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SML0526

Sigma-Aldrich

EHop-016

≥98% (HPLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C25H30N6O
CAS Number:
1380432-32-5
Molecular Weight:
430.55
MDL number:
MFCD23143628
UNSPSC Code:
12352200
PubChem Substance ID:
329825532
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 10 mg/mL, clear

storage temp.

2-8°C

SMILES string

CCn1c2ccccc2c3cc(Nc4ccnc(NCCCN5CCOCC5)n4)ccc13

InChI

1S/C25H30N6O/c1-2-31-22-7-4-3-6-20(22)21-18-19(8-9-23(21)31)28-24-10-12-27-25(29-24)26-11-5-13-30-14-16-32-17-15-30/h3-4,6-10,12,18H,2,5,11,13-17H2,1H3,(H2,26,27,28,29)

InChI key

AFTZZRFCMOAFCR-UHFFFAOYSA-N

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Application

EHop-016 has been used as the EHop inhibitor to study signalling diversity during Chlamydia trachomatis cell entry. It has also been used as a RAC inhibitor.

Biochem/physiol Actions

EHop-016 is a potent and specific inhibitor of Rac1 and Rac3 GTPase activity that inhibits Vav2 interaction with Rac, Rac-activated PAK1, lamellipodia formation, and cell migration. EHop-016 inhibits the Rac activity of MDA-MB-231 metastatic breast cancer cells and reduces Rac-directed lamellipodia formation.

Features and Benefits

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the GTP Binding Proteins (Low Molecular Weight) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Chlamydia exploits filopodial capture and a macropinocytosis-like pathway for host cell entry
Ford C, et al.
PLoS Pathogens, 14(5), e1007051-e1007051 (2018)
Endophilin marks and controls a clathrin-independent endocytic pathway
Boucrot E, et al.
Nature, 517(7535), 460-460 (2015)
Bo Zhang et al.
Cells, 9(3) (2020-03-08)
Rho GTPases, including Rho, Cdc42, Rac and ROP subfamilies, are key signaling molecules in RNA polymerase II (Pol II) transcriptional control. Our prior work has shown that plant ROP and yeast Cdc42 GTPases similarly modulate Ser2 and Ser5 phosphorylation status

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Cyclic nucleotides, including cyclic AMP (cAMP), cyclic GMP (cGMP) and cyclic ADP-ribose, have been extensively studied as second messengers of intracellular events initiated by activation of GPCRs. cAMP modifies cell function in all eukaryotic cells, principally through the activation of cAMP-dependent protein kinase (PKA), but also through cAMP-gated ion channels and guanine nucleotide exchange factors directly activated by cAMP.

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