Development of a New Carbon Monoxide Fluorescent Probe Based on Nitro Reduction and Its Bioimaging Research in Living Cells

doi:10.6023/cjoc202009016

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (3): 1200-1206.DOI: 10.6023/cjoc202009016 Previous Articles Next Articles

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基于硝基还原机理的一氧化碳荧光探针的开发及细胞成像研究

陈恩庆^a, 唐永和^a, 王蕾^b, 任江波^a, 林伟英^a^,^*()

a 广西电化学能源材料重点实验室广西大学光功能材料与化学生物学研究院广西大学化学化工学院南宁 530004
b 南宁市食品药品检验所南宁 530007

收稿日期:2020-09-07 修回日期:2020-10-06 发布日期:2020-10-28
通讯作者: 林伟英
基金资助:
国家自然科学基金(21672083); 国家自然科学基金(21877048); 国家自然科学基金(22077048); 广西大学启动基金(A3040051003); 广西省自然科学基金(2019GXNSFBA245068)

Development of a New Carbon Monoxide Fluorescent Probe Based on Nitro Reduction and Its Bioimaging Research in Living Cells

Enqing Chen^a, Yonghe Tang^a, Lei Wang^b, Jiangbo Ren^a, Weiying Lin^a^,^*()

a Guangxi Key Laboratory of Electrochemical Energy Materials, Institute of Optical Materials and Chemical Biology, School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004
b Nanning Institute for Food and Drug Control, Nanning 530007

Received:2020-09-07 Revised:2020-10-06 Published:2020-10-28
Contact: Weiying Lin
About author:
* Corresponding author. E-mail: weiyinglin2013@163.com
Supported by:
National Natural Science Foundation of China(21672083); National Natural Science Foundation of China(21877048); National Natural Science Foundation of China(22077048); Startup Fund of Guangxi University(A3040051003); Natural Science Foundation of Guangxi Province(2019GXNSFBA245068)

1. cjoc202009016辅助材料.pdf(1175KB)

Abstract

Carbon monoxide (CO), as an important cell signaling molecule, is involved in important physiological and pathological functions in organism. A new fluorescence enhanced CO fluorescent probe NaLy-CO was developed by using naphthalimide dye as fluorescence platform and nitro group as the recognition site. The results of spectrum test in solution showed that the fluorescent probe NaLy-CO had good selectivity and sensitivity to CO. The fluorescent probe NaLy-CO was successfully used to detect exogenous and endogenous CO in living HeLa cells by using confocal fluorescence imaging technology. In addition, the colocation imaging experiments showed that the fluorescent probe NaLy-CO could detect CO in the lysosome of living cells.

Key words: carbon monoxide, fluorescent probe, bioimaging, nitro, naphthalimide

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Enqing Chen, Yonghe Tang, Lei Wang, Jiangbo Ren, Weiying Lin. Development of a New Carbon Monoxide Fluorescent Probe Based on Nitro Reduction and Its Bioimaging Research in Living Cells[J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1200-1206.

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Fig. & Tab. 12

Scheme 1. Sensing mechanism of probe NaLy-CO to CO

Scheme 2. Synthetic route of probe NaLy-CO

Figure 1. Fluorescent curves of probe NaLy-CO (1×10–5 mol/L) encountering with CORM-2 (0~5×10–4 mol/L) In 1×10–2 mol/L PBS buffer (pH 7.4, 10 vol% DMSO) for 40 min. λ ex=430 nm

Figure 2. Linear relationship between the fluorescence intensity of the probe NaLy-CO and the concentration of CORM-2 (0~1×10–5 mol/L) at 523 nm

Figure 3. Time-dependent fluorescent of probe NaLy-CO intensities at F523 nm treated with CORM-2 ▼ 2.50×10–4 mol/L, ▲ 2×10–4 mol/L, ● 1×10–4 mol/L, ■ 5×10–5 mol/L. λ ex=430 nm

Figure 4. Photo-stability profiles of probe NaLy-CO (1×10–5 mol/L) Photo-stability profiles of the probe NaLy-CO (1×10–5 mol/L) in the absence (■) or presence of UV-irradiated (●) (365 nm)

Figure 5. Fluorescent intensity changes of the probe NaLy-CO interacts with various analytes at 523 nm The numbers represent: (1) probe (1×10–5 mol/L), (2) glucose (5×10–4 mol/L), (3) L-Cys (1×10–3 mol/L), (4) ascorbic acid (5×10–4 mol/L), (5) acetone (5×10–4 mol/L), (6) pyruvic acid (5×10–4 mol/L), (7) pyruvic acid sodium (5×10–4 mol/L), (8) NaClO (5×10–4 mol/L), (9) Gly (5×10–4 mol/L), (10) DL-Hcy (5×10–4 mol/L), (11) GSH (5×10–3 mol/L), (12) H2O2(5×10–4 mol/L), (13) FA (5×10–4 mol/L), (14) Na2S (5×10–4 mol/L), (15) NaHS (5×10–4 mol/L), (16) NaSCN (5×10–4 mol/L), (17) TBHP (5×10–4 mol/L), (18) SNP (5×10–4 mol/L), (19) Na2SO3(5×10–4 mol/L), (20) NaHSO3(5×10–4 mol/L), (21) NaNO2 (5×10–4 mol/L), (22) GO (5×10–4 mol/L), (23) CORM-2 (1×10–4 mol/L). λ ex=430 nm

Figure 6. Fluorescence intensity of probe NaLy-CO and CORM-2 in different pH solutions at 523 nm Fluorescence intensity changes of the probe NaLy-CO (1×10–5 mol/L) at different pH values in the absence (●) or presence (■) of CO (1×10–4 mol/L) for 40 min

Figure 7. Fluorescent images of probe NaLy-CO in HeLa cells for detecting exogenous CO A~C: the HeLa cells were incubated with 1×10–5 mol/L probe NaLy-CO for 30 min; D~F: the HeLa cells were incubated with 1× 10–4 mol/L CORM-2 for 30 min; G~I: the HeLa cells were pre-cultured with 1×10–4 mol/L CORM-2 for 30 min, then cultured with 1×10–5 mol/L probe NaLy-CO for another 30 min. λ ex=405 nm, λ em= 500~550 nm, scale bar=50 μm.

Figure 8. Fluorescent images of probe NaLy-CO in HeLa cells for detecting endogenous CO A~C: the HeLa cells were incubated with 1×10–4 mol/L Heme for 2 h; D~F: the HeLa cells were pre-cultured with 1×10–4 mol/L Heme for 2 h, then cultured with 1×10–5 mol/L probe NaLy-CO for another 30 min; G~I: the HeLa cells were pre-cultured with 1×10–4 mol/L Heme for 4 h, then cultured with 1×10–5 mol/L probe NaLy-CO for another 30 min. λ ex=405 nm, λ em=500~550 nm. scale bar=50 μm

Figure 9. Co-location imaging experiment of localized dyes and exogenous CO test system (probe NALy-CO and CORM-2) Co-location imaging experiments between Lyso Tracker Deep Red and probe NALy-CO; (B) Co-location imaging experiments between Mito Tracker Deep Red and probe NALy-CO. The green channel: λ ex=405 nm, λ em=500~550 nm; The deep red channel: λ ex=647 nm, λ em=670~720 nm. Scale bar: 50 μm

	Lyso Tracker Deep Red	Mito Tracker Red
Pearson’s correlation	0.85	0.48

Table 1. Co-localization coefficient of probe NALy-CO and commercial localized dye

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基于硝基还原机理的一氧化碳荧光探针的开发及细胞成像研究

Development of a New Carbon Monoxide Fluorescent Probe Based on Nitro Reduction and Its Bioimaging Research in Living Cells

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