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Progress in Chemistry 2021, Vol. 33 Issue (9): 1496-1510 DOI: 10.7536/PC201116 Previous Articles   Next Articles

• Review •

Small-Molecular Organic Fluorescent Probes for Formaldehyde Recognition and Applications

Xuechuan Wang2(), Yansong Wang1, Qingxin Han2, Xiaolong Sun3   

  1. 1 College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology, Xi'an 710021, China
    2 College of Bioresources Chemical and Materials Engineering, Institute of Biomass and Functional Materials, Shaanxi University of Science and Technology, Xi'an 710021, China
    3 School of Life Science and Technology, Xi'an Jiaotong University, Xi'an 710049, China
  • Received: Revised: Online: Published:
  • Contact: Xuechuan Wang
  • Supported by:
    National Key Research and Development Program of China in the 13th Five-Year Plan(2017YFB0308500); National Natural Science Foundation of China(21907080); National Natural Science Foundation of China(21476134); Natural Science Foundation of Shaanxi Province(2020JM-069); Natural Science Basic Research Program of Shaanxi Province(2019JQ-456)
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Formaldehyde (FA) is not only used as a basic chemical for industrial products, but also a necessary metabolite for regulating human physiological activities. However, excessive intake from the external environment or unbalanced metabolism homeostasis of the internal environment would cause critical diseases to the human body such as organ cancers, Alzheimer?s disease and so on. The high sensitivity and selectivity with visualization and in-situ detection by means of small-molecular fluorescent probe, provides superiority for identification of FA and biological image in vitro and in vivo, and a new detection method for the trace detection of FA in real products as well. In the past five years, fluorescent probes of FA have developed rapidly. This article mainly reviews the research progress of fluorescent probes for FA recognition and applications, including the general reaction mechanisms and the applications in organisms and samples with commercial products. It is concluded that the small molecular fluorescent probes should be continuously improved in structures and optical characteristics to not only assist long-term research in biomedicine, but also lead to the achievable goals of fast (in situ) detecting FA in practice from actual products.

Contents

1 Introduction

2 Reaction mechanisms of FA fluorescent probes

2.1 The 2-aza-Cope rearrangement

2.2 The methylenehydrazine

2.3 The formimine and others

3 Fluorescence imaging applications

3.1 For cell imaging

3.2 For tissue imaging

3.3 For in vivo imaging

4 Detections of FA in samples (products)

4.1 In food

4.2 In air

5 Conclusion and outlook

Key words: formaldehyde, fluorescent probe, reaction mechanisms, bio-imaging, practical applications
Table 1 Summary of formaldehyde fluorescent probes
Name λex, λem
/nm		 time Limit of detection
(the linear range)		 Bio-imaging Applications ref
①The 2-aza-Cope rearrangement
FP1 633, 650 3 h 10 μM
—		 Cell (HEK293TN and NS1) — 38
FAP-1 645, 662 2 h 5 μM
—		 Cell (HEK293T and MCF7) — 39
FAP488 488, 515 2 h 10 μM
—		 — — 40
FAP555 555, 572 2 h 10 μM
—		 Cell (HEK293T) — 40
CFAP540 410, 540 1 h 10 μM
(cp: 10 μM, 25~50 μM)		 Cell (HEK293) — 41
CFAP700 540, 700 1 h —
(cp: 10 μM, 25~50 μM)		 Mice — 41
RFFP 318, 359/451 2 h 59.6 μM
(cp: 10 μM, 0~3 mM)		 Cell (HeLa) Formalin fixative 42
FAP 405, 495/570 2 h 0.5 μM
(cp: 20 μM, 0~200 μM)		 Root tissue of a plant Water samples 43
RFAP-1 420/470, 510 2 h 0.3 μM
(cp: 10 μM, 0~40 μM)		 Cell (HEK293T) — 44
Lyso-TPFP 405, 506 3 h 3.0 μM
(cp: 10 μM, 10~250 μM)		 Cell (HepG2 and HeLa);Mice — 45
MQAP 355, 405/490 2.5 h 4.054 μM
(cp: 10 μM, 0~1 mM)		 Cell (MCF7) — 46
CA 405, 451 3.3 h 41.6 μM
(cp: 10 μM, 0~20 μM)		 Cell (HeLa); zebrafish;
liver tissue		 — 47
CHFA 360, 517 3 h 1.71 μM
(cp: 20 μM, 0~140 μM)		 Cell (HeLa) — 48
FATP1 390, 526 3 h 0.2 μM
(cp: 10 μM, 1~50 μM)		 Cell (HEK293 and MCF7); liver tissue — 49
Name λex, λem
/nm		 time Limit of detection
(the linear range)		 Bio-imaging Applications ref
Probe-1 400, 438/533 3 h 10 μM
(cp: 10 μM, 0~800 μM)		 Cell (MCF7);
tissues of mice		 — 50
TPNF 350, 510 3 h 5 μM
(cp: 20 μM, 0~500 μM)		 Cell (HeLa);zebrafish — 51
Naph-FA 395, 518 3 h 0.22 μM
(cp: 10 μM, 10~350 μM)		 Cell (HeLa) — 52
HBT-FA 350, 462/541 3 h 410 μM
(cp: 20 μM, 0~30 mM)		 — Calf serum;
formaldehyde gas		 53
FA-P 350, 542 3 h 250 μM
(cp: 5 μM, 0~10 mM)		 — Bovine serum;
formaldehyde gas		 54
B1 390, 472 2 h 0.107 μM
(cp: 10 μM, 0~10 μM)		 Cell (HEK293T) — 55
TPE-FA 335, 504 1 h 0.036 mg/m3
(0~1.6 mg/m3)		 — Formaldehyde gas 56
TP-FA 305, 442/488 ~1 h 51 μM
(cp: 40 μM, 0~5.6 mM)		 — Formaldehyde gas 57
PIPBA 350, 440/520 2 h 0.84 μM
(cp: 5 μM, 0~0.6 mM)		 Cell (HeLa); zebrafish; tissues of mice — 58
SO-GJP 366, 393/542 3 h 1.55 μM
(cp: 10 μM, 10~800 μM)		 Cell (HeLa) Formaldehyde gas 59
AENO 390, 513 2.5 h 0.57 μM
(cp: 10 μM, 0~150 μM)		 Cell (HeLa) Toffee 60
PBD-FA 470, 563 3 h 43.5/49.7 nM
(cp: 10 μM, 0~100/200~500 μM)		 Cell (HeLa) — 61
DPFP 455, 555 ~0.5 h 10 μM
(cp: 5 μM, 0~250 μM)		 Cell (HeLa) — 62
P-FA 450, 480/550 1.5 h 0.96 μM
(cp: 10 μM, 0~800 μM)		 Cell (HeLa) — 63
Probe 1 430, 492/552 1.5 h 0.58 μM
(cp: 10 μM, 0~500 μM)		 Cell (MGC-803); zebrafish — 64
PrAK 468, 510 1 h 25 μM
(cp: 0.5 μM, 0~2 mM)		 Cell (HEK293T) — 65
FATP-1 405, 565 3 h 0.3 μM
(cp: 10 μM, 0~2 mM)		 Cell (CCK-8 and SH-SY5Y); epileptic mice — 66
2 and 3 300, 545 1 h 100 nM
(cp: 100 μM, 0~50 μM)		 — Formaldehyde gas 67
②The methylenehydrazine
Probe 1 350, 467 — 0.9 μM
(cp: 10 μM, 0~130 μM)		 — Seafood 68
Na-FA 440, 543 0.5 h 0.71 μM Cell (HeLa);liver tissue Patient urine 69,110
1 and 2 430, 541 8 min 0.78 μM
(cp: 1 μM, 0~10 μM)		 Cell (4T-1 and 3T3);
tumor tissue		 — 70
Na-FA-Lyso 440, 543 0.5 h 5.02 μM
(cp: 5 μM, 0~50 μM)		 Cell (HeLa) — 71
Na-FA-ER 440, 543 ~0.5 h 5.24 μM
(cp: 5 μM, 0~50 μM)		 Cell (HeLa) — 72
Mito-FA-FP 440, 550 ~0.5 h 12.4 μM
(cp: 5 μM, 0~50 μM)		 Cell (HeLa);
zebrafish		 — 73
NaP 440, 550 ~0.5 h 1.62 μM
(cp: 5 μM, 0~10 μM)		 Cell (HeLa) — 74
RBNA 440, 534 5 min 0.21 μM
(cp: 10 μM, 0~120 μM)		 Cell (HeLa);
zebrafish		 Seafood 75
Name λex, λem
/nm		 time Limit of detection
(the linear range)		 Bio-imaging Applications ref
NpFA 325, 550 65 s 8.3 nM
(cp: 1 μM, 0~12 μM)		 Onion tissue; zebrafish Seafood 76
NPz 380, 512 4 min 0.25 ppm
(cp: 10 μM, 0~1.6 mM)		 — Formaldehyde gas 77
NA3 400, 515 9 min 0.104 μM
(cp: 5 μM, 0~200 μM)		 — Formaldehyde gas 78
HyAN 300, 445 5 min 0.23 μM
(cp: 20 μM, 0~200 μM)		 Cell (HeLa) — 79
BHA 420, 466 0.5 h 0.18 μM
(cp: 10 μM, 0~100 μM)		 Cell (HeLa) — 80
Naph-1 405, 510 2 h 0.35 μM
(cp: 10 μM, 0~100 μM)		 Cell (HeLa) — 81
DTH 385, 508/534 ~0.2 h 0.29 μM
(cp: 15 μM, 0~20 μM)		 Cell (HeLa) Formaldehyde gas 82
CmNp-CHO 385, 526/550 1 min 8.3 ± 0.3 nM
(cp: 5 μM, 0~10 μM)		 Cell (HeLa);
onion tissue; zebrafish		 Seafood 83
PDI-HY 540, 582 2 min 1.5 μM
(cp: 5 μM, 2~10 μM)		 Cell (HeLa) — 84
FAP-1 440, 553 1.5 h 0.76 μM
(cp: 5 μM, 0~80 μM)		 — Leather 85
PFM 393, 500 1 min 0.4 μM
(cp: 10 μM, 0~200 μM)		 Cell (HBMECs);
brain slices of mice		 — 86
ANI 440, 518 3 min 0.988 μM
(cp: 10 μM, 0~13 mM)		 Cell (HeLa) — 87
MPAB 365, 525 6 min 20 nM
(cp: 10 μM, 0~30 μM)		 Cell (SMMC-7721) Formaldehyde gas 88
Probe 475, 530/600 5 min 120 nM
(cp: 10 μM, 0~60 μM)		 — Formaldehyde gas 89
FAP 470, 550 ~0.6 h 0.89 μg/L (cp: 12.5 μM, 0.015~0.8 μg/L) — Formaldehyde gas 90
③The formimine and others
dRB-EDA 560, 590 1 h — Cell (L929) — 91
R6-FA 530, 560 10 s 0.77 μM
(cp: 10 μM, 2~10 μM)		 Cell (HeLa) Mushroom;
formaldehyde gas		 92
L 520, 620 5 min 8.3 μM
(cp: 5 μM, 0~5 mM)		 Cell (L929) — 93
BOD-NH2 495, 515 2 h 50 nM
(cp: 10 μM, 0~500 μM)		 Cell (HEK293, etc);
organs; mice		 — 94
AnB 520, 535 — 0.165 μM
(cp: 5 μM, 0~10 mM)		 — — 95
Bodipy-OPDA 482, 548 1.5 h 0.104 μM
(cp: 10 μM, 0~1 mM)		 Cell (HeLa) Formaldehyde gas 96
HCy1 720/800, 820 30 s 3.25 μM
(cp: 10 μM, 0~1 mM)		 — Formaldehyde gas 97
1 365, 415 6 min 10 μM
(cp: 10 μM, 0~23.3 mM)		 — Seafood 98
CHP 363, 480 ~1 h 0.58 mM
(cp: 250 μM, 0~1.2 mM)		 — Formaldehyde gas 99
AIE-FA 370, 530 90 s 40 nM
(cp: 10 μM, 0.1~1 μM)		 Cell (HeLa) — 100
Probe 420, 485 0.5 h 0.24 mM/ 0.7 ppm
—		 — Formaldehyde gas (in
hospital)		 101
Name λex, λem
/nm		 time Limit of detection
(the linear range)		 Bio-imaging Applications ref
NPC 485, 545 2 min 84 nM
(cp: 1 μM, 0~2.5 μM)		 Cell (HADF) Plywood 102
DAB 345, 430 0.25 h 79 nM
(cp: 10 μM, 0~800 μM)		 Cell
(HeLa, HepG2 and WI-38)		 — 103
NP-Lyso 380, 444 1 h 0.27 μM
(cp: 10 μM, 0~200 μM)		 Cell
(L929 and HeLa)		 — 104
NP1/NP2 380, 450 — 1.6/1.8 μM
(cp: 10 μM, 0~100 μM /0~250 μM)		 Cell (L929) — 105
CaP 270, 370/630 1 min — Cell (HeLa);zebrafish;
mice		 — 106
DP 365, 550/635 1 min — Cell (HeLa);
mice		 RNA 107
NP 446, 540/645 5 min — Cell (U251 and HeLa);
mice		 — 108
ABTB 365, 460/525 0.5 h 432 nM
(cp: 10 μM, 0~50 μM)		 Cell (L929);
brain of AD mice		 — 109
Fig.1 Reaction mechanism of probe 1 for FA[38]
Fig.2 Chemical structures of probe 2, 3, and 4[39⇓~41]
Fig.3 Reaction mechanism of probe 5 for FA[42]
Fig.4 Reaction mechanism of probe 6 for FA[43]
Fig.5 Chemical structures of probe 7a~c and reaction mechanism for FA[44]
Fig.6 Reaction mechanism of probe 8 for FA[68]
Fig.7 Chemical structures of probe 9a~g and reaction mechanism for FA[69⇓⇓⇓⇓⇓⇓~76]
Fig.8 Reaction mechanism of probe 10 for aldehydes[91]
Fig.9 Reaction mechanism of probe 11 for FA[94]
Fig.10 Reaction mechanism of probe 12 for FA[97]
Fig.11 Reversible reaction mechanism of probe 13 for sulfur dioxide and FA[106]
Fig.12 Confocal fluorescence microscopy imaging of probe 1 and 2 in normal cells and cancer cells, respectivel[38,39]. Copyright 2015, American Chemical Society
Fig.13 Two-photon fluorescence imaging of probe 9b in liver tissues at different depths[69]. Copyright 2016, John Wiley and Sons
Fig.14 The ratiometric imaging of probe 6 for endogenous and exogenous FA in a plant root tip tissue[43]. Copyright 2017, Royal Society of Chemistry
Fig.15 The ratiometric imaging of probe 14 for endogenous and exogenous FA in zebrafish[58]. Copyright 2017, Royal Society of Chemistry
Fig.16 The near-infrared fluorescence imaging of probe 15 for exogenous FA in anesthetized mice[41]. Copyright 2018, John Wiley and Sons
Fig.17 Chemical structures of probe 8, 16 and 17[60,68,98]
Fig.18 Probe 18 compared with MBTH method to detect FA in mushroom[92]. Copyright 2016, Royal Society of Chemistry
Fig.19 Probe 18 loaded on the filter paper to detect FA gas and indoor air[92]. Copyright 2016, Royal Society of Chemistry
Fig.20 Probe 19 loaded on the TLC plate to detect FA gas[56]. Copyright 2018, American Chemical Society
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