Colorimetric and Fluorescent Probes Based on the Oxidation of o-Phenylenediamine for the Detection of Bio-Molecules

doi:10.7536/PC210927

O-phenylenediamine (OPD) can be easily oxidized by a variety of oxidants to form yellow fluorescent substance 2, 3-diaminophenazine (OPDox), and the unique responding mechanism provides a principle in the design of reaction-based colorimetric/fluorescent probes. Up to now, colorimetric and fluorescent probes based on the OPD oxidative reactions have been widely applied in the detection of metal ions and organic molecules. In recent years, these probes have attracted much attention in the recognition of bio-molecules in cells and tissues due to their high sensitivity, fast response speed and strong anti-interference ability. This review summarizes the development of colorimetric and fluorescent probes based on the OPD oxidative reactions in the detection of important bio-molecules such as biothiols, reactive oxygen species, uric acid, enzyme, antigen and so on. We further make an in-depth perspectives on the application and development prospect of the probes.

Contents

1 Introduction

2 Detection of small bio-molecules

2.1 Biological thiols

2.2 Reactive oxygen species

2.3 Purine and its metabolites

2.4 Other small bio-molecules

3 Detection of biomacromolecules

3.1 Enzyme

3.2 Antigens

3.3 Bacteria and viruses

3.4 Other biomacromolecules

4 Conclusion and outlook

Key words: o-phenylenediamine, colorimetric/fluorescent probe, oxidative reaction, bio-molecules, recognition

Fig. 1 The detection mechanism of biothiols by fluorescence probe based on the oxidation of OPD[19]

Fig. 2 Colorimetric probe of GSH based on the Ag+-OPD autocatalytic oxidation[21]

Fig. 3 The detection mechanism of GSH by colorimetric/fluorometric duel-readout probe[22]

Fig. 4 Ratiometric fluorescence probe of GSH based-on OPD oxidative reaction[25]

Fig. 5 Ratiometric fluorescence probe of H2O2 based on OPD oxidative reaction[29]

Fig. 6 Detection mechanism and cell imaging of ratiometric fluorescence probe of hROS based on the OPD oxidative reaction[32]

Fig. 7 Ratiometric fluorescence/colorimetric probe of xanthine based on the Fe, N-CDs catalyzed OPD oxidative reaction[34]

Fig. 8 Detection mechanism of Uric acid by ratiometric probe based on the cascade catalytic oxidation[36]

Fig. 9 Detection mechanism of cholesterol by ratiometric fluorescence probe based on the OPD oxidative reaction[41]

Fig. 10 Colorimetric probe of PPI based on the OPD oxidative reaction and the photo images of test-paper under different concentrations of PPI[45]

Fig. 11 Detection mechanism of His by fluorescence probe based on OPD oxidative reaction[48]

Fig. 12 Detection mechanism of ATP by ratiometric fluorescence probe based on OPD oxidative reaction[55]

Fig. 13 Detection mechanism of ALP fluorescence probe based on IFE[63]

Fig. 14 Detection mechanism of ALP by the multi-emitting fluorescence probe based on the OPD oxidative reaction[64]

Fig.15 Ratiometric fluorescence probe of ALP based on AuNCs-OPD system[65]

Fig. 16 Dual-readout assay of PPase based on the Cu2+-triggered oxidation of OPD[66]

Fig. 17 Discriminative detection mechanism of AChE and BChE by ratiometric fluorescence probe based on the OPD-CDs system[71]

Fig. 18 Detection mechanism of PSA by fluorescent immunosensor based on the OPD oxidative reaction[80]

Fig. 19 Detection mechanism of HIV-1 virus antigen P24 by fluorescent immunosensor based on the OPD oxidative reaction[83]

Fig. 20 Detection mechanism of H1N1 virus by fluorescent immunosensor based on the OPD oxidative reaction[93]

Fig. 21 Detection mechanism of Listeria monocytogenes by colorimetric probe based on the OPD oxidative reaction[95]

Fig. 22 Detection mechanism of Escherichia coli O157: H7 by fluorescence probe based on the OPD oxidative reaction[97]

Fig. 23 Detection mechanism of DNA by fluorescence probe based on the OPD oxidative reaction[100]

Fig. 24 Detection mechanism of NMP22 by colorimetric/fluorescence probe based on the OPD oxidative reaction[102]

Table 1 Summary of the performance of OPD-based sensors discussed in this review

Analyte	Entry	Sensor category	Linear range	LOD	ref
Cys, HCy, GSH	1	Single-intensity-based fluorescence sensor	0.5 ~ 30.0 μM, 1.0 ~ 45.0 μM, 0.5 ~ 40.0 μM	110 nM, 200 nM, 150 nM	19
GSH	2	Colorimetric sensor	2 nM ~ 1 μM	1.7 nM	21
	3	Colorimetic/fluorometric dual signal sensor	20 ~ 80 μM/ 0.5 ~ 10 μM	0.94 μM/62 nM	22
	4	Ratiometric fluorescence sensor	1 ~ 100 μM	270 nM	25
H₂O₂	5	Ratiometric fluorescence sensor	0 ~ 1 mM	50 nM	29
H₂O₂	6	Ratiometric fluorescence sensor	0 ~ 1 mM	4.66 μM	30
·OH, ClO^-, ONOO^-	7	Ratiometric fluorescence sensor		0.11 μM, 0.50 μM, 0.69 μM	32
Xanthine	8	Colorimetic/fluorometric dual signal sensor	0 ~ 40 μM/ 0 ~ 70 μM	0.023 μM/0.02 μM	34
UA	9	Colorimetic/fluorometric dual signal sensor	0.01~0.8 mM	8.4 μM/0.75 μM	36
	10	Colorimetic/fluorometric dual signal sensor	1.2 ~ 100 μM/1.2 ~ 75 μM	200 nM/125 nM	37
	11	Colorimetic/fluorometric dual signal sensor	5 ~ 100 μM	0.7 μM/0.5 μM	38
Cholesterol	12	Ratiometric fluorescence sensor	0.01 ~ 500 μM	3.6 nM	41
PPI	13	Colorimetric sensor	0 ~ 0.2 μM	4.29 nM	45
His	14	Single-intensity-based fluorescence sensor	0.5 ~ 30 μM	0.33 μM	48
ATP	15	Ratiometric fluorescence sensor	1 ~ 100 μM	0.43 μM	55
ALP	16	Single-intensity-based fluorescence sensor	0.1 ~ 8.0 mU/mL	0.05 mU/mL	63
	17	Multi-emitting fluorescence sensor	0.1 ~ 100 mU/mL	0.06 mU/mL	64
	18	Ratiometric fluorescence sensor	0 ~ 3 U/L	0.0035 U/L	65
PPase	19	Colorimetic/fluorometric dual signal sensor	0.2 ~ 50 mU/mL	0.2 mU/mL	66
AChE, BChE	20	Ratiometric fluorescence sensor	0.2 ~ 14 U/L, 0.1 ~ 5 U/L	0.1 U/L, 0.04 U/L	71
LSD	21	Colorimetic/fluorometric dual signal sensor	0.6 ~ 150 nM	0.5 nM/0.3 nM	75
PSA	22	Single-intensity-based fluorescence sensor	0.5 pg/mL ~ 50 ng/mL	0.1 pg/mL	80
HIV antigen P24	23	Single-intensity-based fluorescence sensor	1.4 ~ 90 pg/mL	0.5 pg/mL	82
Ov	24	Single-intensity-based fluorescence sensor	34.18 ~ 273.44 ng/mL	36.97 ng/mL	87
H1N1 virus	25	Single-intensity-based fluorescence sensor	10^-12~ 10^-8 g/mL	10^-13 g/mL	93
Listeria monocytogenes	26	Colorimetric sensor	10 ~ 10⁶ cfu/mL	10 cfu/mL	95
O157:H7	27	Single-intensity-based fluorescence sensor	10³~ 10⁶ cfu/mL	4.2×10²cfu/mL	97
DNA	28	Ratiometric fluorescence sensor	0.1 pM ~ 20 nM	30 fM	100
NMP 22	29	Colorimetic/fluorometric dual signal sensor	1 ~ 500 pg/mL	0.31 pg/mL	102

Table 1 Summary of the performance of OPD-based sensors discussed in this review

Analyte	Entry	Sensor category	Linear range	LOD	ref
Cys, HCy, GSH	1	Single-intensity-based fluorescence sensor	0.5 ~ 30.0 μM, 1.0 ~ 45.0 μM, 0.5 ~ 40.0 μM	110 nM, 200 nM, 150 nM	19
GSH	2	Colorimetric sensor	2 nM ~ 1 μM	1.7 nM	21
	3	Colorimetic/fluorometric dual signal sensor	20 ~ 80 μM/ 0.5 ~ 10 μM	0.94 μM/62 nM	22
	4	Ratiometric fluorescence sensor	1 ~ 100 μM	270 nM	25
H₂O₂	5	Ratiometric fluorescence sensor	0 ~ 1 mM	50 nM	29
H₂O₂	6	Ratiometric fluorescence sensor	0 ~ 1 mM	4.66 μM	30
·OH, ClO^-, ONOO^-	7	Ratiometric fluorescence sensor		0.11 μM, 0.50 μM, 0.69 μM	32
Xanthine	8	Colorimetic/fluorometric dual signal sensor	0 ~ 40 μM/ 0 ~ 70 μM	0.023 μM/0.02 μM	34
UA	9	Colorimetic/fluorometric dual signal sensor	0.01~0.8 mM	8.4 μM/0.75 μM	36
	10	Colorimetic/fluorometric dual signal sensor	1.2 ~ 100 μM/1.2 ~ 75 μM	200 nM/125 nM	37
	11	Colorimetic/fluorometric dual signal sensor	5 ~ 100 μM	0.7 μM/0.5 μM	38
Cholesterol	12	Ratiometric fluorescence sensor	0.01 ~ 500 μM	3.6 nM	41
PPI	13	Colorimetric sensor	0 ~ 0.2 μM	4.29 nM	45
His	14	Single-intensity-based fluorescence sensor	0.5 ~ 30 μM	0.33 μM	48
ATP	15	Ratiometric fluorescence sensor	1 ~ 100 μM	0.43 μM	55
ALP	16	Single-intensity-based fluorescence sensor	0.1 ~ 8.0 mU/mL	0.05 mU/mL	63
	17	Multi-emitting fluorescence sensor	0.1 ~ 100 mU/mL	0.06 mU/mL	64
	18	Ratiometric fluorescence sensor	0 ~ 3 U/L	0.0035 U/L	65
PPase	19	Colorimetic/fluorometric dual signal sensor	0.2 ~ 50 mU/mL	0.2 mU/mL	66
AChE, BChE	20	Ratiometric fluorescence sensor	0.2 ~ 14 U/L, 0.1 ~ 5 U/L	0.1 U/L, 0.04 U/L	71
LSD	21	Colorimetic/fluorometric dual signal sensor	0.6 ~ 150 nM	0.5 nM/0.3 nM	75
PSA	22	Single-intensity-based fluorescence sensor	0.5 pg/mL ~ 50 ng/mL	0.1 pg/mL	80
HIV antigen P24	23	Single-intensity-based fluorescence sensor	1.4 ~ 90 pg/mL	0.5 pg/mL	82
Ov	24	Single-intensity-based fluorescence sensor	34.18 ~ 273.44 ng/mL	36.97 ng/mL	87
H1N1 virus	25	Single-intensity-based fluorescence sensor	10^-12~ 10^-8 g/mL	10^-13 g/mL	93
Listeria monocytogenes	26	Colorimetric sensor	10 ~ 10⁶ cfu/mL	10 cfu/mL	95
O157:H7	27	Single-intensity-based fluorescence sensor	10³~ 10⁶ cfu/mL	4.2×10²cfu/mL	97
DNA	28	Ratiometric fluorescence sensor	0.1 pM ~ 20 nM	30 fM	100
NMP 22	29	Colorimetic/fluorometric dual signal sensor	1 ~ 500 pg/mL	0.31 pg/mL	102

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Colorimetric and Fluorescent Probes Based on the Oxidation of o-Phenylenediamine for the Detection of Bio-Molecules

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Colorimetric and Fluorescent Probes Based on the Oxidation of o-Phenylenediamine for the Detection of Bio-Molecules