S - (3,4-dichlorobenzyl) isothiourea hydrochloride

Structural formula
General
Surname	S - (3,4-dichlorobenzyl) isothiourea hydrochloride
other names	3,4-dichlorobenzylcarbamimidothioate hydrochloride ( IUPAC ) ; (3,4-dichlorophenyl) methylsulfanyl-methanimidamide; A22;
Molecular formula	C 8 H 9 Cl 3 N 2 S
Brief description	white, hygroscopic solid
External identifiers / databases
EC number	803-561-7
ECHA InfoCard	100.230.352
PubChem	2830968
ChemSpider	2012925
Wikidata	Q279935
properties
Molar mass	271.6 g mol −1
Physical state	firmly
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 302
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

S - (3,4-dichlorobenzyl) isothiourea hydrochloride is a chemical compound that was used under the name A22 hydrochloride to investigate its anti- biofilm activity, as well as its antibacterial , cytostatic and genotoxic activities.

Properties and use

A22 is a colorless, hygroscopic solid that decomposes when exposed to light. The compound is readily soluble in DMSO (> 200 mg / ml) and in water (> 2 mg / ml). However, aqueous solutions are unstable and degrade rapidly; low pH values delay decay. The chemical easily penetrates cell membranes and interacts highly specifically and reversibly with the filament-forming protein MreB, which in many bacteria plays a key role in maintaining the cell shape through the localization of the cell wall- forming enzymes. The interaction disrupts the polymerization of MreB and thus the formation of the filaments. As a result, rod-shaped cells develop after the addition of A22 spheres which ultimately lyse . In 2002 the prokaryotic cytoskeleton was discovered with the help of A22 .

safety instructions

No toxicity data are available. Burning can produce hazardous gases such as carbon monoxide , sulfur oxides, nitrogen oxides , halogenated compounds and hydrogen chloride .

Individual evidence

↑ ^a ^b ^c data sheet MreB Perturbing Compound A22 (PDF) from Calbiochem, accessed on December 8, 2015.
↑ ^a ^b ^c data sheet A22 hydrochloride, ≥95% (HPLC) from Sigma-Aldrich , accessed on February 5, 2013 ( PDF ).
↑ N. Iwai, K. Nagai, M. Wachi: Novel S-Benzylisothiourea Compound That Induces Spherical Cells in Escherichia coli Probably by Acting on a Rod-shape-determining Protein (s) Other Than Penicillin-binding Protein 2. In: Bioscience , Biotechnology, and Biochemistry . 66, 2658 (2002)
^ RB Jensen, SC Wang, L. Shapiro : Dynamic localization of proteins and DNA during a bacterial cell cycle. In: Nat. Rev. Mol. Cell. Biol . 3, 167 (2002)
^ Z. Gitai: The New Bacterial Cell Biology: Moving Parts and Subcellular Architecture. In: Cell 120, 577 (2005)

[Merck-1] ta sheet MreB Perturbing Compound A22 (PDF) from Calbiochem, accessed on December 8, 2015.

[Sigma-2] ta sheet A22 hydrochloride, ≥95% (HPLC) from Sigma-Aldrich , accessed on February 5, 2013 ( PDF ).

[3] N. Iwai, K. Nagai, M. Wachi: Novel S-Benzylisothiourea Compound That Induces Spherical Cells in Escherichia coli Probably by Acting on a Rod-shape-determining Protein (s) Other Than Penicillin-binding Protein 2. In: Bioscience , Biotechnology, and Biochemistry . 66, 2658 (2002)

[4] RB Jensen, SC Wang, L. Shapiro : Dynamic localization of proteins and DNA during a bacterial cell cycle. In: Nat. Rev. Mol. Cell. Biol . 3, 167 (2002)

[5] Z. Gitai: The New Bacterial Cell Biology: Moving Parts and Subcellular Architecture. In: Cell 120, 577 (2005)