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Selective Fluorescent Detection of RNA in Living Cells by Using Imidazolium-Based Cyclophane
Shirinfar, Bahareh,Ahmed, Nisar,Park, Yu Shin,Cho, Gun-Sik,Youn, Il Seung,Han, Jin-Kwan,Nam, Hong Gil,Kim, Kwang S. American Chemical Society 2013 JOURNAL OF THE AMERICAN CHEMICAL SOCIETY - Vol.135 No.1
<P>A water-soluble imidazolium-based fluorescent chemosensor senses RNA selectively through fluorescence enhancement over other biologically relevant biomolecules in aqueous solution at physiological pH 7.4. Fluorescence image detection of RNA in living cells such as onion cells, HeLa cells, and animal model cells was successfully demonstrated which displays a chelation-enhanced fluorescence effect. These affinities can be attributed to the strong electrostatic (C–H)<SUP>+</SUP>···A<SUP>–</SUP> ionic H-bonding and the aromatic moiety driven π-stacking of imidazolium-based cyclophane with the size-complementary major groove of RNA.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/jacsat/2013/jacsat.2013.135.issue-1/ja3112274/production/images/medium/ja-2012-112274_0005.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/ja3112274'>ACS Electronic Supporting Info</A></P>
Ahmed, Nisar,Shirinfar, Bahareh,Geronimo, Inacrist,Kim, Kwang S. American Chemical Society 2011 ORGANIC LETTERS Vol.13 No.20
<P>A new water-soluble and fluorescent imidazolium-anthracene cyclophane (<B>1</B>) effectively recognizes the biologically important GTP and I<SUP>–</SUP> over other anions in a 100% aqueous solution of physiological pH 7.4. Fluorescence and <SUP>1</SUP>H NMR spectra and ab initio calculations demonstrate that emission arises from the formation of an excimer state and quenching occurs upon GTP/I<SUP>–</SUP> binding through (C–H)<SUP>+</SUP>···A<SUP>–</SUP> hydrogen bond interactions.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/orlef7/2011/orlef7.2011.13.issue-20/ol202183t/production/images/medium/ol-2011-02183t_0006.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/ol202183t'>ACS Electronic Supporting Info</A></P>
Yousuf, Muhammad,Ahmed, Nisar,Shirinfar, Bahareh,Miriyala, Vijay Madhav,Youn, Il Seung,Kim, Kwang S. American Chemical Society 2014 ORGANIC LETTERS Vol.16 No.8
<P>Cationic cyclophanes with bridging and spacer groups possess well-organized semirigid cavities and are able to encapsulate and stabilize anionic species through diverse molecular interactions. We highlight the precise tuning of functionalized cyclophanes toward selective recognition of AMP, GTP, and pyrophosphate (PPi) using fluorescence, NMR spectroscopy, and density functional theory (DFT).</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/orlef7/2014/orlef7.2014.16.issue-8/ol500613y/production/images/medium/ol-2014-00613y_0006.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/ol500613y'>ACS Electronic Supporting Info</A></P>
Ahmed, Nisar,Suresh, Vangaru,Shirinfar, Bahareh,Geronimo, Inacrist,Bist, Amita,Hwang, In-Chul,Kim, Kwang S. The Royal Society of Chemistry 2012 Organic & biomolecular chemistry Vol.10 No.10
<P><I>Cyclo</I>-bis-(urea-3,6-dichlorocarbazole) (<B>1</B>) forms a 1 : 2 complex with CH<SUB>3</SUB>CO<SUB>2</SUB><SUP>−</SUP> and H<SUB>2</SUB>PO<SUB>4</SUB><SUP>−</SUP> through hydrogen bonding with the two urea moieties, resulting in fluorescence enhancement <I>via</I> a combined photoinduced electron transfer (PET) and energy transfer mechanism. The binding mechanism involves a conformational change of the two urea receptors to a <I>trans</I> orientation after binding of the first anion, which facilitates the second interaction.</P> <P>Graphic Abstract</P><P><I>Cyclo</I>-bis-(urea-3,6-dichlorocarbazole) (<B>1</B>) forms a 1 : 2 complex with CH<SUB>3</SUB>CO<SUB>2</SUB><SUP>−</SUP> and H<SUB>2</SUB>PO<SUB>4</SUB><SUP>−</SUP> through hydrogen bonding with the two urea moieties, resulting in fluorescence enhancement <I>via</I> a combined photoinduced electron transfer (PET) and energy transfer mechanism. <IMG SRC='http://pubs.rsc.org/services/images/RSCpubs.ePlatform.Service.FreeContent.ImageService.svc/ImageService/image/GA?id=c2ob06994f'> </P>