Phencomycin
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| Category | Antibiotics |
| Catalog number | BBF-02391 |
| CAS | 146615-53-4 |
| Molecular Weight | 282.25 |
| Molecular Formula | C15H10N2O4 |
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Description
It is produced by the strain of Str. sp. HIL Y-9031725. It has weak anti-gram-positive bacterial effect, but also has inhibitory effect against physiologically important enzyme like renin (IC50 is 440 μg/mL).
Specification
| Synonyms | Phenazine-1,6-dicarboxylic acid 1-methyl ester; 1,6-Phenazinedicarboxylic acid, monomethyl ester; Phenocomycin |
| IUPAC Name | 6-methoxycarbonylphenazine-1-carboxylic acid |
| Canonical SMILES | COC(=O)C1=CC=CC2=NC3=C(C=CC=C3N=C21)C(=O)O |
| InChI | InChI=1S/C15H10N2O4/c1-21-15(20)9-5-3-7-11-13(9)17-10-6-2-4-8(14(18)19)12(10)16-11/h2-7H,1H3,(H,18,19) |
| InChI Key | YPYRMWFNCMDUIB-UHFFFAOYSA-N |
Properties
| Appearance | Yellow Crystalline Solid |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Solubility | Soluble in Methanol, Methanol-Hydrochloric acid, Methanol-Sodium hydroxide |
Reference Reading
1. Furanone derivatives from terrestrial Streptomyces spp
Muhammad Arfan, Khaled A Shaaban, Anja Schüffler, Hartmut Laatsch Nat Prod Commun. 2012 Sep;7(9):1199-202.
Chemical investigation of the terrestrial Streptomyces sp. isolates GT2005/020 and ANK148 led to the isolation of two microbial furanone derivatives, 5-hydroxy-4-methylnaphtho[1,2-b]furan-3-one (1) and 4-hydroxy-5-methyl-furan-3-one (2), respectively, which have some similarity to quorum sensing molecules of the AI-2 type. In addition, the known compounds chalcomycin, ferulic acid, indole-3-acetic acid, uracil, thymine, 2'-deoxy-thymidin, monensin B (3), phencomycin, and 1-acetyl-beta-carboline were isolated. The structures of 1 and 2 were deduced from extensive studies of NMR (1D and 2D) and mass spectra. Additionally, the complete NMR shift assignments for monensin B (3) using H-H COSY, HMQC and HMBC experiments are reported here for the first time. We are describing the taxonomy and fermentation of the producing strains, the structure elucidation of the new metabolites and their bioactivity.
2. Induction of Antibacterial Metabolites by Co-Cultivation of Two Red-Sea-Sponge-Associated Actinomycetes Micromonospora sp. UR56 and Actinokinespora sp. EG49
Mohamed S Hifnawy, Hossam M Hassan, Rabab Mohammed, Mohamed M Fouda, Ahmed M Sayed, Ahmed A Hamed, Sameh F AbouZid, Mostafa E Rateb, Hani A Alhadrami, Usama Ramadan Abdelmohsen 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, Micromonospora sp. UR56 and Actinokineospora sp. 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), and p-anisamide (10). Subsequently, the antibacterial, antibiofilm, and cytotoxic properties of these metabolites (1-3, 9, and 10) 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 against Staphylococcus DNA gyrase-B and pyruvate kinase as possible molecular targets together with binding mode studies showed that compounds 1-3 could 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. New phenazine analogues from Streptomyces sp. IFM 11694 with TRAIL resistance-overcoming activities
Mohamed S Abdelfattah, Naoki Ishikawa, Utpal K Karmakar, Kazuki Yamaku, Masami Ishibashi J Antibiot (Tokyo). 2016 Jun;69(6):446-50. doi: 10.1038/ja.2015.129. Epub 2015 Dec 16.
Two new phenazine derivatives, aotaphenazine (1) and 5,10-dihydrophencomycin (2), were isolated from the ethyl acetate extract of Streptomyces sp. IFM 11694. In addition, the known 1-phenazinecarboxylic acid (3), phencomycin (4) and 1,6-phenazinedicarboxylic acid (5) were identified. The structures of the isolated compounds (1-5) were characterized by spectroscopic methods including NMR and mass spectrometry data. Compound 1 showed the ability to overcome tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) resistance at concentration of 12.5 μM. Aotaphenazine (1) enhanced the levels of apoptosis inducing proteins DR4, DR5, p53 and also decreased the levels of cell survival protein Bcl-2 in TRAIL-resistant human gastric adenocarcinoma (AGS) cells in a dose-dependent manner.
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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 ╳
