Evaluation of complexes of DNA duplexes and novel benzoxazoles or benzimidazoles by electrospray ionization mass spectrometry.
Electrospray ionization mass spectrometry is used to compare the metal ion binding and metal-mediated DNA binding of benzoxazole (1, 2, 3, 4) and benzimidazole (5) compounds and to elucidate the putative binding modes and stoichiometries. The observed metal versus non-metal-mediated DNA binding, as...
| Main Authors: | , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
2004
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| _version_ | 1797066085079449600 |
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| author | Oehlers, L Mazzitelli, C Brodbelt, J Rodriguez, M Kerwin, S |
| author_facet | Oehlers, L Mazzitelli, C Brodbelt, J Rodriguez, M Kerwin, S |
| author_sort | Oehlers, L |
| collection | OXFORD |
| description | Electrospray ionization mass spectrometry is used to compare the metal ion binding and metal-mediated DNA binding of benzoxazole (1, 2, 3, 4) and benzimidazole (5) compounds and to elucidate the putative binding modes and stoichiometries. The observed metal versus non-metal-mediated DNA binding, as well as the specificity of DNA binding, is correlated with the biological activities of the analogs. The ESI-MS spectra for the antibacterial benzoxazole and benzimidazole analogs 4 and 5 demonstrated non-specific and non-metal-mediated binding to DNA, with the appearance of DNA complexes containing multiple ligands. The anticancer analog 2 demonstrates a clear preference for metal-mediated DNA interactions, with an apparent selectivity for Ni2+ -mediated binding over the more physiologically relevant Mg2+ or Zn2+ cations. Complexation between DNA and the biologically inactive analog 1 was not observed, either in the absence or presence of metal cations. |
| first_indexed | 2024-03-06T21:37:19Z |
| format | Journal article |
| id | oxford-uuid:46b5c69c-6b65-4c45-8d2c-83daeddd7246 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T21:37:19Z |
| publishDate | 2004 |
| record_format | dspace |
| spelling | oxford-uuid:46b5c69c-6b65-4c45-8d2c-83daeddd72462022-03-26T15:15:21ZEvaluation of complexes of DNA duplexes and novel benzoxazoles or benzimidazoles by electrospray ionization mass spectrometry.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:46b5c69c-6b65-4c45-8d2c-83daeddd7246EnglishSymplectic Elements at Oxford2004Oehlers, LMazzitelli, CBrodbelt, JRodriguez, MKerwin, SElectrospray ionization mass spectrometry is used to compare the metal ion binding and metal-mediated DNA binding of benzoxazole (1, 2, 3, 4) and benzimidazole (5) compounds and to elucidate the putative binding modes and stoichiometries. The observed metal versus non-metal-mediated DNA binding, as well as the specificity of DNA binding, is correlated with the biological activities of the analogs. The ESI-MS spectra for the antibacterial benzoxazole and benzimidazole analogs 4 and 5 demonstrated non-specific and non-metal-mediated binding to DNA, with the appearance of DNA complexes containing multiple ligands. The anticancer analog 2 demonstrates a clear preference for metal-mediated DNA interactions, with an apparent selectivity for Ni2+ -mediated binding over the more physiologically relevant Mg2+ or Zn2+ cations. Complexation between DNA and the biologically inactive analog 1 was not observed, either in the absence or presence of metal cations. |
| spellingShingle | Oehlers, L Mazzitelli, C Brodbelt, J Rodriguez, M Kerwin, S Evaluation of complexes of DNA duplexes and novel benzoxazoles or benzimidazoles by electrospray ionization mass spectrometry. |
| title | Evaluation of complexes of DNA duplexes and novel benzoxazoles or benzimidazoles by electrospray ionization mass spectrometry. |
| title_full | Evaluation of complexes of DNA duplexes and novel benzoxazoles or benzimidazoles by electrospray ionization mass spectrometry. |
| title_fullStr | Evaluation of complexes of DNA duplexes and novel benzoxazoles or benzimidazoles by electrospray ionization mass spectrometry. |
| title_full_unstemmed | Evaluation of complexes of DNA duplexes and novel benzoxazoles or benzimidazoles by electrospray ionization mass spectrometry. |
| title_short | Evaluation of complexes of DNA duplexes and novel benzoxazoles or benzimidazoles by electrospray ionization mass spectrometry. |
| title_sort | evaluation of complexes of dna duplexes and novel benzoxazoles or benzimidazoles by electrospray ionization mass spectrometry |
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