Chandrananimycin C
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| Category | Antibiotics |
| Catalog number | BBF-00529 |
| CAS | |
| Molecular Weight | 296.32 |
| Molecular Formula | C17H16N2O3 |
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Description
It is produced by the strain of Actinomadura sp. M048. Chandrananimycin C has anti-mucor activity, and anti-CCL HT29, MFXF 529L, MACL McF-7 et al tumor cell activity. It is also have anti-gram-positive bacteria and algae activities.
Specification
| IUPAC Name | 1-methoxy-3-methyl-1,2,3,4-tetrahydropyrido[3,2-a]phenoxazin-5-one |
| Canonical SMILES | CC1CC(C2=C(N1)C(=O)C=C3C2=NC4=CC=CC=C4O3)OC |
| InChI | InChI=1S/C17H16N2O3/c1-9-7-13(21-2)15-16(18-9)11(20)8-14-17(15)19-10-5-3-4-6-12(10)22-14/h3-6,8-9,13,18H,7H2,1-2H3 |
| InChI Key | MXSILDMPRHIENH-UHFFFAOYSA-N |
Properties
| Appearance | Orange Solid |
| Antibiotic Activity Spectrum | Gram-positive bacteria; neoplastics (Tumor); fungi |
| Solubility | Soluble in Methanol |
Reference Reading
1. New aminophenoxazinones from a marine Halomonas sp.: fermentation, structure elucidation, and biological activity
Jens Bitzer, Thomas Grosse, Linzhu Wang, Siegmund Lang, Winfried Beil, Axel Zeeck J Antibiot (Tokyo). 2006 Feb;59(2):86-92. doi: 10.1038/ja.2006.12.
The addition of anthranilic acid to the culture medium of the marine derived Halomonas sp. strain GWS-BW-H8hM completely altered the secondary metabolite pattern relative to the standard conditions. The red-orange color of the culture filtrate extract was the result of the production of 2-aminophenoxazin-3-one (1), chandrananimycin C (5) and three new derivatives of 1 with a previously unknown substitution pattern: 2-amino-, 2-amino-8-benzoyl-, and 2-amino-8-(4-hydroxybenzoyl)-6-hydroxyphenoxazin-3-one (2-4). The compounds were determined to have antibacterial and cytotoxic activities; a mode of action other than DNA intercalation is discussed.
2. 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.
3. Interaction of marine Streptomyces compounds with selected cancer drug target proteins by in silico molecular docking studies
Amulya Ruby Lankapalli, K Kannabiran Interdiscip Sci. 2013 Mar;5(1):37-44. doi: 10.1007/s12539-013-0146-0. Epub 2013 Apr 19.
The criteria currently followed for selecting antitumor compounds include agents that can target apoptosis inhibitor proteins and cancer cell markers. In silico studies are often used to identify suitable antitumor compounds for the cancer targets. The aim of the present study is to evaluate the interactions of some antitumor compounds reported from marine Streptomyces with cancer target proteins. Nine compounds were selected from marine Streptomyces based on previous reports and evaluated for their interactions with cancer target proteins by in silico molecular docking approach. Interactions of the selected ligand with target proteins were studied by PatchDock bioinformatics docking tool. Among the compounds tested marmycin A was interacted very effectively with human epidermal growth factor receptor 2 (HER2) and showed a least binding energy of -472.92 kcal/mol. The compound altemicidin showed a least binding energy of -415.66 kcal/mol with cyclin dependent kinase 4 (CDK4). The ligands resistoflavine and resistomycin also interacted with HER2 and showed the binding energy of -402.10 kcal/mol and -377.78 kcal/mol respectively. Other ligands proximycin A, chandrananimycin C, echinosporin, streptochlorin and streptokordin also showed the binding energy of -341.11 kcal/mol, -313.31 kcal/mol, -305.64 kcal/mol, -291.91 kcal/mol and 222.34 kcal/mol respectively with CDK4 protein. These results of our study suggest that HER2 and CDK4 are better cancer drug targets for therapy.
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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 ╳
