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SML1309

Sigma-Aldrich

SQ109

≥98% (HPLC)

Synonym(s):

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]-NŒ-tricyclo[3.3.1.13,7]dec-2-yl-1,2-ethanediamine, NSC 722041

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About This Item

Empirical Formula (Hill Notation):
C22H38N2
CAS Number:
502487-67-4
Molecular Weight:
330.55
UNSPSC Code:
12352200
PubChem Substance ID:
329825775
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

oil

color

colorless to yellow

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

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

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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.
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
Tae Sung Kim et al.
Scientific reports, 7(1), 3431-3431 (2017-06-15)
The induction of host cell autophagy by various autophagy inducers contributes to the antimicrobial host defense against Mycobacterium tuberculosis (Mtb), a major pathogenic strain that causes human tuberculosis. In this study, we present a role for the newly identified cyclic

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