Triazole-Tailored Guanosine Dinucleosides as Biomimetic Ion Channels to Modulate Transmembrane Potential

被引:24
作者
Kumar, Y. Pavan [1 ]
Das, Rabindra Nath [2 ]
Kumar, Sonu [2 ]
Schuette, Ole Mathis [3 ]
Steinem, Claudia [3 ]
Dash, Jyotirmayee [1 ,2 ]
机构
[1] Indian Assoc Cultivat Sci, Dept Organ Chem, Kolkata 700032, India
[2] Indian Inst Sci Educ & Res Kolkata, Dept Chem Sci, Mohanpur 741252, India
[3] Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
关键词
amphiphilic guanosine; click chemistry; ion channels; inhibition; phospholipid bilayers; G-QUADRUPLEX DNA; AMPHIPHILIC HEPTAPEPTIDE; CUBIC PHASE; NILE RED; MEMBRANES; MODELS; PORES; CARBOXYFLUORESCEIN; FLUORESCENT; TRANSPORT;
D O I
10.1002/chem.201304530
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A click ion channel platform has been established by employing a clickable guanosine azide or alkyne with covalent spacers. The resulting guanosine derivatives modulated the traffic of ions across the phospholipid bilayer, exhibiting a variation in conductance spanning three orders of magnitude (pS to nS). Forster resonance energy transfer studies of the dansyl fluorophore with the membrane binding fluorophore Nile red revealed that the dansyl fluorophore is deeply embedded in the phospholipid bilayer. Complementary cytosine can inhibit the conductance of the supramolecular guanosine channels in the phospholipid bilayers.
引用
收藏
页码:3023 / 3028
页数:6
相关论文
共 63 条
  • [1] Self-assembled nucleolipids: from supramolecular structure to soft nucleic acid and drug delivery devices
    Allain, Vanessa
    Bourgaux, Claudie
    Couvreur, Patrick
    [J]. NUCLEIC ACIDS RESEARCH, 2012, 40 (05) : 1891 - 1903
  • [2] Cu(I)-Catalyzed Huisgen Azide-Alkyne 1,3-Dipolar Cycloaddition Reaction in Nucleoside, Nucleotide, and Oligonucleotide Chemistry
    Amblard, Franck
    Cho, Jong Hyun
    Schinazi, Raymond F.
    [J]. CHEMICAL REVIEWS, 2009, 109 (09) : 4207 - 4220
  • [3] LIPOSOME ELECTROFORMATION
    ANGELOVA, MI
    DIMITROV, DS
    [J]. FARADAY DISCUSSIONS, 1986, 81 : 303 - +
  • [4] Nucleobase-containing gelators
    Araki, K
    Yoshikawa, I
    [J]. LOW MOLECULAR MASS GELATORS: DESIGN, SELF-ASSEMBLY, FUNCTION, 2005, 256 : 133 - 165
  • [5] Balasubramanian S, 2006, RSC BIOMOL SCI, pV
  • [6] Targeting G-quadruplexes in gene promoters: a novel anticancer strategy?
    Balasubramanian, Shankar
    Hurley, Laurence H.
    Neidle, Stephen
    [J]. NATURE REVIEWS DRUG DISCOVERY, 2011, 10 (04) : 261 - 275
  • [7] Enhanced resonator sensitivity with nanostructured porous silica coatings
    Bhansali, S. H.
    Jarvis, J. M.
    Aksay, I. A.
    Carbeck, J. D.
    [J]. LANGMUIR, 2006, 22 (15) : 6676 - 6682
  • [8] Metal-Organic Transmembrane Nanopores
    Boccalon, Mariangela
    Iengo, Elisabetta
    Tecilla, Paolo
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (50) : 20310 - 20313
  • [9] Biosensing with conically shaped nanopores and nanotubes
    Choi, Youngseon
    Baker, Lane A.
    Hillebrenner, Heather
    Martin, Charles R.
    [J]. PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2006, 8 (43) : 4976 - 4988
  • [10] The application of DNA and RNA G-quadruplexes to therapeutic medicines
    Collie, Gavin W.
    Parkinson, Gary N.
    [J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (12) : 5867 - 5892