8-Aza-2 `-deoxyisoguanosine Forms Fluorescent Hydrogels whereas 8-Aza-2 `-deoxyguanosine Assembles into Nucleoside Nanotubes

Autor(en): Zhao, Hang
Jiang, Dawei
Schaefer, Andreas H.
Seela, Frank
Stichwörter: 8-aza-2-deoxyguanosine; 8-aza-2-deoxyiso- guanosine; ANALOGS; ANTIPARALLEL CHAIN ORIENTATION; BASE; Chemistry; Chemistry, Multidisciplinary; DNA; fluorescence; ISOGUANOSINE PENTAMERS; NUCLEOBASE; nucleoside hydrogels; OLIGONUCLEOTIDE DUPLEXES; PI-GELS; self-assembly; SUPRAMOLECULAR GELS; TAUTOMERISM
Erscheinungsdatum: 2017
Herausgeber: WILEY-V C H VERLAG GMBH
Journal: CHEMPLUSCHEM
Volumen: 82
Ausgabe: 5
Startseite: 778
Seitenende: 784
Zusammenfassung: 
Fluorescent hydrogels have attracted attention for applications in tissue engineering, drug delivery or as molecular machines. This study describes a nucleoside hydrogel formed by 8-aza-2-deoxyisoguanosine (z(8)isoG(d)). The new hydrogel is the first guanosine gel that has intrinsic fluorescence. It has long-term stability and a higher thermal stability (T-gel=77 degrees C) than gels of 2-deoxyisoguanosine (T-gel=67 degrees C) and 2-deoxyguanosine (T-gel=50 degrees C). Furthermore, the minimum gel concentration is lower at 0.3mg per 100L for z(8)isoG(d) compared to 0.7mg for 2-deoxyisoguanosine. Scanning electron microscopy images show that the z(8)isoG(d) gel forms dense bundles of fibers. The related nucleoside 8-aza-2-deoxyguanosine does not form a hydrogel but forms nanotube-like structures in the solid state. The fluorescence of the z(8)isoG(d) hydrogel responds to external stimuli such as the addition of alkali metal ions, pH change, heat, and UV irradiation. In binary mixtures with nucleoside shape mimics such as 7-deaza-2-deoxyisoguanosine, the z(8)isoG(d) hydrogel disintegrates.
ISSN: 21926506
DOI: 10.1002/cplu.201700156

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