Pyrrolidinyl
peptide nucleic acid internally-labeled with cyanine-styryl dye as a
fluorescence DNA probe
My
research question is to find excellent the environment-sensitive fluorescence labels, alkyne-modified cyanine-styryl
derivatives (STR), which were labeled
onto pyrrolidinyl peptide nucleic acid with
D-proline/(1S,2S)-2-aminocyclopentanecarboxylic
acid backbone (acpcPNA) via sequential reductive alkylation-Click strategy with
the aim to create self-reporting PNA probes that exhibit fluorescence change in
response to the correct DNA target.
The styryl dye family
has received increasing attention as a photostable DNA label that revealed the
excellent colorimetric response in difference microenvironments.
Researchers who have
looked at this subject are Wen-hai Zhan and Rubner. Both of
studies focused on the synthesis and evaluation of styryl dyes capable of
exhibiting turn-on fluorescence through sequence-specific interaction with
nucleic acid in fluorescence spectroscopy and diagnostic application.
Zhan
et al. (2005) argue that the 2-propynyl substituted hemicyanine dyes were
synthesized in a facile route and showed good optical properties that have a
strong absorbance as well as a large strokes shift of the fluorescence emission
maxima. The terminal alkynyl group of dyes was successfully employed for
bioconjugation through a Click strategy with azide-modified cowpea mosaic virus
(CPMV).
Rubner
et al. (2012) argue that the alkyne-modified indole-quinoline styryl dye
(CyIQ) was synthesized and incorporated it into DNA via click chemistry. The
CyIQ dye exhibit good brightness and give excellent photostability.
Debate centers on this
basic issue of the fluorescent properties of cyanine-styryl dyes
which exhibit good brightness. Thus, we are interested in synthesizing new
clickable styryl dyes for attachment onto acpcPNAs with the aim to use them as
DNA sensing probes.
My
work will be closer to Rubner’s in the focus on the synthesis of the alkyne-modified
styryl family for fluorescent labeling and incorporated into nucleic acid as
fluorescent probes.
Hopefully my
contribution will be to synthesize and incorporate into acpcPNA which discriminate
between the complementary DNA and single mismatch DNA and apply in SNP
detection for diagnosis.
Reference
list
Zhan, W-h., Barnhill, H. N., Sivakumar,
K., Tian, H., Wang, Q. (2005). Synthesis of hemicyanine dyes for ‘click’
bioconjugation. Tetrahedron Letters, 46, 1691-1695.
Rubner, M. M., Holzhauser, C.,
Bohlander, P. R., Wagenknecht, H-A. (2012). A “Clickable” Styryl Dye for
Fluorescent DNA labeling by Excitron and Energy Transfer Interactions. Chemistry
- A European Journal, 18, 1299-1302.
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