MedKoo Cat#: 463363 | Name: Ambigol A

Description:

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

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

Ambigol A
Ambigol A
CAS#151487-20-6

Theoretical Analysis

MedKoo Cat#: 463363

Name: Ambigol A

CAS#: 151487-20-6

Chemical Formula: C18H8Cl6O3

Exact Mass: 481.8605

Molecular Weight: 484.96

Elemental Analysis: C, 44.58; H, 1.66; Cl, 43.86; O, 9.90

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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Related CAS #
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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

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
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.