Duocarmycin B2
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| Category | Antibiotics |
| Catalog number | BBF-01184 |
| CAS | 124325-94-6 |
| Molecular Weight | 588.40 |
| Molecular Formula | C26H26BrN3O8 |
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Description
It is produced by the strain of (Pyridamycin) Streptomyces sp. DO-88. It has anti-tumor activity.
Specification
| Synonyms | DUMB2; Benzo1,2-b:4,3-bdipyrrole-2-carboxylic acid, 8-(bromomethyl)-1,2,3,6,7,8-hexahydro-4-hydroxy-2-methyl-1-oxo-6-(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl-, methyl ester, (2R,8S)- |
| IUPAC Name | methyl (2R,8S)-8-(bromomethyl)-4-hydroxy-2-methyl-1-oxo-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-7,8-dihydro-3H-pyrrolo[3,2-e]indole-2-carboxylate |
| Canonical SMILES | CC1(C(=O)C2=C3C(CN(C3=CC(=C2N1)O)C(=O)C4=CC5=CC(=C(C(=C5N4)OC)OC)OC)CBr)C(=O)OC |
| InChI | InChI=1S/C26H26BrN3O8/c1-26(25(34)38-5)23(32)18-17-12(9-27)10-30(14(17)8-15(31)20(18)29-26)24(33)13-6-11-7-16(35-2)21(36-3)22(37-4)19(11)28-13/h6-8,12,28-29,31H,9-10H2,1-5H3/t12-,26-/m1/s1 |
| InChI Key | UQPQXFUURNIVNJ-MZHQLVBMSA-N |
Properties
| Appearance | Orange Crystal |
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Melting Point | 214-215 °C |
| Solubility | Soluble in Ethanol, Methanol, Chloroform, DMSO |
Reference Reading
1. Nucleosome Assembly Alters the Accessibility of the Antitumor Agent Duocarmycin B2 to Duplex DNA
Tingting Zou, Seiichiro Kizaki, Ganesh N Pandian, Hiroshi Sugiyama Chemistry. 2016 Jun 20;22(26):8756-8. doi: 10.1002/chem.201600950. Epub 2016 May 11.
To evaluate the reactivity of antitumor agents in a nucleosome architecture, we conducted in vitro studies to assess the alkylation level of duocarmycin B2 on nucleosomes with core and linker DNA using sequencing gel electrophoresis. Our results suggested that the alkylating efficiencies of duocarmycin B2 were significantly decreased in core DNA and increased at the histone-free linker DNA sites when compared with naked DNA conditions. Our finding that nucleosome assembly alters the accessibility of duocarmycin B2 to duplex DNA could advance its design as an antitumor agent.
2. Investigating Nucleosome Accessibility for MNase, FeII Peplomycin, and Duocarmycin B2 by Using Capillary Electrophoresis
Tingting Zou, Seiichiro Kizaki, Hiroshi Sugiyama Chembiochem. 2018 Apr 4;19(7):664-668. doi: 10.1002/cbic.201700643. Epub 2018 Feb 12.
Capillary electrophoresis, coupled with DNA 5' Texas Red labeling, was used to investigate the ability of MNase, FeII peplomycin, and duocarmycin B2 to access the nucleosome. Distinct accessibility patterns of these species to the nucleosome were observed. MNase was completely prevented from approaching the nucleosome core and exhibited a higher site specificity for targeting DNA sites located close to the core region. Intercalation of peplomycin in the nucleosomal core region was highly suppressed, but reaction sites located at the ends of the nucleosomal core remained accessible, which implied flexibility of the core DNA end. Duocarmycin B2 was able to enter and react in the core region, although its alkylating efficiency decreased significantly.
3. Duocarmycins--natures prodrugs?
Mark Searcey Curr Pharm Des. 2002;8(15):1375-89. doi: 10.2174/1381612023394539.
The duocarmycins and (+)-CC-1065 are amongst the most potent antitumour antibiotics discovered to date and yet have not progressed into the clinic. The natural products are extremely stable to nucleophilic attack until bound to their DNA target and are not substrates for any other biological nucleophile. The mechanism for this target activation of the duocarmycins is discussed with relation to both an acid-catalyzed activation and a binding-induced conformational change leading to ground state destabilization. It is suggested that targeting of the duocarmycins to their site of action in a tumour may be more important than introducing systemically-activated prodrugs as the natural product itself can be considered to be a type of prodrug, activated only on binding to its targets. Methods that have been used to target CC-1065 and the duocarmycins are reviewed as well as efforts towards systemically activated prodrugs. A simple analysis of the approaches that could be taken to vary the structure for targeting is suggested.
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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 ╳
