Rapid characterization of cross-links, mono-adducts, and non-covalent binding of psoralens to deoxyoligonucleotides by LC-UV/ESI-MS and IRMPD mass spectrometry
Open accessAbstract
Upon UV photoactivation, psoralen analogs form covalent mono-adducts and cross-links with DNA at thymine residues. Electrospray ionization mass spectrometric analysis allowed rapid and efficient determination of the reaction percentages of each psoralen analog with DNA duplexes containing different binding sites after exposure to UV irradiation. The distribution of cross-linked products and mono-adducts was monitored by both LC-UV and IRMPD-MS methods with the highest ratio of cross-linked products to mono-adducts obtained for 8-methoxypsoralen (8-MOP), psoralen (P), and 5-methoxypsoralen (5-MOP). Reactions at 5'-TA sites were favored over 5'-AT sites, and duplexes containing two and three binding sites showed extensive binding by the psoralens. 4'-Aminomethyl-4,5',8-trimethylpsoralen (AMP) bound non-selectively via non-covalent interactions and was the only psoralen analog to show significant binding in the absence of UV irradiation. 8-MOP binding displayed the greatest sequence selectivity among the psoralen analogs. The sites of interstrand cross-linking were determined by fragmentation of the duplex/psoralen complexes by infrared multiphoton dissociation (IRMPD), which produced cross-linked product ions containing an intact single strand, the psoralen analog, and either a w(n) or a(n)-B portion of the complementary strand. IRMPD of DNA/AMP complexes after UV irradiation also produced high abundances of the intact single strands with the AMP ligand attached, products indicative of a significant population of mono-adducts.
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A complementary analytical tool involving liquid chromatography with UV/ESI-MS or IR multiphoton dissociation mass spectrometry is available for monitoring distribution of psoralen mono- and bi-adducts to pyrimidine bases in duplex oligodeoxynucleotides.
“A complementary analytical tool for monitoring the distribution of psoralen mono-and bi-adducts to pyrimidine bases in duplex oligodeoxynucleotides that involves the association of liquid chromatography with either UV ⁄ ESI-MS or IR multiphoton dissociation mass spectrometry has recently become available (173).”
From Photoinduced Damage to Cellular DNA: Direct and Photosensitized Reactions<sup>†</sup> (2012) · cites this paper as [173]
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- Authors
- Smith, S. I., & Brodbelt, J. S.
- Affiliations
- The University of Texas at Austin (US)
- Corresponding author
- Brodbelt, Jennifer S.
- Venue
- The Analyst
- Publisher
- Royal Society of Chemistry (RSC)
- Published
- 2010
- Volume
- 135
- Issue
- 5
- Pages
- 943
- ISSN
- 0003-2654 (ISSN-L)
- 1364-5528
- PMC
- PMC2890229
- OpenAlex
- W1967245942
- Cited by
- 25
- References
- 62
- Citations by year
- 2026: 1 · 2024: 2 · 2023: 2 · 2021: 3 · 2020: 1 · 2019: 2 · 2018: 1 · 2014: 2 · 2013: 3 · 2012: 4
- FWCI
- 1.47
- Type
- journal article
- Language
- en
- Open access
- green
- www.ncbi.nlm.nih.gov
- Locations
- The Analyst (publishedVersion)
- PubMed (publishedVersion)
- PubMed Central (acceptedVersion)
- Funders
- National Institute of General Medical Sciences (R01GM65956, R01GM065956)
- Topics
- Physical Sciences › Chemistry › Spectroscopy › Mass Spectrometry Techniques and Applications
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › DNA and Nucleic Acid Chemistry
- Physical Sciences › Chemistry › Organic Chemistry › Synthesis and pharmacology of benzodiazepine derivatives
- Keywords
- psoralen, DNA cross-linking, monoadducts, UV photoactivation, 8-methoxypsoralen, 5-methoxypsoralen, non-covalent DNA binding, sequence selectivity, interstrand cross-links, double-stranded DNA
- MeSH terms
- 5-Methoxypsoralen, Chromatography, High Pressure Liquid, Methoxsalen, Oligodeoxyribonucleotides, Furocoumarins, Thymine, Ultraviolet Rays, DNA Adducts, Spectrometry, Mass, Electrospray Ionization
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