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Merck
CN

475951

A22 hydrochloride

≥95% (HPLC),cell-permeable isothiourea compound, solid

Synonym(s):

MreB Perturbing Compound A22, S-(3,4-Dichlorobenzyl)isothiourea, HCl

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About This Item

Empirical Formula (Hill Notation):
C8H8Cl2N2S · xHCl
CAS Number:
22816-60-0
Molecular Weight:
235.13 (free base basis)
UNSPSC Code:
51111800
NACRES:
NA.77
MDL number:
MFCD00035050

Key Documents

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Product Name

MreB Perturbing Compound A22, A cell-permeable isothiourea compound that specifically, rapidly and reversibly perturbs MreB function without affecting eukaryotic actin polymerization.

SMILES string

S(Cc1cc(c(cc1)Cl)Cl)\C(=N\[H])\N.Cl

InChI

1S/C8H8Cl2N2S.ClH/c9-6-2-1-5(3-7(6)10)4-13-8(11)12;/h1-3H,4H2,(H3,11,12);1H

InChI key

VBJNMXMOMSWRDV-UHFFFAOYSA-N

assay

≥95% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
desiccated (hygroscopic)
protect from light

color

white

solubility

water: 2 mg/mL
DMSO: 200 mg/mL

shipped in

ambient

storage temp.

2-8°C

Quality Level

100

Related Categories

Other Notes

Gitai, Z., et al. 2005. Cell120, 329.
Jensen, R.B., et al. 2002. Nat. Rev. Mol. Cell Biol.3, 167.
Iwai, N., et al. 2002. Biosci. Biotechnol. Biochem.66, 2658.

Packaging

Packaged under inert gas

Biochem/physiol Actions

Cell permeable: yes
Primary Target
MreB
Product does not compete with ATP.
Reversible: yes

Disclaimer

Toxicity: Standard Handling (A)

General description

A cell-permeable isothiourea compound that specifically, rapidly and reversibly perturbs MreB function without affecting eukaryotic actin polymerization. Reported to affect the growth and morphology of Caulobacter crescentus, convert rod-shaped E. coli to round cells, and block DNA segregation without affecting DNA replication. Suggested to interact with MreB′s nucleotide binding pocket and is useful for the temporal analysis of MreB function.

Preparation Note

Following reconstitution in DMSO, aliquot and freeze (-20°C. DMSO stock solutions are stable for up to 1 month at -20°C. Reconstitute in H₂O just prior to use; aqueous stock solutions are stable for up to 12 hr. Stable for up to 2 days in acidic medium.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class

11 - Combustible Solids

wgk

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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Zemer Gitai et al.
Cell, 120(3), 329-341 (2005-02-15)
Faithful chromosome segregation is an essential component of cell division in all organisms. The eukaryotic mitotic machinery uses the cytoskeleton to move specific chromosomal regions. To investigate the potential role of the actin-like MreB protein in bacterial chromosome segregation, we
Noritaka Iwai et al.
Bioscience, biotechnology, and biochemistry, 66(12), 2658-2662 (2003-02-25)
Random screening for inhibitors of chromosome partitioning in Escherichia coli was done by the anucleate cell blue assay. A novel S-benzylisothiourea derivative, S-(3,4-dichlorobenzyl)isothiourea, tentatively named A22, was found to induce spherical cells and spherical anucleate cells in E. coli. Mecillinam
Rasmus B Jensen et al.
Nature reviews. Molecular cell biology, 3(3), 167-176 (2002-05-08)
A cellular differentiation programme that culminates in an asymmetric cell division is an integral part of the cell cycle in the bacterium Caulobacter crescentus. Recent work has uncovered mechanisms that ensure the execution of many events at different times during
Abhishek Shrivastava et al.
Science advances, 6(10), eaay6616-eaay6616 (2020-03-18)
The gliding bacterium Flavobacterium johnsoniae is known to have an adhesin, SprB, that moves along the cell surface on a spiral track. Following viscous shear, cells can be tethered by the addition of an anti-SprB antibody, causing spinning at 3

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