NSC23766 3HCl | CAS#1177865-17-6 | RAC-1 inhibitor

MedKoo Cat#: 510327 | Name: NSC23766 3HCl

Description:

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

NSC23766 is a potent Rac1 inhibitor. NSC23766 disrupted polar secretion of adhesive, polarization of endomembranes, and tip-focused growth in the rhizoid. NSC23766 can acts as a competitive antagonist at muscarinic acetylcholine receptors. NSC23766 exerts anti-influenza virus properties by affecting the viral polymerase complex activity. NSC23766 suppresses CREB signaling by targeting NMDA receptor function.

Chemical Structure

NSC23766 3HCl

CAS#1177865-17-6 (HCl)

Theoretical Analysis

MedKoo Cat#: 510327

Name: NSC23766 3HCl

CAS#: 1177865-17-6 (HCl)

Chemical Formula: C24H35N7

Exact Mass: 0.0000

Molecular Weight: 530.97

Elemental Analysis:

Price and Availability

Size	Price	Availability
50mg	USD 450.00	2 Weeks
100mg	USD 750.00	2 Weeks
200mg	USD 1,250.00	2 Weeks
500mg	USD 2,650.00	2 Weeks
1g	USD 4,250.00	2 Weeks
2g	USD 6,650.00	2 Weeks

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Related CAS #

733767-34-5 (free base) 1177865-17-6 (HCl)

Synonym

NSC23766; NSC23766; NSC 23766; NSC23766 3HCl salt; NSC23766 trihydrochloride; NSC23766 hydrochloride.

IUPAC/Chemical Name

N6-(2-((5-(diethylamino)pentan-2-yl)amino)-6-methylpyrimidin-4-yl)-2-methylquinoline-4,6-diamine trihydrochloride

InChi Key

CPUHORIUXPQCHW-UHFFFAOYSA-N

InChi Code

InChI=1S/C24H35N7.3ClH/c1-6-31(7-2)12-8-9-16(3)27-24-28-18(5)14-23(30-24)29-19-10-11-22-20(15-19)21(25)13-17(4)26-22;;;/h10-11,13-16H,6-9,12H2,1-5H3,(H2,25,26)(H2,27,28,29,30);3*1H

SMILES Code

NC1=CC(C)=NC2=CC=C(NC3=NC(NC(CCCN(CC)CC)C)=NC(C)=C3)C=C12.[H]Cl.[H]Cl.[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# 1177865-17-6 (NSC23766·3HCl), 733767-34-5 (NSC23766 free base)

Product Data

Product Data

Instruction

View handling instruction

Biological target:

NSC 23766 trihydrochloride is an inhibitor of Rac1 activation.

In vitro activity:

The chemical compound NSC23766 was identified by a structure-based virtual screening of compounds that fit into a surface groove of Rac1 known to be critical for GEF specification. In vitro it could effectively inhibit Rac1 binding and activation by the Rac-specific GEF Trio or Tiam1 in a dose-dependent manner without interfering with the closely related Cdc42 or RhoA binding or activation by their respective GEFs or with Rac1 interaction with BcrGAP or effector PAK1. In cells, it potently blocked serum or platelet-derived growth factor-induced Rac1 activation and lamellipodia formation without affecting the activity of endogenous Cdc42 or RhoA. Reference: Proc Natl Acad Sci U S A. 2004 May 18;101(20):7618-23. https://pubmed.ncbi.nlm.nih.gov/15128949/

In vivo activity:

Data shown in Fig. 1 (Panel B) demonstrate a marked reduction in the development of hyperglycemia in NOD mice treated with NSC23766. At the beginning of the study (8 wks.), the blood glucose values corresponded to l27 ± l.50 mg/dl and l09 ± ll.4 4 mg/dl for Balb/c and NOD mice, respectively. At 32 wks., the blood glucose values remained unchanged in Balb/c mice treated with either vehicle (96 ± 6 mg/dl) or NSC23766 (91 ± 5 mg/dl). As expected, blood glucose levels were significantly higher in NOD mice at 32 wks. (370 ± 50 mg/dl). NSC23766 treatment of NOD mice significantly reduced their blood glucose levels (187 ± 46 mg/dl). Reference: Cell Physiol Biochem. 2016;39(2):760-7. https://pubmed.ncbi.nlm.nih.gov/27467102/

	Solvent	mg/mL	mM
Solubility
	DMF	2.0	3.77
	DMSO	35.5	66.82
	Ethanol	4.0	7.53
	PBS (pH 7.2)	10.0	18.83
	Water	42.6	80.14

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 530.97 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. Akbar H, Cancelas J, Williams DA, Zheng J, Zheng Y. Rational design and applications of a Rac GTPase-specific small molecule inhibitor. Methods Enzymol. 2006;406:554-65. doi: 10.1016/S0076-6879(06)06043-5. PMID: 16472687. 2. Gao Y, Dickerson JB, Guo F, Zheng J, Zheng Y. Rational design and characterization of a Rac GTPase-specific small molecule inhibitor. Proc Natl Acad Sci U S A. 2004 May 18;101(20):7618-23. doi: 10.1073/pnas.0307512101. Epub 2004 May 5. PMID: 15128949; PMCID: PMC419655. 3. Veluthakal R, Sidarala V, Kowluru A. NSC23766, a Known Inhibitor of Tiam1-Rac1 Signaling Module, Prevents the Onset of Type 1 Diabetes in the NOD Mouse Model. Cell Physiol Biochem. 2016;39(2):760-7. doi: 10.1159/000445666. Epub 2016 Jul 29. PMID: 27467102; PMCID: PMC6686134. 4. Wang Y, Lu YF, Li CL, Sun W, Li Z, Wang RR, He T, Yang F, Yang Y, Wang XL, Guan SM, Chen J. Involvement of Rac1 signalling pathway in the development and maintenance of acute inflammatory pain induced by bee venom injection. Br J Pharmacol. 2016 Mar;173(5):937-50. doi: 10.1111/bph.13413. Epub 2016 Feb 10. PMID: 26700000; PMCID: PMC4761090.

In vitro protocol:

In vivo protocol:

1. Veluthakal R, Sidarala V, Kowluru A. NSC23766, a Known Inhibitor of Tiam1-Rac1 Signaling Module, Prevents the Onset of Type 1 Diabetes in the NOD Mouse Model. Cell Physiol Biochem. 2016;39(2):760-7. doi: 10.1159/000445666. Epub 2016 Jul 29. PMID: 27467102; PMCID: PMC6686134. 2. Wang Y, Lu YF, Li CL, Sun W, Li Z, Wang RR, He T, Yang F, Yang Y, Wang XL, Guan SM, Chen J. Involvement of Rac1 signalling pathway in the development and maintenance of acute inflammatory pain induced by bee venom injection. Br J Pharmacol. 2016 Mar;173(5):937-50. doi: 10.1111/bph.13413. Epub 2016 Feb 10. PMID: 26700000; PMCID: PMC4761090.

1: Hou H, ChÃ¡vez AE, Wang CC, Yang H, Gu H, Siddoway BA, Hall BJ, Castillo PE, Xia H. The Rac1 inhibitor NSC23766 suppresses CREB signaling by targeting NMDA receptor function. J Neurosci. 2014 Oct 15;34(42):14006-12. doi: 10.1523/JNEUROSCI.1659-14.2014. PubMed PMID: 25319697; PubMed Central PMCID: PMC4198541. 2: Zhu S, Chen P, Wu Y, Xiong S, Sun H, Xia Q, Shi L, Liu H, Ouyang HW. Programmed Application of Transforming Growth Factor β3 and Rac1 Inhibitor NSC23766 Committed Hyaline Cartilage Differentiation of Adipose-Derived Stem Cells for Osteochondral Defect Repair. Stem Cells Transl Med. 2014 Oct;3(10):1242-51. doi: 10.5966/sctm.2014-0042. Epub 2014 Aug 25. PubMed PMID: 25154784; PubMed Central PMCID: PMC4181399. 3: Liao J, Ye Z, Huang G, Xu C, Guo Q, Wang E. Delayed treatment with NSC23766 in streptozotocin-induced diabetic rats ameliorates post-ischemic neuronal apoptosis through suppression of mitochondrial p53 translocation. Neuropharmacology. 2014 Oct;85:508-16. doi: 10.1016/j.neuropharm.2014.06.008. Epub 2014 Jun 20. PubMed PMID: 24953831. 4: Dierkes R, Warnking K, Liedmann S, Seyer R, Ludwig S, Ehrhardt C. The Rac1 inhibitor NSC23766 exerts anti-influenza virus properties by affecting the viral polymerase complex activity. PLoS One. 2014 Feb 11;9(2):e88520. doi: 10.1371/journal.pone.0088520. eCollection 2014. PubMed PMID: 24523909; PubMed Central PMCID: PMC3921225. 5: Zhu S, Lu P, Liu H, Chen P, Wu Y, Wang Y, Sun H, Zhang X, Xia Q, Heng BC, Zhou Y, Ouyang HW. Inhibition of Rac1 activity by controlled release of NSC23766 from chitosan microspheres effectively ameliorates osteoarthritis development in vivo. Ann Rheum Dis. 2015 Jan;74(1):285-93. doi: 10.1136/annrheumdis-2013-203901. Epub 2013 Nov 20. PubMed PMID: 24257023. 6: Levay M, Krobert KA, Wittig K, Voigt N, Bermudez M, Wolber G, Dobrev D, Levy FO, Wieland T. NSC23766, a widely used inhibitor of Rac1 activation, additionally acts as a competitive antagonist at muscarinic acetylcholine receptors. J Pharmacol Exp Ther. 2013 Oct;347(1):69-79. doi: 10.1124/jpet.113.207266. Epub 2013 Jul 25. PubMed PMID: 23887096. 7: Milsom MD, Lee AW, Zheng Y, Cancelas JA. Fanca-/- hematopoietic stem cells demonstrate a mobilization defect which can be overcome by administration of the Rac inhibitor NSC23766. Haematologica. 2009 Jul;94(7):1011-5. doi: 10.3324/haematol.2008.004077. Epub 2009 Jun 2. PubMed PMID: 19491337; PubMed Central PMCID: PMC2704313. 8: Hable WE, Reddy S, Julien L. The Rac1 inhibitor, NSC23766, depolarizes adhesive secretion, endomembrane cycling, and tip growth in the fucoid alga, Silvetia compressa. Planta. 2008 Apr;227(5):991-1000. doi: 10.1007/s00425-007-0673-1. Epub 2008 Jan 9. PubMed PMID: 18183417.