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Merck
CN

SML2477

Squarunkin A hydrochloride

≥98% (HPLC)

Synonym(s):

4-[[3,4-Dioxo-2-[[2-[4-[3-(trifluoromethyl)phenyl]-1-piperazinyl]ethyl]amino]-1-cyclobuten-1-yl]amino]-1-piperidinecarboxylic acid ethyl ester, hydrochloride, Ethyl 4-(3,4-dioxo-2-(2-(4-(3-(trifluoromethyl)phenyl)piperazin-1-yl)ethylamino)cyclobut-1-enylamino)piperidine-1-carboxylate, hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C25H32F3N5O4 · xHCl
CAS Number:
2101958-02-3
Molecular Weight:
523.55 (free base basis)
UNSPSC Code:
12352200

Key Documents

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InChI key

ZKITWOVRRSBKFG-UHFFFAOYSA-N

InChI

1S/C25H32F3N5O4/c1-2-37-24(36)33-9-6-18(7-10-33)30-21-20(22(34)23(21)35)29-8-11-31-12-14-32(15-13-31)19-5-3-4-17(16-19)25(26,27)28/h3-5,16,18,29-30H,2,6-15H2,1H3

SMILES string

FC(F)(F)c1cc(ccc1)N2CCN(CC2)CCNC3=C(C(=O)C3=O)NC4CCN(CC4)C(=O)OCC

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

Biochem/physiol Actions

Non-cytotoxic, potent and specific UNC119-cargo interation blocker that inhibits Lck localization at T-cell immune synpase and Src activation.
Squarunkin A is a non-cytotoxic, potent and specific UNC119-cargo interation blocker (IC50 = 10 nM against 800 nM myristoylated Src N-terminal peptide for GST-UNC119A) that targets UNC119A/B myristoyl-binding pocket without affecting the interaction of geranylgeranylated Rab1 to RhoGDI22, or farnesylated Rheb to PDE6d, AIPL1, and calmodulin. Squarunkin A blocks Lck localization at staphylococcal E enterotoxin-induced Jurkat T-cell synpase (2 μM) and prevents MDA-MB-231 cellular Src activation (37/62% reduced Src pY416 post 24 hr 78/625 nM Squarunkin A incubation) without growth inhibition or apoptosis induction (10 μM for >35 hrs).

wgk

WGK 3

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000076777
0000076778
0000072554

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Tom Mejuch et al.
Angewandte Chemie (International ed. in English), 56(22), 6181-6186 (2017-05-05)
N-Terminal myristoylation facilitates membrane binding and activity of proteins, in particular of Src family kinases, but the underlying mechanisms are only beginning to be understood. The chaperones UNC119A/B regulate the cellular distribution and signaling of N-myristoylated proteins. Selective small-molecule modulators
Nelli Erwin et al.
Chembiochem : a European journal of chemical biology, 19(14), 1482-1487 (2018-04-28)
Plasma membrane localization of myristoylated c-Src, a proto-oncogene protein-tyrosine kinase, is required for its signaling activity. Recent studies proposed that UNC119 protein functions as a solubilizing factor for myristoylated proteins, thereby regulating their subcellular distribution and signaling. The underlying molecular
Louise A Stephen et al.
Developmental cell, 47(1), 122-132 (2018-09-18)
Upon engagement of the T cell receptor with an antigen-presenting cell, LCK initiates TCR signaling by phosphorylating its activation motifs. However, the mechanism of LCK activation specifically at the immune synapse is a major question. We show that phosphorylation of the

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