Dynemicin M
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| Category | Antibiotics |
| Catalog number | BBF-01190 |
| CAS | 127003-54-7 |
| Molecular Weight | 529.49 |
| Molecular Formula | C29H23NO9 |
| Purity | ≥98% |
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Description
It is produced by the strain of Micromonospora chersina sp. M 956-I and M. globosa. The cyclic enediyne part of enediyne antibiotics is cycled by Bergman to form aromatic diradicals, which quickly seize hydrogen atoms from the DNA skeleton and break the DNA strand, thus killing tumor cells.
Specification
| Synonyms | (1R)-3,4,4a,13,14,14a-Hexahydro-4a,6,8,11,14a-pentahydroxy-3β-methoxy-1β-methyl-4,14-[1,2]benzenonaphtho[2,3-c]phenanthridine-2,7,12(1H)-trione |
| IUPAC Name | (8R,9R,14S,17S,18R,20R)-1,4,6,8,17-pentahydroxy-20-methoxy-18-methyl-8,9,14,15-tetrahydro-8,14,9-(epibutane[1,1,4]triyl)anthra[1,2-b]benzo[f]azocine-5,16,19-trione |
Properties
| Appearance | Blue Amorphous Powder |
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Boiling Point | 816.9 °C at 760 mmHg |
| Melting Point | 238-240 °C |
| Density | 1.67 g/cm3 |
| Solubility | Soluble in DMSO, DMF, Dioxane; Fairly soluble in Methanol, Ethanol, Isopropanol, Ethyl Acetate; Insoluble in Water, Hexane |
Reference Reading
1. Dynemicins O, P and Q: novel antibiotics related to dynemicin A isolation, characterization and biological activity
M Miyoshi-Saitoh, N Morisaki, Y Tokiwa, S Iwasaki, M Konishi, K Saitoh, T Oki J Antibiot (Tokyo). 1991 Oct;44(10):1037-44. doi: 10.7164/antibiotics.44.1037.
New antibiotics, dynemicins O (3), P (4) and Q (5), were isolated from the culture broth of Micromonospora chersina M956-1, the dynemicin A (1)-producing strain. An ethyl acetate extract of a tank culture was roughly separated by a column of Diaion SP-800 and was further purified by combining a variety of column chromatographies to afford a few mg of compounds 3, 4 and 5. Their structures, analyzed from the spectral data, had a bridging phenylene group, a vic-diol and an oxo group in place of the respective 1,5-diyn-3-ene bridge, the epoxide ring and the carboxyl group in dynemicin A. Their biological activities were evaluated against bacteria and tumor cells.
2. Cytotoxicity and DNA-binding property of non-diynene class of dynemicins and aza-anthraquinones
R Shirai, R Shimazawa, M Shichita, M Takahashi, Y Hashimoto, S Iwasaki Nucleic Acids Symp Ser. 1995;(34):151-2.
Dynemicin A is a potent antibacterial and antitumor antibiotic having a striking hybrid structure of both anthraquinone as a DNA intercalator and diynene as a DNA strand breaker. We have investigated the DNA-binding property and cytotoxicity of non-diynene class of dynemicins (H, L, M, O and Q) and several related synthetic tri- and pentacyclic aza-anthraquinones 1a-3a (R = H) and 1b-3b (R = CH3). Among them, dynemicin H, L, M, O, Q, 1a, 1b and 2b exhibited DNA-binding property. All non-diynene class of dynemicins investigated exhibited intercalative binding activity, however, synthetic aza-anthraquinones 1a-3a did not show such ability. Dynemicin H, Q, 2a, 2b and 3b showed cytotoxicity against HL-60 and K-562 cell lines.
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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 ╳
