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Murale, Dhiraj P.,Kim, Hwajin,Choi, Wan Sung,Churchill, David G. American Chemical Society 2013 Organic letters Vol.15 No.14
<P>Chemodosimetric action in detection of cysteine and homocysteine (310- and 290-fold) and superoxide inputs (336-fold increase) gives significant fluorescence intensity increases. Detection limits of 2.13 × 10<SUP>–5</SUP> M, 1.37 × 10<SUP>–5</SUP> M, and 2.71 × 10<SUP>–5</SUP> M, respectively, are biorelevant and are consistent with “OR” logic gating, demonstrated in intracellular biothiol detection in neuronal cells by way of novel fluorescein derivatization. As per our knowledge, this is the first example of a novel fluorescent probe based on the nucleophilic substitution reaction of biothiols and superoxide through ester cleavage.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/orlef7/2013/orlef7.2013.15.issue-14/ol401480w/production/images/medium/ol-2013-01480w_0007.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/ol401480w'>ACS Electronic Supporting Info</A></P>
Fluorescence probing of the ferric Fenton reaction <i>via</i> novel chelation
Murale, Dhiraj P.,Manjare, Sudesh T.,Lee, Yoon-Sup,Churchill, David G. The Royal Society of Chemistry 2014 Chemical communications Vol.50 No.3
<P>A new probe-chelator PET dyad was synthesised, which can be used to detect Fe<SUP>3+</SUP><I>via</I> fluorescence enhancement to discriminate between Fe<SUP>2+</SUP> and Fe<SUP>3+</SUP><I>via</I> Fenton chemistry involving hydrogen peroxide. This is the first BODIPY which works as a 2 : 1 multiplexer for Fe<SUP>3+</SUP>, Fe<SUP>2+</SUP> and H<SUB>2</SUB>O<SUB>2</SUB>.</P> <P>Graphic Abstract</P><P>A new probe-chelator PET dyad was synthesised, which can be used to detect Fe<SUP>3+</SUP><I>via</I> fluorescence enhancement to discriminate between Fe<SUP>2+</SUP> and Fe<SUP>3+</SUP><I>via</I> Fenton chemistry involving hydrogen peroxide. <IMG SRC='http://pubs.rsc.org/services/images/RSCpubs.ePlatform.Service.FreeContent.ImageService.svc/ImageService/image/GA?id=c3cc47038e'> </P>
Highly Selective Excited State Intramolecular Proton Transfer (ESIPT)-Based Superoxide Probing
Murale, Dhiraj P.,Kim, Hwajin,Choi, Wan Sung,Churchill, David G. American Chemical Society 2013 Organic letters Vol.15 No.15
<P>Two novel fluorescent probe conjugates of 2-(benzothiazol-2-yl)-phenol (HBT) enable ratiometric and selective superoxide detection by an established <I>excited state intramolecular proton transfer</I> (ESIPT) mechanism giving a 60-fold intensity increase.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/orlef7/2013/orlef7.2013.15.issue-15/ol4017222/production/images/medium/ol-2013-017222_0007.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/ol4017222'>ACS Electronic Supporting Info</A></P>
Ha, Yonghwang,Murale, Dhiraj P.,Yun, Changsuk,Manjare, Sudesh T.,Kim, Hyungjun,Kwak, Juhyoun,Lee, Yoon Sup,Churchill, David G. The Royal Society of Chemistry 2015 Chemical communications Vol.51 No.29
<P>A novel Schiff base probe exhibited strong ‘turn-ON’ fluorescence for Cu<SUP>2+</SUP> at 345 nm, Al<SUP>3+</SUP> at 445 nm, and Cu<SUP>+</SUP> at 360 nm in the presence of Al<SUP>3+</SUP> in organic solvent (acetonitrile), which allowed for construction of molecular logic gates ‘INH’ and ‘1:2 DEMULTIPLEXING.’ H<SUP>+</SUP> generated from Al<SUP>3+</SUP> contributed greatly to Cu<SUP>+</SUP> chemosensing based on a redox non-innocence mechanism.</P> <P>Graphic Abstract</P><P>A novel logic gate containing protecting groups interacts with various species (acetonitrile) with fluorescence responses relating to ligand non innocence. <IMG SRC='http://pubs.rsc.org/services/images/RSCpubs.ePlatform.Service.FreeContent.ImageService.svc/ImageService/image/GA?id=c4cc10025e'> </P>
Solvent-controlled Novel Cu+ and Cu+/2+ Fluorescent “Turn-ON” Probing
하용황,Dhiraj P. Murale,Sudesh T. Manjare,Minseong Kim,Jeong A. Jeong,처칠 대한화학회 2016 Bulletin of the Korean Chemical Society Vol.37 No.1
A novel Schiff base probe, carbamoyl salicylimine benzothiazole hydrazine, was prepared and measured for its probing ability. High sensitivity was shown for Cu+ and Cu2+. When solvent polarity was regulated through a combination of H2O and acetonitrile, selective sensing of Cu+ or the total amount of Cu+ and Cu2+ was possible. In addition, a linear hypsochromic fluorescent shift of about 30 nm was shown. A binding stoichiometry of 1:1 exists at low concentration. Time-dependent emission measurement showed an exponential decay curve (τ1 = 2.99 × 103 s, 10 equiv of Cu+) and a linear decay line (slope = –0.0216, 5 equiv of Cu+). Interference experiments in 50% acetonitrile in H2O showed that the emission produced by Cu+ and Cu2+ was not disturbed by other metal ions or by acidity or basicity. Peroxynitrite changed the emission trends; Cu+ emission decreased (78%) and Cu2+ fluorescence increased (28-fold). Biothiols, l-cysteine, dl-homocysteine, reduced glutathione, and N-acetyl-l-cysteine affected the complete reversibility of Cu+-induced emission in 50% (v/v) acetonitrile in H2O, relative to partial reversibility of Cu2+ emission. Thus, by regulating the ratio between acetonitrile and H2O, Cu+ and Cu+/2+ can be probed selectively.
Singh, Atul P.,Murale, Dhiraj P.,Ha, Yonghwang,Liew, Hyunjeong,Lee, Kang Mun,Segev, Aviv,Suh, Yoo-Hun,Churchill, David G. The Royal Society of Chemistry 2013 Dalton transactions Vol.42 No.10
<P>Novel, high “<I>turn-on</I>” Hg<SUP>2+</SUP> and O<SUB>2</SUB><SUP>−</SUP> fluorescence behaviour (∼25-fold) with probes bearing [<I>S</I><SUB>thi</SUB><I>N</I><SUB>py</SUB>] and [<I>S</I><SUB>thi</SUB><I>N</I><SUB>py</SUB><I>N</I><SUB>py</SUB>] binding receptors, joined by oxidizable sulphides, may involve <I>S</I>-bound transient ROS species; such optical O<SUB>2</SUB><SUP>−</SUP> behaviour operates moderately in neuroblastoma.</P> <P>Graphic Abstract</P><P>Probes bearing [<I>S</I><SUB>thi</SUB><I>N</I><SUB>py</SUB>] binding atoms and joined by oxidizable sulphides engage in selective novel high “<I>turn-on</I>” Hg<SUP>2+</SUP>“<I>AND</I>” O<SUB>2</SUB><SUP>−</SUP> fluorescence behaviour (∼25 times, <I>λ</I><SUB>em</SUB> = 524 nm); transient ROS species may be involved. <IMG SRC='http://pubs.rsc.org/services/images/RSCpubs.ePlatform.Service.FreeContent.ImageService.svc/ImageService/image/GA?id=c2dt32135a'> </P>
Jang, Yoon Jeong,Murale, Dhiraj P.,Churchill, David G. The Royal Society of Chemistry 2014 The Analyst Vol.139 No.7
<P>Herein, we present fluorescein as a reversible fluorescent sensor for nerve agent simulants diethylchlorophosphate (DCP), diethyl methylphosphonate (DEMP), and diethyl cyanophosphonate (DECP). The superoxide allows for an “off–on” mechanism to regenerate fluorescein. The order of decrease in fluorescence intensity for nerve agent simulants is DCP > DEMP ≫ DECP.</P> <P>Graphic Abstract</P><P>A reversible fluorescent sensor for nerve agent simulants diethylchlorophosphate (DCP), diethyl methylphosphonate (DEMP), and diethyl cyanophosphonate (DECP) has been developed (DCP > DEMP ≫ DECP). The superoxide allows for an “off–on” mechanism in which fluorescein is regenerated. <IMG SRC='http://pubs.rsc.org/services/images/RSCpubs.ePlatform.Service.FreeContent.ImageService.svc/ImageService/image/GA?id=c3an02267f'> </P>
Crosstalk between Oxidative Stress and Tauopathy
Haque, Md. Mamunul,Murale, Dhiraj P.,Kim, Yun Kyung,Lee, Jun-Seok MDPI 2019 INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES Vol.20 No.8
<P>Tauopathy is a collective term for neurodegenerative diseases associated with pathological modifications of tau protein. Tau modifications are mediated by many factors. Recently, reactive oxygen species (ROS) have attracted attention due to their upstream and downstream effects on tauopathy. In physiological conditions, healthy cells generate a moderate level of ROS for self-defense against foreign invaders. Imbalances between ROS and the anti-oxidation pathway cause an accumulation of excessive ROS. There is clear evidence that ROS directly promotes tau modifications in tauopathy. ROS is also highly upregulated in the patients’ brain of tauopathies, and anti-oxidants are currently prescribed as potential therapeutic agents for tauopathy. Thus, there is a clear connection between oxidative stress (OS) and tauopathies that needs to be studied in more detail. In this review, we will describe the chemical nature of ROS and their roles in tauopathy.</P>
Novel and selective detection of Tabun mimics
Jang, Yoon Jeong,Tsay, Olga G.,Murale, Dhiraj P.,Jeong, Jeong A.,Segev, Aviv,Churchill, David G. The Royal Society of Chemistry 2014 Chemical communications Vol.50 No.56
<P>Detection of nerve agent-related molecules based on BODIPY–salicylaldehyde oxime conjugation was studied. Fluorescence intensity of the B–SAL–OXIME species increases in the presence of DECP, whereas it decreases in the presence of DCP and DEMP (limit of detection = 997 nM). Benzonitrile formation in the novel fluorescent B–SAL–OXIME system was elucidated using model substrates.</P> <P>Graphic Abstract</P><P>Detection of nerve agent-related molecules based on BODIPY–salicylaldehyde oxime conjugation was studied. <IMG SRC='http://pubs.rsc.org/services/images/RSCpubs.ePlatform.Service.FreeContent.ImageService.svc/ImageService/image/GA?id=c4cc02689f'> </P>