MAC13243 - CAS 1071638-38-4
Catalog number: 1071638-38-4
Category: Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C20H25Cl2N3O2S
Molecular Weight:
442.4
COA:
Inquire
Targets:
Antibacterial
Description:
MAC13243, an antibacterial agent, is a likely inhibitor of the bacterial lipoprotein targeting chaperone, LolA.
Purity:
>98%
MSDS:
Inquire
InChIKey:
VCJIDISBDZWDOJ-UHFFFAOYSA-N
InChI:
InChI=1S/C20H24ClN3O2S.ClH/c1-25-18-8-5-15(11-19(18)26-2)9-10-24-13-22-20(23-14-24)27-12-16-3-6-17(21)7-4-16;/h3-8,11H,9-10,12-14H2,1-2H3,(H,22,23);1H
Canonical SMILES:
COC1=C(C=C(C=C1)CCN2CNC(=NC2)SCC3=CC=C(C=C3)Cl)OC.Cl
1.Degradation of MAC13243 and studies of the interaction of resulting thiourea compounds with the lipoprotein targeting chaperone LolA.
Barker CA1, Allison SE, Zlitni S, Nguyen ND, Das R, Melacini G, Capretta AA, Brown ED. Bioorg Med Chem Lett. 2013 Apr 15;23(8):2426-31. doi: 10.1016/j.bmcl.2013.02.005. Epub 2013 Feb 13.
The discovery of novel small molecules that function as antibacterial agents or cellular probes of biology is hindered by our limited understanding of bacterial physiology and our ability to assign mechanism of action. We previously employed a chemical genomic strategy to identify a novel small molecule, MAC13243, as a likely inhibitor of the bacterial lipoprotein targeting chaperone, LolA. Here, we report on the degradation of MAC13243 into the active species, S-(4-chlorobenzyl)isothiourea. Analogs of this compound (e.g., A22) have previously been characterized as inhibitors of the bacterial actin-like protein, MreB. Herein, we demonstrate that the antibacterial activity of MAC13243 and the thiourea compounds are similar; these activities are suppressed or sensitized in response to increases or decreases of LolA copy number, respectively. We provide STD NMR data which confirms a physical interaction between LolA and the thiourea degradation product of MAC13243, with a Kd of ~150 μM.
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CAS 1071638-38-4 MAC13243

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