MedKoo Cat#: 208148 | Name: Armeniaspirol A

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Armeniaspirols, a novel class of natural products isolated from Streptomyces armeniacus, have been previously identified as antibacterial agents against Gram-positive pathogens. Studies found that armeniaspirol A (ARM1) exhibited potent antibacterial activity against H. pylori, including multidrug-resistant strains, with MIC range values of 4-16 μg ml-1 . The underlying mechanism of action of ARM1 against H. pylori involved the disruption of bacterial cell membranes.

Chemical Structure

Armeniaspirol A
CAS#1206881-47-1

Theoretical Analysis

MedKoo Cat#: 208148

Name: Armeniaspirol A

CAS#: 1206881-47-1

Chemical Formula: C18H19Cl2NO4

Exact Mass: 383.0691

Molecular Weight: 384.25

Elemental Analysis: C, 56.26; H, 4.98; Cl, 18.45; N, 3.65; O, 16.65

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Synonym
ArmeniaspirolA, Armeniaspirol -A, armeniaspirol-a
IUPAC/Chemical Name
(2R)-3',4'-Dichloro-7-hexyl-6-hydroxy-1'-methylspiro[1-benzofuran-2,5'-pyrrole]-2',3-dione
InChi Key
ZSUZJBBHPTXKIV-SFHVURJKSA-N
InChi Code
InChI=1S/C18H19Cl2NO4/c1-3-4-5-6-7-10-12(22)9-8-11-14(10)25-18(16(11)23)15(20)13(19)17(24)21(18)2/h8-9,22H,3-7H2,1-2H3/t18-/m0/s1
SMILES Code
O=C(C(Cl)=C1Cl)N(C)[C@@]21OC3=C(C=CC(O)=C3CCCCCC)C2=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 384.25 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Jia J, Zhang C, Liu Y, Huang Y, Bai Y, Hang X, Zeng L, Zhu D, Bi H. Armeniaspirol A: a novel anti-Helicobacter pylori agent. Microb Biotechnol. 2022 Feb;15(2):442-454. doi: 10.1111/1751-7915.13807. Epub 2021 Mar 29. PMID: 33780131; PMCID: PMC8867979. 2: Arisetti N, Fuchs HLS, Coetzee J, Orozco M, Ruppelt D, Bauer A, Heimann D, Kuhnert E, Bhamidimarri SP, Bafna JA, Hinkelmann B, Eckel K, Sieber SA, Müller PP, Herrmann J, Müller R, Winterhalter M, Steinem C, Brönstrup M. Total synthesis and mechanism of action of the antibiotic armeniaspirol A. Chem Sci. 2021 Nov 24;12(48):16023-16034. doi: 10.1039/d1sc04290d. PMID: 35024125; PMCID: PMC8672772. 3: Dufour C, Wink J, Kurz M, Kogler H, Olivan H, Sablé S, Heyse W, Gerlitz M, Toti L, Nußer A, Rey A, Couturier C, Bauer A, Brönstrup M. Isolation and structural elucidation of armeniaspirols A-C: potent antibiotics against gram- positive pathogens. Chemistry. 2012 Dec 7;18(50):16123-8. doi: 10.1002/chem.201201635. Epub 2012 Nov 9. PMID: 23143837. 4: Labana P, Dornan MH, Lafrenière M, Czarny TL, Brown ED, Pezacki JP, Boddy CN. Armeniaspirols inhibit the AAA+ proteases ClpXP and ClpYQ leading to cell division arrest in Gram-positive bacteria. Cell Chem Biol. 2021 Dec 16;28(12):1703-1715.e11. doi: 10.1016/j.chembiol.2021.07.001. Epub 2021 Jul 21. PMID: 34293284. 5: Qiao Y, Yan J, Jia J, Xue J, Qu X, Hu Y, Deng Z, Bi H, Zhu D. Characterization of the Biosynthetic Gene Cluster for the Antibiotic Armeniaspirols in Streptomyces armeniacus. J Nat Prod. 2019 Feb 22;82(2):318-323. doi: 10.1021/acs.jnatprod.8b00753. Epub 2019 Feb 12. PMID: 30747534.