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Merck
CN

SML1309

SQ109

≥98% (HPLC), Antibiotic, oil

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

Key Documents

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Product Name

SQ109, ≥98% (HPLC)

Quality Level

100

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

Related Categories

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000418363
0000418363
0000240740
0000240740
0000230092

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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)
Sergey Bukhdruker et al.
International journal of molecular sciences, 21(20) (2020-10-22)
Spreading of the multidrug-resistant (MDR) strains of the one of the most harmful pathogen Mycobacterium tuberculosis (Mtb) generates the need for new effective drugs. SQ109 showed activity against resistant Mtb and already advanced to Phase II/III clinical trials. Fast SQ109
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