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Fluorescent probes and functional materials for biomedical applications

《化学科学与工程前沿（英文）》 2022年 第16卷 第10期   页码 1425-1437 doi: 10.1007/s11705-022-2163-1

摘要： Due to their simplicity in preparation, sensitivity and selectivity, fluorescent probes have become the analytical tool of choice in a wide range of research and industrial fields, facilitating the rapid detection of chemical substances of interest as well as the study of important physiological and pathological processes at the cellular level. In addition, many long-wavelength fluorescent probes developed have also proven applicable for in vivo biomedical applications including fluorescence-guided disease diagnosis and theranostics (e.g., fluorogenic prodrugs). Impressive progresses have been made in the development of sensing agents and materials for the detection of ions, organic small molecules, and biomacromolecules including enzymes, DNAs/RNAs, lipids, and carbohydrates that play crucial roles in biological and disease-relevant events. Here, we highlight examples of fluorescent probes and functional materials for biological applications selected from the special issues “Fluorescent Probes” and “Molecular Sensors and Logic Gates” recently published in this journal, offering insights into the future development of powerful fluorescence-based chemical tools for basic biological studies and clinical translation.

关键词： fluorescent probes     imaging     cell     biomedicine     biomolecules    

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Recent advances of small-molecule fluorescent probes for detecting biological hydrogen sulfide

《化学科学与工程前沿（英文）》 2022年 第16卷 第1期   页码 34-63 doi: 10.1007/s11705-021-2050-1

摘要： H2S is well-known as a colorless, acidic gas, with a notoriously rotten-egg smell. It was recently revealed that H2S is also an endogenous signaling molecule that has important biological functions, however, most of its physiology and pathology remains elusive. Therefore, the enthusiasm for H2S research remains. Fluorescence imaging technology is an important tool for H2S biology research. The development of fluorescence imaging technology has realized the study of H2S in subcellular organelles, facilitated by the development of fluorescent probes. The probes reviewed in this paper were categorized according to their chemical mechanism of sensing and were divided into three groups: H2S reducibility-based probes, H2S nucleophilicity-based probes, and metal sulfide precipitation-based probes. The structure of the probes, their sensing mechanism, and imaging results have been discussed in detail. Moreover, we also introduced some probes for hydrogen polysulfides.

关键词： hydrogen sulfide     fluorescent probe     reducibility     nucleophilicity     copper sulfide precipitate     hydrogen polysulfides    

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Special issue on “Fluorescent probes”

Adam C. Sedgwick, Tony D. James

《化学科学与工程前沿（英文）》 2020年 第14卷 第1期   页码 1-3 doi: 10.1007/s11705-019-1910-4

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Recent advances in small molecule fluorescent probes for simultaneous imaging of two bioactive molecules

Yongqing Zhou, Xin Wang, Wei Zhang, Bo Tang, Ping Li

《化学科学与工程前沿（英文）》 2022年 第16卷 第1期   页码 4-33 doi: 10.1007/s11705-021-2041-2

摘要： The interrelationships and synergistic regulations of bioactive molecules play pivotal roles in physiological and pathological processes involved in the initiation and development of some diseases, such as cancer and neurodegenerative and cardiovascular diseases. Therefore, the simultaneous, accurate and timely detection of two bioactive molecules is crucial to explore their roles and pathological mechanisms in related diseases. Fluorescence imaging associated with small molecular probes has been widely used in the imaging of bioactive molecules in living cells and due to its excellent performances, including high sensitivity and selectivity, noninvasive properties, real-time and high spatial temporal resolution. Single organic molecule fluorescent probes have been successively developed to simultaneously monitor two biomolecules to uncover their synergistic relationships in living systems. Hence, in this review, we focus on summarizing the design strategies, classifications, and bioimaging applications of dual-response fluorescent probes over the past decade. Furthermore, future research directions in this field are proposed.

关键词： bioactive molecules     fluorescent probes     in living cells and in vivo     review    

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N-Positive ion activated rapid addition and mitochondrial targeting ratiometric fluorescent probes

Yan Shi, Fangjun Huo, Yongkang Yue, Caixia Yin

《化学科学与工程前沿（英文）》 2022年 第16卷 第1期   页码 64-71 doi: 10.1007/s11705-021-2048-8

摘要： Heterocyclic compound quinoline and its derivatives exist in natural compounds and have a broad spectrum of biological activity. They play an important role in the design of new structural entities for medical applications. Similarly, indoles and their derivatives are found widely in nature. Amino acids, alkaloids and auxin are all derivatives of indoles, as are dyes, and their condensation with aldehydes makes it easy to construct reaction sites for nucleophilic addition agents. In this work, we combine these two groups organically to construct a rapid response site (within 30 s) for H S, and at the same time, a ratiometric fluorescence response is presented throughout the process of H S detection. As such, the lower detection limit can reach 55.7 nmol/L for H S. In addition, cell imaging shows that this probe can be used for the mitochondrial targeted detection of endogenous and exogenous H S. Finally, this probe application was verified by imaging H S in nude mice.

关键词： heterocyclic compound     hydrogen sulfide     ratiometric     mitochondrial targeted    

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Information gathering and processing with fluorescent molecules

Brian DALY,Jue LING,A. Prasanna de SILVA

《化学科学与工程前沿（英文）》 2014年 第8卷 第2期   页码 240-251 doi: 10.1007/s11705-014-1432-z

摘要： Molecular information gathering and processing — a young field of applied chemistry — is undergoing good growth. The progress is occurring both in terms of conceptual development and in terms of the strengthening of older concepts with new examples. This review critically surveys these two broad avenues. We consider some cases where molecules emulate one of the building blocks of electronic logic gates. We then examine molecular emulation of various Boolean logic gates carrying one, two or three inputs. Some single-input gates are popular information gathering devices. Special systems, such as ‘lab-on-a-molecule’ and molecular keypad locks, also receive attention. A situation deviating from the Boolean blueprint is also discussed. Some pointers are offered for maintaining the upward curve of the field.

关键词： molecular logic     molecular computation     molecular sensor     fluorescent molecular device     fluorescent sensor    

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Fluorescent properties and

Hong GAO,Jie SONG,Shibin SHANG,Zhanqian SONG

《农业科学与工程前沿（英文）》 2017年 第4卷 第1期   页码 106-115 doi: 10.15302/J-FASE-2017133

摘要： A series of dehydroabietic acid-based diarylamines have been synthesized in order to investigate their fluorescent properties, photostability, cell toxicity and fluorescence imaging. The geometries as well as their molecular properties were optimized at the B3LYP/6-31G* level using Gaussian 03. The results indicate that molecular geometry, HOMO and LUMO energies, and energy gaps are important to predict absorption and fluorescent properties. Five of the compounds can be effectively taken up by human cervical carcinoma, human hepatocellular carcinoma SMMC-7721, human gastric cancer SGC-7901 and human lung adenocarcinoma A549 cells and strong blue fluorescent signals are detected in these cells. These compounds are potential candidates for fluorescent probes in biological diagnosis.

关键词： dehydroabietic acid-based diarylamine     DFT study     fluorescent probe     in vitro imaging    

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A novel flavonol-based colorimetric and turn-on fluorescent probe for rapid determination of hydrazine

《化学科学与工程前沿（英文）》 2023年 第17卷 第1期   页码 24-33 doi: 10.1007/s11705-022-2171-1

摘要： Hydrazine is extremely toxic and causes severe harm to human body. Herein, a novel fluorescent probe 4-oxo-2-styryl-4H-chromen-3-yl thiophene-2-carboxylate (FHT) was synthesized for detecting hydrazine by using natural cinnamaldehyde as starting material. This probe exhibited significantly enhanced fluorescence response towards hydrazine over various common metal ions, anions, and amine compounds. The detection limit of probe FHT for hydrazine was as low as 0.14 μmol·L–1, significantly lower than that of the threshold value of 0.312 μmol·L–1, imposed by the Environmental Protection Agency. Moreover, the proposed probe was able to detect hydrazine within wide pH (5–10) and linear detection ranges (0–110 μmol·L–1). This probe was employed for determining trace hydrazine in different environmental water samples. The probe FHT-loaded filter paper strips were able to conveniently detect hydrazine of low concentration through distinct naked-eye and fluorescent color changes. Importantly, the probe FHT with low cytotoxicity was successfully applied to visualize hydrazine in living Hela cells and zebrafish.

关键词： cinnamaldehyde     3-hydroxychromone derivative     hydrazine     fluorescent probe    

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Novel lysosome-targeted anticancer fluorescent agents used in zebrafish and nude mouse tumour imaging

《化学科学与工程前沿（英文）》 2022年 第16卷 第1期   页码 112-120 doi: 10.1007/s11705-021-2075-5

摘要： The design of three novel fatty nitrogen mustard-based anticancer agents with fluorophores incorporated into the alkene structure (CXL 118, CXL121, and CXL122) is described in this report. The results indicated that these compounds are selectively located in lysosomes and exhibit effective antitumour activity. Notably, these compounds can directly serve as both reporting and imaging agents in vitro and in vivo without the need to add other fluorescent tagging agents.

关键词： fluorescent drug     lysosomal     anticancer     zebrafish     nude-mouse tumour imaging    

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Design and use of group-specific primers and probes for real-time quantitative PCR

Juntaek LIM, Seung Gu SHIN, Seungyong LEE, Seokhwan HWANG

《环境科学与工程前沿（英文）》 2011年 第5卷 第1期   页码 28-39 doi: 10.1007/s11783-011-0302-x

摘要： Real-time quantitative polymerase chain reaction (qPCR) has gained popularity as a technique to detect and quantify a specific group of target microorganisms from various environmental samples including soil, water, sediments, and sludge. Although qPCR is a very useful technique for nucleic acid quantification, accurately quantifying the target microbial group strongly depends on the quality of the primer and probe used. Many aspects of conducting qPCR assays have become increasingly routine and automated; however, one of the most important aspects, designing and selecting primer and probe sets, is often a somewhat arcane process. In many cases, failed or non-specific amplification can be attributed to improperly designed primer-probe sets. This paper is intended to provide guidelines and general principles for designing group-specific primers and probes for qPCR assays. We demonstrate the effectiveness of these guidelines by reviewing the use of qPCR to study anaerobic processes and biologic nutrient removal processes. qPCR assays using group-specific primers and probes designed with this method, have been used to successfully quantify 16S ribosomal Ribonucleic Acid (16S rRNA) gene copy numbers from target methanogenic and ammonia- oxidizing bacteria in various laboratory- and full-scale biologic processes. Researchers with a good command of primer and probe design can use qPCR as a valuable tool to study biodiversity and to develop more efficient control strategies for biologic processes.

关键词： absolute quantification     design guideline     primer     probe     real-time quantitative polymerase chain reaction (qPCR)    

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A highly selective fluorescent probe for real-time imaging of UDP-glucuronosyltransferase 1A8 in living

《化学科学与工程前沿（英文）》 2022年 第16卷 第1期   页码 103-111 doi: 10.1007/s11705-021-2064-8

摘要： Uridine diphosphate (UDP)-glucuronosyltransferases (UGTs) are enzymes involved in the biotransformation of important endogenous compounds such as steroids, bile acids, and hormones as well as exogenous substances including drugs, environmental toxicants, and carcinogens. Here, a novel fluorescent probe BDMP was developed based on boron-dipyrromethene (BODIPY) with high sensitivity for the detection of UGT1A8. The glucuronidation of BDMP not only exhibited a red-emission wavelength (λex/λem = 500/580 nm), but also displayed an excellent UGT1A8-dependent fluorescence signal with a good linear relationship with UGT1A8 concentration. Based on this perfect biocompatibility and cell permeability, BDMP was successfully used to image endogenous UGT1A8 in human cancer cell lines (LoVo and HCT15) in real time. In addition, BDMP could also be used to visualize UGT1A8 in tumor tissues. These results suggested that BDMP is a promising molecular tool for the investigation of UGT1A8-mediated physiological function in humans.

关键词： UDP-glucuronosyltransferase 1A8     fluorescent probe     subtype selectivity     fluorescence imaging    

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Near-infrared benzodiazoles as small molecule environmentally-sensitive fluorophores

《化学科学与工程前沿（英文）》 2022年 第16卷 第1期   页码 128-135 doi: 10.1007/s11705-021-2080-8

摘要： The development of fluorophores emitting in the near-infrared spectral window has gained increased attention given their suitable features for biological imaging. In this work, we have optimised a general and straightforward synthetic approach to prepare a small library of near-infrared-emitting C-bridged nitrobenzodiazoles using commercial precursors. C-bridged benzodiazoles have low molecular weight and neutral character as important features that are not common in most near-infrared dyes. We have investigated their fluorescence response in the presence of a wide array of 60 different biomolecules and identified compound 3i as a potential chemosensor to discriminate between Fe2+ and Fe3+ ions in aqueous media.

关键词： fluorescence     probes     iron     screening     library    

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Enhancement of open circuit voltage in organic solar cells by doping a fluorescent red dye

Qing LI, Junsheng YU, Yue ZANG, Nana WANG, Yadong JIANG

《能源前沿（英文）》 2012年 第6卷 第2期   页码 179-183 doi: 10.1007/s11708-012-0177-y

摘要： The open circuit voltage ( ) of small-molecule organic solar cells (OSCs) could be improved by doping suitable fluorescent dyes into the donor layers. In this paper, 4-(dicyanomethylene)-2-t-butyl-6-(1,1,7,7-tetramethyljulolidyl-9-enyl)-4H-pyran (DCJTB) was used as a dopant, and the performance of the OSCs with different DCJTB concentration in copper phthalocyanine (CuPc) was studied. The results showed that the of the OSC with 50% of DCJTB in CuPc increased by 15%, compared with that of the standard CuPc/fullerene (C ) device. The enhancement of the was attributed to the lower highest occupied molecular orbital (HOMO) level in the DCJTB than that in the CuPc. Also, the light absorption intensity is enhanced between 400 and 550 nm, where CuPc and C have low absorbance, leading to a broad absorption spectrum.

关键词： organic solar cells (OSCs)     open circuit voltage     fluorescent dye doping     4-(dicyanomethylene)-2-t-butyl-6-(1     1     7     7-tetramethyljulolidyl-9-enyl)-4H-pyran (DCJTB)    

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Valorization of agro-industrial fruit peel waste to fluorescent nanocarbon sensor: Ultrasensitive detection

《环境科学与工程前沿（英文）》 2022年 第16卷 第3期 doi: 10.1007/s11783-021-1461-z

摘要：

• Transformation of agro-industrial waste to value-added material via green chemistry.

关键词： Agro-industrial waste     Orange peel     Valorization     Nanodiamond-like carbon     Atropine sulphate     Fluorescence sensing    

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A minimized fluorescent chemosensor array utilizing carboxylate-attached polythiophenes on a chip for

Yui Sasaki, Xiaojun Lyu, Zhoujie Zhang, Tsuyoshi Minami

《化学科学与工程前沿（英文）》 2022年 第16卷 第1期   页码 72-80 doi: 10.1007/s11705-021-2037-y

摘要： Chemosensor arrays have a great potential for on-site applications in real-world scenarios. However, to fabricate on chemosensor array a number of chemosensors are required to obtain various optical patterns for multi-analyte detection. Herein, we propose a minimized chemosensor array composed of only two types of carboxylate-functionalized polythiophene derivatives for the detection of eight types of metal ions. Upon recognition of the metal ions, the polythiophenes exhibited changes in their fluorescence intensity and various spectral shifts. Although both chemosensors have the same polymer backbone and recognition moiety, only the difference in the number of methylene groups contributed to the difference in the fluorescence response patterns. Consequently, the metal ions in aqueous media were successfully discriminated qualitatively and quantitatively by the chemosensor microarray on the glass chip. This study offers an approach for achieving a minimized chemosensor array just by changing the alkyl chain lengths without the necessity for many receptors and reporters.

关键词： metal ions     polythiophene     chemosensor array     fluorescence     pattern recognition    

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标题 作者 时间 类型 操作

Fluorescent probes and functional materials for biomedical applications

期刊论文

Recent advances of small-molecule fluorescent probes for detecting biological hydrogen sulfide

期刊论文

Special issue on “Fluorescent probes”

Adam C. Sedgwick, Tony D. James

期刊论文

Recent advances in small molecule fluorescent probes for simultaneous imaging of two bioactive molecules

Yongqing Zhou, Xin Wang, Wei Zhang, Bo Tang, Ping Li

期刊论文

N-Positive ion activated rapid addition and mitochondrial targeting ratiometric fluorescent probes

Yan Shi, Fangjun Huo, Yongkang Yue, Caixia Yin

期刊论文

Information gathering and processing with fluorescent molecules

Brian DALY,Jue LING,A. Prasanna de SILVA

期刊论文

Fluorescent properties and

Hong GAO,Jie SONG,Shibin SHANG,Zhanqian SONG

期刊论文

A novel flavonol-based colorimetric and turn-on fluorescent probe for rapid determination of hydrazine

期刊论文

Novel lysosome-targeted anticancer fluorescent agents used in zebrafish and nude mouse tumour imaging

期刊论文

Design and use of group-specific primers and probes for real-time quantitative PCR

Juntaek LIM, Seung Gu SHIN, Seungyong LEE, Seokhwan HWANG

期刊论文

A highly selective fluorescent probe for real-time imaging of UDP-glucuronosyltransferase 1A8 in living

期刊论文

Near-infrared benzodiazoles as small molecule environmentally-sensitive fluorophores

期刊论文

Enhancement of open circuit voltage in organic solar cells by doping a fluorescent red dye

Qing LI, Junsheng YU, Yue ZANG, Nana WANG, Yadong JIANG

期刊论文

Valorization of agro-industrial fruit peel waste to fluorescent nanocarbon sensor: Ultrasensitive detection

期刊论文

A minimized fluorescent chemosensor array utilizing carboxylate-attached polythiophenes on a chip for

Yui Sasaki, Xiaojun Lyu, Zhoujie Zhang, Tsuyoshi Minami

期刊论文