P-stilbazole moieties as artificial base pairs for photo-cross-linking of DNA duplex

被引：0
|
作者：
机构：
[1] Kashida, Hiromu
[2] Doi, Tetsuya
[3] Sakakibara, Takumi
[4] Hayashi, Takamitsu
[5] Asanuma, Hiroyuki
来源：
Kashida, H. (kashida@nubio.nagoya-u.ac.jp) | 1600年 / American Chemical Society卷 / 135期
关键词：
In this study; we report a photo-cross-linking reaction between p-stilbazole moieties. p-Stilbazoles were introduced into base-paring positions of complementary DNA strands. The [2 + 2] photocycloaddition reaction occurred rapidly upon light irradiation at 340 nm. Consequently; duplex was cross-linked and highly stabilized after 3 min irradiation. The CD spectrum of the cross-linked duplex indicated that the B-form double-helical structure was not severely distorted. NMR analysis revealed only one conformation of the duplex prior to UV irradiation; whereas two diastereomers were detected after the photo-cross-linking reaction. Before UV irradiation; p-stilbazole can adopt two different stacking modes because of rotation around the single bond between the phenyl and vinyl groups; these conformations cannot be discriminated on the NMR time scale due to rapid interconversion. However; photo-cross-linking fixed the conformation and enabled discrimination both by NMR and HPLC. The artificial base pair of p-methylstilbazolium showed almost the same reactivity as p-stilbazole; indicating that positive charge does not affect the reactivity. When a natural nucleobase was present in the complementary strand opposite p-stilbazole; the duplex was significantly destabilized relative to the duplex with paired p-stilbazole moieties and no photoreaction occurred between p-stilbazole and the nucleobase. The p-stilbazole pair has potential as a third base pair for nanomaterials due to its high stability and superb orthogonality. © 2013 American Chemical Society;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
Journal article (JA)
引用
收藏
相关论文
共 50 条
  • [31] PSORALEN COVALENTLY LINKED TO OLIGODEOXYRIBONUCLEOTIDES - SYNTHESIS, SEQUENCE SPECIFIC RECOGNITION OF DNA AND PHOTO-CROSS-LINKING TO PYRIMIDINE RESIDUES OF DNA
    PIELES, U
    ENGLISCH, U
    NUCLEIC ACIDS RESEARCH, 1989, 17 (01) : 285 - 299
  • [32] Structure of the LexA repressor-DNA complex probed by affinity cleavage and affinity photo-cross-linking
    Dumoulin, P
    Ebright, RH
    Knegtel, R
    Kaptein, R
    GrangerSchnarr, M
    Schnarr, M
    BIOCHEMISTRY, 1996, 35 (14) : 4279 - 4286
  • [33] WAVELENGTH DEPENDENCE FOR THE PHOTOREACTIONS OF DNA-PSORALEN MONOADDUCTS .2. PHOTO-CROSS-LINKING OF MONOADDUCTS
    SHI, YB
    HEARST, JE
    BIOCHEMISTRY, 1987, 26 (13) : 3792 - 3798
  • [34] Bioorthogonal Labeling of 5-Hydroxymethylcytosine in Genomic DNA and Diazirine-Based DNA Photo-Cross-Linking Probes
    Song, Chun-Xiao
    He, Chuan
    ACCOUNTS OF CHEMICAL RESEARCH, 2011, 44 (09) : 709 - 717
  • [35] Laser-induced photo-cross-linking of cisplatin-modified DNA to HMG-domain proteins
    Mikata, Y
    He, Q
    Lippard, SJ
    BIOCHEMISTRY, 2001, 40 (25) : 7533 - 7541
  • [36] Critical Evaluation of Photo-cross-linking Parameters for the Implementation of Efficient DNA-Encoded Chemical Library Selections
    Sannino, Alessandro
    Gironda-Martinez, Adrian
    Gorre, Emile M. D.
    Prati, Luca
    Piazzi, Jacopo
    Scheuermann, Joerg
    Neri, Dario
    Donckele, Etienne J.
    Samain, Florent
    ACS COMBINATORIAL SCIENCE, 2020, 22 (04) : 204 - 212
  • [37] Identification of tyrosine 204 as the photo-cross-linking site in the DNA -: EcoRI DNA methyltransferase complex by electrospray ionization mass spectrometry
    Wong, DL
    Reich, NO
    BIOCHEMISTRY, 2000, 39 (50) : 15410 - 15417
  • [38] Photo-cross-linking reactions in RNA-DNA heteroduplexes using photoreactive DNA incorporated with diazirine and aryl azide warheads
    Matsuo, Kazuya
    Kitamura, Machiko
    Kobata, Kentaro
    Unita, Daiki
    Waku, Tomonori
    Kobori, Akio
    CHEMISTRY LETTERS, 2024, 53 (08)
  • [39] TELOMERIC PROTEIN-DNA POINT CONTACTS IDENTIFIED BY PHOTO-CROSS-LINKING USING 5-BROMODEOXYURIDINE
    HICKE, BJ
    WILLIS, MC
    KOCH, TH
    CECH, TR
    BIOCHEMISTRY, 1994, 33 (11) : 3364 - 3373
  • [40] Synthesis of trifunctional PNA-benzophenone derivatives for mitochondrial targeting, selective DNA binding, and photo-cross-linking
    Ross, GF
    Smith, PM
    McGregor, A
    Turnbull, DM
    Lightowlers, RN
    BIOCONJUGATE CHEMISTRY, 2003, 14 (05) : 962 - 966
12345