title: Biochemical properties of phosphonoacetate and thiophosphonoacetate oligodeoxyribonucleotides.
abstract: Phosphorus-modified phosphonoacetate and thiophosphonoacetate oligodeoxyribonucleotides were chemically synthesized and their biochemical properties evaluated. Under physiological pH, these DNA analogs possess negative charge and form stable, complementary A-like DNA:RNA heteroduplexes when analyzed via circular dichroism spectroscopy. Phosphonoacetate and thiophosphonoacetate oligomers were found to stimulate RNase H activity and to be completely resistant to degradation by snake venom phosphodiesterase, DNase I and HeLa cell nuclear extract. Further research has demonstrated that neutral, esterified forms of these analogs can be taken up by cells. Phosphonoacetate and thiophosphonoacetate oligomers therefore represent a new class of oligodeoxyribonucleotide analogs having phosphorus- carbon bonds with considerable potential for use in biological research.
authors.affiliation: Department of Chemistry and Biochemistry, University of Colorado, Boulder, CO 80309, USA.
authors.forename: David
authors.initials: D
authors.lastname: Sheehan
authors.forename: Benjamin
authors.initials: B
authors.lastname: Lunstad
authors.forename: Christina M
authors.initials: CM
authors.lastname: Yamada
authors.forename: Brian G
authors.initials: BG
authors.lastname: Stell
authors.forename: Marvin H
authors.initials: MH
authors.lastname: Caruthers
authors.forename: Douglas J
authors.initials: DJ
authors.lastname: Dellinger
mesh_terms: D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism; D003850:Deoxyribonuclease I / Q000378:metabolism; D006801:Humans; D006863:Hydrogen-Ion Concentration; D009691:Nucleic Acid Denaturation; D009838:Oligodeoxyribonucleotides / Q000737:chemistry* / Q000235:genetics / Q000378:metabolism; D010746:Phosphonoacetic Acid / Q000737:chemistry*; D016914:Ribonuclease H / Q000378:metabolism; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013696:Temperature; D013873:Thionucleotides / Q000737:chemistry / Q000235:genetics / Q000378:metabolism; D014162:Transfection; D014407:Tumor Cells, Cultured
chemical_list: D009838:Oligodeoxyribonucleotides; D013873:Thionucleotides; D003850:Deoxyribonuclease I; D016914:Ribonuclease H; C078856:ribonuclease HI; D010746:Phosphonoacetic Acid