- Cell-Permeable Fluorogenic Probes for Identification and Imaging Nitroreductases in Live Bacterial Cells
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Enzyme-activated fluorogenic probes, which invoke enzymatic catalysis to trigger the generation of fluorescence, provide a versatile platform for monitoring biological processes. The development of fluorogenic probes that can readily penetrate the cell envelopes of bacteria are essential to examine intracellular targets of live bacterial cells. Herein, we present the design, synthesis, properties, and biological applications of two series of fluorogenic probes based on cyanine 5 for identification of bacterial nitroreductase (NTR). The selected fluorogenic probe 3 generates a rapid 10-fold fluorescence response after being catalytically reduced by NTR to the intermediate para-aminobenzyl substituted which then underwent a rearrangement elimination reaction. Moreover, probe 3 is cell permeable for both Gram-positive and Gram-negative bacterial cell envelopes and is selective for NTR over other biological analytes, thus minimizing the background signal and enabling the real-time intracellular imaging of NTR in live bacterial cells.
- Ji, Yubin,Wang, Yali,Zhang, Na,Xu, Shengnan,Zhang, Leilei,Wang, Qinghua,Zhang, Qingyang,Hu, Hai-Yu
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- Synthesis, characterization, and UV–visible study of some new photochromic formyl-containing 1′,3′,3′-trimethylspiro[chromene-2,2′-indoline] derivatives
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The spiropyran derivatives can exist in two forms, the closed-ring spiropyran form and the open-ring merocyanine (MC) form. The SP form could be converted into the MC form upon UV irradiation. In this work, some 1′,3′,3′-trimethylspiro[chromene-2,2′-indoline] derivatives containing the nitro and formyl groups are synthesized via the reaction of 1,3,3-trimethyl-2-methylene-5-nitroindoline with the corresponding salicylaldehyde derivatives. These compounds have different photochromic behaviors. The synthesized photochromic molecules are characterized by the FT-IR, 1H-NMR, and 13C-NMR spectroscopic techniques. In order to investigate the photochromic properties of these compounds, the UV–visible spectroscopic analyses of their methanolic solutions before and after exposure to a UV lamp (in the spectral range of 360–400?nm) are studied. Graphic abstract: [Figure not available: see fulltext.].
- Sepehr, Zeinalabedin,Nasr-Isfahani, Hossein,Mahdavian, Ali Reza,Amin, Amir Hossein
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p. 3061 - 3067
(2021/05/27)
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- Comparative Evaluation of Substituent Effect on the Photochromic Properties of Spiropyrans and Spirooxazines
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Spiropyrans and spirooxazines represent an important class of photochromic compounds with a wide variety of applications. In order to effectively utilize and design these photoswitches it is desirable to understand how the substituents affect photochromic properties, and how the different structural motifs compare under identical conditions. In this work a small library of photoswitches was synthesized in order to comparatively evaluate the effect of substituent modifications and structure on photochromism. The library was designed to modify positions that were believed to have the greatest effect on C-O bond lability and therefore the photochromic properties. Herein we report a comparative analysis of the UV and visible light responses of 30 spiropyrans, spiroindolinonaphthopyrans, and spirooxazines. The influence of gadolinium(III) binding was also investigated on the library of compounds to determine its effect on photoswitching. Both assays demonstrated different trends in substituent and structural requirements for optimal photochromism.
- Balmond, Edward I.,Tautges, Brandon K.,Faulkner, Andrea L.,Or, Victor W.,Hodur, Blanka M.,Shaw, Jared T.,Louie, Angelique Y.
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p. 8744 - 8758
(2016/10/14)
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- Radioactivity-synchronized fluorescence enhancement using a radionuclide fluorescence-quenched dye
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(Chemical Equation Presented) We demonstrate the first evidence of radioactivity-synchronized fluorescence quenching of a near-infrared light-emitting dye by a radionuclide, 64Cu, and subsequent fluorescence enhancement upon 64Cu decay to the daughter isotopes 64Ni and 64Zn. The dynamic switch from high radioactivity and low fluorescence to low radioactivity and high fluorescence is potentially useful for developing complementary multimodal imaging and detection platforms for chemical, environmental, and biomedical applications as well as for unraveling the mechanisms of metal-induced dynamic fluorescence changes.
- Berezin, Mikhail Y.,Guo, Kevin,Teng, Bao,Edwards, W. Barry,Anderson, Carolyn J.,Vasalatiy, Olga,Gandjbakhche, Amir,Griffiths, Gary L.,Achilefu, Samuel
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supporting information; experimental part
p. 9198 - 9200
(2009/12/05)
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- Synthesis of some new substituted photochromic N,N′-bis(spiro[1- benzopyran-2,2′-indolyl])diazacrown systems with substituent control over ion chelation
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The reversible photochemical ion chelation of the newly synthesised substituted N,N′-bis(spiro[1-benzopyran-2,2′-indolyl])diazacrown systems 15a-c and the subsequent molecular electronic control of this process using appropriately placed substituent groups on the spiro-benzopyran skeleton is reported. The principle of molecular electronic control of ion chelation is demonstrated by comparing the behaviour of the newly synthesised nitro-substituted and pyrido-annulated spiro-benzopyran system 9b with that of the unsubstituted compound 9a. Electronic substituent control over ion chelation is then exemplified for the new N,N′-bis(5′-nitrospiro[1- benzopyran-2,2′-indolyl])diazacrown system 15c and further exemplified for the corresponding 5′-trifluoromethyl derivative 15b, which contains the photochemically more robust trifluoromethyl group. The crown system 15a, unsubstituted in the spiro-indole moiety, is also reported. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
- Roxburgh, Craig J.,Sammes, Peter G.
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p. 1050 - 1056
(2007/10/03)
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- Synthesis and structure of indoline spiropyrans of the coumarin series
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New indoline spiropyrans of the coumarin series were synthesized by the condensation of indoline and hydroxyformylcoumarin derivatives. Spiropyrans, viz., derivatives of 8-formyl-7-hydroxy-4-methylcoumarin and 5-formyl-6-hydroxy-4-methylcoumarin, under irradiation are transformed into open forms, which are recyclized in the dark. The compounds formed by the condensation of the indoline derivatives with 3-formyl-4-hydroxycoumarin have an open structure of the merocyanine dyes and are transformed into spiro forms neither in the dark nor under irradiation with the visible light.
- Traven,Miroshnikov,Chibisova,Barachevsky,Venidiktova,Strokach
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p. 2417 - 2424
(2007/10/03)
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- Cyanine Borate Salts That Form Penetrated Ion Pairs in Benzene Solution: Synthesis, Properties, and Structure
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A series of cyanine borate salts were prepared and studied by laser spectroscopy, fluorescence spectroscopy, NMR spectral methods, and computer modeling.Analysis of the chemical, physical, and spectral properties of these salts shows that, in benzene solution, they form penetrated ion pairs.The center-to-center distance between the ions is less than the sum of the individual ionic radii.We call such structures penetrated ion pairs.Penetration affects the properties of the cyanine dyes in unique ways that are described.
- Murphy, Sean,Yang, Xiquiang,Schuster, Gary B.
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p. 2411 - 2422
(2007/10/02)
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- SYNTHESE DE QUELQUES SPIRO ET SPIRO PHOTOCHROMIQUES. APPLICATION DE LA METHODOLOGIE DE LA RECHERCHE EXPERIMENTALE
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Some spiro I and spiro II substituted by different groups were synthesized in order to evaluate their photochromic properties and to optimize the preparation of spiroheterocyclic systems.In addition, some spiro III were also prepared as reference compounds.Their physical and spectroscopic characteristics (UV, 1H and 13C) were determined.A study using the experimental design methodology allowed to point out the most important factors for improving the reaction yields. KEYWORDS: Photochromism, spirooxazines, spiropyrans, synthesis, 1H NMR, experimental design methodology.
- Pottier, E.,Sergent, M.,Luu, R. Phan Tan,Guglielmetti, R.
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p. 719 - 740
(2007/10/02)
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- PHOTOCHROMISM. SYNTHESIS AND PROPERTIES OF INDOLINOSPIROBENZOTHIOPYRANS
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Novel photochromic compounds, indolinospirobenzothiopyrans, were prepared and their properties in polymer films were examined.The absorption bands of the colored form lie around 100 nm deeper in the long-wave region of the spectrum than are the case with the common spiropyrans.
- Arakawa, Sei'ichi,Kondo, Hirofumi,Seto, Jun'etsu
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p. 1805 - 1808
(2007/10/02)
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