed to block the NMDA-induced effect. In vitro experiments using purified proteins demonstrated direct phosphorylation and activation of CYLD by the beta catalytic subunit of IKK. Activation of IKK in isolated PSDs also promoted phosphorylation of CYLD and an increase in endogenous deubiquitinase activity for K63-linked polyubiquitins. Altogether, the results suggest that in the absence of excitatory conditions, constitutive IKK activity at the PSD regulates CYLD and maintains basal levels of K63-linkage specific deubiquitination at the synapse. Reference: Biochem Biophys Res Commun. 2014 Jul 18;450(1):550-4. https://pubmed.ncbi.nlm.nih.gov/24928390/
In vivo activity: Treatment of septic mice with IKK 16 at 1 hour after surgery significantly attenuated (P<0.05) the rises in serum creatinine (Fig. 2D) and lung MPO activity (Fig. 2F), and ameliorated the rise in ALT (Fig. 2E, P>0.05). Thus, treatment of septic mice with IKK 16 attenuated the sepsis-induced MOD (multiple organ dysfunction). Reference: Dis Model Mech. 2013 Jul;6(4):1031-42. https://pubmed.ncbi.nlm.nih.gov/23649820/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 5.0 9.61
DMSO 45.3 87.16
DMSO:PBS (pH 7.2) (1:2) 0.3 0.58

Preparing Stock Solutions

The following data is based on the product molecular weight 520.09 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. Thein S, Pham A, Bayer KU, Tao-Cheng JH, Dosemeci A. IKK regulates the deubiquitinase CYLD at the postsynaptic density. Biochem Biophys Res Commun. 2014 Jul 18;450(1):550-4. doi: 10.1016/j.bbrc.2014.06.019. Epub 2014 Jun 10. PMID: 24928390; PMCID: PMC4126652. 2. Tandon M, Johnson J, Li Z, Xu S, Wipf P, Wang QJ. New pyrazolopyrimidine inhibitors of protein kinase d as potent anticancer agents for prostate cancer cells. PLoS One. 2013 Sep 23;8(9):e75601. doi: 10.1371/journal.pone.0075601. PMID: 24086585; PMCID: PMC3781056. 3. Sordi R, Chiazza F, Johnson FL, Patel NS, Brohi K, Collino M, Thiemermann C. Inhibition of IκB Kinase Attenuates the Organ Injury and Dysfunction Associated with Hemorrhagic Shock. Mol Med. 2015 Jun 18;21(1):563-75. doi: 10.2119/molmed.2015.00049. PMID: 26101953; PMCID: PMC4607620. 4. Coldewey SM, Rogazzo M, Collino M, Patel NS, Thiemermann C. Inhibition of IκB kinase reduces the multiple organ dysfunction caused by sepsis in the mouse. Coldewey SM, Rogazzo M, Collino M, Patel NS, Thiemermann C. Inhibition of IκB kinase reduces the multiple organ dysfunction caused by sepsis in the mouse. Dis Model Mech. 2013 Jul;6(4):1031-42. doi: 10.1242/dmm.012435. Epub 2013 May 2. PMID: 23649820; PMCID: PMC3701222.doi: 10.1242/dmm.012435. Epub 2013 May 2. PMID: 23649820; PMCID: PMC3701222.
In vitro protocol: 1. Thein S, Pham A, Bayer KU, Tao-Cheng JH, Dosemeci A. IKK regulates the deubiquitinase CYLD at the postsynaptic density. Biochem Biophys Res Commun. 2014 Jul 18;450(1):550-4. doi: 10.1016/j.bbrc.2014.06.019. Epub 2014 Jun 10. PMID: 24928390; PMCID: PMC4126652. 2. Tandon M, Johnson J, Li Z, Xu S, Wipf P, Wang QJ. New pyrazolopyrimidine inhibitors of protein kinase d as potent anticancer agents for prostate cancer cells. PLoS One. 2013 Sep 23;8(9):e75601. doi: 10.1371/journal.pone.0075601. PMID: 24086585; PMCID: PMC3781056.
In vivo protocol: 1. Sordi R, Chiazza F, Johnson FL, Patel NS, Brohi K, Collino M, Thiemermann C. Inhibition of IκB Kinase Attenuates the Organ Injury and Dysfunction Associated with Hemorrhagic Shock. Mol Med. 2015 Jun 18;21(1):563-75. doi: 10.2119/molmed.2015.00049. PMID: 26101953; PMCID: PMC4607620. 2. Coldewey SM, Rogazzo M, Collino M, Patel NS, Thiemermann C. Inhibition of IκB kinase reduces the multiple organ dysfunction caused by sepsis in the mouse. Coldewey SM, Rogazzo M, Collino M, Patel NS, Thiemermann C. Inhibition of IκB kinase reduces the multiple organ dysfunction caused by sepsis in the mouse. Dis Model Mech. 2013 Jul;6(4):1031-42. doi: 10.1242/dmm.012435. Epub 2013 May 2. PMID: 23649820; PMCID: PMC3701222.doi: 10.1242/dmm.012435. Epub 2013 May 2. PMID: 23649820; PMCID: PMC3701222.

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1: Tandon M, Johnson J, Li Z, Xu S, Wipf P, Wang QJ. New pyrazolopyrimidine inhibitors of protein kinase d as potent anticancer agents for prostate cancer cells. PLoS One. 2013 Sep 23;8(9):e75601. doi: 10.1371/journal.pone.0075601. PubMed PMID: 24086585; PubMed Central PMCID: PMC3781056.

2: Mehmood T, Maryam A, Zhang H, Li Y, Khan M, Ma T. Deoxyelephantopin induces apoptosis in HepG2 cells via oxidative stress, NF-κB inhibition and mitochondrial dysfunction. Biofactors. 2016 Sep 15. doi: 10.1002/biof.1324. [Epub ahead of print] PubMed PMID: 27628030.

3: Shu YS, Tao W, Miao QB, Zhu YB, Yang YF. Improvement of ventilation-induced lung injury in a rodent model by inhibition of inhibitory κB kinase. J Trauma Acute Care Surg. 2014 Jun;76(6):1417-24. doi: 10.1097/TA.0000000000000229. PubMed PMID: 24854310.

4: Coldewey SM, Rogazzo M, Collino M, Patel NS, Thiemermann C. Inhibition of IκB kinase reduces the multiple organ dysfunction caused by sepsis in the mouse. Dis Model Mech. 2013 Jul;6(4):1031-42. doi: 10.1242/dmm.012435. PubMed PMID: 23649820; PubMed Central PMCID: PMC3701222.

5: Ansbro MR, Shukla S, Ambudkar SV, Yuspa SH, Li L. Screening compounds with a novel high-throughput ABCB1-mediated efflux assay identifies drugs with known therapeutic targets at risk for multidrug resistance interference. PLoS One. 2013 Apr 10;8(4):e60334. doi: 10.1371/journal.pone.0060334. PubMed PMID: 23593196; PubMed Central PMCID: PMC3622673.

6: Chen J, Kieswich JE, Chiazza F, Moyes AJ, Gobbetti T, Purvis GS, Salvatori DC, Patel NS, Perretti M, Hobbs AJ, Collino M, Yaqoob MM, Thiemermann C. IκB Kinase Inhibitor Attenuates Sepsis-Induced Cardiac Dysfunction in CKD. J Am Soc Nephrol. 2016 May 6. pii: ASN.2015060670. [Epub ahead of print] PubMed PMID: 27153924.

7: Shu Y, Liu Y, Li X, Cao L, Yuan X, Li W, Cao Q. Aspirin-Triggered Resolvin D1 Inhibits TGF-β1-Induced EndMT through Increasing the Expression of Smad7 and Is Closely Related to Oxidative Stress. Biomol Ther (Seoul). 2016 Mar 1;24(2):132-9. doi: 10.4062/biomolther.2015.088. PubMed PMID: 26869523; PubMed Central PMCID: PMC4774493.

8: Dobritsa SV, Kuok IT, Nguyen H, Webster JC, Spragg AM, Morley T, Carr GJ. Development of a high-throughput cell-based assay for identification of IL-17 inhibitors. J Biomol Screen. 2013 Jan;18(1):75-84. doi: 10.1177/1087057112459350. PubMed PMID: 22983163.