Zaragozic acid A
- Product Name
- Zaragozic acid A
- CAS No.
- 142561-96-4
- Chemical Name
- Zaragozic acid A
- Synonyms
- Aids111671;Gr 105155x;Aids-111671;Squalestatin A;Zaragozic Acid;Squalestatin 1;ZARAGOZIC ACID A;DFKDOZMCHOGOBR-NCSQYGPNSA-N;Squalestatin A, Squalestatin S1, L 694599;L-Erythro-L-glycero-D-altro-7-trideculo-7,4-furanosonic acid, 2,7-anhydro-3,4-di-C-carboxy-8,9,10,12,13-pentadeoxy-10-methylene-12-(phenylmethyl)-, 11-acetate 5-[(2E,4S,6S)-4,6-dimethyl-2-octenoate], (7S)-
- CBNumber
- CB1505421
- Molecular Formula
- C35H46O14
- Formula Weight
- 690.73
- MOL File
- 142561-96-4.mol
Zaragozic acid A Property
- alpha
- D22 +18.3° (c = 0.60 in CHCl3); D25 +37° (c = 1.29 in methanol)
- Boiling point:
- 850.1±65.0 °C(Predicted)
- Density
- 1.35±0.1 g/cm3(Predicted)
- storage temp.
- −20°C
- solubility
- Soluble in DMSO
- form
- solid
- pka
- 1.47±0.70(Predicted)
- color
- white to light tan
- CAS DataBase Reference
- 142561-96-4
Safety
- WGK Germany
- 3
N-Bromosuccinimide Price
- Product number
- 17452
- Product name
- Zaragozic Acid A
- Purity
- ≥98%
- Packaging
- 1mg
- Price
- $194
- Updated
- 2024/03/01
- Product number
- 17452
- Product name
- Zaragozic Acid A
- Purity
- ≥98%
- Packaging
- 5mg
- Price
- $483
- Updated
- 2024/03/01
- Product number
- Z150605
- Product name
- ZaragozicAcidA
- Packaging
- 0.5mg
- Price
- $395
- Updated
- 2021/12/16
- Product number
- A1624
- Product name
- ZaragozicAcidA
- Packaging
- 5mg
- Price
- $549
- Updated
- 2021/12/16
- Product number
- 8496CP
- Product name
- ZaragozicacidA
- Packaging
- 5mg
- Price
- $637
- Updated
- 2021/12/16
Zaragozic acid A Chemical Properties,Usage,Production
Chemical Properties
White to light tan solid. Soluble in ethanol (10 mg/ml), methanol, DMF, DMSO (10 mg/ml), and water (moderate).
Uses
Zaragozic acid A is the major metabolite of a class of unusual bicyclic tricarboxylic acids, produced by a number of fungi in the genera Curvularia, Exserohilum, Setosphaeria and others, discovered at Merck and Glaxo in the early 1990s. In nature, zaragozic acid A acts as broad spectrum antifungal but its mode of action as an inhibitor of squalene synthase, involved in sterol biosynthesis, lead to investigation as a cholesterol lowering agent. Zaragozic acid A prepared by BioAustralis is presented as the free acid rather than the tri-sodium salt to avoid stability problems associated with hydrolysis of the salt.
Definition
ChEBI: Zaragozic acid A is a polyketide isolated from fungi that is a potent inhibitor of fungal and mammalian squalene synthase. It has a role as an EC 2.5.1.21 (squalene synthase) inhibitor and a fungal metabolite. It is a tricarboxylic acid, an acetate ester, a cyclic ketal, an oxabicycloalkane, a tertiary alcohol and a polyketide.
Application
Zaragozic Acid A is a squalene synthetase inhibitor. it targeted squalene synthase and lowered the cholesterol levels in vivo of marmosets.
Biological Activity
Zaragozic acid A is an inhibitor of acute liver cholsterol synthesis (50% inhibition dose 200 μg/ kg) with Ki value of 78pM. It inhibited cholesterol synthesis in Hep G2 cells.
in vitro
zaragozic acid a, as well as it two analogs zaragozic acid b and c were discovered from an unidentified sterile fungal culture, spororniella intermedia, and leptodontium elatius, respectively. zaragozic acid a, b and c were reported to be three potent competitive inhibitors of rat liver squalene synthase with ki values of 78 pm, 29 pm, and 45 pm, respectively. in addition, zaragozic acid a, b and c could also inhibite cholesterol synthesis in hep g2 cells [1].
in vivo
in the mouse model, zaragozic acid a was found to be an inhibitor of acute hepatic cholesterol synthesis (50% inhibitory dose of 200 μg/kg). the in-vivo inhibition of squalene synthase was accompanied by an accumulation of label from [3hjmevalonate into farnesyl diphosphate, farnesol, as well as organic acids. in summary, these data showed the zaragozic acids were a new class of therapeutic agents with potential for the hypercholesterolemia treatment [1].
References
[1] bergstrom jd,kurtz mm,rew dj,amend am,karkas jd,bostedor rg,bansal vs,dufresne c,vanmiddlesworth fl,hensens od, et al. zaragozic acids: a family of fungal metabolites that are picomolar competitive inhibitors of squalene synthase. proc natl acad sci u s a.1993 jan 1;90(1):80-4.
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