CAS 1380432-32-5|EHop-016

Introduction：Basic information about CAS 1380432-32-5|EHop-016, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. EHop-016 BiologicalActivity
3. Chemical & Physical Properties
4. Safety Information
5. Synonyms

Common Name	EHop-016
CAS Number	1380432-32-5	Molecular Weight	430.54500
Density	1.27	Boiling Point	/
Molecular Formula	C₂₅H₃₀N₆O	Melting Point	/
MSDS	USA	Flash Point	/

Names

Name	4-N-(9-ethylcarbazol-3-yl)-2-N-(3-morpholin-4-ylpropyl)pyrimidine-2,4-diamine
Synonym	More Synonyms

EHop-016 BiologicalActivity

Description	EHop-016 is a novel potent and selective inhibitor of Rac GTPase; inhibits Rac1 activity in MDA-MB-435 cells with an IC50 of 1.1 uM.IC50 value: 1.1 uM (MDA-MB-435 cell) [1]Target: Rac1 inhibitorin vitro: The IC(50) of 1.1 μM for Rac inhibition by EHop-016 is ～100-fold lower than for NSC23766. EHop-016 is specific for Rac1 and Rac3 at concentrations of ≤5 μM. At higher concentrations, EHop-016 inhibits the close homolog Cdc42. In MDA-MB-435 cells that demonstrate high active levels of the Rac GEF Vav2, EHop-016 inhibits the association of Vav2 with a nucleotide-free Rac1(G15A), which has a high affinity for activated GEFs. EHop-016 also inhibits the Rac activity of MDA-MB-231 metastatic breast cancer cells and reduces Rac-directed lamellipodia formation in both cell lines. EHop-016 decreases Rac downstream effects of PAK1 (p21-activated kinase 1) activity and directed migration of metastatic cancer cells. Moreover, at effective concentrations (<5 μM), EHop-016 does not affect the viability of transformed mammary epithelial cells (MCF-10A) and reduces viability of MDA-MB-435 cells by only 20% [1]. At higher concentrations (10μM), EHop-016 inhibits the related Rho GTPase Cdc42, but not Rho, and also reduces cell viability. Moreover, EHop-016 inhibits the activation of the Rac downstream effector p21-activated kinase, extension of motile actin-based structures, and cell migration [2].in vivo: As quantified by UPLC MS/MS, EHop-016 was detectable in the plasma of nude mice at 17 to 23 ng/ml levels at 12 h following intraperitoneal (i.p.) administration of 10 to 25 mg/kg BW EHop-016. The EHop-016 mediated inhibition of angiogenesis In Vivo was confirmed by immunohistochemistry of excised tumors and by In Vitro tube formation assays of endothelial cells. Moreover, EHop-016 affected cell viability by down-regulating Akt and Jun kinase activities and c-Myc and Cyclin D expression, as well as increasing caspase 3/7 activities in metastatic cancer cells [3].
Related Catalog	Signaling Pathways >>GPCR/G Protein >>RasResearch Areas >>Cancer
References	[1]. Montalvo-Ortiz BL, et al. Characterization of EHop-016, novel small molecule inhibitor of Rac GTPase. J Biol Chem. 2012 Apr 13;287(16):13228-38. [2]. Dharmawardhane S, et al. Development of EHop-016: a small molecule inhibitor of Rac. Enzymes. 2013;33 Pt A:117-46. [3]. Castillo-Pichardo L, et al. The Rac Inhibitor EHop-016 Inhibits Mammary Tumor Growth and Metastasis in a Nude Mouse Model. Transl Oncol. 2014 Oct 24;7(5):546-55.

Description

EHop-016 is a novel potent and selective inhibitor of Rac GTPase; inhibits Rac1 activity in MDA-MB-435 cells with an IC50 of 1.1 uM.IC50 value: 1.1 uM (MDA-MB-435 cell) [1]Target: Rac1 inhibitorin vitro: The IC(50) of 1.1 μM for Rac inhibition by EHop-016 is ～100-fold lower than for NSC23766. EHop-016 is specific for Rac1 and Rac3 at concentrations of ≤5 μM. At higher concentrations, EHop-016 inhibits the close homolog Cdc42. In MDA-MB-435 cells that demonstrate high active levels of the Rac GEF Vav2, EHop-016 inhibits the association of Vav2 with a nucleotide-free Rac1(G15A), which has a high affinity for activated GEFs. EHop-016 also inhibits the Rac activity of MDA-MB-231 metastatic breast cancer cells and reduces Rac-directed lamellipodia formation in both cell lines. EHop-016 decreases Rac downstream effects of PAK1 (p21-activated kinase 1) activity and directed migration of metastatic cancer cells. Moreover, at effective concentrations (<5 μM), EHop-016 does not affect the viability of transformed mammary epithelial cells (MCF-10A) and reduces viability of MDA-MB-435 cells by only 20% [1]. At higher concentrations (10μM), EHop-016 inhibits the related Rho GTPase Cdc42, but not Rho, and also reduces cell viability. Moreover, EHop-016 inhibits the activation of the Rac downstream effector p21-activated kinase, extension of motile actin-based structures, and cell migration [2].in vivo: As quantified by UPLC MS/MS, EHop-016 was detectable in the plasma of nude mice at 17 to 23 ng/ml levels at 12 h following intraperitoneal (i.p.) administration of 10 to 25 mg/kg BW EHop-016. The EHop-016 mediated inhibition of angiogenesis In Vivo was confirmed by immunohistochemistry of excised tumors and by In Vitro tube formation assays of endothelial cells. Moreover, EHop-016 affected cell viability by down-regulating Akt and Jun kinase activities and c-Myc and Cyclin D expression, as well as increasing caspase 3/7 activities in metastatic cancer cells [3].

Related Catalog

Signaling Pathways >>GPCR/G Protein >>RasResearch Areas >>Cancer

References

[1]. Montalvo-Ortiz BL, et al. Characterization of EHop-016, novel small molecule inhibitor of Rac GTPase. J Biol Chem. 2012 Apr 13;287(16):13228-38.

[2]. Dharmawardhane S, et al. Development of EHop-016: a small molecule inhibitor of Rac. Enzymes. 2013;33 Pt A:117-46.

[3]. Castillo-Pichardo L, et al. The Rac Inhibitor EHop-016 Inhibits Mammary Tumor Growth and Metastasis in a Nude Mouse Model. Transl Oncol. 2014 Oct 24;7(5):546-55.

Chemical & Physical Properties

Density	1.27
Molecular Formula	C₂₅H₃₀N₆O
Molecular Weight	430.54500
Exact Mass	430.24800
PSA	73.70000
LogP	3.26390
Appearance of Characters	powder,white to beige
InChIKey	AFTZZRFCMOAFCR-UHFFFAOYSA-N
SMILES	CCn1c2ccccc2c2cc(Nc3ccnc(NCCCN4CCOCC4)n3)ccc21
Storage condition	2-8°C
Water Solubility	DMSO: soluble10mg/mL, clear

Safety Information

RIDADR	NONH for all modes of transport
WGK Germany	3

Synonyms

EHop-016

N4-(9-ethyl-9H-carbazol-3-yl)-N2-(3-morpholin-4-yl-propyl)-pyrimidine-2,4-diamine

S7319

N4-(9-Ethyl-9H-carbazol-3-yl)-N2-[3-(4-morpholinyl)propyl]-2,4-pyrimidinediamine

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