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SML0471

Sigma-Aldrich

A22 hydrochloride

≥95% (HPLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C8H8Cl2N2S · HCl
CAS Number:
22816-60-0
Molecular Weight:
271.59
MDL number:
MFCD00035050
UNSPSC Code:
51111800
PubChem Substance ID:
329825427
NACRES:
NA.77

assay

≥95% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

H2O: 2 mg/mL (clear solution, warmed)

storage temp.

2-8°C

SMILES string

Cl.NC(=N)SCc1ccc(Cl)c(Cl)c1

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

Application

A22 hydrochloride has been used to study its anti-biofilm activity, antibacterial, cyto and genotoxic activities. It is also used as a MreB polymerization inhibitor to understand the role of MreB polymers in Candidatus Thiosymbion oneisti and Candidatus T. hypermnestrae division.

Biochem/physiol Actions

A22 is an inhibitor of MreB, an actin-like bacterial protein, and has been shown to act as an antiobiotic adjuvant. A22 inhibition of MreB disrupts the bacterial actin cytoskeleton, which can cause an increase in cell permeability and altered transport. A22 has been shown to have synergistic effects with several antibiotics including novobiocin and rifampin in gram negative bacteria.

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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Anti-biofilm activity of A22 ((S-3, 4-dichlorobenzyl) isothiourea hydrochloride) against Pseudomonas aeruginosa: Influence on biofilm formation, motility and bioadhesion.
Bonez P C, et al.
Microbial Pathogenesis, 111, 6-13 (2017)
Host-polarized cell growth in animal symbionts.
Pende N, et al.
Current Biology, 28(7), 1039-1051 (2018)
Alam García-Heredia et al.
eLife, 10 (2021-02-06)
Many antibiotics target the assembly of cell wall peptidoglycan, an essential, heteropolymeric mesh that encases most bacteria. In rod-shaped bacteria, cell wall elongation is spatially precise yet relies on limited pools of lipid-linked precursors that generate and are attracted to
Antibacterial, cyto and genotoxic activities of A22 compound ((S-3, 4-dichlorobenzyl) isothiourea hydrochloride).
Bonez P C, et al.
Microbial Pathogenesis, 99, 14-18 (2016)
Jan Lennings et al.
International journal of medical microbiology : IJMM, 309(6), 151335-151335 (2019-08-06)
The type VI secretion system (T6SS) injects effector proteins into neighboring bacteria and host cells. Effector translocation is driven by contraction of a tubular sheath in the cytoplasm that expels an inner needle across the cell envelope. The AAA + ATPase ClpV

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