Exfoliazone
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| Category | Antibiotics |
| Catalog number | BBF-00891 |
| CAS | 132627-73-7 |
| Molecular Weight | 284.27 |
| Molecular Formula | C15H12N2O4 |
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Description
Exfoliazone is a phenoxazine antibiotic produced by Streptomyces exfoliatus. It has the activity of resisting Valsa ceratosperma, and the ED50 that inhibits mycelial growth is 70 μg/mL.
Specification
| IUPAC Name | N-[8-(hydroxymethyl)-3-oxophenoxazin-2-yl]acetamide |
| Canonical SMILES | CC(=O)NC1=CC2=NC3=C(C=CC(=C3)CO)OC2=CC1=O |
| InChI | InChI=1S/C15H12N2O4/c1-8(19)16-10-5-12-15(6-13(10)20)21-14-3-2-9(7-18)4-11(14)17-12/h2-6,18H,7H2,1H3,(H,16,19) |
| InChI Key | AUBMZQABQDPFKS-UHFFFAOYSA-N |
Properties
| Appearance | Orange Needle Crystal |
| Boiling Point | 568.1°C at 760 mmHg |
| Melting Point | 294-296°C |
| Density | 1.45 g/cm3 |
Reference Reading
1. Marine Actinomycetes-Derived Secondary Metabolites Overcome TRAIL-Resistance via the Intrinsic Pathway through Downregulation of Survivin and XIAP
Mohammed I Y Elmallah, Sheron Cogo, Andrei A Constantinescu, Selene Elifio-Esposito, Mohammed S Abdelfattah, Olivier Micheau Cells. 2020 Jul 22;9(8):1760. doi: 10.3390/cells9081760.
Resistance of cancer cells to tumor necrosis factor-related apoptosis-inducing ligand (TRAIL)-induced apoptosis represents the major hurdle to the clinical use of TRAIL or its derivatives. The discovery and development of lead compounds able to sensitize tumor cells to TRAIL-induced cell death is thus likely to overcome this limitation. We recently reported that marine actinomycetes' crude extracts could restore TRAIL sensitivity of the MDA-MB-231 resistant triple negative breast cancer cell line. We demonstrate in this study, that purified secondary metabolites originating from distinct marine actinomycetes (sharkquinone (1), resistomycin (2), undecylprodigiosin (3), butylcyclopentylprodigiosin (4), elloxizanone A (5) and B (6), carboxyexfoliazone (7), and exfoliazone (8)), alone, and in a concentration-dependent manner, induce killing in both MDA-MB-231 and HCT116 cell lines. Combined with TRAIL, these compounds displayed additive to synergistic apoptotic activity in the Jurkat, HCT116 and MDA-MB-231 cell lines. Mechanistically, these secondary metabolites induced and enhanced procaspase-10, -8, -9 and -3 activation leading to an increase in PARP and lamin A/C cleavage. Apoptosis induced by these compounds was blocked by the pan-caspase inhibitor QvD, but not by a deficiency in caspase-8, FADD or TRAIL agonist receptors. Activation of the intrinsic pathway, on the other hand, is likely to explain both their ability to trigger cell death and to restore sensitivity to TRAIL, as it was evidenced that these compounds could induce the downregulation of XIAP and survivin. Our data further highlight that compounds derived from marine sources may lead to novel anti-cancer drug discovery.
2. New phenoxazinone-related alkaloids from strain Streptomyces sp. KIB-H1318
Feng-Xian Yang, Guan-Xiong Hou, Jianying Luo, Jing Yang, Yijun Yan, Sheng-Xiong Huang J Antibiot (Tokyo). 2018 Nov;71(12):1040-1043. doi: 10.1038/s41429-018-0099-y. Epub 2018 Sep 14.
Chemical investigation of a strain Streptomyces sp. KIB-H1318 isolated from soil sample led to the discovery of three new phenoxazinone-related alkaloids 1-3, as well as two known analogs exfoliazone (4) and viridobrunnine A (5). Their structures were determined on the basis of extensive spectroscopic analysis. The antimicrobial activity and cytotoxicity of the isolates were assayed. Exfoliazone and viridobrunnine A exhibited minor antibacterial activity against Escherichia coli ATCC 8099, Bacillus subtilis ATCC 6633, and Staphylococcus aureus ATCC 6538. Compound 2 exhibited low cytotoxicity against two human cancer cell lines HeLa and SW480 with the IC50 values of 36.8 and 37.8 μM, respectively.
3. Venezuelines A-G, new phenoxazine-based alkaloids and aminophenols from Streptomyces venezuelae and the regulation of gene target Nur77
Jinwei Ren, Dong Liu, Li Tian, Yangye Wei, Peter Proksch, Jinzhang Zeng, Wenhan Lin Bioorg Med Chem Lett. 2013 Jan 1;23(1):301-4. doi: 10.1016/j.bmcl.2012.10.096. Epub 2012 Oct 30.
Five new phenoxazine-based alkaloids venezuelines A-E (1-5) and two new aminophenols venezuelines F-G (6-7), as well as three known analogues exfoliazone, chandrananimycin D and carboxyexfoliazone were isolated from the fermentation broth of the marine-derived bacterium Streptomyces venezuelae. The structures of new compounds were determined on the basis of extensive spectroscopic analysis. The cytotoxic activity of these compounds against a panel of tumor cell lines were tested, while the regulation of gene target Nur77 of 2 and exfoliazone (8) were evaluated.
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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 ╳
