Jump to main content
Jump to site search

Issue 48, 2019
Previous Article Next Article

Solvent-dependent regioselectivity of 2′-deoxyadenosine alkylation by 9-aminomethyl derivatives of SN38

Author affiliations

Abstract

The mechanism of alkylation of the 2′-deoxyadenosine (dA) by potential topoisomerase I (Top I) inhibitors, from the camptothecin family, is described in water and in DMSO-d6. The products of the reactions depend on the solvent; however in both cases the thermodynamic products are formed. The investigated compounds in DMSO solution unexpectedly alkylate the N9 nitrogen atom of 2′-deoxyadenosine, preceded by an irreversible deglycosylation process, whereas the N6 nitrogen atom is alkylated in buffered water solution. The products of the reaction have been confirmed by NMR and MS techniques. This is the first evidence of spontaneous alkylation of 2′-deoxyadenosine by compounds from the camptothecin family, which are biologically active in vitro against several cancer cells.

Graphical abstract: Solvent-dependent regioselectivity of 2′-deoxyadenosine alkylation by 9-aminomethyl derivatives of SN38

Back to tab navigation

Supplementary files

Publication details

The article was received on 23 Sep 2019, accepted on 18 Nov 2019 and first published on 26 Nov 2019


Article type: Letter
DOI: 10.1039/C9NJ04828F
New J. Chem., 2019,43, 18975-18978

  •   Request permissions

    Solvent-dependent regioselectivity of 2′-deoxyadenosine alkylation by 9-aminomethyl derivatives of SN38

    B. Naumczuk, W. Bocian, J. Sitkowski, R. Kawęcki and L. Kozerski, New J. Chem., 2019, 43, 18975
    DOI: 10.1039/C9NJ04828F

Search articles by author

Spotlight

Advertisements