SML0009
AI-1
≥98% (HPLC)
Synonym(s):
4-Chloro-1,2-dihydro-1-methyl-2-oxo-3-quinolinecarboxylic acid ethyl ester, Ethyl 4-chloro-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate
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About This Item
Empirical Formula (Hill Notation):
C13H12ClNO3
CAS Number:
Molecular Weight:
265.69
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
MDL number:
form
powder
color
white to tan
assay
≥98% (HPLC)
InChI
1S/C13H12ClNO3/c1-3-18-13(17)10-11(14)8-6-4-5-7-9(8)15(2)12(10)16/h4-7H,3H2,1-2H3
SMILES string
ClC(C1=C(N2C)C=CC=C1)=C(C(OCC)=O)C2=O
InChI key
XUJQDJGGHFNYDY-UHFFFAOYSA-N
solubility
DMSO: ≥15 mg/mL
storage temp.
2-8°C
Biochem/physiol Actions
AI-1 positively regulates antioxidant response element (ARE)-driven gene transcription through the activation of Nuclear factor E2-related factor 2 (Nrf2), an ARE-binding transcription factor.
AI-1 promotes Nrf2 activation via the covalent modification of Kelch-like ECH-associated protein 1 (Keap1), a negative regulator of Nrf2. Biochemical studies indicate that an aromatic chloride present within the AI-1 molecule undergoes a nucleophilic aromatic substitution reaction with cysteine thiols of Keap1.
Storage Class
11 - Combustible Solids
wgk
WGK 3
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Tiziana Fuoco et al.
Biomacromolecules, 21(1), 188-198 (2019-09-25)
The advancement of 3D printing technologies in the fabrication of degradable scaffolds for tissue engineering includes, from the standpoint of the polymer chemists, an urgent need to develop new materials that can be used as ink and are suitable for
Kyoko Hosohama-Saito et al.
PloS one, 11(1), e0147114-e0147114 (2016-01-23)
Capnocytophaga ochracea is present in the dental plaque biofilm of patients with periodontitis. Biofilm cells change their phenotype through quorum sensing in response to fluctuations in cell-population density. Quorum sensing is mediated by auto-inducers (AIs). AI-2 is involved in intercellular
Kristina Stephens et al.
Nature communications, 10(1), 4129-4129 (2019-09-13)
Synthetic biology and metabolic engineering have expanded the possibilities for engineered cell-based systems. The addition of non-native biosynthetic and regulatory components can, however, overburden the reprogrammed cells. In order to avoid metabolic overload, an emerging area of focus is on engineering
Suman Mukhopadhyay et al.
Cancer research, 80(8), 1630-1643 (2020-01-09)
Pancreatic cancer is a disease with limited therapeutic options. Resistance to chemotherapies poses a significant clinical challenge for patients with pancreatic cancer and contributes to a high rate of recurrence. Oncogenic KRAS, a critical driver of pancreatic cancer, promotes metabolic
Rong Gao et al.
Applied and environmental microbiology, 81(23), 7993-8007 (2015-09-13)
Burkholderia glumae PG1 is a soil-associated motile plant-pathogenic bacterium possessing a cell density-dependent regulation system called quorum sensing (QS). Its genome contains three genes, here designated bgaI1 to bgaI3, encoding distinct autoinducer-1 (AI-1) synthases, which are capable of synthesizing QS
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