Synthesis, Properties and Dynamics of BODIPY-based Fluorophores

基于 BODIPY 的荧光团的合成、性质和动力学

• 批准号: 1800126
• 负责人: Maria Vicente
• 金额: $ 42万
• 依托单位: Louisiana State University
• 依托单位国家: 美国
• 项目类别: Standard Grant
• 财政年份: 2018
• 资助国家: 美国
• 起止时间: 2018-08-15 至 2022-07-31
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=1800126&HistoricalAwards=false
• 关键词: Synthesis; Properties; Dynamics; BODIPY; based

In this project funded by the Chemical Structure, Dynamic & Mechanism B Program of the Chemistry Division, Professor Maria G Vicente of the Department of Chemistry at Louisiana State University, in collaboration with Professor Petia N Bobadova-Parvanova of the Department of Chemistry at Rockhurst University, are developing fluorescent dyes for use in biological and material applications, including in bioimaging, and chemosensing. The goal of this research is to design, synthesize and then investigate the photophysical, electrochemical, and cellular properties of the new dyes toward the development of near-infrared absorbing and emitting fluorophores that can be conjugated with proteins and other biomolecules. The project involves both computational and experimental methods to design, synthesize and evaluate new fluorescent dyes and their conjugates, of enhanced stability, biocompatibility and performance for practical applications. This project involves organic and inorganic chemistry, spectroscopy, chemical kinetics, computational modeling, cell and molecular biology, molecular recognition, and biomedical imaging, and is therefore well suited to the education of scientists at all levels. This group is also well-positioned to provide the highest level of education and training for students underrepresented in science. Outreach activities involving K-12 students will also be part of the funded project. Boron dipyrromethene (BODIPY) dyes display a rich array of photophysical and optoelectronic properties, including intense absorption and emission profiles, high molar extinction coefficients, high fluorescence quantum yields and long fluorescence lifetimes. Previous work demonstrated that reactions of the basic BODIPY core can be used for the tuning of the absorption and emission wavelengths, Stokes shifts, stability, quantum yields, water-solubility, and for introduction of functionality for conjugation. The proposed syntheses will afford BODIPY-based systems with enhanced stability, solubility, and photophysical properties for practical applications in bioimaging and biosensing. In this project, the main strategies are 1) use of benzo-annelation via efficient intramolecular cyclizations to produce fused BODIPY systems with enhanced rigidity, and near-IR absorptions/emissions, 2) regioselective functionalizations to create push-pull BODIPY systems and BODIPY dyads with enhanced molar extinction coefficients, fluorescence emissions, Stokes shifts, as well as with increased oxidation potentials and solubility, and 3) use of polyfluorination for enhancement of cellular permeability, stability, and biocompatibility. The project takes advantage of computational methods to assist the target design and to model BODIPY mechanisms and properties, and explores new methodologies for the synthesis and functionalization of BODIPYs.This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.

在这个由化学部化学结构、动力学机制B计划资助的项目中，路易斯安那州立大学化学系的Maria G Vicente教授与罗克赫斯特大学化学系的Petia N Bobadova-Parvanova教授合作，正在开发用于生物和材料应用的荧光染料，包括生物成像和化学传感。 本研究的目标是设计，合成，然后研究新染料的生物物理，电化学和细胞特性，以开发可与蛋白质和其他生物分子缀合的近红外吸收和发射荧光团。 该项目涉及计算和实验方法来设计、合成和评估新的荧光染料及其缀合物，具有增强的稳定性、生物相容性和实际应用性能。该项目涉及有机和无机化学，光谱学，化学动力学，计算建模，细胞和分子生物学，分子识别和生物医学成像，因此非常适合各级科学家的教育。 该小组也有能力为科学领域代表性不足的学生提供最高水平的教育和培训。 涉及K-12学生的外联活动也将是资助项目的一部分。 硼二吡咯亚甲基（BODIPY）染料显示出丰富的物理和光电性质，包括强的吸收和发射曲线、高的摩尔消光系数、高的荧光量子产率和长的荧光寿命。以前的工作表明，基本BODIPY核心的反应可用于调谐的吸收和发射波长，斯托克斯位移，稳定性，量子产率，水溶性，并为共轭功能的引入。所提出的合成将提供基于BODIPY的系统，其具有增强的稳定性、溶解性和生物物理性质，用于生物成像和生物传感的实际应用。 在该项目中，主要策略是1）通过有效的分子内环化使用苯并-环化物以产生具有增强的刚性和近红外吸收/发射的稠合BODIPY系统，2）区域选择性官能化以产生具有增强的摩尔消光系数、荧光发射、斯托克斯位移以及增加的氧化电位和溶解度的推拉BODIPY系统和BODIPY二联体，和3）使用聚乙烯醇来增强细胞渗透性、稳定性和生物相容性。该项目利用计算方法来协助目标设计和模拟BODIPY的机制和属性，并探索新的方法合成和功能化的BODIPYs.This奖项反映了NSF的法定使命，并已被认为是值得通过评估使用基金会的智力价值和更广泛的影响审查标准的支持。

项目成果

Synthesis, Characterization, and Evaluation of Near-IR Boron Dipyrromethene Bioconjugates for Labeling of Adenocarcinomas by Selectively Targeting the Epidermal Growth Factor Receptor

• DOI: 10.1021/acs.jmedchem.8b01746
• 发表时间: 2019-04-11
• 期刊: JOURNAL OF MEDICINAL CHEMISTRY
• 影响因子: 7.3
• 作者: Kaufman, Nichole E. M.;Meng, Qianli;Vicente, M. Graca H.
• 通讯作者: Vicente, M. Graca H.

Surface modification strategy based on the conjugation of NaYF4:5%Eu luminescent nanoprobe with organic aromatic compounds for application in bioimaging assays

• DOI: 10.1007/s11051-018-4422-0
• 发表时间: 2019-01
• 期刊: Journal of Nanoparticle Research
• 影响因子: 2.5
• 作者: Rodrigo Silva Viana;Luciana Amaral Mascena Costa;A. N. Leal;Tyrslai M. Williams;Liquian Luan;Guanyun Zhang;Maodie Wang;A. Harmon;J. V. Anjos;R. Cueto;M. A. G. Filho;E. Falcão;M. Vicente;S. Júnior;J. Mathis

Structure Based Modulation of Electron Dynamics in meso-(4-Pyridyl)-BODIPYs: A Computational and Synthetic Approach.

• DOI: 10.1021/acs.jpca.8b05153
• 发表时间: 2018-08-09
• 期刊: The journal of physical chemistry. A
• 作者: LaMaster DJ;Kaufman NEM;Bruner AS;Vicente MGH
• 通讯作者: Vicente MGH

Novel phthalocyanines activated by dim light for mosquito larva- and cell-inactivation with inference for their potential as broad-spectrum photodynamic insecticides

• DOI: 10.1371/journal.pone.0217355
• 发表时间: 2019-05
• 期刊: PLoS ONE
• 影响因子: 3.7
• 作者: Shin-Hong Shiao;Shih-Che Weng;Liqiang Luan;M. Vicente;Xiong-Jie Jiang;D. Ng;B. Kolli;K. Chang

Synthesis, photodynamic activities, and cytotoxicity of new water-soluble cationic gallium(III) and zinc(II) phthalocyanines

• DOI: 10.1016/j.jinorgbio.2018.11.013
• 发表时间: 2019-03-01
• 期刊: JOURNAL OF INORGANIC BIOCHEMISTRY
• 影响因子: 3.9
• 作者: Fujishiro, Rei;Sonoyama, Hayato;Ikeue, Takahisa
• 通讯作者: Ikeue, Takahisa