Azinomycin A
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| Category | Antibiotics |
| Catalog number | BBF-00241 |
| CAS | 106486-77-5 |
| Molecular Weight | 595.60 |
| Molecular Formula | C30H33N3O10 |
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Description
Azinomycin A is produced by the strain of Streptomyces griseofuscus. It was highly cytotoxic, and the cytotoxicity of A and B to L5178Y cell IC50 was 0.07 g/mL and 0.11 g/mL, respectively.
Specification
| Synonyms | 1-Naphthalenecarboxylic acid, 3-methoxy-5-methyl-, 2-((1-(3-(acetyloxy)-4-hydroxy-1-azabicyclo(3.1.0)hex-2-ylidene)-2-oxo-2-((2-oxopropyl)amino)ethyl)amino)-1-(2-methyloxiranyl)-2-oxoethyl ester |
| IUPAC Name | [(1S)-2-[[(1E)-1-[(3R,4R,5S)-3-acetyloxy-4-hydroxy-1-azabicyclo[3.1.0]hexan-2-ylidene]-2-oxo-2-(2-oxopropylamino)ethyl]amino]-1-[(2S)-2-methyloxiran-2-yl]-2-oxoethyl] 3-methoxy-5-methylnaphthalene-1-carboxylate |
| Canonical SMILES | CC1=C2C=C(C=C(C2=CC=C1)C(=O)OC(C(=O)NC(=C3C(C(C4N3C4)O)OC(=O)C)C(=O)NCC(=O)C)C5(CO5)C)OC |
| InChI | InChI=1S/C30H33N3O10/c1-14-7-6-8-18-19(14)9-17(40-5)10-20(18)29(39)43-26(30(4)13-41-30)28(38)32-22(27(37)31-11-15(2)34)23-25(42-16(3)35)24(36)21-12-33(21)23/h6-10,21,24-26,36H,11-13H2,1-5H3,(H,31,37)(H,32,38)/b23-22+/t21-,24+,25+,26+,30-,33?/m0/s1 |
| InChI Key | PBRHVAKBKPQZAF-CMMHMAGGSA-N |
Properties
| Appearance | Achromatic Flake Crystalline |
| Boiling Point | 868.9°C at 760 mmHg |
| Melting Point | 140 °C |
| Density | 1.43 g/cm3 |
Reference Reading
1. Priming of Azabicycle Biosynthesis in the Azinomycin Class of Antitumor Agents
Shogo Mori, Keshav K Nepal, Gilbert T Kelly, Vasudha Sharma, Dinesh Simkhada, Vishruth Gowda, Dioscar Delgado, Coran M H Watanabe Biochemistry. 2017 Feb 14;56(6):805-808. doi: 10.1021/acs.biochem.6b01108. Epub 2017 Feb 6.
The biosynthesis of the azabicyclic ring system of the azinomycin family of antitumor agents represents the "crown jewel" of the pathway and is a complex process involving at least 14 enzymatic steps. This study reports on the first biosynthetic step, the inroads, in the construction of the novel aziridino [1,2-a]pyrrolidine, azabicyclic core, allowing us to support a new mechanism for azabicycle formation.
2. The Fate of Molecular Oxygen in Azinomycin Biosynthesis
Gilbert T Kelly, Lauren A Washburn, Coran M H Watanabe J Org Chem. 2019 Mar 1;84(5):2991-2996. doi: 10.1021/acs.joc.8b03007. Epub 2019 Feb 11.
The azinomycins are a family of aziridine-containing antitumor antibiotics and represent a treasure trove of biosynthetic reactions. The formation of the azabicyclo[3.1.0]hexane ring and functionalization of this ring system remain the least understood aspects of the pathway. This study reports the incorporation of 18O-labeled molecular oxygen in azinomycin biosynthesis including both oxygens of the diol that ultimately adorn the aziridino[1,2- a]pyrrolidine moiety. Likewise, two other sites of heavy atom incorporation are observed.
3. Mode of action and biosynthesis of the azabicycle-containing natural products azinomycin and ficellomycin
Jennifer Foulke-Abel, Hillary Agbo, Huitu Zhang, Shogo Mori, Coran M H Watanabe Nat Prod Rep. 2011 Apr;28(4):693-704. doi: 10.1039/c0np00049c. Epub 2011 Feb 15.
Only a handful of aziridine-containing natural products have been identified out of the more than 100,000 natural products characterized to date. Among this class of compounds, only the azinomycins (azinomycin A and B) and ficellomycin contain an unusual 1-azabicyclo[3.1.0]hexane ring system, which has been reported to be the reason for theDNAcrosslinking abilities and cytotoxicity of these metabolites. Both families of natural products are produced by Streptomyces species, Streptomyces sahachiroi and Streptomyces ficellus, respectively. Up until recently, much of the work on these molecules has focused on the synthesis of these natural products or their corresponding analogs for in vitro investigations evaluating their DNA selectivity. While one of the most intriguing aspects of these natural products is their biosynthesis, progress made in this area was largely impeded by difficulties with obtaining a reliable culture method and securing a consistent source of these natural products. In this review, we will cover the discovery and biological activity of the azinomycins, their mode of action, related synthetic analogs and biosynthesis, and finish with a discussion on the less studied metabolite, ficellomycin.
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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 ╳
