pH-Dependent Optical Properties of Synthetic Fluorescent Imidazoles

Mikhail Y. Berezin; Jeff Kao; Samuel Achilefu

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pH-Dependent Optical Properties of Synthetic Fluorescent Imidazoles

机译：合成荧光咪唑的pH依赖性光学性质

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An imidazole moiety is oftenfound as an integral part of fluorophoresin a variety of fluorescent proteins and many such proteins display pH-dependent light emission.In contrast,synthetic fluorescentcompounds with incorporated imidazoles are rare and have not been studied as pH probes.In this report,the richness of imidazole optical properties, includingpH sensitivity,was demonstrated bymeans of a novel imidazole-based fluorophore1H-imidazol-5-yl-vinylbenz[e]indolium.Three species corresponding to protonated,neutral,and deprotonated imidazoles were identified in the broad range of pH 1-12.The absorption and emission bands of each species were assigned by comparativespectral analysis with synthesizedmono-and di-N-methylated fluorescentimidazole analogues.pKa analysis in the ground and the excited states showed photoacidic properties of the fluorescent imidazoles due to the excitedstate proton transfer(ESPT).Thiseffect was negligible for substitutedimidazoles.The assessment of a pHsensitivecenter in the imidazolering revealed the switching of the pH-sensitivecenters from 1-N in the groundstate to 3-N in the excited state.The effect was attributed to the uniquekind of the excited state charge transfer(ESCT)resulting in a positivecharge swapping between two nitrogens.

机译：通常在各种荧光蛋白中发现咪唑部分是荧光团的组成部分，许多此类蛋白显示出pH依赖的发光。相反，掺有咪唑的合成荧光化合物很少见，因此尚未作为pH探针进行研究。通过新型咪唑基荧光团1H-咪唑-5-基-乙烯基苯并[e]吲哚的方法证明了咪唑光学性质的丰富性，包括pH敏感性。 pH值1-12。通过合成的单和二-N-甲基化的荧光咪唑类似物的比较光谱分析确定每个物种的吸收和发射谱带。在地面和激发态下的pKa分析表明，荧光咪唑的光酸性是由于激发态质子转移（ESPT）。对于取代的咪唑而言，这一影响可以忽略不计。咪唑环中的vecenter揭示了pH敏感中心从基态的1-N转换为激发态的3-N，其影响归因于激发态电荷转移（ESCT）的独特种类，导致电荷之间的正电荷交换两个氮。

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《Chemistry: A European journal》 |2009年第14期|共7页
作者
Mikhail Y. Berezin; Jeff Kao; Samuel Achilefu;
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正文语种 eng
中图分类应用化学;
关键词
charge transfer; emissionspectroscopy; energy transfer; imidazole; pH sensitivity; sensors;

机译：电荷转移发射光谱能量转移咪唑pH敏感度传感器;

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1. pH-Dependent Optical Properties of Synthetic Fluorescent Imidazoles [J] . Mikhail Y. Berezin, Jeff Kao, Samuel Achilefu Chemistry: A European journal . 2009,第14期

机译：合成荧光咪唑的pH依赖性光学性质
2. Interaction of tobacco mosaic virus protein with synthetic polynucleotides containing a fluorescent label: optical properties of poly (A,εA) and poly (C,εC) copolymers and energy migration from the tryptophan to 1,N6 or 3,N4-ethenocytosine residues in RNP [J] . A.A. Bogdanov, A.A. Kost, A.P. Razjivin, Nucleic acids research . 1978,第11期

机译：烟草叶片病毒蛋白与含有荧光标记的合成多核苷酸的相互作用：聚（a，εaaa）和聚（c，εc）共聚物的光学性质和从色氨酸至1，n6或3，RNP中的N4- ethenocytosine残基
3. Interaction of tobacco mosaic virus protein with synthetic polynucleotides containing a fluorescent label: optical properties of poly (A,εA) and poly (C,εC) copolymers and energy migration from the tryptophan to 1,N6 or 3,N4-ethenocytosine residues in RNP [J] . A.A. Bogdanov, A.A. Kost, A.P. Razjivin, Nucleic acids research . 1978,第11期

机译：烟草叶片病毒蛋白与含有荧光标记的合成多核苷酸的相互作用：聚（a，εaaa）和聚（c，εc）共聚物的光学性质和从色氨酸至1，n6或3，RNP中的N4- ethenocytosine残基
4. Electronic, nonlinear optical and optical limiting properties of 2-amino-3-(1H-imidazole-4-yl) propanoic tetrafluoroborate (2A3PT) single crystal [C] . M. Madhangi, RO. MU. Jauhar, P. Murugakoothan DAE Solid State Physics Symposium . 2020

机译：2-氨基-3-（1H-咪唑-4-基）的电子，非线性光学和光学限制性质的2-氨基-3-（1H-咪唑-4-基）丙酸四氟硼酸盐（2A3PT）单晶
5. Synthetic analogs of bilirubin: Syntheses, conformational analysis, circular dichroism, and metabolism and novel fluorescent probes: Xanthoglow syntheses and optical properties. [D] . Brower, Justin Orion. 2001

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6. pH-Dependent Optical Properties of Synthetic Fluorescent Imidazoles [O] . Mikhail Y. Berezin, Jeff Kao, Samuel Achilefu -1

机译：合成荧光咪唑的pH依赖性光学性质
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8. Coastal Benthic Optical Properties (CoBOP) of Coral Reef Environments: Small Scale Fluorescent Optical Signatures and Hyperspectral Remote Sensing of Coral Reef Habitats. [R] . Lesser, M. P. 2003

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pH-Dependent Optical Properties of Synthetic Fluorescent Imidazoles

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