Mitochondria-targeted near-infrared fluorescent probe for the detection of carbon monoxide in vivo

Mitochondria-targeted near-infrared fluorescent probe for the detection of carbon monoxide in vivo
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用于体内一氧化碳检测的线粒体靶向近红外荧光探针

DOI:
10.1016/j.talanta.2018.06.046
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发表时间:
2018-10-01
期刊:
影响因子:
6.1
通讯作者:
Li, Chun-Yan
Li, Chun-Yan
中科院分区:
化学1区
文献类型:
--
作者:
Li, Song-Jiao;Zhou, Dong-Ye;Li, Chun-Yan

文献摘要

被引文献

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一氧化碳是体内一种重要的气体递质,与线粒体呼吸有关。到目前为止,人们已经提出了各种针对CO的荧光探针,但仍然存在两个主要问题。其一是,大多数探针不是以线粒体为靶点的,即使这些探针声称能够在活细胞中检测到一氧化碳。二是CO探针在紫外光或可见光范围内表现出激发和发射,这阻碍了其在体内的应用。本文首次合成了一种基于半花菁的近红外(NIR)荧光探针CyAPC,并将其用于检测线粒体一氧化碳。探针CyAPC的特点如下:(1)该传感系统的荧光发射波长为736 nm,属于近红外区,适合活体生物成像。(2)CyAPC是一种带正电的分子,在细胞线粒体中有较高的定位倾向。(3)探针的荧光变化归因于Pd~(2+)引起的CO裂解探针上的甲酸烯丙酯基团,荧光关闭时的CyAPC转变为荧光开启时的CyOH,这一点经高效液相、质谱分析和密度泛函理论计算证实。(4)将近红外荧光探针应用于细胞、组织和活体等多种生物样品中外源性和内源性CO的检测,结果令人满意。
Carbon monoxide is a critical gasotransmitter in the body and related with mitochondrial respiration. To date, various fluorescent probes for CO have been well proposed, but two main problems remain. One is that most of the probes are not mitochondria-targeting, even if the probes claim to be able to detect CO in living cells. The other is that the probes for CO display excitation and emission within the ultraviolet or visible range, which hinders their applications in vivo. Herein, a hemicyanine-based near-infrared (NIR) fluorescent probe named CyAPC is first synthesized and used to detect mitochondrial CO. The characteristics of probe CyAPC are as follows: (1) The fluorescence emission of the sensing system is at 736 nm belonging to NIR region, which is suitable for bioimaging in vivo. (2) CyAPC, a positively charged molecule, would have a high tendency to localize in mitochondria of cells. (3) The fluorescence change of the probe is attributed to the fact that CO with Pd2+ induced cleavage of the allyl formate group from the probe and CyAPC (fluorescence off) is transformed into CyOH (fluorescence on), which is proved by HPLC, MS and DFT calculation. (4) The NIR fluorescent probe is applied for the detection of exogenous and endogenous CO in various biological samples such as cell, tissue and in vivo with satisfactory results.