502487-67-4

Usage

Uses

Used in Antitubercular Applications:
SQ109 is used as an antitubercular agent for studying its interactions with mycobacterial membrane proteins large 3 (MmpL3) binding pocket. This interaction is crucial for understanding the compound's effectiveness against Mycobacterium tuberculosis (Mtb).
Used in Determining Minimum Inhibitory Concentration (MIC):
SQ109 serves as a positive control to determine the minimum inhibitory concentration (MIC) of ohmyungsamycins (OMS) A and B against Mycobacterium tuberculosis (Mtb) using the resazurin microtiter assay (REMA) plate method. This application helps in evaluating the potency of other compounds in inhibiting the growth of Mtb.
Used in Inhibiting MmpL3:
SQ109 is used as an inhibitor of MmpL3 to explore the utility of mycobacterial CRISPR interference for validating target gene essentiality and compound mode of action. By inhibiting MmpL3, SQ109 aids in understanding the role of this protein in the pathogenesis of tuberculosis and the potential of targeting it for therapeutic intervention.

Biochem/physiol Actions

SQ109 exhibits activity against Helicobacter pylori and the fungi Candida albicans. It might also possess anti-bacterial activity.

Upstream product

• 6138-90-5 trans-geranyl bromide 
• 1227090-46-1 (E)-N'-(3,7-dimethylocta-2,6-dienyl)ethane-1,2-diamine 
• 700-58-3 2-Adamantanone 

Relevant academic research and scientific papers

Novel polycyclic 'cage'-1,2-diamines as potential anti-tuberculosis agents

A series of polycyclic 'cage' derivatives of N-geranyl-1,2 diamines were synthesized and screened for their anti-mycobacterial activity against H 37Rv, multidrug resistant (MDR) and extensively drug-resistant (XDR) strains of tuberculosis. By substituting the adamantyl skeleton of SQ109 with trishomocubanyl (9), oxa-pentacycloundecyl (14, 16), pentacycloundecyl, PCU, (10, 15) and azapentacycloundecyl (22, 23), the effect of other polycyclic "cage" skeletons could be investigated. Compound 9 (trishomocubanyl moiety) proved to be the most active (MICs: 0.5-2 μg/mL) while PCU hydroxyl derivatives (15 and 23), oxa-pentacycloundecyl and azapentacycloundecyl derivatives displayed similar activity to SQ109 (MICs: 0.5-4 μg/mL) against all three strains of TB used in this study.

Novel linear diamine disubstituted polycyclic 'cage' derivatives as potential antimycobacterial candidates

As a part of an ongoing project to develop highly potent antituberculosis therapeutics, a series novel polycyclic 'cage' tetra-amines were synthesized and screened for in-vitro antituberculosis activities against the H37Rv strain of tuberculosis. Three disubstituted polycyclic moieties, namely pentacyclodecane, pentacycloundecane, and tricyclodecane, were used in this study. Compounds 5 and 7 showed similar activity to SQ109 at a MIC of 1μm while compounds 4, 6 and 8 displayed MIC activity at 137Rv strain of tuberculosis. Compounds 5, 7 and SQ109 were selected for further screening against, multi-drug resistant, (R1097) and extensively drug resistant, (X149) strains of tuberculosis. Compound 5 showed anti-TB activity of a MIC=1μm against multi-drug resistant strain (R1097) and 2,5.03,9.04,8]decane as a potential therapeutic agent.

Synthesis and evaluation of SQ109 analogues as potential anti-tuberculosis candidates

As part of an ongoing project to develop highly potent anti-tuberculosis therapeutics, six SQ109 derivatives were synthesized and screened in vitro for their anti-tuberculosis activity against the ATCC strain H37Rv and the extensively drug-resistant clinical strain XDR 173. Compound 16 with an extended alkene chain was the most active against both strains of Mycobacterium tuberculosis within a MIC range of 0.5-0.25 μM. Compound 12 and SQ109 were potent within a MIC range of 1-0.5 μM, whilst compound 18 displayed an activity within the MIC range of 0.5-2 μM against both Mycobacterium tuberculosis strains.

Methods of use and compositions for the diagnosis and treatment of infectious disease

Methods and compositions for treating disease caused by microorganisms, particularly tuberculosis. In particular, methods and compositions comprising substituted ethylene diamines for the treatment of infectious diseases are provided. In one embodiment, t