Acetohydroxamic acid - CAS 546-88-3
Not Intended for Therapeutic Use. For research use only.
Category:
Inhibitor
Product Name:
Acetohydroxamic acid
Catalog Number:
546-88-3
Synonyms:
AHA N-hydroxyacetamide;
CAS Number:
546-88-3
Description:
Acetohydroxamic acid is a potent and irreversible inhibitor used in the synthesis of pyrogallol and catechol derivatives as Helicobacter pylori urease inhibitors.
Molecular Weight:
75.06
Molecular Formula:
C2H5NO2
Quantity:
Grams-Kilos
Quality Standard:
Enterprise Standard/USP
COA:
Inquire
MSDS:
Inquire
Canonical SMILES:
CC(=O)NO
InChI:
1S/C2H5NO2/c1-2(4)3-5/h5H,1H3,(H,3,4)
InChIKey:
RRUDCFGSUDOHDG-UHFFFAOYSA-N
Targets:
Antibacterial
Chemical Structure
CAS 546-88-3 Acetohydroxamic acid

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Reference Reading


1.Synergistic activity of acetohydroxamic acid on prokaryotes under oxidative stress: the role of reactive nitrogen species.
Yadav R1, Goldstein S2, Nasef MO1, Lee W1, Samuni U3. Free Radic Biol Med. 2014 Dec;77:291-7. doi: 10.1016/j.freeradbiomed.2014.09.020. Epub 2014 Sep 28.
One-electron oxidation of acetohydroxamic acid (aceto-HX) initially gives rise to nitroxyl (HNO), which can be further oxidized to nitric oxide (NO) or react with potential biological targets such as thiols and metallo-proteins. The distinction between the effects of NO and HNO in vivo is masked by the reversible redox exchange between the two congeners and by the Janus-faced behavior of NO and HNO. The present study examines the ability of aceto-HX to serve as an HNO donor or an NO donor when added to Escherichia coli and Bacillus subtilis subjected to oxidative stress by comparing its effects to those of NO and commonly used NO and HNO donors. The results demonstrate that: (i) the effects of NO and HNO on the viability of prokaryotes exposed to H2O2 depend on the type of the bacterial cell; (ii) NO synergistically enhances H2O2-induced killing of E. coli, but protects B. subtilis depending on the extent of cell killing by H2O2; (iii) the HNO donor Angeli׳s salt alone has no effect on the viability of the cells; (iv) Angeli׳s salt synergistically enhances H2O2-induced killing of B.
2.Lectin-Conjugated Clarithromycin and Acetohydroxamic Acid-Loaded PLGA Nanoparticles: a Novel Approach for Effective Treatment of H. pylori.
Jain SK1, Haider T2, Kumar A2, Jain A2. AAPS PharmSciTech. 2015 Nov 13. [Epub ahead of print]
Helicobacter pylori infection remains challenging as it mainly colonized beneath the deep gastric mucosa and adheres to epithelial cells of the stomach. Concanavalin-A (Con-A)-conjugated gastro-retentive poly (lactic-co-glycolic acid) (PLGA) nanoparticles of acetohydroxamic acid (AHA) and clarithromycin (CLR) were prepared and evaluated under in vitro conditions. Solvent evaporation method was employed for preparation of nanoparticles and characterized for particle size distribution, surface morphology, percent drug entrapment, and in vitro drug release in simulated gastric fluid. Optimized nanoparticles were conjugated with Con-A and further characterized for Con-A conjugation efficiency and mucoadhesion and tested for in vitro anti-H. pylori activity. The conjugation with Con-A further sustained the drug release over a period of 8 h when compared to non-conjugated nanoparticles of AHA and CLR. In vitro anti H. pylori study confirmed that Con-A-conjugated nanoparticles containing both drugs, i.