NSC305787 | CAT#785718-37-8 | ezrin inhibitor

MedKoo Cat#: 462527 | Name: NSC305787

Featured

Description:

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

NSC305787 is a small molecule ezrin inhibitor. Ezrin is a key driver of tumor progression and metastatic spread of osteosarcoma. NSC305787 directly binds to ezrin and inhibits its functions in promoting invasive phenotype. NSC-305787 reduces the incidence of lung metastasis in a genetically engineered mouse model of osteosarcoma. NSC305787 exhibits antineoplastic activity in pancreatic cancer cells

Chemical Structure

NSC305787

CAS#785718-37-8 (free base)

Theoretical Analysis

MedKoo Cat#: 462527

Name: NSC305787

CAS#: 785718-37-8 (free base)

Chemical Formula: C25H30Cl2N2O

Exact Mass: 444.1735

Molecular Weight: 445.43

Elemental Analysis: C, 67.41; H, 6.79; Cl, 15.92; N, 6.29; O, 3.59

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 750.00	2 Weeks
10mg	USD 1,250.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

785718-37-8 (free base) 53868-26-1 (HCl)

Synonym

NSC305787; NSC 305787; NSC-305787

IUPAC/Chemical Name

(2-(adamantan-1-yl)-6,8-dichloroquinolin-4-yl)(piperidin-2-yl)methanol

InChi Key

YNGQUUFYBFKLNH-UHFFFAOYSA-N

InChi Code

InChI=1S/C25H30Cl2N2O/c26-17-8-18-19(24(30)21-3-1-2-4-28-21)10-22(29-23(18)20(27)9-17)25-11-14-5-15(12-25)7-16(6-14)13-25/h8-10,14-16,21,24,28,30H,1-7,11-13H2

SMILES Code

OC(C1NCCCC1)C2=CC(C3(C4)CC5CC4CC(C5)C3)=NC6=C(Cl)C=C(Cl)C=C26

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

Shelf Life

>3 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

Instruction

View handling instruction

Biological target:

NSC305787 is an inhibitor of ezrin with a Kd of 5.85 μM, inhibits the phosphorylation of ezrin caused by PKCΙ with an IC50 of 8.3 μM.

In vitro activity:

This study assessed the potential antineoplastic effects of NSC305787 in pancreatic cancer cell lines. In pancreatic cells, NSC305787 reduced cell viability, clonal growth, and migration. This study’s exploratory molecular studies identified that NSC305787 modulates the expression and activation of key regulators of the cell cycle, proliferation, DNA damage, and apoptosis, favoring a tumor-suppressive molecular network. Reference: Invest New Drugs. 2022 Aug;40(4):728-737. https://pubmed.ncbi.nlm.nih.gov/35477813/

In vivo activity:

Treatment of mice with NSC305787 significantly suppressed pulmonary metastasis compared with the vehicle-treated control. Lung metastasis was observed only in 40% (4 of 10) of NSC305787-treated animals (p = 0.039, Fisher's exact test) (Fig. 3A). Taken together, these findings suggest that NSC305787 treatment inhibits ezrin-dependent lung metastasis of osteosarcoma. Reference: J Biol Chem. 2016 Jun 17;291(25):13257-70. https://pubmed.ncbi.nlm.nih.gov/27137931/

	Solvent	mg/mL	mM
Solubility
	DMSO	6.0	13.47

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 445.43 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. Lipreri da Silva JC, Carvalho MFL, de Miranda LBL, de Almeida BO, Lima K, Machado-Neto JA. NSC305787, a pharmacological ezrin inhibitor, exhibits antineoplastic activity in pancreatic cancer cells. Invest New Drugs. 2022 Aug;40(4):728-737. doi: 10.1007/s10637-022-01249-z. Epub 2022 Apr 28. PMID: 35477813. 2. Chen C, Ye C, Xia J, Zhou Y, Wu R. Ezrin T567 phosphorylation regulates migration and invasion of ectopic endometrial stromal cells by changing actin cytoskeleton. Life Sci. 2020 Aug 1;254:117681. doi: 10.1016/j.lfs.2020.117681. Epub 2020 May 5. PMID: 32380081. 3. Çelik H, Bulut G, Han J, Graham GT, Minas TZ, Conn EJ, Hong SH, Pauly GT, Hayran M, Li X, Özdemirli M, Ayhan A, Rudek MA, Toretsky JA, Üren A. Ezrin Inhibition Up-regulates Stress Response Gene Expression. J Biol Chem. 2016 Jun 17;291(25):13257-70. doi: 10.1074/jbc.M116.718189. Epub 2016 May 2. PMID: 27137931; PMCID: PMC4933238. 4. Bulut G, Hong SH, Chen K, Beauchamp EM, Rahim S, Kosturko GW, Glasgow E, Dakshanamurthy S, Lee HS, Daar I, Toretsky JA, Khanna C, Uren A. Small molecule inhibitors of ezrin inhibit the invasive phenotype of osteosarcoma cells. Oncogene. 2012 Jan 19;31(3):269-81. doi: 10.1038/onc.2011.245. Epub 2011 Jun 27. PMID: 21706056; PMCID: PMC3513970.

In vitro protocol:

In vivo protocol:

1. Çelik H, Bulut G, Han J, Graham GT, Minas TZ, Conn EJ, Hong SH, Pauly GT, Hayran M, Li X, Özdemirli M, Ayhan A, Rudek MA, Toretsky JA, Üren A. Ezrin Inhibition Up-regulates Stress Response Gene Expression. J Biol Chem. 2016 Jun 17;291(25):13257-70. doi: 10.1074/jbc.M116.718189. Epub 2016 May 2. PMID: 27137931; PMCID: PMC4933238. 2. Bulut G, Hong SH, Chen K, Beauchamp EM, Rahim S, Kosturko GW, Glasgow E, Dakshanamurthy S, Lee HS, Daar I, Toretsky JA, Khanna C, Uren A. Small molecule inhibitors of ezrin inhibit the invasive phenotype of osteosarcoma cells. Oncogene. 2012 Jan 19;31(3):269-81. doi: 10.1038/onc.2011.245. Epub 2011 Jun 27. PMID: 21706056; PMCID: PMC3513970.

1: Lipreri da Silva JC, Saldanha-Araujo F, de Melo RCB, Vicari HP, Silva- Carvalho AE, Rego EM, Buccheri V, Machado-Neto JA. Ezrin is highly expressed and a druggable target in chronic lymphocytic leukemia. Life Sci. 2022 Dec 15;311(Pt B):121146. doi: 10.1016/j.lfs.2022.121146. Epub 2022 Nov 3. PMID: 36336127. 2: Lipreri da Silva JC, Carvalho MFL, de Miranda LBL, de Almeida BO, Lima K, Machado-Neto JA. NSC305787, a pharmacological ezrin inhibitor, exhibits antineoplastic activity in pancreatic cancer cells. Invest New Drugs. 2022 Aug;40(4):728-737. doi: 10.1007/s10637-022-01249-z. Epub 2022 Apr 28. PMID: 35477813. 3: Lipreri da Silva JC, Coelho-Silva JL, Lima K, Vicari HP, Lazarini M, Costa- Lotufo LV, Traina F, Machado-Neto JA. Comprehensive analysis of cytoskeleton regulatory genes identifies ezrin as a prognostic marker and molecular target in acute myeloid leukemia. Cell Oncol (Dordr). 2021 Oct;44(5):1105-1117. doi: 10.1007/s13402-021-00621-0. Epub 2021 Jul 1. PMID: 34196912. 4: Chen C, Ye C, Xia J, Zhou Y, Wu R. Ezrin T567 phosphorylation regulates migration and invasion of ectopic endometrial stromal cells by changing actin cytoskeleton. Life Sci. 2020 Aug 1;254:117681. doi: 10.1016/j.lfs.2020.117681. Epub 2020 May 5. PMID: 32380081. 5: Penchev VR, Chang YT, Begum A, Ewachiw T, Gocke C, Li J, McMillan RH, Wang Q, Anders R, Marchionni L, Maitra A, Uren A, Rasheed Z, Matsui W. Ezrin Promotes Stem Cell Properties in Pancreatic Ductal Adenocarcinoma. Mol Cancer Res. 2019 Apr;17(4):929-936. doi: 10.1158/1541-7786.MCR-18-0367. Epub 2019 Jan 17. PMID: 30655325; PMCID: PMC6445733. 6: Çelik H, Bulut G, Han J, Graham GT, Minas TZ, Conn EJ, Hong SH, Pauly GT, Hayran M, Li X, Özdemirli M, Ayhan A, Rudek MA, Toretsky JA, Üren A. Ezrin Inhibition Up-regulates Stress Response Gene Expression. J Biol Chem. 2016 Jun 17;291(25):13257-70. doi: 10.1074/jbc.M116.718189. Epub 2016 May 2. PMID: 27137931; PMCID: PMC4933238. 7: Saygideğer-Kont Y, Minas TZ, Jones H, Hour S, Çelik H, Temel I, Han J, Atabey N, Erkizan HV, Toretsky JA, Üren A. Ezrin Enhances EGFR Signaling and Modulates Erlotinib Sensitivity in Non-Small Cell Lung Cancer Cells. Neoplasia. 2016 Feb;18(2):111-20. doi: 10.1016/j.neo.2016.01.002. PMID: 26936397; PMCID: PMC5005263. 8: Russo CM, Adhikari AA, Wallach DR, Fernandes S, Balch AN, Kerr WG, Chisholm JD. Synthesis and initial evaluation of quinoline-based inhibitors of the SH2-containing inositol 5'-phosphatase (SHIP). Bioorg Med Chem Lett. 2015 Nov 15;25(22):5344-8. doi: 10.1016/j.bmcl.2015.09.034. Epub 2015 Sep 15. PMID: 26453006; PMCID: PMC4628863. 9: Çelik H, Hong SH, Colón-López DD, Han J, Kont YS, Minas TZ, Swift M, Paige M, Glasgow E, Toretsky JA, Bosch J, Üren A. Identification of Novel Ezrin Inhibitors Targeting Metastatic Osteosarcoma by Screening Open Access Malaria Box. Mol Cancer Ther. 2015 Nov;14(11):2497-507. doi: 10.1158/1535-7163.MCT-15-0511. Epub 2015 Sep 10. PMID: 26358752; PMCID: PMC4636458. 10: Çelik H, Sajwan KP, Selvanathan SP, Marsh BJ, Pai AV, Kont YS, Han J, Minas TZ, Rahim S, Erkizan HV, Toretsky JA, Üren A. Ezrin Binds to DEAD-Box RNA Helicase DDX3 and Regulates Its Function and Protein Level. Mol Cell Biol. 2015 Sep;35(18):3145-62. doi: 10.1128/MCB.00332-15. Epub 2015 Jul 6. PMID: 26149384; PMCID: PMC4539380. 11: Ren L, Khanna C. Role of ezrin in osteosarcoma metastasis. Adv Exp Med Biol. 2014;804:181-201. doi: 10.1007/978-3-319-04843-7_10. PMID: 24924175. 12: Bulut G, Hong SH, Chen K, Beauchamp EM, Rahim S, Kosturko GW, Glasgow E, Dakshanamurthy S, Lee HS, Daar I, Toretsky JA, Khanna C, Uren A. Small molecule inhibitors of ezrin inhibit the invasive phenotype of osteosarcoma cells. Oncogene. 2012 Jan 19;31(3):269-81. doi: 10.1038/onc.2011.245. Epub 2011 Jun 27. PMID: 21706056; PMCID: PMC3513970.