高等学校化学学报 ›› 2018, Vol. 39 ›› Issue (5): 897-903.doi: 10.7503/cjcu20170672

• 有机化学 • 上一篇    下一篇

双氰基二苯代乙烯型双光子荧光铅离子探针

黄池宝, 潘淇, 陈华仕, 梁兴, 吕国岭   

  1. 遵义师范学院化学化工学院, 遵义 563002
  • 收稿日期:2017-10-11 出版日期:2018-04-08 发布日期:2018-04-08
  • 作者简介:

    联系人简介: 黄池宝, 男, 博士, 教授, 主要从事双光子荧光探针方面的研究. E-mail: huangchibao@163.com

  • 基金资助:
    贵州省高层次创新型人才培养计划项目“百”层次人才(批准号: 黔科合平台人才[2016]5683)、 国家自然科学基金(批准号: 21562050)、 贵州省第八批科技创新人才团队建设专项基金[批准号: 黔科合人才团队(2015)4007]、 贵州省科学技术基金项目(批准号: 黔科合J字[2015]2146)、 贵州省教育厅自然科学重点研究项目(批准号: 黔教合KY字[2014]296)、 贵州省教育厅省级本科教学工程建设项目(批准号: 黔教[2014]JXGChcb)、 遵义市“15851人才精英工程”项目[批准号: (2015)4007]和遵义市红花岗区科学技术项目(批准号: 遵红科合社字[2015]18)资助.

Dicyanostilbene-derived Two-photon Fluorescence Probe for Lead Ions

HUANG Chibao*, PAN Qi, CHEN Huashi, LIANG Xing, LÜ Guoling   

  1. Chemistry and Chemical Engineering College, Zunyi Normal University, Zunyi 563002, China
  • Received:2017-10-11 Online:2018-04-08 Published:2018-04-08
  • Contact: HUANG Chibao
  • Supported by:
    † Supported by the Guizhou Provincial High-level Innovative Talents Training ProjectHundred Talents Program, China(No.[2016]5683), the National Natural Science Foundation of China(No.21562050), the Special Fund Project of the Construction of the Eighth Batch of Scientific and Technological Innovation Talent Team in Guizhou Province, China[No.(2015)4007], the Guizhou Science and Technology Fund Project, China(No.J[2015]2146), the Key Project of Education Department of Guizhou Province, China(No.KY[2014]296), the Teaching Contents and Curriculum System Reform Project of Higher Education in Guizhou Province, China(No.KY[2014]JXGChcb), the Project of “15851 Talents Elite Project” in Zunyi City, China(No.[2015]4007) and the Science and Technology Project of Zunyi City Honghuagang District, China(No.[2015]18).

摘要:

以4-甲基-2,5-二氰基-4'-氨基二苯代乙烯(DCS)和双[2-(2-氨基苯基硫基)乙基]胺(BSA)分别作为双光子荧光团和铅离子配体, 构建了1个新型的双光子荧光Pb2+探针(DPb), 并对其结构和性能进行了表征. 结果表明, 该探针具有分子尺寸小、 双光子吸收截面大(δTPA, 1020 GM)、 长波长发射(λmax=609 nm)、 斯托克斯位移大(209 nm)、 光稳定性好、 水溶性适宜、 细胞渗透性优良、 无细胞毒性及在生理环境下对pH不依赖等优点. 该探针能选择性地检测细胞与组织中的Pb2+, 猝灭常数KsvTP=7.58×105 L/mol.

关键词: 双光子荧光探针, 铅离子, 活体成像, 双光子吸收截面

Abstract:

One-photon microscopy(OPM) uses a single photon of higher energy to excite the fluorophore, while two-photon microscopy(TPM) uses two photons of lower energy as the excitation source. Therefore, TPM has such distinct advantages as improvement of penetration depth, localized two-photon excitation, reduction of photo-damage and photobleaching, small absorption coefficient of light in tissue, and lower tissue autofluorescence. These advantages make TPM more popular among biologists. Lead is a common contaminant and has inherent toxic effects on human health and environment. Pb2+ ion contamination can affect a wide variety of diseases such as anemia, irritability, memory loss, and muscle paralysis. For these reasons, there is an urgent need to develop some effective two-photon fluorescence probes to detect trace amounts of Pb2+ ions in live cells and tissues. A novel two-photon fluorescence probe for Pb2+ derived from 4-methyl-2,5-dicyano-4'-amino stilbene as a two-photon fluorophore and bis[2-(2-aminophenylsulfanyls)ethyl]amine as a novel Pb2+ ligand was developed. The probe possessed small molecule size, large two-photon absorption cross-section(1020 GM), noncytotoxic effect, long-wavelength emission at 609 nm, large Stokes shift(209 nm), excellent photostability, moderate water-solubility, good cell-permeability and pH-insensitivity in the biologically relevant range. The probe was able to selectively detect Pb2+ ions in live cells and living tissues without interference from other metal ions and the membrane-bound probes, and its quenching constant(KsvTP) was 7.58×105 L/mol.

Key words: Two-photon fluorescence probe, Lead ion, Live-imaging, Two-photon absorption across-section

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