Photo-cross-linking of psoralen-derivatized oligonucleoside methylphosphonates to single-stranded DNA

Purshotam Bhan, Paul S. Miller

Research output: Contribution to journalArticle

Abstract

The preparation of oligodeoxyribonucleoside methylphosphonates derivatized with 3-[(2-aminoethyl)carbamoyl]psoralen [(ae)CP] is described. These derivatized oligomers are capable of cross-linking with single-stranded DNA via formation of a photoadduct between the furan side of the psoralen ring and a thymidine of the target DNA when the oligomer-target duplex is irradiated with 365-nm light. The photoreactions of (ae)CP-derivatized methylphosphonate oligomers with single-stranded DNA targets in which the position of the psoralen-linking site is varied are characterized and compared to results obtained with oligomers derivatized with 4′-[[N-(aminoethyl)amino]methyl]-4,5′,8-trimethylpsoralen [(ae)AMT]. It appears that the psoralen ring can stack on the terminal base pair formed between the oligomer and its target DNA or can intercalate between, the last two base pairs of the oligomer-target duplex. Oligomers derivatized with (ae)CP cross-link efficiently to a thymidine located in the last base pair (n position) or 3′ to the last base pair (n + 1 position) of the target, whereas the (ae)AMT-derivatized oligomers cross-link most efficiently to a thymidine located in the n + 1 position. The results show that both the extent and kinetics of cross-linking are influenced by the location of the psoralen-linking site in the oligomer-target duplex.

Original languageEnglish (US)
Pages (from-to)82-88
Number of pages7
JournalBioconjugate Chemistry
Volume1
Issue number1
StatePublished - 1990

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Ficusin
Single-Stranded DNA
Oligomers
Base Pairing
DNA
Thymidine
Trioxsalen
Light
methylphosphonic acid
3-((2-aminoethyl)carbamoyl)psoralen
Kinetics

ASJC Scopus subject areas

  • Chemistry(all)
  • Organic Chemistry
  • Clinical Biochemistry
  • Biochemistry, Genetics and Molecular Biology(all)
  • Biochemistry

Cite this

Photo-cross-linking of psoralen-derivatized oligonucleoside methylphosphonates to single-stranded DNA. / Bhan, Purshotam; Miller, Paul S.

In: Bioconjugate Chemistry, Vol. 1, No. 1, 1990, p. 82-88.

Research output: Contribution to journalArticle

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