Dioxamycin
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| Category | Antibiotics |
| Catalog number | BBF-01159 |
| CAS | 134861-62-4 |
| Molecular Weight | 736.72 |
| Molecular Formula | C38H40O15 |
| Purity | >95% |
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Description
It is produced by the strain of Streptomyces xantholiticus. It has anti-gram-positive bacterial activity. It can inhibit Staphylococcus aureus 209P with MIC of 3.12 μg/mL. It inhibits the growth of L1210, P388, IMC, LX-1 and SC-6 cells with IC50 (μg/mL) of 2.7, 1.4, 6.0, 2.0 and 2.5, respectively.
Specification
| Synonyms | 1,3-Dioxolane-2-carboxylic acid, 2,4-dimethyl-5-(7-oxo-7-((tetrahydro-2-methyl-6-(1,2,3,4,4a,7,12,12b-octahydro-2,3,4a,8,12b-pentahydroxy-3-methyl-1,7,12-trioxobenz(a)anthracen-9-yl)-2H-pyran-3-yl)oxy)-1,3,5-heptatrienyl)-, (2-alpha,3-alpha,4a-alpha, 9(2R*,3S*(1E(2S*,4S*,5S*),3E,5E)6R*),12b-alpha)-(+)- |
| IUPAC Name | (2S,4S,5S)-4-[(1E,3E,5E)-7-[(2R,6R)-6-[(2R,3S,4aR,12bS)-2,3,4a,8,12b-pentahydroxy-3-methyl-1,7,12-trioxo-2,4-dihydrobenzo[a]anthracen-9-yl]-2-methyloxan-3-yl]oxy-7-oxohepta-1,3,5-trienyl]-2,5-dimethyl-1,3-dioxolane-2-carboxylic acid |
| Canonical SMILES | CC1C(CCC(O1)C2=C(C3=C(C=C2)C(=O)C4=C(C3=O)C=CC5(C4(C(=O)C(C(C5)(C)O)O)O)O)O)OC(=O)C=CC=CC=CC6C(OC(O6)(C)C(=O)O)C |
| InChI | InChI=1S/C38H40O15/c1-18-23(51-26(39)10-8-6-5-7-9-24-19(2)52-36(4,53-24)34(45)46)13-14-25(50-18)20-11-12-21-27(29(20)40)30(41)22-15-16-37(48)17-35(3,47)32(43)33(44)38(37,49)28(22)31(21)42/h5-12,15-16,18-19,23-25,32,40,43,47-49H,13-14,17H2,1-4H3,(H,45,46)/b6-5+,9-7+,10-8+/t18-,19+,23?,24+,25-,32+,35+,36+,37+,38-/m1/s1 |
| InChI Key | HWMMBHOXHRVLCU-QOUANJGESA-N |
Properties
| Appearance | Orange Powder |
| Antibiotic Activity Spectrum | Gram-posotive becteria; Neoplastics (Tumor) |
| Boiling Point | 941.5 °C at 760 mmHg |
| Melting Point | 176-178 °C (dec.) |
| Density | 1.54 g/cm3 |
| Solubility | Soluble in Methanol |
Reference Reading
1. Waldiomycin, a novel WalK-histidine kinase inhibitor from Streptomyces sp. MK844-mF10
Masayuki Igarashi, Takafumi Watanabe, Tomohiro Hashida, Maya Umekita, Masaki Hatano, Yohei Yanagida, Hirokazu Kino, Tomoyuki Kimura, Naoko Kinoshita, Kunio Inoue, Ryuichi Sawa, Yoshio Nishimura, Ryutaro Utsumi, Akio Nomoto J Antibiot (Tokyo). 2013 Aug;66(8):459-64. doi: 10.1038/ja.2013.33. Epub 2013 May 1.
WalK, a histidine kinase, and WalR, a response regulator, make up a two-component signal transduction system that is indispensable for the cell-wall metabolism of low GC Gram-positive bacteria. WalK inhibitors are likely to show bactericidal effects against methicillin-resistant Staphylococcus aureus . We discovered a new WalK inhibitor, designated waldiomycin, by screening metabolites from actinomycetes. Waldiomycin belongs to the family of angucycline antibiotics and is structurally related to dioxamycin. Waldiomycin inhibits WalK from S. aureus and Bacillus subtilis at IC50s 8.8 and 10.2 μM, respectively, and shows antibacterial activity with MICs ranging from 4 to 8 μg ml(-1) against methicillin-resistant S. aureus and B. subtilis.
2. Dioxamycin, a new benz[a]anthraquinone antibiotic
R Sawa, N Matsuda, T Uchida, T Ikeda, T Sawa, H Naganawa, M Hamada, T Takeuchi J Antibiot (Tokyo). 1991 Apr;44(4):396-402. doi: 10.7164/antibiotics.44.396.
A new antibiotic, dioxamycin (1) was isolated from the culture broth of the strain MH406-SF1, which was closely related to Streptomyces xantholiticus. This antibiotic was purified by countercurrent chromatography, column chromatography and preparative HPLC. The molecular formula of 1 was determined to be C38H40O15 by HRFAB-MS. The structure was determined by spectral analysis of 2D NMR; 1H-1H COSY, 13C-1H COSY, long range 13C-1H COSY (HMBC) and NOESY. The antibiotic is active in vitro against Gram-positive bacteria and some tumor cells. Dioxamycin is a benz[a]anthraquinone antibiotic related to capoamycin.
3. Streptomyces cocklensis sp. nov., a dioxamycin-producing actinomycete
Byung-Yong Kim, Tiago Domingues Zucchi, Hans-Peter Fiedler, Michael Goodfellow Int J Syst Evol Microbiol. 2012 Feb;62(Pt 2):279-283. doi: 10.1099/ijs.0.029983-0. Epub 2011 Mar 11.
The taxonomic position of a streptomycete isolated from soil collected from Cockle Park Experimental Farm, Northumberland, UK, was determined by using a polyphasic approach. The organism had chemical and morphological features consistent with its classification in the genus Streptomyces. 16S rRNA gene sequence analysis supported classification of the strain in the genus Streptomyces and showed that it formed a distinct phyletic line loosely associated with members of the Streptomyces yeochonensis clade. It was related most closely to Streptomyces paucisporeus 1413(T) (98.6 %16S rRNA gene sequence similarity), but could be distinguished from the latter based on the low level of DNA-DNA relatedness (40 %). It was readily distinguished from the type strains of all species assigned to the S. yeochonensis clade based on a combination of phenotypic properties. Strain BK168(T) ( = KACC 20908(T) = NCIMB 14704(T)) should therefore be classified as the type strain of a novel species of the genus Streptomyces, for which the name Streptomyces cocklensis sp. nov. is proposed. The organism produces the antibiotic dioxamycin.
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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 ╳
