Chinese Journal of Organic Chemistry >
Construction of a Lipid Droplets Targeted Fluorescent Probe for Visualization of Liver Tumor Cells
Received date: 2023-09-08
Revised date: 2023-11-29
Online published: 2023-12-21
Supported by
Key Project of Anhui Provincial Department of Education(2023AH051883); Key Project of Anhui Provincial Department of Education(2022AH051632); Horizontal Project from Dalian Jindian Biotechnology Co., Ltd(880988); Shanghai Qingzhen Test Technology Co., Ltd(881242)
Lipid droplets (LDs) are involved in the metabolic processes of many living cells, and their anomalies are highly associated with a variety of diseases, such as fatty liver, diabetes and cancers. But it is still a great challenge to elucidate the intrinsic relationship between various diseases and LDs. In particular, there has been only a few studies on the visualization of abnormal LDs in liver tumor cells. Therefore, in this paper, a lipid droplets targeted fluorescent probe was easily prepared through a two-step procedure by using triphenylamine as the electron donor and polycyanide heterocyclic compound as the electron acceptor. The fluorescent probe TCN-Tph possesses good ability to target LDs in living cells through their co- localization imaging experiments. In comparison with other carcinoma cells, the liver tumor cells have good response and uptake of TCN-Tph. The slices images of liver tissues in different states further show that the probe TCN-Tph can also distinguish liver tissues and normal liver tissues effectively, which provide an experimental basis for the early diagnosis of liver tumor cells in clinic.
Key words： lipid droplets; fluorescent probe; liver tumor cell; visualization
Dongqing Xu , Haishan Tong , Jie Shen , Wanwei Qiu , Lisheng Qian . Construction of a Lipid Droplets Targeted Fluorescent Probe for Visualization of Liver Tumor Cells[J]. Chinese Journal of Organic Chemistry, 2024 , 44(4) : 1240 -1246 . DOI: 10.6023/cjoc202309008
| [1] | Guo L.; Tian M.; Zhang Z.; Lu Q.; Liu Z.; Niu G.; Yu X. J. Am. Chem. Soc. 2021, 143, 3169. |
| [2] | Wu C.-J.; Li X.-Y.; Zhu T.; Zhao M.; Song Z.; Li.; Shan G.-G.; Niu, G. Anal. Chem. 2022, 94, 3881. |
| [3] | Xiao H.; Li P.; Tang B. Chem. Rev. 2021, 427, 213582. |
| [4] | Wang L.; Ma Y.; Li Z.; Li S.; Lin W. Chem. Eng. J. 2023, 451, 139023. |
| [5] | Cao M.; Zhu T.; Zhao M.; Meng F.; Liu Z.; Wang J.; Niu G.; Yu X. Anal. Chem. 2022, 94, 10676. |
| [6] | Zhang X.; Yuan L.; Jiang J.; Hu J.; Du R.; Cao H.; Zhang R.; Tian X.; Zhang F.; Ma Y.; Zhang Z.; Uvdal K.; Hu Z. Anal. Chem. 2020, 92, 3613. |
| [7] | Roberts M.; Olzmann J. Annu. Rev. Cell Dev. Biol. 2020, 36, 115. |
| [8] | Sun Z.; Gong J.; Wu H.; Xu W.; Wu L.; Xu D.; Gao J.; Wu J.; Yang H.; Yang M.; Li P. Nat. Commun. 2013, 4, 1594. |
| [9] | Fu Y.; Finney N. S. RSC Adv. 2018, 8, 29051. |
| [10] | Tian H.; Sedgwick A. C.; Han H.-H.; Sen S.; Chen G.-R.; Zang Y.; Sessler J. L.; James T. D.; Li J.; He X.-P. Coord. Chem. Rev. 2021, 427, 213577. |
| [11] | Wang K.; Ma S.; Ma Y.; Zhao Y.; Xing M.; Zhou L.; Cao D.; Lin W. Anal. Chem. 2020, 92, 6631. |
| [12] | Thiam A.-R.; Farese Jr R.-V.; Walther T.-C. Nat. Rev. Mol. Cell Biol. 2013, 14, 775. |
| [13] | Samanta S.; Huang M.; Lin F.; Das P.; Chen B.; Yan W.; Chen J.; Ji K.; Liu L.; Qu J.; Yang Z. Anal. Chem. 2020, 92, 1541. |
| [14] | Herker E.; Vieyres G.; Beller M.; Krahmer N.; Bohnert M. Trends Cell Biol. 2021, 345. |
| [15] | Farmer B. C.; Walsh A. E.; Kluemper J. C.; Johnson L. A. Front. Neurosci. 2020, 14, 742.. |
| [16] | Xue K.; Zhao Y.; Sun S.; Li Y.; Liang J.; Qi Z. Chem. Eng. J. 2023, 470, 144125. |
| [17] | Pennetta G.; Welte M.-A. Dev. Cell 2018, 45, 427. |
| [18] | Wang X.; Tang Y.; Liang J.; Zhao Y.; Yang L.; Qi Z. Chem. Eng. J. 2023, 453, 139838. |
| [19] | Pei S.; Li H.; Li J.; Liu Y.; Zhang G.; Shi L.; Liang W.; Zhang C.; Shuang S.; Dong C. ACS Biomater. Sci. Eng. 2023, 9, 3590. |
| [20] | Huo Z.; Cao X.; Sun D.; Xu W.; Yang B.; Xu S. ACS Sens. 2023, 8, 1939. |
| [21] | Liu M.-X.; Chen X.-B.; Liu W.-Y.; Zou G.-Y.; Yu Y.-L.; Chen S.; Wang J.-H. Anal. Chem. 2023, 95, 5087. |
| [22] | Zhu X.; Feng L.; Cao S.; Wang J.; Niu G. Org. Lett. 2022, 24, 8305. |
| [23] | Greenspan P.; Mayer E. P.; Fowler S. D. J. Cell Biol. 1985, 100, 965. |
| [24] | Ou M.; Lin C.; Wang Y.; Lu Y.; Wang W.; Li Z.; Zeng W.; Zeng X.; Ji X.; Mei L.; J. Contro. Release. 2022, 345,755.. |
| [25] | Qiu B.; Simon M.-C. Biol. Protoc. 2016, 6, 17. |
| [26] | Spangenburg E.-E.; Pratt S.-J.; Wohlers L.-M.; Lovering R.-M. J. Biomed. Biotechnol. 2011, 598358. |
| [27] | Collot M.; Fam T.; Ashokkumar P.; Faklaris O.; Galli T.; Danglot L.; Klymchenko A.-S. J. Am.Chem. Soc. 2018, 140, 5401. |
| [28] | Tatenaka Y.; Kato H.; Ishiyama M.; Sasamoto K.; Shiga M.; Nishitoh H.; Ueno Y. Biochem. 2019, 58, 6499. |
| [29] | Collot M.; Bou S.; Fam T.-K.; Richert L.; Mely Y.; Danglot ?L.; Klymchenko A.-S. Anal. Chem. 2019, 91, 1928. |
| [30] | Yin J.; Peng M.; Lin W. Sens. Actuators B Chem. 2019, 288, 251. |
| [31] | Guo L.; Tian M.; Feng R.; Zhang G.; Zhang R.; Li X.; Liu Z.; He X.; Sun J. Z.; Yu X. ACS Appl. Mater. Interfaces 2018, 10, 10706. |
| [32] | Zeng S.-T.; Shao W., Yu Z.-Y.; Fang L.; Tang G.-X.; Fang Y.-Y.; Chen S.-B.; Huang Z.-S.; Tan J.-H.; Chen X.-C. ACS Sens. 2023, 8, 40. |
| [33] | He L.; Cao J.-J.; Zhang D.-Y.; Hao L.; Zhang M.-F.; Tan C.-P.; Ji L.-N.; Mao Z.-W. Sens. Actuators, B Chem. 2018, 262, 313. |
| [34] | Purevsuren K.; Shiozaki S.; Mizukami K.; Tobita S.; Yoshihara T. Anal. Chem. 2023, 95, 3729. |
| [35] | Liu H.; Yan N.; Wong T.; Lam H.; Lam J.; Kwok R.; Sun J.; Tang B. ACS Nano. 2022, 16, 14973. |
| [36] | Shao T.; Liu T.; Liu H.; Zhang M.; Shen Y.; Gao A.; Tian X.; Zhang Q.; Wu J.; Tian Y. J. Mater. Chem. B 2019, 7, 3704. |
| [37] | Cao S.; Tian X.; Cao M.; Wang J.; Niu G.; Tang B.-Z. Chem. Mater. 2023, 35, 2472. |
| [38] | Liang K.; Zhong W.; Wei M.; Tan L.-L.; Shang L. Anal. Chem. 2023, 95, 8077. |
| [39] | Fan L.; Wang X.; Ge J.; Li F.; Wang X.; Wang J.; Shuang S.; Dong C. Chem. Commun. 2019, 55, 4703. |
| [40] | Fan L.; Wang X.; Ge J.; Li F.; Zhang C.; Lin B.; Shuang S.; Dong C. Chem. Commun. 2019, 55, 6685. |
| [41] | Yin J.; Peng M.; Lin W. Anal. Chem. 2019, 91, 8415. |
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