Interaction of psoralen-derivatized oligodeoxyribonucleoside methylphosphonates with single-stranded DNA

Journal Article · Tue May 03 04:00:00 EDT 1988 · Biochemistry; (United States)

DOI:https://doi.org/10.1021/bi00409a011· OSTI ID:6998084

Lee, B L; Murakami, A; Blake, K R; Lin, S B; Miller, P S

Oligodeoxyribonucleoside methylphosphonates derivatized at the 5' end with 4'-(amino-alkyl)-4,5',8-trimethylpsoralen were prepared. The interaction of these psoralen-derivatized methyl-phosphonate oligomers with synthetic single-stranded DNAs 35 nucleotides in length was studied. Irradiation of a solution containing the 35-mer and its complementary methylphosphonate oligomer at 365 nm gave a cross-linked duplex produced by cycloaddition between the psoralen pyrone ring of the derivatized methylphosphonate oligomer and a thymine base of the DNA. Photoadduct formation could be reversed by irradiation at 254 nm. The rate and extent of cross-linking were dependent upon the length of the aminoalkyl linker between the trimethylpsoralen group and the 5' end of the methylphosphonate oligomer. Methylphosphonate oligomers derivatized with 4'-((N-(2-aminoethyl)amino)methyl)-4,5',8-trimethylpsoralen gave between 70% and 85% cross-linked product when irradiated for 20 min at 4 /sup 0/C. These results suggest that the methylphosphonate oligomers undergo both cross-linking and deactivation reactions when irradiated at 365 nm. The cross-linking reaction was dependent upon the fidelity of base-pairing interactions between the methylphosphonate oligomers and the single-stranded DNA. The extent and sequence specificity of photoinduced cross-linking, combined with the known ability of methylphosphonate oligomers to be taken up by living cells, suggest that psoralen-derivatized oligonucleoside methylphosphonates may be useful probes of cellular gene expression.

• Research Organization: Johns Hopkins Univ., Baltimore, MD (USA)
• OSTI ID: 6998084
• Journal Information: Biochemistry; (United States), Journal Name: Biochemistry; (United States) Vol. 27:9; ISSN BICHA
• Country of Publication: United States
• Language: English

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560120* -- Radiation Effects on Biochemicals
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63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
ADDUCTS
ANTICOAGULANTS
ATP
BETA DECAY RADIOISOTOPES
BETA-MINUS DECAY RADIOISOTOPES
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HEMATOLOGIC AGENTS
HETEROCYCLIC COMPOUNDS
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LIQUID COLUMN CHROMATOGRAPHY
NEAR ULTRAVIOLET RADIATION
NUCLEI
NUCLEIC ACIDS
NUCLEOTIDES
ODD-ODD NUCLEI
OLIGONUCLEOTIDES
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
ORGANIC PHOSPHORUS COMPOUNDS
PHOSPHONIC ACID ESTERS
PHOSPHORUS 32
PHOSPHORUS ISOTOPES
POLYMERIZATION
PSORALEN
RADIATIONS
RADIOINDUCTION
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SEPARATION PROCESSES
SPECTRA
ULTRAVIOLET RADIATION
ULTRAVIOLET SPECTRA