A22 (antibiotic)

A22

Names
Preferred IUPAC name

(3,4-Dichlorophenyl)methyl carbamimidothioate

Other names

3,4-Dichlorobenzyl carbamimidothioate

Identifiers

CAS Number

* 22297-13-8

3D model (JSmol)

* Interactive image

ChEMBL |

* ChEMBL1229059

PubChem CID

* 348494

InChI

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

Key: LZTCFLDZLBOLDW-UHFFFAOYSA-N

SMILES

* C1=CC(=C(C=C1CSC(=N)N)Cl)Cl

Properties

Chemical formula

| C8H8Cl2N2S
Molar mass | 235.13 g·mol−1

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Tracking categories (test):

* SizeSet

A22, also known as S-(3,4-dichlorobenzyl) isothiourea, is a chemical compound with antibiotic activity. It is colorless, hygroscopic, and light-sensitive.[1]

## Antibiotic activity

A22 acts as a reversible inhibitor of the bacterial cell wall protein MreB, causing bacterial rod-shaped cells to form coccoid cells.[2] The antibiotic activity of A22 has been studied primarily in Pseudomonas aeruginosa. However, A22 does not seem to be useful as an antibiotic in humans due to its cytotoxic and genotoxic effects on human peripheral blood mononuclear cells (PBMCs).[2]

## A22 as a research tool

Despite its cytotoxic effects in human cells, A22 has been used as a research tool to investigate the bacterial cytoskeleton. A22 binds directly to the actin homolog MreB in its nucleotide-binding pocket, blocking simultaneous ATP binding. As a consequence, A22 inhibits MreB polymerization and thus disrupts the cytoskeleton of bacteria, causing defects of morphology and chromosome segregation.[3]

## References

1. ↑ "MreB Perturbing Compound A22". http://www.emdmillipore.com/US/en/product/MreB-Perturbing-Compound-A22-CAS-22816-60-0-Calbiochem,EMD_BIO-475951.
2. ↑ 2.0 2.1 "Antibacterial, cyto and genotoxic activities of A22 compound ((S-3, 4 -dichlorobenzyl) isothiourea hydrochloride)". Microbial Pathogenesis 99: 14–18. October 2016. doi:10.1016/j.micpath.2016.07.007. PMID 27427089.
3. ↑ "A22 disrupts the bacterial actin cytoskeleton by directly binding and inducing a low-affinity state in MreB". Biochemistry 48 (22): 4852–7. June 2009. doi:10.1021/bi900014d. PMID 19382805.

0.00

(0 votes)

Original source: https://en.wikipedia.org/wiki/A22 (antibiotic). Read more

|

Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:A22_(antibiotic)&oldid=805219"
*[CID]: Compound ID