Dynemicin O
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| Category | Antibiotics |
| Catalog number | BBF-01192 |
| CAS | 138370-12-4 |
| Molecular Weight | 545.49 |
| Molecular Formula | C29H23NO10 |
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Description
It is produced by the strain of Micromonospora chersina M956-1. Although the activity of this antibiotic is lower than Dynemicin A, it still has strong anti-gram-positive bacterial activity, such as Staphylococcus aureus FDA 209P (MIC is 0.08 μg/mL).
Specification
| Synonyms | (1R)-3,4,4a,13,14,14a-Hexahydro-4a,6,8,11,14a,17-hexahydroxy-3β-methoxy-1β-methyl-4,14-[1,2]benzenonaphtho[2,3-c]phenanthridine-2,7,12(1H)-trione; (8R-(8alpha,9beta,14beta,17S*,18R*))-8,9,14,15-Tetrahydro-1,4,6,8,10,17-hexahydroxy-20-methoxy-18-methyl-9,8,14-(1)butanyl(4)ylideneanthra(1,2-b)benz(f)azocine-5,16,19-trione |
| IUPAC Name | (2R,3S,4R,6R,7R,14S)-2,3,9,20,23,27-hexahydroxy-6-methoxy-4-methyl-15-azaheptacyclo[14.12.0.02,7.03,14.08,13.017,26.019,24]octacosa-1(28),8(13),9,11,16,19,21,23,26-nonaene-5,18,25-trione |
| Canonical SMILES | CC1C(=O)C(C2C3=C(C=CC=C3O)C4C1(C2(C5=CC(=C6C(=C5N4)C(=O)C7=C(C=CC(=C7C6=O)O)O)O)O)O)OC |
| InChI | InChI=1S/C29H23NO10/c1-9-23(35)26(40-2)21-16-10(4-3-5-12(16)31)27-28(9,38)29(21,39)11-8-15(34)19-20(22(11)30-27)25(37)18-14(33)7-6-13(32)17(18)24(19)36/h3-9,21,26-27,30-34,38-39H,1-2H3/t9-,21+,26+,27-,28-,29-/m0/s1 |
| InChI Key | DXAZISIKQHCJNJ-ZCRFVMIVSA-N |
Properties
| Appearance | Blue Powder |
| Antibiotic Activity Spectrum | gram-posotive becteria |
| Boiling Point | 816.2 °C at 760 mmHg |
| Density | 1.81 g/cm3 |
| Solubility | Soluble in Methanol, DMSO, Benzene |
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 ╳
