کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5218974 1383343 2013 8 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Fluorescent p-substituted-phenyl-imidazolo-cytidine analogues
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Fluorescent p-substituted-phenyl-imidazolo-cytidine analogues
چکیده انگلیسی

The synthesis and spectral properties of modified cytidine analogues are described here. To confer fluorescent properties, the cytidine fluorophore was extended by a cinnamyl moiety at the cytidine 5-position, (analogues 1a-c), or extended by a phenyl-imidazolo ring, (analogues 3a-d). Those compounds were synthesized via the Suzuki-Miyaura coupling reaction and via condensation of 5-amino-cytidine with p-substituted benzaldehydes, respectively. All analogues were fluorescent in the blue region (λem: 402-436 nm). Among the above mentioned analogues, p-CF3-phenyl-imidazolo-cytidine, 3d, was found to be a promising fluorescent probe, exhibiting a quantum yield 7000-fold larger than cytidine (Φ=0.617) and a red-shift of ca. 108 nm of maximum emission (411 nm). Its retained Watson-Crick hydrogen bonding face allows 3d to base-pair specifically with guanosine, similar to cytidine. In addition, phenyl-imidazolo-cytidine analogues prefer anti conformation and the C3′-endo (N) sugar puckering. These properties make 3d an attractive fluorescent probe for potential use in the various facets of nucleic acid chemistry.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron - Volume 69, Issue 18, 6 May 2013, Pages 3698-3705
نویسندگان
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