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Merck

SML0921

AR7

≥98% (HPLC)

Synonym(s):

7-Chloro-3-(4-methylphenyl)-2H-1,4-benzoxazine; 7-Chloro-3-p-tolyl-2H-benzo[b][1,4]oxazine, Atypical retinoid 7

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About This Item

Empirical Formula (Hill Notation):
C15H12ClNO
CAS Number:
80306-38-3
Molecular Weight:
257.71
UNSPSC Code:
12352200
NACRES:
NA.77

Key Documents

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InChI key

PUXHKTZKBDGXBB-UHFFFAOYSA-N

SMILES string

Clc1cc2c(cc1)NC(=CO2)c3ccc(cc3)C

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

2-8°C

Quality Level

100

Application

AR7 has been used:
  • as chaperone-mediated autophagy (CMA) activator to study the activity of CMA in rat liver lysosomes
  • as a CMA activator to study its effects on expression of DEAD-box helicase 3 X-linked (DDX3X), eukaryotic translation initiation factor 4A1 (EIF4A1), and eukaryotic translation initiation factor 4H (EIF4H) in cancer cells
  • to study its effects on synuclein α (SNCA) oligomer levels in mature primary cortical neurons

Biochem/physiol Actions

AR7 is an atypical retinoic acid receptor α (RARα) antagonist.
AR7 is an atypical retinoic acid receptor α (RARα) antagonist. There is high interest in retinoic acid receptors for cancer and for differentiation studies. Recently, it has been found that signaling through retinoic acid receptor α (RARα) inhibits chaperone-mediated autophagy (CMA). Disruption of RARα signaling has a stimulatory effect on CMA, but can lead to inhibition of macroautophagy. AR7 antagonizes only the CMA inhibitory effect without affecting macroautophagy, allowing the two RARα effects on autophagy to be studied independently.

pictograms

Environment
GHS09

signalword

Warning

hcodes

H410

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

SML0921-25MG: + SML0921-VAR: + SML0921-BULK: + SML0921-5MG:

jan

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Certificates of Analysis (COA)

Lot/Batch Number
0000401383
0000401380
0000401383
0000401380
0000184193

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Y R Juste et al.
Methods in molecular biology (Clifton, N.J.), 1880, 703-727 (2019-01-06)
Chaperone-mediated autophagy (CMA) is a selective type of autophagy whereby a specific subset of intracellular proteins is targeted to the lysosome for degradation. These proteins are identified by a chaperone that targets them to lysosomes. There, they are translocated into
You-Jin Choi et al.
Molecular metabolism, 76, 101784-101784 (2023-08-01)
Alterations in lipid metabolism are associated with aging and age-related diseases. Chaperone-mediated autophagy (CMA) is a lysosome-dependent process involved in specific protein degradation. Heat shock cognate 71 kDa protein (Hsc70) recognizes cytosolic proteins with KFERQ motif and allows them to enter
Yuqing Hao et al.
Autophagy, 15(9), 1558-1571 (2019-03-02)
Chaperone-mediated autophagy (CMA) is a lysosomal degradation pathway of select soluble proteins. Nearly one-third of the soluble proteins are predicted to be recognized by this pathway, yet only a minor fraction of this proteome has been identified as CMA substrates
Panagiota Mavroeidi et al.
Autophagy, 18(9), 2104-2133 (2022-01-11)
Accumulation of the neuronal protein SNCA/alpha-synuclein and of the oligodendroglial phosphoprotein TPPP/p25A within the glial cytoplasmic inclusions (GCIs) represents the key histophathological hallmark of multiple system atrophy (MSA). Even though the levels/distribution of both oligodendroglial SNCA and TPPP/p25A proteins are
Philip Wing-Lok Ho et al.
Autophagy, 16(2), 347-370 (2019-04-16)
Parkinson disease (PD) is an age-related neurodegenerative disorder associated with misfolded SNCA/α-synuclein accumulation in brain. Impaired catabolism of SNCA potentiates formation of its toxic oligomers. LRRK2 (leucine-rich repeat kinase-2) mutations predispose to familial and sporadic PD. Mutant LRRK2 perturbs chaperone-mediated-autophagy
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