Showdomycin
Antibiotic
From Wikipedia, the free encyclopedia
Showdomycin is a nucleoside antibiotic derived from Streptomyces showdoensis. It is known for its antitumor and antimicrobial properties.[1] Showdomycin was first isolated in the 1960s and has since been studied for its potential applications in cancer research and microbiology.[2][3]
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| Names | |
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| IUPAC name
(1S)-1,4-Anhydro-1-(2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl)-D-ribitol | |
Other names
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| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| MeSH | Showdomycin |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C9H11NO6 | |
| Molar mass | 229.188 g·mol−1 |
| Melting point | 153–154 °C (307–309 °F; 426–427 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Discovery and History
Showdomycin was first discovered in 1964 by Japanese researchers during a screening of Streptomyces species for novel antibiotics. It was isolated from Streptomyces showdoensis, a soil bacterium, and its structure was elucidated shortly thereafter. The compound gained attention for its unusual structure, which includes a maleimide ring fused to a ribose sugar, distinguishing it from other nucleoside antibiotics.[4]
Chemical Structure
Showdomycin is a C-nucleoside, meaning the sugar is directly bonded to a carbon atom of the maleimide ring rather than a nitrogen atom, as seen in typical nucleosides. Its chemical formula is C9H11NO6, and its systematic name is 1-β-D-ribofuranosyl-1H-pyrrole-2,5-dione. The maleimide moiety is responsible for its reactivity, particularly its ability to act as a Michael acceptor in biochemical reactions.[1][5] It displays a high similarity with uridine and pseudouridine.[6][7]
Mechanism of Action
Showdomycin exhibits its biological activity through several mechanisms:
- Antitumor Activity: Showdomycin and its derivatives act as uridine mimics, thereby delaying RNA extension and hence RNA synthysis. This makes it effective against rapidly dividing cancer cells.[1][8]
- Antimicrobial Activity: It inhibits the growth of various fungi and bacteria, especially Streptococcus hemolyticus[3] and Streptococcus pyogenes[9] by disrupting essential metabolic pathways.[10]
- Inhibition of Enzymes: It is a sulfhydryl reactive agent and acts as an inhibitor of certain enzymes, particularly those with thiol groups, by forming covalent bonds with cysteine residues.[6]
Applications
Showdomycin is a compound commonly used in biochemical research to investigate enzyme mechanisms and protein interactions.[6] It works by selectively modifying thiol groups, making it a valuable tool for studying protein structure and function.[1] Although it has not been developed into a commercial drug, researchers have explored its potential therapeutic uses. Preclinical studies have shown that showdomycin possesses both antitumor and antimicrobial properties.[2] It has demonstrated effectiveness against certain antibiotic-resistant pathogens,[3][7] making it a potential candidate for future drug development. However its use in therapeutic applications is limited by its lack of selectivity, which can lead to adverse effects on healthy cells.