The application of natural drug-curcumin in the detection hypochlorous acid of real sample and its bioimaging

Abstract The detection property of natural drug-curcumin (1) was firstly reported by us. Experimental details showed 1 acts as an excellent UV–vis and fluorescent selectivity, sensitivity probe for the detection of hypochlorous acid, while other reactive oxygen species (ROS) and reactive nitrogen species (RNS) induced no changes in UV–vis spectra and fluorescence quench properties of 1. A possible detection mechanism is that HOCl oxidized phenol of 1 into quinone resulting in a non-fluorescent curcumin derivative. Furthermore, the ability of probe to detect ClO− in living cells was also evaluated (HepG2 cells) via a cancelation of the fluorescence. Moreover, the application of 1 in quantitative analysis of hypochlorite in 84 disinfectant was also illustrated.

[1]  M. Davies,et al.  Absolute rate constants for the reaction of hypochlorous acid with protein side chains and peptide bonds. , 2001, Chemical research in toxicology.

[2]  Yue Wu,et al.  Binding of curcumin with bovine serum albumin in the presence of ι-carrageenan and implications on the stability and antioxidant activity of curcumin. , 2013, Journal of agricultural and food chemistry.

[3]  T. Masuda,et al.  Structural identification of new curcumin dimers and their contribution to the antioxidant mechanism of curcumin. , 2002, Journal of agricultural and food chemistry.

[4]  Youngjoo Lee,et al.  Curcumin and genistein coloaded nanostructured lipid carriers: in vitro digestion and antiprostate cancer activity. , 2013, Journal of agricultural and food chemistry.

[5]  J. Qin,et al.  A highly specific rhodamine-based colorimetric probe for hypochlorites: a new sensing strategy and real application in tap water. , 2011, Chemical communications.

[6]  J. Qin,et al.  Colorimetric hypochlorite detection using an azobenzene acid in pure aqueous solutions and real application in tap water , 2012 .

[7]  M. Davies,et al.  Evidence for rapid inter- and intramolecular chlorine transfer reactions of histamine and carnosine chloramines: implications for the prevention of hypochlorous-acid-mediated damage. , 2006, Biochemistry.

[8]  I. Shin,et al.  A rhodamine-hydroxamic acid-based fluorescent probe for hypochlorous acid and its applications to biological imagings. , 2009, Organic letters.

[9]  Weiying Lin,et al.  A ratiometric fluorescent probe for hypochlorite based on a deoximation reaction. , 2009, Chemistry.

[10]  Robert A Newman,et al.  Bioavailability of curcumin: problems and promises. , 2007, Molecular pharmaceutics.

[11]  Hongtao Zhao,et al.  Superoxide reacts with hydroethidine but forms a fluorescent product that is distinctly different from ethidium: potential implications in intracellular fluorescence detection of superoxide. , 2003, Free radical biology & medicine.

[12]  Deqing Zhang,et al.  4,5-dimethylthio-4'-[2-(9-anthryloxy)ethylthio]tetrathiafulvalene, a highly selective and sensitive chemiluminescence probe for singlet oxygen. , 2004, Journal of the American Chemical Society.

[13]  Tak W. Kee,et al.  Diamide linked γ-cyclodextrin dimers as molecular-scale delivery systems for the medicinal pigment curcumin to prostate cancer cells. , 2013, Molecular pharmaceutics.

[14]  Y. Surh,et al.  Curcumin exerts antidifferentiation effect through AMPKalpha-PPAR-gamma in 3T3-L1 adipocytes and antiproliferatory effect through AMPKalpha-COX-2 in cancer cells. , 2009, Journal of agricultural and food chemistry.

[15]  J. Qin,et al.  Simple triphenylamine-based luminophore as a hypochlorite chemosensor , 2010 .

[16]  P. Tam,et al.  A highly specific BODIPY-based fluorescent probe for the detection of hypochlorous acid. , 2008, Organic letters.

[17]  Y. Urano,et al.  Development of an Si-rhodamine-based far-red to near-infrared fluorescence probe selective for hypochlorous acid and its applications for biological imaging. , 2011, Journal of the American Chemical Society.

[18]  Dengqing Zhang.  Highly selective and sensitive colorimetric probes for hypochlorite anion based on azo derivatives. , 2010, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[19]  W. Lee,et al.  Ratiometric and turn-on monitoring for heavy and transition metal ions in aqueous solution with a fluorescent peptide sensor. , 2009, Talanta.

[20]  B. Aggarwal,et al.  Potential therapeutic effects of curcumin, the anti-inflammatory agent, against neurodegenerative, cardiovascular, pulmonary, metabolic, autoimmune and neoplastic diseases. , 2009, The international journal of biochemistry & cell biology.

[21]  R. Basha,et al.  The impact of curcumin on breast cancer. , 2012, Integrative biology : quantitative biosciences from nano to macro.

[22]  Weihong Zhu,et al.  Steric hindrance-enforced distortion as a general strategy for the design of fluorescence "turn-on" cyanide probes. , 2013, Chemical communications.

[23]  Rupesh Kumar Basniwal,et al.  Curcumin nanoparticles: preparation, characterization, and antimicrobial study. , 2011, Journal of agricultural and food chemistry.

[24]  Zhong-Ning Chen,et al.  An iridium(III) complex of oximated 2,2'-bipyridine as a sensitive phosphorescent sensor for hypochlorite. , 2011, The Analyst.

[25]  Huan Yu,et al.  Oxidative cleavage-based near-infrared fluorescent probe for hypochlorous acid detection and myeloperoxidase activity evaluation. , 2014, Analytical chemistry.

[26]  Jianbin Chao,et al.  A fluorescein-based highly specific colorimetric and fluorescent probe for hypochlorites in aqueous solution and its application in tap water , 2012 .

[27]  P. Pizzo,et al.  Grp94 acts as a mediator of curcumin-induced antioxidant defence in myogenic cells , 2010, Journal of Cellular and Molecular Medicine.

[28]  T. Osawa,et al.  Involvement of the beta-diketone moiety in the antioxidative mechanism of tetrahydrocurcumin. , 1996, Biochemical pharmacology.

[29]  Deqing Zhang,et al.  A highly selective naked-eye probe for hypochlorite with the p-methoxyphenol-substituted aniline compound , 2010 .

[30]  Zhaoxin Lu,et al.  Study on the antibiotic activity of microcapsule curcumin against foodborne pathogens. , 2009, International journal of food microbiology.

[31]  G. Nair,et al.  Antimicrobial Activity of Curcumin against Helicobacter pylori Isolates from India and during Infections in Mice , 2009, Antimicrobial Agents and Chemotherapy.

[32]  Jiahuai Han,et al.  A self-referenced nanodosimeter for reaction based ratiometric imaging of hypochlorous acid in living cells , 2013 .

[33]  Juyoung Yoon,et al.  A highly specific fluorescent probe for hypochlorous acid and its application in imaging microbe-induced HOCl production. , 2013, Journal of the American Chemical Society.

[34]  J. Qin,et al.  Naked-eye visible and fluorometric dual-signaling chemodosimeter for hypochlorous acid based on water-soluble p-methoxyphenol derivative. , 2011, Organic & biomolecular chemistry.