Deacetylravidomycin
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| Category | Antibiotics |
| Catalog number | BBF-01694 |
| CAS | 88580-27-2 |
| Molecular Weight | 521.56 |
| Molecular Formula | C29H31NO8 |
| Purity | >95% by HPLC |
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Description
Deacetyiravidomycin is an antibiotic produced by Streptomyces sp. WK-6326. It has anti-Gram-positive bacteria activity with a MIC of 3.0-5.0 μg/mL.
Specification
| Synonyms | Desacetylravidomycin; 6H-Benzo(d)naphtho(1,2-b)pyran-6-one, 4-(3,6-dideoxy-3-(dimethylamino)-alpha-altopyranosyl)-10,12-dimethoxy-8-ethenyl-1-hydroxy- |
| Storage | -20°C |
| IUPAC Name | 4-[(2R,3S,4R,5S,6R)-4-(dimethylamino)-3,5-dihydroxy-6-methyloxan-2-yl]-8-ethenyl-1-hydroxy-10,12-dimethoxynaphtho[1,2-c]isochromen-6-one |
| Canonical SMILES | CC1C(C(C(C(O1)C2=C3C(=C(C=C2)O)C(=CC4=C3OC(=O)C5=C4C(=CC(=C5)C=C)OC)OC)O)N(C)C)O |
| InChI | InChI=1S/C29H31NO8/c1-7-14-10-17-21(19(11-14)35-5)16-12-20(36-6)23-18(31)9-8-15(22(23)27(16)38-29(17)34)28-26(33)24(30(3)4)25(32)13(2)37-28/h7-13,24-26,28,31-33H,1H2,2-6H3/t13-,24-,25-,26+,28-/m1/s1 |
| InChI Key | ZHXCTIMNNKVMJM-JSPLCZCHSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | Light Yellow Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Solubility | Soluble in DMF or DMSO. Moderately soluble in methanol or ethanol. Poor water solubility. |
Reference Reading
1. Deacetylravidomycin M, a new inhibitor of IL-4 signal transduction, produced by Streptomyces sp. WK-6326. II. Structure elucidation
M Arai, N Ishiguro, H Tomoda, S Kobayashi, N Tabata, S Omura J Antibiot (Tokyo) . 2001 Jul;54(7):562-6. doi: 10.7164/antibiotics.54.562.
The structure of deacetylravidomycin M, an inhibitor of interleukin-4 signal transduction, was elucidated to be 6H-benzo[d]naphtho[1,2-b]pyran-6-one, 4-[3,6-dideoxy-3-(dimethylamino)-alpha-altropyranosyl]-1-hydroxy-10,12-dimethoxy-8-methyl- by spectroscopic studies including NMR measurements.
2. Deacetylravidomycin M, a new inhibitor of IL-4 signal transduction, produced by Streptomyces sp. WK-6326. I. Taxonomy, fermentation, isolation and biological activities
M Arai, A Matsumoto, N Ishiguro, B H Woodruff, H Tomoda, S Kobayashi, Y Takahashi, S Omura J Antibiot (Tokyo) . 2001 Jul;54(7):554-61. doi: 10.7164/antibiotics.54.554.
Streptomyces sp. WK-6326, a soil isolate, was found to produce an inhibitor of interleukin (IL)-4 signal transduction. Two structurally related compounds, a novel one designated deacetylravidomycin M and the known deacetylravidomycin, were isolated from the culture broth by solvent extraction, silica gel column chromatography and HPLC. Deacetylravidomycin M inhibited IL-4-induced CD23 expression in U937 cells without any cytotoxic effect, whereas deacetylravidomycin showed no inhibitory activity.
3. Light-dependent activity of the antitumor antibiotics ravidomycin and desacetylravidomycin
R Yeung, W M Maiese, M Greenstein, T Monji, R J White Antimicrob Agents Chemother . 1986 May;29(5):861-6. doi: 10.1128/AAC.29.5.861.
The antitumor antibiotics ravidomycin and desacetylravidomycin were studied by the biochemical lambda prophage induction assay. In this assay, induction of the enzyme beta-galactosidase is measured as a specific indication of the ability of an agent to directly or indirectly damage DNA. Induction was observed only when these two antibiotics were irradiated with light in the presence of the indicator organism. Drug treated with light followed by incubation with the indicator organism in the dark did not cause induction. Light in both the near UV and visible wave length ranges activated these antibiotics; near UV and visible blue wavelengths were most effective, while 597-nm light was totally ineffective. The amount of induction caused by these drugs varied directly with the dosage of light provided. Bacterial growth inhibition, as well as cytotoxicity for a human colon carcinoma cell line, was also dramatically enhanced by light. These data suggest that ravidomycin and desacetylravidomycin are potent photosensitizing, DNA-damaging agents.
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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 ╳
