Wu Cuiyan, Ni Ziqi, Li Peijuan, Li Yaqian, Pang Xiao, Xie Ruihua, Zhou Zile, Li Haitao, Zhang Youyu
Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education), College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha, 410081, PR China.
Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education), College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha, 410081, PR China.
Talanta. 2020 Nov 1;219:121307. doi: 10.1016/j.talanta.2020.121307. Epub 2020 Jul 2.
β-Galactosidase (β-gal) which is overexpressed in primary ovarian cancer can be employed as a valuable biomarker for ovarian cancer. Thus, monitoring and imaging endogenous β-gal in living cells is of great importance. Herein, a dicyanoisophorone-based near-infrared (NIR) fluorescent probe 2-(5,5-dimethyl-3-((E)-4-(((2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)styryl)cyclohex-2-en-1-ylidene)malononitrile named DP-βgal, was rationally designed and synthesized for the monitoring of β-gal activity in living cells. In the presence of β-gal, with the breaking of the glycosidic bond, the NIR fluorescence of the dicyanoisophorone derivative gradually recovered, enabling the fluorescence "off-on" quantitative determination of β-gal activity. DP-βgal has the advantages of good selectivity and high sensitivity for the detection of β-gal, with the limit of detection (LOD) of 3.2 × 10 U. Furthermore, based on its advantages of long-wavelength emission and excellent biocompatibility, the practical applications of DP-βgal in NIR imaging of β-gal in living ovarian cancer cells (SKOV-3) were demonstrated.
β-半乳糖苷酶（β-gal）在原发性卵巢癌中过表达，可作为卵巢癌的一种有价值的生物标志物。因此，监测和成像活细胞中的内源性β-gal非常重要。在此，合理设计并合成了一种基于二氰基异佛尔酮的近红外（NIR）荧光探针2-(5,5-二甲基-3-((E)-4-(((2R,3S,4R,5S,6S)-3,4,5-三羟基-6-(羟甲基)四氢-2H-吡喃-2-基)氧基)苯乙烯基)环己-2-烯-1-亚基)丙二腈，命名为DP-βgal，用于监测活细胞中的β-gal活性。在β-gal存在下，随着糖苷键的断裂，二氰基异佛尔酮衍生物的近红外荧光逐渐恢复，从而实现对β-gal活性的荧光“关-开”定量测定。DP-βgal对β-gal的检测具有选择性好、灵敏度高的优点，检测限（LOD）为3.2×10 U。此外，基于其长波长发射和优异的生物相容性优势，证明了DP-βgal在活卵巢癌细胞（SKOV-3）中β-gal近红外成像的实际应用。
