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Göteborgs universitets publikationer

Second-Generation Fluorescent Quadracyclic Adenine Analogues: Environment-Responsive Probes with Enhanced Brightness

Författare och institution:
B. Dumat (Institutionen för kemi och kemiteknik, Fysikalisk kemi, Chalmers); Mattias Bood (Institutionen för kemi och molekylärbiologi); Moa Sandberg Wranne (Institutionen för kemi och kemiteknik, Fysikalisk kemi, Chalmers); Chris Lawson (Institutionen för kemi och molekylärbiologi); Anders Foller Larsen (Institutionen för kemi och kemiteknik, Fysikalisk kemi, Chalmers); S. Preus (-); J. Streling (Institutionen för kemi och molekylärbiologi); H. Gradén (-); E. Wellner (-); Morten Grøtli (Institutionen för kemi och molekylärbiologi); Marcus Wilhelmsson (Institutionen för kemi och kemiteknik, Fysikalisk kemi, Chalmers)
Publicerad i:
Chemistry - A European Journal, 21 ( 10 ) s. 4039-4048
ISSN:
0947-6539
E-ISSN:
1521-3765
Publikationstyp:
Artikel, refereegranskad vetenskaplig
Publiceringsår:
2015
Språk:
engelska
Fulltextlänk:
Fulltextlänk (lokalt arkiv):
Sammanfattning (abstract):
Fluorescent base analogues comprise a group of increasingly important molecules for the investigation of nucleic acid structure, dynamics, and interactions with other molecules. Herein, we report on the quantum chemical calculation aided design, synthesis, and characterization of four new putative quadracyclic adenine analogues. The compounds were efficiently synthesized from a common intermediate through a two-step pathway with the Suzuki-Miyaura coupling as the key step. Two of the compounds, qAN1 and qAN4, display brightnesses (εΦF) of 1700 and 2300, respectively, in water and behave as wavelength-ratiometric pH probes under acidic conditions. The other two, qAN2 and qAN3, display lower brightnesses but exhibit polarity-sensitive dual-band emissions that could prove useful to investigate DNA structural changes induced by DNA-protein or -drug interactions. The four qANs are very promising microenvironment-sensitive fluorescent adenine analogues that display considerable brightness for such compounds. Polarity and pH probes: 2-Aminopurine has long been the standard for fluorescent base analogues. Four new fluorescent probes suitable for the replacement of adenine in nucleic acids are presented. Based on their high structural similarity to their parent compound, quadracyclic adenine, they have the potential to be excellent A analogues. Their improved photophysical properties also suggest that they could be significantly brighter than 2-aminopurine inside nucleic acid systems (see figure; ΦF: fluorescence quantum yield).
Ämne (baseras på Högskoleverkets indelning av forskningsämnen):
NATURVETENSKAP ->
Kemi
NATURVETENSKAP ->
Kemi ->
Fysikalisk kemi
NATURVETENSKAP ->
Kemi ->
Fysikalisk kemi ->
Biofysikalisk kemi
NATURVETENSKAP ->
Kemi ->
Fysikalisk kemi ->
Spektroskopi
NATURVETENSKAP ->
Kemi ->
Organisk kemi ->
Fysikalisk organisk kemi
NATURVETENSKAP ->
Kemi ->
Organisk kemi ->
Bioorganisk kemi
Nyckelord:
Aromatic substitution , C-C coupling , Fluorescent probes , Nucleic acids , Nucleobases
Chalmers styrkeområden:
Livsvetenskaper
Nanovetenskap och nanoteknik
Postens nummer:
215167
Posten skapad:
2015-04-13 20:27
Posten ändrad:
2016-06-02 10:56

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