SML1309
SQ109
≥98% (HPLC), Antibiotic, oil
别名:
N-[(2E)-3,7-Dimethyl-2,6-octadienyl]-N′-tricyclo[3.3.1.13,7]dec-2-yl-1,2-ethanediamine, N-[(2E)-3,7-dimethyl-2,6-octadienyl]-NŒ-tricyclo[3.3.1.13,7]dec-2-yl-1,2-ethanediamine, NSC 722041
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关于此项目
经验公式（希尔记法）:
C22H38N2
化学文摘社编号:
分子量:
330.55
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
产品名称
SQ109, ≥98% (HPLC)
Quality Level
storage temp.
2-8°C
SMILES string
C/C(CCC=C(C)C)=C\CNCCNC1[C@@H]2C[C@@H]3C[C@H]1C[C@H](C2)C3
InChI
1S/C22H38N2/c1-16(2)5-4-6-17(3)7-8-23-9-10-24-22-20-12-18-11-19(14-20)15-21(22)13-18/h5,7,18-24H,4,6,8-15H2,1-3H3/b17-7+
InChI key
JFIBVDBTCDTBRH-REZTVBANSA-N
assay
≥98% (HPLC)
form
oil
color
colorless to yellow
General description
SQ109 is a 1,2-ethylenediamine, which is related to ethambutol.
Application
SQ109 has been used:
- as an antitubercular agent to study its interactions with mycobacterial membrane proteins large 3 (MmpL3) binding pocket
- 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
- as an inhibitor of MmpL3 to explore the utility of mycobacterial CRISPR interference for validating target gene essentiality and compound mode of action
Biochem/physiol Actions
Antitubercular; Inhibitor of MmpL3, a mycolic acid transporter required for incorporation of mycolic acid into the Mycobacterium tuberculosis cell wall.
SQ109 exhibits activity against Helicobacter pylori and the fungi Candida albicans. It might also possess anti-bacterial activity.
SQ109 is an antitubercular developed for the treatment of multidrug-resistant tuberculosis (MDR-TB). SQ109 inhibits the activity of MmpL3, a mycolic acid transporter required for incorporation of mycolic acid into the Mycobacterium tuberculosis cell wall.
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Utilization of CRISPR Interference To Validate MmpL3 as a Drug Target in Mycobacterium tuberculosis.
Matthew B McNeil et al.
Antimicrobial agents and chemotherapy, 63(8) (2019-06-05)
There is an urgent need for novel therapeutics to treat Mycobacterium tuberculosis infections. Genetic strategies for validating novel targets are available, yet their time-consuming nature limits their utility. Here, using MmpL3 as a model target, we report on the application
Katherine A Sacksteder et al.
Future microbiology, 7(7), 823-837 (2012-07-26)
Existing drugs have limited efficacy against the rising threat of drug-resistant TB, have significant side effects, and must be given in combinations of four to six drugs for at least 6 months for drug-sensitive TB and up to 24 months
Matthew B McNeil et al.
mSphere, 5(5) (2020-10-16)
The Mycobacterium tuberculosis protein MmpL3 performs an essential role in cell wall synthesis, since it effects the transport of trehalose monomycolates across the inner membrane. Numerous structurally diverse pharmacophores have been identified as inhibitors of MmpL3 largely based on the
Utilization of CRISPR interference to validate MmpL3 as a drug target in Mycobacterium tuberculosis
McNeil MB and Cook GM
Antimicrobial Agents and Chemotherapy, 63(8), e00629-e00619 (2019)
SQ109 targets MmpL3, a membrane transporter of trehalose monomycolate involved in mycolic acid donation to the cell wall core of Mycobacterium tuberculosis
Tahlan K, et al.
Antimicrobial Agents and Chemotherapy, 56(4), 1797-1809 (2012)
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