Ambigol A

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

MedKoo CAT#: 463363

CAS#: 151487-20-6

Description: Ambigol A is an antibiotic against Serratia sp. ATCC 39006 (S39006) strain. The terrestrial cyanobacterium Fischerella ambigua 108b produces the three polychlorinated triphenyls ambigol A–C that exhibit interesting antimicrobial, antiviral and cytotoxic activities. They are structurally related to polybrominated diphenylethers synthesized by diverse marine bacteria that are known to be highly toxic and are bioaccumulating in natural food webs. All ambigols display unusual connectivities: Ambigols A and B exhibit chlorination and ambigol C biaryl-ether bonds in the relative meta position at the central phenol unit, which is flanked by two 2,4-dichlorophenol units in all three compounds. Here we report on the identification of the biosynthetic gene cluster (BGC) reponsible for ambigol production in F. ambigua.

Chemical Structure

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Ambigol A
CAS# 151487-20-6
Instruction

Theoretical Analysis

MedKoo Cat#: 463363
Name: Ambigol A
CAS#: 151487-20-6
Chemical Formula: C18H8Cl6O3
Exact Mass: 481.86
Molecular Weight: 484.959
Elemental Analysis: C, 44.58; H, 1.66; Cl, 43.86; O, 9.90

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: Ambigol A; Ambigol-A;

IUPAC/Chemical Name: 3',4,5',6-tetrachloro-3-(2,4-dichlorophenoxy)-[1,1'-biphenyl]-2,2'-diol

InChi Key: AHLSIYMTIQLHAO-UHFFFAOYSA-N

InChi Code: InChI=1S/C18H8Cl6O3/c19-7-1-2-14(10(21)4-7)27-18-13(24)6-11(22)15(17(18)26)9-3-8(20)5-12(23)16(9)25/h1-6,25-26H

SMILES Code: OC1=C(OC2=CC=C(Cl)C=C2Cl)C(Cl)=CC(Cl)=C1C3=CC(Cl)=CC(Cl)=C3O

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: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

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 484.96 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: Chilczuk T, Monson R, Schmieder P, Christov V, Enke H, Salmond G, Niedermeyer THJ. Ambigols from the Cyanobacterium Fischerella ambigua Increase Prodigiosin Production in Serratia spp. ACS Chem Biol. 2020 Nov 20;15(11):2929-2936. doi: 10.1021/acschembio.0c00554. Epub 2020 Nov 4. PMID: 33143417.


2: Wright AD, Papendorf O, König GM, Oberemm A. Effects of cyanobacterium Fischerella ambigua isolates and cell free culture media on zebrafish (Danio rerio) embryo development. Chemosphere. 2006 Oct;65(4):604-8. doi: 10.1016/j.chemosphere.2006.02.004. Epub 2006 Mar 22. PMID: 16554083.


3: Wright AD, Papendorf O, König GM. Ambigol C and 2,4-dichlorobenzoic acid, natural products produced by the terrestrial cyanobacterium Fischerella ambigua. J Nat Prod. 2005 Mar;68(3):459-61. doi: 10.1021/np049640w. PMID: 15787461.


4: Falch BS, König GM, Wright AD, Sticher O, Angerhofer CK, Pezzuto JM, Bachmann H. Biological activities of cyanobacteria: evaluation of extracts and pure compounds. Planta Med. 1995 Aug;61(4):321-8. doi: 10.1055/s-2006-958092. PMID: 7480178.