Synthesis of a Colorimetric Fluorescent Probe of Cr 3+ and Its Application in Cell Imaging †

doi:10.7503/cjcu20190354

Abstract

Abstract:

Colorimetric fluorescence probe B was synthesized from 2,3,3-trimethyl-3H-benzo[e]indole and p-dimethylaminobenzaldehyde using acidic solvent as catalyst and ethanol as solvent. In the mixed system(pH=7.4) of V(EtOH)∶V(HEPES)=9∶1, the color of solution B changed from pale yellow to purple-red after added Cr ³⁺ to probe B solution, indicating that probe B can recognize Cr ³⁺ with naked-eye. Fluorescence emission spectra shows that probe B had good selectivity of Cr ³⁺, high sensitivity and good recognition ability with EDTA. The binding constant(K_a) of probe B on Cr ³⁺ was 0.28×10 ² mol/L and the detection limit was 1.90×10 ^-8 mol/L. The detection limit was lower than the maximum Cr ³⁺ content(9.60×10 ^-8 mol/L) in drinking water stipulated by WHO. In addition, the concentration of Cr ³⁺in actual water samples was quantitatively detected by fluorescence emission spectra. Probe B has been applied to the detection of Cr ³⁺ in living cells, which has a good application prospect and practical value.

Key words: Benzindole, Fluorescence probe, Cr ³⁺, Water sample, Cell

CLC Number:

O659

TrendMD:

Yingying ZHANG,Yiwen HUANG,Bing ZHAO,Liyan WANG,Bo SONG. Synthesis of a Colorimetric Fluorescent Probe of Cr ³⁺ and Its Application in Cell Imaging ^†[J]. Chem. J. Chinese Universities, 2019, 40(12): 2486.

Figures/Tables 12

Scheme 1 Synthetic procedure of probe B

Fig.1 Photos of probe B solutions in the presence of different metal ions

Fig.2 Absorption spectra(A) and fluorescence emission spectra(B) of probe B solutions in the presence of different metal ions

Fig.3 Fluorescence recognition of probe B in the presence of Cr3+ and other metal ions a. Probe B; b. probe B+Cr3+; c. probe B+K++Cr3+; d. probe B+Ca2++Cr3+; e. probe B+Na++Cr3+; f. probe B+Mg2++Cr3+; g. probe B+Al3++Cr3+; h. probe B+Zn2++Cr3+; i. probe B+Cd2++Cr3+; j. probe B+Co2++Cr3+; l. probe B+Pb2++Cr3+; l. probe B+Ni2++Cr3+; m. probe B+Hg2++Cr3+; n. probe B+Ag++Cr3+; o. probe B+Cu2+ +Cr3+; p. probe B+Fe3+ +Cr3+.

Fig.4 Fluorescence intensity of probe B in the presence of different concentrations of Cr3+(A) and the linear relationship of probe B with the concentrations of Cr3+(B) Inset: the fluorescence intensity change of probe B with the increase of Cr3+ concentration.

Fig.5 SEM images of probe B(A) and probe B+Cr3+(B)

Fig.6 Job’s curve of probe B and Cr3+

Fig.7 Fluorescence intensity of probe B+Cr3+ and EDTA(A) and the reversible identification of EDTA by the complex probe B+Cr3+ with EDTA(B)

Fig.8 Time-stability of probe B(a), probe B+Cr3+(b), probe B+Cr3++EDTA(c)

Sample	Cr³⁺ added/(μmol·L^-1)	Cr³⁺detected/(μmol·L^-1)	Recovery(100%)	RSD^*(%)
Tap water	0	ND
	2.0	2.11	105	2.08
	4.0	3.72	93	1.89
	6.0	6.02	100	2.19
Drinking water	0	ND
	2.0	1.98	99	1.21
	4.0	4.12	103	2.11
	6.0	5.90	98	3.01
River water	0	ND
	2.0	2.21	110	2.04
	4.0	4.02	100	1.09
	6.0	5.98	99	2.31

Fig.9 Cell viability of Hela cells

Fig.10 Fluorescence microscopy images of probe B(10 μmol/L) and Cr3+ in Hela cells (A) Bright field of the probe B; (B) fluorescence field of the probe B; (C) overlay of the (A) and (B); (D) bright field of the probe with Cr3+; (E) the fluorescence field of the probe B with Cr3+; (F) the overlay of the (D) and (E). λex=421 nm.

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Synthesis of a Colorimetric Fluorescent Probe of Cr ³⁺ and Its Application in Cell Imaging ^†

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