ArticleChembiochem : a European journal of chemical biology2008
Generation of new derivatives of the antitumor antibiotic mithramycin by altering the glycosylation pattern through combinatorial biosynthesis.
Article in Chembiochem : a European journal of chemical biology, 2008. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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Who cites it
21 citing papers in PubMed, 50 citations in OpenAlex.
- Mithramycin targets head and neck cancer stem cells by inhibiting Sp1 and UFMylation.Cancer cell international · 2024Article
- Pathway Engineering of Anthracyclines: Blazing Trails in Natural Product Glycodiversification.The Journal of organic chemistry · 2020Article
- Heterologous reconstitution of the biosynthesis pathway for 4-demethyl-premithramycinone, the aglycon of antitumor polyketide mithramycin.Microbial cell factories · 2020Article
- New Sipanmycin Analogues Generated by Combinatorial Biosynthesis and Mutasynthesis Approaches Relying on the Substrate Flexibility of Key Enzymes in the Biosynthetic Pathway.Applied and environmental microbiology · 2020Article
- The Mithralog EC-7072 Induces Chronic Lymphocytic Leukemia Cell Death by Targeting Tonic B-Cell Receptor Signaling.Frontiers in immunology · 2019Article
- Structures of mithramycin analogues bound to DNA and implications for targeting transcription factor FLI1.Nucleic acids research · 2016Article
- Increasing antibiotic production yields by favoring the biosynthesis of precursor metabolites glucose-1-phosphate and/or malonyl-CoA in Streptomyces producer strains.The Journal of antibiotics · 2016Article
- Tailoring pathway modularity in the biosynthesis of erythromycin analogs heterologously engineered in E. coli.Science advances · 2015Article
- Genome-wide modulation of gene transcription in ovarian carcinoma cells by a new mithramycin analogue.PloS one · 2014Article
- Recent biotechnological progress in enzymatic synthesis of glycosides.Journal of industrial microbiology & biotechnology · 2013Review
- Molecular insight into substrate recognition and catalysis of Baeyer-Villiger monooxygenase MtmOIV, the key frame-modifying enzyme in the biosynthesis of anticancer agent mithramycin.ACS chemical biology · 2013Article
- In silico biosynthesis of virenose, a methylated deoxy-sugar unique to Coxiella burnetii lipopolysaccharide.Proteome science · 2012Article
- Cooperation of two bifunctional enzymes in the biosynthesis and attachment of deoxysugars of the antitumor antibiotic mithramycin.Angewandte Chemie (International ed. in English) · 2012Article
- A novel mithramycin analogue with high antitumor activity and less toxicity generated by combinatorial biosynthesis.Journal of medicinal chemistry · 2012Article
- Article
- Investigating Mithramycin deoxysugar biosynthesis: enzymatic total synthesis of TDP-D-olivose.Chembiochem : a European journal of chemical biology · 2011Article
- Chromomycin SA analogs from a marine-derived Streptomyces sp.Bioorganic & medicinal chemistry · 2011Article
- Characterization of the TDP-D-ravidosamine biosynthetic pathway: one-pot enzymatic synthesis of TDP-D-ravidosamine from thymidine-5-phosphate and glucose-1-phosphate.Organic & biomolecular chemistry · 2011Article
- The chromomycin CmmA acetyltransferase: a membrane-bound enzyme as a tool for increasing structural diversity of the antitumour mithramycin.Microbial biotechnology · 2011Article
- Molecular insights on the biosynthesis of antitumour compounds by actinomycetes.Microbial biotechnology · 2011Review
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Authors and funding
6 authors at 3 institutions in 2 countries.
Funding
Abstract
Mithramycin is an antitumor drug produced by Streptomyces argillaceus. It consists of a tricyclic aglycone and five deoxyhexoses that form a disaccharide and a trisaccharide chain, which are important for target interaction and therefore for the antitumor activity. Using a combinatorial biosynthesis approach, we have generated nine mithramycin derivatives, seven of which are new compounds, with alterations in the glycosylation pattern. The wild-type S. argillaceus strain and the mutant S. argillaceus M7U1, which has altered D-oliose biosynthesis, were used as hosts to express various "sugar plasmids", each one directing the biosynthesis of a different deoxyhexose. The newly formed compounds were purified and characterized by MS and NMR. Compared to mithramycin, they contained different sugar substitutions in the second (D-olivose, D-mycarose, or D-boivinose instead of D-oliose) and third (D-digitoxose instead of D-mycarose) sugar units of the trisaccharide as well as in the first (D-amicetose instead of D-olivose) sugar unit of the disaccharide. All compounds showed antitumor activity against different tumor cell lines. Structure-activity relationships are discussed on the basis of the number and type of deoxyhexoses present in these mithramycin derivatives.
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