Chandrananimycin A
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| Category | Antibiotics |
| Catalog number | BBF-00527 |
| CAS | 664355-12-8 |
| Molecular Weight | 270.24 |
| Molecular Formula | C14H10N2O4 |
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Description
It is produced by the strain of Actinomadura sp. M048. Chandrananimycin A has anti-mucor activity, and anti-CCL HT29, MFXF 529L, MACL McF-7 et al tumor cell activity.
Specification
| Synonyms | Acetamide, N-(9-hydroxy-3-oxo-3H-phenoxazin-2-yl)- |
| IUPAC Name | N-(9-hydroxy-3-oxophenoxazin-2-yl)acetamide |
| Canonical SMILES | CC(=O)NC1=CC2=NC3=C(C=CC=C3OC2=CC1=O)O |
| InChI | InChI=1S/C14H10N2O4/c1-7(17)15-8-5-9-13(6-11(8)19)20-12-4-2-3-10(18)14(12)16-9/h2-6,18H,1H3,(H,15,17) |
| InChI Key | VRKDUDPRCAZBHW-UHFFFAOYSA-N |
Properties
| Appearance | Orange Solid |
| Antibiotic Activity Spectrum | neoplastics (Tumor); fungi |
| Solubility | Soluble in Methanol |
Reference Reading
1. attB site disruption in marine Actinomyces sp. M048 via DNA transformation of a site-specific integration vector
Yan-Hua Hou, Quan-Fu Wang, Ling Ding, Fu-Chao Li, Song Qin Biotechnol Appl Biochem. 2008 May;50(Pt 1):11-6. doi: 10.1042/BA20070124.
An efficient conjugation method has been developed for the marine Actinomyces sp. isolate M048 to facilitate the genetic manipulation of the chandrananimycin biosynthesis gene cluster. A phiC31-derived integration vector pIJ8600 containing oriT and attP fragments was introduced into strain M048 by bi-parental conjugation from Escherichia coli ET12567 to strain M048. Transformation efficiency was (6.38+/-0.41)x10(-5) exconjugants per recipient spore. Analysis of eight exconjugants showed that the plasmid pIJ8600 was stably integrated at a single chromosomal site (attB) of the Actinomyces genome. The DNA sequence of the attB was cloned and shown to be conserved. The results of antimicrobial activity analysis indicated that the insertion of plasmid pIJ8600 seemed to affect the biosynthesis of antibiotics that could strongly inhibit the growth of E. coli and Mucor miehei (Tü284). HPLC-MS analysis of the extracts indicated that disruption of the attB site resulted in the complete abolition of chandrananimycin A-C production, proving the identity of the gene cluster. Instead of chandrananimycins, two bafilomycins were produced through disruption of the attB site from the chromosomal DNA of marine Actinomyces sp. M048.
2. Aminophenoxazinones as inhibitors of indoleamine 2,3-dioxygenase (IDO). Synthesis of exfoliazone and chandrananimycin A
Raffaele Pasceri, David Siegel, David Ross, Christopher J Moody J Med Chem. 2013 Apr 25;56(8):3310-7. doi: 10.1021/jm400049z. Epub 2013 Apr 10.
A range of 2-aminophenoxazin-3-ones has been prepared by oxidative cyclocondensation of 2-aminophenols, including the natural products exfoliazone and chandrananimycin A, both synthesized for the first time. The compounds were evaluated for their ability to inhibit indoleamine 2,3-dioxygenase. Compounds containing additional electron-withdrawing carboxylate groups, such as cinnabarinic acid, showed modest inhibitory activity with a dose response.
3. Chandrananimycins A approximately C: production of novel anticancer antibiotics from a marine Actinomadura sp. isolate M048 by variation of medium composition and growth conditions
Rajendra P Maskey, Fuchao Li, Song Qin, Heinz H Fiebig, Hartmut Laatsch J Antibiot (Tokyo). 2003 Jul;56(7):622-9. doi: 10.7164/antibiotics.56.622.
In our screening of marine actinomycetes for bioactive principles, three novel antibiotics designated as chandrananimycin A (3c), B (3d) and C (4) were isolated from the culture broth of a marine Actinomadura sp. isolate M045. The structures of the new antibiotics were determined by detailed interpretation of mass, 1D and 2D NMR spectra.
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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 ╳
