AJI-9561
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| Category | Mycotoxins |
| Catalog number | BBF-03198 |
| CAS | 339300-34-4 |
| Molecular Weight | 386.36 |
| Molecular Formula | C22H14N2O5 |
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Description
AJI-9561 is a benzoxazole derivative produced by Streptomyces sp. AJ9561. It has cytotoxic activity with IC50 of 0.88 µmol/L and 1.63 µmol/L for Jorkat and P388 cells, respectively. Its mechanism of action is the same as that of UK-1, which can inhibit DNA topoisomerase U.
Specification
| Synonyms | (2,4'-Bibenzoxazole)-4-carboxylic acid, 2'-(2-hydroxy-6-methylphenyl)- |
| IUPAC Name | 2-[2-(2-hydroxy-6-methylphenyl)-1,3-benzoxazol-4-yl]-1,3-benzoxazole-4-carboxylic acid |
| Canonical SMILES | CC1=C(C(=CC=C1)O)C2=NC3=C(C=CC=C3O2)C4=NC5=C(C=CC=C5O4)C(=O)O |
| InChI | InChI=1S/C22H14N2O5/c1-11-5-2-8-14(25)17(11)21-24-18-12(6-3-9-15(18)29-21)20-23-19-13(22(26)27)7-4-10-16(19)28-20/h2-10,25H,1H3,(H,26,27) |
| InChI Key | OKZZJMABRRSZAW-UHFFFAOYSA-N |
Properties
| Appearance | White Powder |
| Boiling Point | 600.2±50.0°C at 760 mmHg |
| Melting Point | 251-252°C |
| Density | 1.4±0.1 g/cm3 |
Reference Reading
1. Genome Mining of Streptomyces sp. Tü 6176: Characterization of the Nataxazole Biosynthesis Pathway
Carolina Cano-Prieto, Raúl García-Salcedo, Marina Sánchez-Hidalgo, Alfredo F Braña, Hans-Peter Fiedler, Carmen Méndez, José A Salas, Carlos Olano Chembiochem. 2015 Jul 6;16(10):1461-73. doi: 10.1002/cbic.201500153. Epub 2015 May 26.
Streptomyces sp. Tü 6176 produces the cytotoxic benzoxazole nataxazole. Bioinformatic analysis of the genome of this organism predicts the presence of 38 putative secondary-metabolite biosynthesis gene clusters, including those involved in the biosynthesis of AJI9561 and its derivative nataxazole, the antibiotic hygromycin B, and ionophores enterobactin and coelibactin. The nataxazole biosynthesis gene cluster was identified and characterized: it lacks the O-methyltransferase gene required to convert AJI9561 into nataxazole. This O-methyltransferase activity might act as a resistance mechanism, as AJI9561 shows antibiotic activity whereas nataxazole is inactive. Moreover, heterologous expression of the nataxazole biosynthesis gene cluster in S. lividans JT46 resulted in the production of AJI9561. Nataxazole biosynthesis requires the shikimate pathway to generate 3-hydroxyanthranilate and an iterative type I PKS to generate 6-methylsalicylate. Production of nataxazole was improved up to fourfold by disrupting one regulatory gene in the cluster. An additional benzoxazole, 5-hydroxynataxazole is produced by Streptomyces sp. Tü 6176. 5-Hydroxynataxazole derives from nataxazole by the activity of an as yet unidentified oxygenase; this implies cross-talk between the nataxazole biosynthesis pathway and an unknown pathway.
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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 ╳
