Fluorescent Probe for Rapid Detection of H2S with Benzimidazole Naphthalimide as the Core

doi:10.19894/j.issn.1000-0518.210232

Chinese Journal of Applied Chemistry ›› 2022, Vol. 39 ›› Issue (3): 489-497.DOI: 10.19894/j.issn.1000-0518.210232

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Fluorescent Probe for Rapid Detection of H₂S with Benzimidazole Naphthalimide as the Core

Cheng-Lu ZHANG(), Yi-Ming WANG, Zhi-Xuan REN, Lu LI, Yu-Qing LI, Fu-Lu SONG

College of Chemistry and Chemical Engineering，Liaoning Normal University，Dalian 116029，China

Received:2021-05-13 Accepted:2021-07-26 Published:2022-03-01 Online:2022-03-15
Contact: Cheng-Lu ZHANG
About author:zhangchenglu@lnnu.edu.cn
Supported by:
the National Natural Science Foundation of China(21641012)

Abstract

Abstract:

A naphthalimide derivative 3-azido-7H-benzo［de］benzo［4，5］imidazole［2，1-a］（DBNG） was synthesized starting from 1，8-naphthalenedicarboxylic acid anhydride isoquinoline and characterized by using infrared spectroscopy （IR） and nuclear magnetic resonance spectroscopy （NMR）. It was used as a small molecule fluorescent probe to detect H₂S. The results show that probe DBNG can detect H₂S with high selectivity and rapid fluorescence response， and exhibits good fluorescence performance in a wide pH range with a detection limit as low as 0.82 μmol/L. It can be used to detect actual water samples with H₂S and has been successfully applied to cell imaging experiments.

Key words: Naphthalimide, Hydrogen sulfide, Azide, Fluorescent probe

CLC Number:

O626

Cheng-Lu ZHANG, Yi-Ming WANG, Zhi-Xuan REN, Lu LI, Yu-Qing LI, Fu-Lu SONG. Fluorescent Probe for Rapid Detection of H₂S with Benzimidazole Naphthalimide as the Core[J]. Chinese Journal of Applied Chemistry, 2022, 39(3): 489-497.

Figures/Tables 16

Fig.1 Schematic diagram of azide reduced by H2S

Fig.2 UV titration spectra of fluorescent probe DBNG with H2S

Fig.3 （A） The titration experiment of probe DBNG fluorescence recognition of H2S and （B） the relationship of fluorescence intensity of probe with the concentration of H2S at 515 nm

Fig.4 Selective experiment of DBNG fluorescence recogniton of H2S

Fig.5 Interference experiment of probe DBNG fluorescence recognition of H2S（1.Gly； 2. Cl； 3. Br； 4.SO32； 5.NO2； 6.H2PO4； 7.H2O2；8.Cys； 9.Hcy； 10.GSH； 11.Pro； 12.Try； 13.Met； 14.Val； 15.Asp； 16.Ser； 17.Leu； 18.Ala； 19.Phe； 20.blank where H2S is 20 μmol/L and for interfering substances is 50 μmol/L）

Fig.6 Time response of the fluorescent probe DBNG

Fig.7 The effect of pH on probe DBNG fluorescence recognition of H2S

Fig.8 The mechanism of DBNG fluorescence recognition of H2S

Fig.9 Electrostatic potential （ESP） maps of sensors DBNG?N 3 （left） and DBNG?NH 2 （right）

Fig.10 Spatial distribution of HOMO and LUMO of DBNG?N 3and DBNG?NH 2

Fig.11 NBO charge distribution of sensors DBNG?N 3 （left） and DBNG?NH 2 （right）

Fig.12 Fluorescence spectra of fluorescent probe DBNG in the presence of H2S （30 μmol/L） in different actual water samples

Table 1 Determination of H2S in different water samples with fluorescent probe DBNG

样品 Sample	添加浓度 c（H₂S spiked）/（μmol·L^-1）	检测浓度 c（total H₂S found）/（μmol·L^-1）	H₂S回收率 Recovery of H₂S/%
自来水 Tap water	10	9.89	98.9
	20	19.79	98.9
	30	29.39	97.9
河水 River water	10	9.93	99.3
	20	20.21	101.05
	30	30.09	100.3
海水 Sea water	10	10.04	100.4
	20	19.86	99.3
	30	30.65	102.1

Fig.13 Cell survival rates of 8 h were cultured at different probe concentrations （10~50 μmol/L）

Fig.14 Fluorescence images of H2S in HeLa cells. Cells were treated with probe DBNG （45 min）， washed， and subjected to different treatments（A） control （no H2S donor）；（B） 20 μmol/L H2S donor （60 min）；（C） 50 μmol/L H2Sdonor （60 min）；（D） 90 μmol/L H2S donor （60 min）

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Fluorescent Probe for Rapid Detection of H₂S with Benzimidazole Naphthalimide as the Core

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