Tubermycin B
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| Category | Antibiotics |
| Catalog number | BBF-03428 |
| CAS | 2538-68-3 |
| Molecular Weight | 224.21 |
| Molecular Formula | C13H8N2O2 |
| Purity | >98% by HPLC |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-03428 | 250 mg | $199 | In stock |
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Add to cartDescription
A simple phenazine produced by several species of pseudomonas and actinomycetes. It is a weakly active antibacterial compound that plays a role in the biocontrol of plant diseases by several pseudomonas strains.
Specification
| Related CAS | 1144-02-1 (hydrochloride) |
| Synonyms | 1-Phenazinecarboxylic acid; 1-Carboxylic acid phenazine; NRRL B-1576; NSC 15851; BRN 0183818 |
| Storage | Store at-20°C |
| IUPAC Name | phenazine-1-carboxylic acid |
| Canonical SMILES | C1=CC=C2C(=C1)N=C3C=CC=C(C3=N2)C(=O)O |
| InChI | InChI=1S/C13H8N2O2/c16-13(17)8-4-3-7-11-12(8)15-10-6-2-1-5-9(10)14-11/h1-7H,(H,16,17) |
| InChI Key | JGCSKOVQDXEQHI-UHFFFAOYSA-N |
| Source | Pseudomonas aeruginosa |
Properties
| Appearance | Yellow solid |
| Antibiotic Activity Spectrum | mycobacteria |
| Boiling Point | 494.6°C at 760 mmHg |
| Melting Point | 242-244°C |
| Density | 1.431±0.06 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF or DMSO. Poor water solubility. |
Reference Reading
1. Fatty acids enhanced tubermycin production by Pseudomonas strain 2HS
J K Huang, A C Lanser, L Wen, K C Keudell, M O Bagby, W E Klopfenstein, R D Plattner, D Weisleder, R E Peterson Microbios . 2000;102(401):27-38.
A new microbial isolate, Pseudomonas 2HS, produced trace amounts of a greenish-yellow pigment when grown aerobically in a 1% yeast extract medium at 30 degrees C and shaken at 250 rpm for 5 days. In contrast, cells produced more greenish-yellow pigment (2.16 mg/15 ml culture) when grown in the presence of 0.5% 12-hydroxyoctadecanoic acid (w/v). The greenish-yellow pigment was identified as phenazine-1-carboxylic acid (tubermycin B), and the Pseudomonas 2HS was identified as P. aeruginosa 2HS. This is the first report that 12-hydroxyoctadecanoic, ricinoleic and other fatty acids can enhance the production of phenazine-1-carboxylic acid by a Pseudomonas species.
2. Induction of Antibacterial Metabolites by Co-Cultivation of Two Red-Sea-Sponge-Associated Actinomycetes Micromonospora sp. UR56 and Actinokinespora sp. EG49
Hossam M Hassan, Mostafa E Rateb, Ahmed A Hamed, Usama Ramadan Abdelmohsen, Mohamed S Hifnawy, Sameh F AbouZid, Hani A Alhadrami, Mohamed M Fouda, Ahmed M Sayed, Rabab Mohammed Mar Drugs . 2020 May 5;18(5):243. doi: 10.3390/md18050243.
Liquid chromatography coupled with high resolution mass spectrometry (LC-HRESMS)-assisted metabolomic profiling of two sponge-associated actinomycetes,Micromonosporasp. UR56 andActinokineosporasp. EG49, revealed that the co-culture of these two actinomycetes induced the accumulation of metabolites that were not traced in their axenic cultures. Dereplication suggested that phenazine-derived compounds were the main induced metabolites. Hence, following large-scale co-fermentation, the major induced metabolites were isolated and structurally characterized as the already known dimethyl phenazine-1,6-dicarboxylate (1), phenazine-1,6-dicarboxylic acid mono methyl ester (phencomycin;2), phenazine-1-carboxylic acid (tubermycin;3), N-(2-hydroxyphenyl)-acetamide (9), andp-anisamide (10). Subsequently, the antibacterial, antibiofilm, and cytotoxic properties of these metabolites (1-3,9, and10) were determined in vitro. All the tested compounds except 9 showed high to moderate antibacterial and antibiofilm activities, whereas their cytotoxic effects were modest. Testing againstStaphylococcusDNA gyrase-B and pyruvate kinase as possible molecular targets together with binding mode studies showed that compounds1-3could exert their bacterial inhibitory activities through the inhibition of both enzymes. Moreover, their structural differences, particularly the substitution at C-1 and C-6, played a crucial role in the determination of their inhibitory spectra and potency. In conclusion, the present study highlighted that microbial co-cultivation is an efficient tool for the discovery of new antimicrobial candidates and indicated phenazines as potential lead compounds for further development as antibiotic scaffold.
3. Metabolites of microorganisms. 247. Phenazines from Streptomyces antibioticus, strain Tü 2706
H Zähner, W Keller-Schierlein, A Geiger, M Brandl J Antibiot (Tokyo) . 1988 Nov;41(11):1542-51. doi: 10.7164/antibiotics.41.1542.
From a strain of Streptomyces antibioticus seven yellow phenazines were isolated. The antibacterially most active antibiotic was identified as (-)-saphenamycin, a second one with compound DC-86-Y (saphenic acid). Three compounds were new: Saphenic acid methyl ether, 6-acetylphenazine-1-carboxylic acid and an inseparable mixture of fatty acid esters of saphenic acid. Two simple phenazines were phenazine-1-carboxylic acid (tubermycin B) and unsubstituted phenazine, which was isolated for the first time from a microorganism.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
