Solid-phase synthesis of oligomers carrying several chromophore units linked by phosphodiester backbones

被引:10
作者
Avino, Anna [1 ,2 ,5 ]
Navarro, Isabel [4 ,5 ]
Farrera-Sinfreu, Josep [3 ]
Royo, Miriam [2 ,3 ]
Aymami, Juan [4 ,7 ]
Delgado, Antonio [6 ,8 ]
Llebaria, Amadeu [6 ]
Albericio, Fernando [1 ,2 ,9 ]
Eritja, Ramon [1 ,2 ,5 ]
机构
[1] IRB Barcelona, Inst Biomed Res, E-08028 Barcelona, Spain
[2] CIBER BBN, Networking Ctr Bioengn Biomat & Nanomed, E-08028 Barcelona, Spain
[3] PCB, Combinatorial Chem Unit, E-08028 Barcelona, Spain
[4] Crystax Pharmaceut SL, E-08028 Barcelona, Spain
[5] CSIC, Spanish Res Council, Inst Adv Chem Catalonia, IQAC, E-08034 Barcelona, Spain
[6] CSIC, Spanish Res Council, Res Unit BioAct Mol, E-08034 Barcelona, Spain
[7] Univ Politecn Cataluna, Dept Engn Quim, E-08028 Barcelona, Spain
[8] Univ Barcelona, Fac Farm, CSIC, Unitat Associada,Unitat Quim Farmaceut, E-08028 Barcelona, Spain
[9] Univ Barcelona, Dept Organ Chem, E-08028 Barcelona, Spain
关键词
chromophore; fluorescence; oligonucleotides; solid-phase synthesis; phosphite-triester; DNA-intercalating drugs;
D O I
10.1016/j.bmcl.2008.02.074
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A method for the preparation of oligomers by linking chromophore units is described. Specifically, the synthesis of chromophore units having a protected-hydroxyl group and a phosphoramidite function is described, along with a method to link several units using solid-phase phosphite-triester protocols. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2306 / 2310
页数:5
相关论文
共 16 条
  • [1] Reaching into the major groove of B-DNA: Synthesis and nucleic acid binding of a neomycin-Hoechst 33258 conjugate
    Arya, DP
    Willis, B
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (41) : 12398 - 12399
  • [2] DNA-dye conjugates for controllable H* aggregation
    Asanuma, H
    Shirasuka, K
    Takarada, T
    Kashida, H
    Komiyama, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (08) : 2217 - 2223
  • [3] ASSELINE U, 1997, NEW J CHEM, V212, P5
  • [4] Solid-phase synthesis of acridine-based threading intercalator peptides
    Carlson, CB
    Beal, PA
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (17) : 1979 - 1982
  • [5] CARUTHERS MH, 1987, METHOD ENZYMOL, V154, P287
  • [6] Intercalating nucleic acids containing insertions of 1-O-(1-pyrenylmethyl)glycerol:: stabilisation of dsDNA and discrimination of DNA over RNA
    Christensen, UB
    Pedersen, EB
    [J]. NUCLEIC ACIDS RESEARCH, 2002, 30 (22) : 4918 - 4925
  • [7] Oligomeric fluorescent labels for DNA
    Cuppoletti, A
    Cho, YJ
    Park, JS
    Strässler, C
    Kool, ET
    [J]. BIOCONJUGATE CHEMISTRY, 2005, 16 (03) : 528 - 534
  • [8] Design of a sequence-specific DNA bisintercalator
    Fechter, EJ
    Olenyuk, B
    Dervan, PB
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (27) : 3591 - 3594
  • [9] Synthesis of DNA with phenanthridinium as an artificial DNA base
    Huber, R
    Amann, N
    Wagenknecht, HA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (03) : 744 - 751
  • [10] THE AUTOMATED SYNTHESIS OF SULFUR-CONTAINING OLIGODEOXYRIBONUCLEOTIDES USING 3H-1,2-BENZODITHIOL-3-ONE 1,1-DIOXIDE AS A SULFUR-TRANSFER REAGENT
    IYER, RP
    PHILLIPS, LR
    EGAN, W
    REGAN, JB
    BEAUCAGE, SL
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (15) : 4693 - 4699