α-Піридинові аналоги 2,5-диарилоксазолу як хемосенсорні сполуки, чутливі до іонів важких металів
Анотація
Синтезовано декілька оксазольних похідних на основі α-піридикарбонової кислоти, досліджені їх спектрально-флуоресцентні властивості, протолітичні взаємодії та комплексоутворення з іонами важких металів - кадмію та ртуті. Показана перспективність сполук цього класу для подальшої розробки на їх основі флуоресцентних хемосенсорів з чутливістю до іонів полівалентних металів-токсикантів.
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Hutchinson T.C., Meema K.M. Lead, Mercury, Arsenic and Cadmium in the Environment.- Wiley: New York, 1987.- P. 1-8.
Scoullos G.H., Vonkeman M.J., Thorton L., Makuch Z. Mercury, Cadmium, and Lead: Hand-book for Sustainable Heavy Metals Policy and Regulation (Environment & Policy), vol. 31.- Kluwer Academic: Norwell, MA, 2001.
Coester C.J. Trends in environmental analysis // Anal. Chem.- 2005.- V. 77.- P. 3737-3754.
Richardson S.D., Temes T.A. Water analysis: emerging contaminants and current issues // Anal. Chem.- 2005.- V. 77.- P. 3807-3838.
Mercury Update Impact on Fish Advisories, EPA Fact Sheet EPA-823-F-01-011. EPA, Office of Water: Washington, DC, 2001.- P. 1-10.
Safavi A., Bagheri M. Design and characteristics of a mercury (II) optode based on immobili-zation of dithizone on a triacetylcellulose membrane // Sens. Actuators B.- 2004.- V. 99.- P. 608–612.
Shamsipur M., Hosseini M., Alizadeh K., Alizadeh N., Yari A., Caltagirone C., Lippolis V. Novel fluorimetric bulk optode membrane based on a dansylamidopropyl pendant arm deriva-tive of 1-aza-4,10-dithia-7-oxacyclododecane ([12]aneNS2O) for selective subnanomolar de-tection of Hg(II) // Anal. Chem. Acta.- 2005.- V. 533.- P. 17-24.
Bennun L., Gomez G. Determination of mercury by total-reflection X-ray fluorescence using amalgamation with gold // Spectrochim. Acta B.- 1999.- V. 54.- P.1291-1301.
Powell M.J., Quan E.S.K., Boomer D.W., Wiederin D.R. Inductively coupled plasma mass spectrometry with direct injection nebulization for mercury analysis of drinking water // Anal. Chem.- 1992.- V. 64.- P. 2253-2257.
Burrini C., Cagnini A. Determination of mercury in urine by ET-AAS using complexation with dithizone and extraction with cyclohexane // Talanta.- 1997.- V. 44.- P. 1219-1223.
Shafawi A., Ebdon L., Foulkes M., Stockwell P., Corns W. Determination of total mercury in hydrocarbons and natural gas condensate by atomic fluorescence spectrometry // Analyst.- 1999.- V. 124.- P. 185-189.
Yamini Y., Alizadeh N., Shamsipour M. Solid phase extraction and determination of ultra trace amounts of mercury(II) using octadecyl silica membrane disks modified by hexathia-18-crown-6-tetraone and cold vapour atomic absorption spectrometry // Anal. Chim. Acta.- 1997.- V. 355.- P. 69-74.
Anthemidis A.N., Zachariadis G.A., Michos C.E., Stratis J.A. Time-based on-line preconcen-tration cold vapour generation procedure for ultra-trace mercury determination with induc-tively coupled plasma atomic emission spectrometry // Anal. Bioanal. Chem.- 2004.- V. 379.- P. 764-769.
Meng W., Weiyue F., Junwen S., Weiyue F., Fang Z., Bing W., Motao Z., Bai L., Yuliang Z., Zhifang C. Development of a mild mercaptoethanol extraction method for determination of mercury species in biological samples by HPLC–ICP-MS // Talanta.- 2007.- V. 71.- P. 2034-2039.
Nolan E.M., Lippard S.J. Tools and tactics for the optical detection of mercury ion // Chem. Rev.- 2008.- V. 108.- P. 3443-3480.
Coskun A., Yilmaz M.D., Akkaya E.U. Bis(2-pyridyl)-substituted boratriazaindacene as an NIR-emitting chemosensor for Hg(II) // Org. Lett.- 2007.- V. 9.- P. 607-609.
Liu B., Tian H. A selective fluorescent ratiometric chemodosimeter for mercury ion // Chem. Commun.- 2005.- P. 3156–3158.
Zhu X.J., Fu S.T., Wong W.K., Guo H.P., Wong W.Y. A near-infrared-fluorescent chemodo-simeter for mercuric ion based on an expanded porphyrin // Angew. Chem. Int. Ed.- 2006.- V. 45.- P.- 3150-3154.
Zheng H., Qian Z.H., Xu L., Yuan F.F., Lan L.D., Xu J.G. Switching the recognition prefer-ence of rhodamine B spirolactam by replacing one atom: design of Rhodamine B thiohy-drazide for recognition of Hg(II) in aqueous solution // Org. Lett.- 2006.- V. 8.- P. 859-861.
Chen P., He C. A general strategy to convert the MerR family proteins into highly sensitive and selective fluorescent biosensors for metal ions // J. Am. Chem. Soc.- 2004.- V. 126.- P. 728-729.
Ono A., Togashi H. Highly selective oligonucleotide-based sensor for Mercury(II) in aqueous solutions // Angew. Chem. Int. Ed.- 2004.- V. 43.- P. 4300-4302.
Wu J.S., Hwang I.C., Kim K.S., Kim J.S. Rhodamine-based Hg2+-selective chemodosimeter in aqueous solution: fluorescent OFF–ON // Org. Lett.- 2007.- V. 9.- P. 907-910.
Wang J., Qian X., Cui J. Detecting Hg2+ ions with an ICT fluorescent sensor molecule: re-markable emission spectra shift and unique selectivity // J. Org. Chem.- 2006.- V. 71.- P. 4308-4311.
Nolan E.M., Lippard S.J. MS4, a seminaphthofluorescein-based chemosensor for the ratiomet-ric detection of Hg(II) // J. Mater. Chem.- 2005.- V. 15.- P. 2778-2783.
Nolan E.M., Lippard S.J. Turn-On and ratiometric mercury sensing in water with a red-emitting probe // J. Am. Chem. Soc.- 2007.- V. 129.- P. 5910-5918.
Guo W., Yuan J., Wang E. Oligonucleotide-stabilized Ag nanoclusters as novel fluorescence probes for the highly selective and sensitive detection of the Hg2+ ion // Chem. Commun.- 2009.- P. 3395–3397.
Wang Z., Lee J.H., Lu Y. Highly sensitive “turn-on” fluorescent sensor for Hg2+ in aqueous solution based on structure-switching DNA // Chem. Commun.- 2008.- P. 6005–6007.
Yang R., Jin J., Long L., Wang L., Wang H., Tan W. Reversible molecular switching of mo-lecular beacon: controlling DNA hybridization kinetics and thermodynamics using mer-cury(II) ions // Chem. Commun.- 2009.- P. 322–324.
Tian M., Ihmels H. Selective ratiometric detection of mercury(II) ions in water with an acrid-izinium-based fluorescent probe // Chem. Commun.- 2009.- P.- 3175–3177.
Li H., Li Y., Dang Y., Ma L., Wu Y., Hou G., Wu L. An easily prepared hypersensitive water-soluble fluorescent probe for mercury(II) ions // Chem. Commun.- 2009.- P. 4453–4455.
Jana A., Kim J.S., Jung H.S., Bharadwaj P.K. A cryptand based chemodosimetric probe for naked-eye detection of mercury(II) ion in aqueous medium and its application in live cell im-aging // Chem. Commun.- 2009.- P. 4417–4419.
Joshi B.P., Lohani C.R., Lee K.H. A highly sensitive and selective detection of Hg(II) in 100% aqueous solution with fluorescent labeled dimerized Cys residues // Org. Bio. Chem.- 2010.- V. 8.- P. 3220-3226.
Yoon S., Miller E.W., He Q., Do P.H., Chang C. A bright and specific fluorescent sensor for mercury in water, cells, and tissue // Angew. Chem. Int. Ed.- 2007.- V. 46.- P. 6658-6661.
Ma L.J., Li Y., Li L., Sun J., Tian C., Wu Y. A protein-supported fluorescent reagent for the highly-sensitive and selective detection of mercury ions in aqueous solution and live cells // Chem. Commun.- 2008.- P. 6345–6347.
Yang M.H., Lohani C.R., Cho H., Lee K.H. A methionine-based turn-on chemical sensor for selectively monitoring Hg2+ ions in 100% aqueous solution // Org. Biomol. Chem.- 2011.- V. 9.- P. 2350-2356.
Nolan E.M., Lippard S.J.A. Turn-on fluorescent sensor for the selective detection of mercuric ion in aqueous media // J. Am. Chem. Soc.- 2003.- V. 125.- P. 14270-14271.
Melhuish W.H. Absolute spectrofluorometry // J. Res. Nat. Bur. Stand. USA.– 1972.– V. 76A.– P. 547-560
Albert A., Serjeant E.P. The determination of ionization constants: a laboratory manual.- Chapman and Hall: London.- 1971.
Krasovitskii B.M., Bolotin B.M. Organic Luminescent Materials.- VCH: New York.- 1988.
Reichardt C. Solvatochromic dyes as solvent polarity indicators // Chem. Rev.- 1994.- V. 94.- P. 2319-2358.
Grabowski Z.R., Rotkiewicz K., Siemiarczuk A., Cowley D.J., Baumann W. Twisted in-tramolecular charge transfer states (TICT). A new class of excited states with a full charge separation // // Nouv. J. Chim.-1979.- V. 3.- P. 443-454.
Grabowski Z.R., Rotkiewicz K., Rettig W. Structural changes accompanying intramolecular electron transfer: focus on Twisted Intramolecular Charge-Transfer states and structures // Chem. Rev.- 2003.- V. 103.- P. 3899-4031.
Iliashenko R.Yu., Zozulia O.S., Doroshenko A.O. High Stokes shift long-wavelength energy gap regulated fluorescence in the series of nitro/dimethylamino-substituted ortho-analogs of POPOP // Cent. Eur. J. Chem.- 2011.- V.9.- P.962-971.
Luzanov A.V. The structure of the electronic excitation of molecules in quantum-chemical models // Russ. Chem. Rev.- 1980.- V. 49.- P. 1033-1048.
Luzanov A.V., Zhikol O.A. Electron invariants and excited state structural analysis for electronic transitions within CIS, RPA, and TDDFT models // Int. J. Quant. Chem.- 2010.- V. 110.- P. 902-924.
Parker C. Photoluminescence in solutions.- Elsevier: Amsterdam-Londnon-New York, 1968.