Page last updated: 2024-12-07
rhodomycinone
Description
Rhodomycinone is a potent antitumor antibiotic produced by the bacterium Streptomyces purpurascens. It is known for its complex structure, which includes a highly oxygenated anthraquinone core. The compound exhibits a wide range of biological activities, including cytotoxic activity against several cancer cell lines. Notably, rhodomycinone has shown promising anticancer effects in preclinical studies, with potential applications in treating leukemia, lymphoma, and breast cancer. The synthesis of rhodomycinone remains a significant challenge due to its intricate molecular architecture. Researchers are actively investigating various approaches to synthesizing rhodomycinone, including biocatalytic methods and total synthesis strategies. The understanding of rhodomycinone's biosynthesis and its potential anticancer properties has sparked considerable research interest in the development of new antitumor agents. Studying rhodomycinone is crucial for exploring its therapeutic potential and understanding the mechanisms of action underlying its biological effects. The complex structure of this compound also serves as a fascinating target for synthetic chemistry research, pushing the boundaries of organic synthesis and providing valuable insights into molecular complexity.'
rhodomycinone: anthracycline antibiotic [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
epsilon-rhodomycinone : A carboxylic ester that is the methyl ester of (1R,2R,4S)-2-ethyl-2,4,5,7,12-pentahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylic acid. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]
Cross-References
Synonyms (14)
Synonym |
21288-60-8 |
epsilon-rhodomycinone |
rhodomycinone |
e-rhodomycinone |
chebi:75291 , |
CHEMBL22025 |
AC1L40QH , |
methyl (1r,2r,4s)-2-ethyl-2,4,5,7,12-pentahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate |
AKOS004902751 |
1-naphthacenecarboxylic acid, 2-ethyl-1,2,3,4,6,11-hexahydro-2,4,5,7,12-pentahydroxy-6,11-dioxo-, methyl ester, (1r-(1alpha,2beta,4beta))- |
nsc 196524 |
methyl (1r,2r,4s)-2-ethyl-2,4,5,7,12-pentahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate |
Q27105038 |
epsilon-rhodomycinon |
Drug Classes (5)
Class | Description |
tetracenomycin | A polyketide based on a tetracene ring structure. |
polyphenol | Members of the class of phenols that contain 2 or more benzene rings each of which is substituted by at least one hydroxy group. |
carbopolycyclic compound | A polyclic compound in which all of the ring members are carbon atoms. |
tetracenequinones | |
methyl ester | Any carboxylic ester resulting from the formal condensation of a carboxy group with methanol. |
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] |
Bioassays (10)
Assay ID | Title | Year | Journal | Article |
AID1354667 | Cytotoxicity against human HepG2 cells after 48 hrs by MTT assay | 2018 | Journal of natural products, 05-25, Volume: 81, Issue:5
| Cytotoxic Anthracycline Metabolites from a Recombinant Streptomyces. |
AID70892 | Compound is evaluated for lambda-phage induction activity in Escherichia coli (dose at 50 ug/mL); Toxic to culture | 1980 | Journal of medicinal chemistry, Nov, Volume: 23, Issue:11
| 8-Hydroxyanthracyclinones from epsilon-rhodomycinone. |
AID333401 | Antibacterial activity against Bacillus subtilis ATCC 6633 after 24 hrs by microtiter plate assay | 2004 | Journal of natural products, Oct, Volume: 67, Issue:10
| Blanchaquinone: a new anthraquinone from an Australian Streptomyces sp. |
AID70889 | Compound is evaluated for lambda-phage induction activity in Escherichia coli (dose at 25 ug/mL) | 1980 | Journal of medicinal chemistry, Nov, Volume: 23, Issue:11
| 8-Hydroxyanthracyclinones from epsilon-rhodomycinone. |
AID1354666 | Cytotoxicity against human HCT116 cells after 48 hrs by MTT assay | 2018 | Journal of natural products, 05-25, Volume: 81, Issue:5
| Cytotoxic Anthracycline Metabolites from a Recombinant Streptomyces. |
AID1354668 | Cytotoxicity against human MCF10A cells after 48 hrs by MTT assay | 2018 | Journal of natural products, 05-25, Volume: 81, Issue:5
| Cytotoxic Anthracycline Metabolites from a Recombinant Streptomyces. |
AID1354664 | Cytotoxicity against human NCI-H460 cells after 48 hrs by MTT assay | 2018 | Journal of natural products, 05-25, Volume: 81, Issue:5
| Cytotoxic Anthracycline Metabolites from a Recombinant Streptomyces. |
AID70888 | Compound is evaluated for lambda-phage induction activity in Escherichia coli (dose at 12.5 ug/mL) | 1980 | Journal of medicinal chemistry, Nov, Volume: 23, Issue:11
| 8-Hydroxyanthracyclinones from epsilon-rhodomycinone. |
AID1354663 | Cytotoxicity against human MDA-MB-435 cells after 48 hrs by MTT assay | 2018 | Journal of natural products, 05-25, Volume: 81, Issue:5
| Cytotoxic Anthracycline Metabolites from a Recombinant Streptomyces. |
AID1354665 | Cytotoxicity against human MDA-MB-231 cells after 48 hrs by MTT assay | 2018 | Journal of natural products, 05-25, Volume: 81, Issue:5
| Cytotoxic Anthracycline Metabolites from a Recombinant Streptomyces. |
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Research
Studies (31)
Timeframe | Studies, This Drug (%) | All Drugs % |
pre-1990 | 9 (29.03) | 18.7374 |
1990's | 9 (29.03) | 18.2507 |
2000's | 6 (19.35) | 29.6817 |
2010's | 6 (19.35) | 24.3611 |
2020's | 1 (3.23) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Study Types
Publication Type | This drug (%) | All Drugs (%) |
Trials | 0 (0.00%) | 5.53% |
Reviews | 2 (6.45%) | 6.00% |
Case Studies | 0 (0.00%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 29 (93.55%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |