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SML1309

Sigma-Aldrich

SQ109

≥98% (HPLC)

Synonyme(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

Formule empirique (notation de Hill):
C22H38N2
Numéro CAS:
502487-67-4
Poids moléculaire :
330.55
Code UNSPSC :
12352200
ID de substance PubChem :
329825775
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

oil

Couleur

colorless to yellow

Température de stockage

2-8°C

Chaîne SMILES 

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+

Clé InChI

JFIBVDBTCDTBRH-REZTVBANSA-N

Description générale

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

Actions biochimiques/physiologiques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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
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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