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SML0462

Sigma-Aldrich

Alda-1

≥98% (HPLC)

Synonym(s):

N-(1,3-Benzodioxol-5-ylmethyl)-2,6-dichlorobenzamide

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About This Item

Empirical Formula (Hill Notation):
C15H11Cl2NO3
CAS Number:
Molecular Weight:
324.16
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 10 mg/mL (clear solution)

storage temp.

2-8°C

SMILES string

Clc1cccc(Cl)c1C(=O)NCc2ccc3OCOc3c2

InChI

1S/C15H11Cl2NO3/c16-10-2-1-3-11(17)14(10)15(19)18-7-9-4-5-12-13(6-9)21-8-20-12/h1-6H,7-8H2,(H,18,19)

InChI key

NMKJFZCBCIUYHI-UHFFFAOYSA-N

Application

Alda-1 has been used as an aldehyde dehydrogenase 2 (ALDH2) agonist:
  • to study its cryoprotective effects on H2O2-induced Achilles tendinopathy in mice Achilles tenocytes
  • to study its protective effects against alcohol-derived DNA damage in ALDH2 knock out mice
  • to study its effects on cutaneous wound healing in mice

Biochem/physiol Actions

Alda-1 is an ALDH2 agonist; cell-permeable activator of both the wild-type ALDH2*1 and the asian E487K mutant ALDH2*2 forms of mitochondrial aldehyde dehydrogenase 2. ALDH2 is the oxidative enzyme, which removes the ethanol metabolite acetaldehyde and other aliphatic aldehydes. Also. ALDH2 is involved in bioconversion of vasodilator nitroglycerin to nitric oxide. Alda-1 increases acetaldehyde oxidation by ALDH2*1 (wild type) and ALDH2*2 9 Asian variant) approximately 1.5- and 6-fold, respectively. It appears that Alda-1 stimulates acetaldehyde oxidation by ALDH2 by improving NAD binding, but does not improve the nitroglycerin binding affinity of the Asian variant.
Alda-1 plays a role in reducing the damage caused by oxidative stress in several human cells like lung endothelial, umbilical vein endothelial, and hepatic cells.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3


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Jianlu Guo et al.
Nan fang yi ke da xue xue bao = Journal of Southern Medical University, 38(11), 1288-1293 (2018-12-06)
To investigate whether CaN-NFAT3 pathway mediates the protective effects of aldehyde dehydrogenase (ALDH) 2 in high glucose-treated neonatal rat ventricular myocytes. The ventricular myocytes were isolated from the heart of neonatal (within 3 days) SD rats by enzyme digestion and
Weiming Yan et al.
BMC ophthalmology, 20(1), 55-55 (2020-02-20)
Retinitis pigmentosa (RP) is a kind of inherited retinal degenerative diseases characterized by the progressive loss of photoreceptors. RP has been a conundrum without satisfactory countermeasures in clinic until now. Acetaldehyde dehydrogenase 2 (ALDH2), a major enzyme involved in aldehyde
Qiankun Zhu et al.
Clinical science (London, England : 1979), 131(11), 1123-1136 (2017-03-23)
Many studies demonstrate that activation of aldehyde dehydrogenase 2 (ALDH2) protects against oxidative stress via detoxification of cytotoxic aldehydes, and could attenuate cardiac, cerebral, lung and renal ischaemia-reperfusion (I/R) injuries. However, the effect of ALDH2 in intestinal I/R is unknown. The
Che-Hong Chen et al.
EBioMedicine, 55, 102753-102753 (2020-05-14)
Aldehyde dehydrogenase 2 (ALDH2) catalyzes the detoxification of aliphatic aldehydes, including acetaldehyde. About 45% of Han Chinese (East Asians), accounting for 8% of humans, carry a single point mutation in ALDH2*2 (E504K) that leads to accumulation of toxic reactive aldehydes.
Sahebgowda Sidramagowda Patil et al.
Frontiers in pharmacology, 11, 597942-597942 (2021-02-19)
Acute lung injury (ALI), a milder form of acute respiratory distress syndrome (ARDS), is a leading cause of mortality in older adults with an increasing prevalence. Oxygen therapy, is a common treatment for ALI, involving exposure to a high concentration

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