ArticleChemistry (Weinheim an der Bergstrasse, Germany)2018
Sequence-Dependent Diastereospecific and Diastereodivergent Crosslinking of DNA by Decarbamoylmitomycin C.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- Synthesis of Oligonucleotides Containing a Dna Distorting Interstrand Crosslink Produced by Mitomycins.Chembiochem : a European journal of chemical biology · 2025Article
- Stereoisomeric mitomycins interstrand crosslinks differently impact gene expression in MCF-7 and K562 cancer cells.Chemico-biological interactions · 2025Article
- Mitomycin C and its analog trigger cytotoxicity in MCF-7 and K562 cancer cells through the regulation of RAS and MAPK/ERK pathways.Chemico-biological interactions · 2024Article
- Insight Into Factors Governing Formation, Synthesis and Stereochemical Configuration of DNA Adducts Formed by Mitomycins.Chemical record (New York, N.Y.) · 2023Review
- Cytotoxicity, crosslinking and biological activity of three mitomycins.Bioorganic chemistry · 2022Article
- Synthesis of Oligonucleotides Containing Trans Mitomycin C DNA Adducts at NChemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Synthesis of Oligonucleotides containing the cis-Interstrand Crosslink Produced by Mitomycins in their Reaction with DNA.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Synthesis of Mitomycin C and decarbamoylmitomycin C NBioorganic chemistry · 2019Article
- Interdependent Sequence Selectivity and Diastereoselectivity in the Alkylation of DNA by Decarbamoylmitomycin C.Chemistry (Weinheim an der Bergstrasse, Germany) · 2018Article
- Isolation and Rationale for the Formation of Isomeric Decarbamoylmitomycin C- NChemical research in toxicology · 2018Article
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Authors and funding
6 authors.
Funding
Abstract
Mitomycin C (MC), a potent antitumor drug, and decarbamoylmitomycin C (DMC), a derivative lacking the carbamoyl group, form highly cytotoxic DNA interstrand crosslinks. The major interstrand crosslink formed by DMC is the C1'' epimer of the major crosslink formed by MC. The molecular basis for the stereochemical configuration exhibited by DMC was investigated using biomimetic synthesis. The formation of DNA-DNA crosslinks by DMC is diastereospecific and diastereodivergent: Only the 1''S-diastereomer of the initially formed monoadduct can form crosslinks at GpC sequences, and only the 1''R-diastereomer of the monoadduct can form crosslinks at CpG sequences. We also show that CpG and GpC sequences react with divergent diastereoselectivity in the first alkylation step: 1"S stereochemistry is favored at GpC sequences and 1''R stereochemistry is favored at CpG sequences. Therefore, the first alkylation step results, at each sequence, in the selective formation of the diastereomer able to generate an interstrand DNA-DNA crosslink after the "second arm" alkylation. Examination of the known DNA adduct pattern obtained after treatment of cancer cell cultures with DMC indicates that the GpC sequence is the major target for the formation of DNA-DNA crosslinks in vivo by this drug.
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