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Progress in Chemistry 2021, Vol. 33 Issue (1): 111-123 DOI: 10.7536/PC200557 Previous Articles   Next Articles

• Review •

Metal Complexes in Application of Two-Photon Luminescence Probes

Jiaen Xie1, Yuheng Luo1, Qianling Zhang1, Pingyu Zhang1,*()   

  1. 1 College of Chemistry and Environmental Engineering, Shenzhen University, Shenzhen 518055, China
  • Received: Revised: Online: Published:
  • Contact: Pingyu Zhang
  • Supported by:
    the National Natural Science Foundation of China(21701113); the Science and Technology Foundation of Shenzhen(JCYJ20190808153209537); the Peacock Talent Fund(827-000389); the Natural Science Foundation of SZU(2018036)
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During the past years, metal complexes have attracted intensive research interest in biological sensors and imaging of cellular dynamics during a series of biological events. This is due to their unique advantages includes the following:(1) easily tunable chemical and photophysical properties resulting from their synthetic versatility;(2) high emission quantum yields and long phosphorescence lifetimes, which may avoid interferences from background auto-fluorescence;(3) large Stokes shifts for effective discrimination of excitation and emission wavelengths, as well as prevention of fluorescence quenching induced by self-absorption, and(4) emissive properties that are sensitive to subtle changes in the local environment. In recent years, metal complexes with obvious two-photon absorption have been attracted extensive attention in luminescence detection of biomolecules and organelle dyes because of their superior depth resolution and low light damage compared with traditional one-photon absorption. This review describes the latest two-photon absorption metal complexes with detection of biomolecules(pH, O2, HClO, NO, SO2, GSH, DNA, and so on) for diagnosis of diseases, as well as organelle probes(mitochondria, lysosomes, lipid droplets, nucleus, and so on) for intracellular dynamic behaviors and evolution processes. Finally, the perspectives of metal complexes in application of biomolecular probes and organelle dyes were analyzed and discussed.

Contents

1 Introduction

2 Two-photon technology

2.1 Two-photon absorption

2.2 Two-photon emission and two-photon absorption parameters measurement

2.3 Study on two-photon luminescent probes of metal complexes

3 Two-photon luminescent biosensors

3.1 O2

3.2 Amino acids

3.3 DNA

3.4 pH

3.5 SO2

3.6 HClO

3.7 NO

3.8 Metal ions

4 Two-photon luminescent organelle dyes

4.1 Mitochondria

4.2 Lysosomes

4.3 Lipid droplets

4.4 Nucleus

5 Conclusion and outlook

Key words: metal complexes, two-photon absorption, biosensors, organelle dyes
Fig. 1 Jablonski diagrams of two-photon(A) and one-photon(B) excitation[42]
Fig. 2 (A) Schematic illustration of the ruthenium(Ⅱ) anthraquinone complexes 1a~c as two-photon luminescent hypoxia probes;(B) Two-photon luminescence confocal microscopy images of A549 cancer cells incubated with complex 1c at various oxygen concentrations for 1 h;(C) Two-photon confocal luminescence images of the head of zebrafish under hypoxia after incubation of 1c for 1 h[46]
Fig. 3 Detection mechanism of the mitochondrial O2-sensitive iridium(Ⅲ)-anthraquinone complexes 2a~d[47]
Fig. 4 (A) Schematic diagram of complex 3 coated on gold nanoparticles;(B) OPM and TPM images of HeLa cells incubated with RuNH2@AuNPS for 1 h;(C) HeLa cells pre-treated with N-ethylmaleimide(NEM) and then treated with RuNH2@AuNPS for 1 h[57]
Fig. 5 The chemical structures of complexes 4a,b for Cys/Hcy two-photon probes[58]
Fig. 6 (A)The reaction scheme of gold(Ⅰ) complexes 5a~d with R-SH in the dark or upon irradiation;(B) One- and two-photon fluorescence images of HepG2 cells treated with 10 μM of 5b for 1 h[69]
Fig. 7 Fig. 7 (A) The chemical structure of complex 6;(B) Confocal two-photon fluorescence images of living HepG2 cells incubated with 10 μM complex 6 for 10 min(λex= 820 nm, λem = 580~620 nm);(C) The STED micrographs of complex 6 staining the nucleus;(D and E) Amplified confocal two-photon fluorescence imaging and STED micrographs of living HepG2 cells incubated with 10 μM complex 6.(F) The fluorescence intensity profile from confocal two-photon fluorescence imaging and the STED micrographs(inset: S/N ratio of confocal and STED microscopy). The scale bar = 5 μm[71]
Fig. 8 Chemical structures of complexes 7a,b[75] and 8[76]
Fig. 9 The protonated chemical structures of complexes 9a,b[80]
Fig. 10 The chemical structure of complex 10[86]
Fig. 11 Reaction mechanism and chemical structure of complex 11[90]
Fig. 12 (A) Illustration of the reaction of probe complex 12 with NO;(B) One-photon and two-photon phosphorescence and bright field images of the complex 12-loaded RAW 264.7cells after adding different concentrations of NO;(C) PLIM images of the complex 12-loaded RAW 264.7 cells incubated with LPS, IFN-γ and L-Arg at different times. Scale bar: 10 μm[95]
Fig. 13 Illustration of the reaction of complex 13 and NO[96]
Fig. 14 (A) The reaction mechanism of complex 14 and Cu 2+;(B) OPM and(C) TPM images of HeLa cells incubated with complex 14 before and after the exogenous Cu source treatment;(D) Luminescence imaging of five-day-old zebrafish incubated with complex 14 for 1 h;(E) Zebrafish incubated with complex 14, then further incubated with the exogenous Cu source treatment[103]
Fig. 15 Reaction mechanism and chemical structure of complex 15[113]
Fig. 16 Chemical structures of complexes 16a~f[116]
Fig. 17 Chemical structures of complexes 17a~e[123]
Fig. 18 (A) Synthetic route to complexes 18;(B)Two-photon phosphorescent images of 3D tumor spheroids after incubation with complexes 18(2 μM) for 6 h;(C) The two-photon 3D Z-stack images of an intact tumor spheroid;(D) The two-photon Z-stack images from different sections from top to bottom. λex = 750 nm[131]
Fig. 19 Schematic diagram of the self-assembly process of complexes 19a,b[132]
Fig. 20 Chemical structures of complexes(A) 20a,b[135] and(B) 21[136]
Fig. 21 Chemical structures of complexes(A)22a~d[138] and(B)23a,b[139]
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