Armeniaspirol A

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

MedKoo CAT#: 208148

CAS#: 1206881-47-1

Description: 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

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Armeniaspirol A
CAS# 1206881-47-1
Instruction

Theoretical Analysis

MedKoo Cat#: 208148
Name: Armeniaspirol A
CAS#: 1206881-47-1
Chemical Formula: C18H19Cl2NO4
Exact Mass: 383.07
Molecular Weight: 384.250
Elemental Analysis: C, 56.26; H, 4.98; Cl, 18.45; N, 3.65; O, 16.65

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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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:

Biological target:
In vitro activity:
In vivo activity:

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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.