Duazomycin A
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| Category | Antibiotics |
| Catalog number | BBF-01385 |
| CAS | 2508-89-6 |
| Molecular Weight | 213.19 |
| Molecular Formula | C8H11N3O4 |
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Description
Duazomycin A is produced by the strain of Streptomyces ambofaciens. It has the activity of anti-gram-positive bacteria, yeast and yeast-like fungi, and has strong inhibitory effect on sarcoma 180 and adenocarcinoma 755.
Specification
| Synonyms | Duazomycine; Duazomycinum; N-Acetyl-6-diazo-5-oxo-L-norleucine |
| IUPAC Name | (2S)-2-acetamido-6-diazo-5-oxohexanoic acid |
| Canonical SMILES | CC(=O)NC(CCC(=O)C=[N+]=[N-])C(=O)O |
| InChI | InChI=1S/C8H11N3O4/c1-5(12)11-7(8(14)15)3-2-6(13)4-10-9/h4,7H,2-3H2,1H3,(H,11,12)(H,14,15)/t7-/m0/s1 |
| InChI Key | WBSWOKCKZUNHQV-ZETCQYMHSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; fungi; yeast; neoplastics (Tumor) |
| Solubility | Soluble in Water, Methylene chloride, Chloroform |
Reference Reading
1. Model studies towards prodrugs of the glutamine antagonist 6-diazo-5-oxo-l-norleucine (DON) containing a diazo precursor
Run-Duo Gao, Niyada Hin, Eva Prchalová, Arindom Pal, Jenny Lam, Rana Rais, Barbara S Slusher, Takashi Tsukamoto Bioorg Med Chem Lett. 2021 Oct 15;50:128321. doi: 10.1016/j.bmcl.2021.128321. Epub 2021 Aug 13.
Two distinct diazo precursors, imidazotetrazine and nitrous amide, were explored as promoieties in designing prodrugs of 6-diazo-5-oxo-l-norleucine (DON), a glutamine antagonist. As a model for an imidazotetrazine-based prodrug, we synthesized (S)-2-acetamido-6-(8-carbamoyl-4-oxoimidazo[5,1-d][1,2,3,5]tetrazin-3(4H)-yl)-5-oxohexanoic acid (4) containing the entire scaffold of temozolomide, a precursor of the DNA-methylating agent clinically approved for the treatment of glioblastoma multiforme. For a nitrous amide-based prodrug, we synthesized 2-acetamido-6-(((benzyloxy)carbonyl)(nitroso)amino)-5-oxohexanoic acid (5) containing a N-nitrosocarbamate group, which can be converted to a diazo moiety via a mechanism similar to that of streptozotocin, a clinically approved diazomethane-releasing drug containing an N-nitrosourea group. Preliminary characterization confirmed formation of N-acetyl DON (6), also known as duazomycin A, from compound 4 in a pH-dependent manner while compound 5 did not exhibit sufficient stability to allow further characterization. Taken together, our model studies suggest that further improvements are needed to translate this prodrug approach into glutamine antagonist-based therapy.
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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 ╳
