Research Progress in Activatable NIR-Ⅱ Small Molecule Fluorescent Probes

doi:10.19894/j.issn.1000-0518.230264

Chinese Journal of Applied Chemistry ›› 2024, Vol. 41 ›› Issue (1): 39-59.DOI: 10.19894/j.issn.1000-0518.230264

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Research Progress in Activatable NIR-Ⅱ Small Molecule Fluorescent Probes

Xin-Yu ZHAO, Zuo-Jia QIN, Xiao-Bing ZHANG, Lin YUAN()

State Key Laboratory of Chemo/Biosensing and Chemometrics，College of Chemistry and Chemical Engineering，Hunan University，Changsha 410082，China

Received:2023-09-01 Accepted:2023-11-17 Published:2024-01-01 Online:2024-01-30
Contact: Lin YUAN
About author:lyuan@hnu.edu.cn
Supported by:
the National Natural Science Foundation of China(22074036)

Abstract

Abstract:

Fluorescence imaging in the second near-infrared region （NIR-Ⅱ?） has been widely used in biomedical due to its deep tissue penetration and high spatial resolution. Compared with the “always on” fluorescent probes， the activatable probes that change fluorescence signals only in the presence of specific biomarkers have higher signal-to-background ratio， resulting in better accuracy and reliability of detection. In this review， from the classification of disease models， we introduce the recent NIR-Ⅱ activatable probes. Moreover， the limitation and perspectives of NIR-Ⅱ activatable probes are briefly discussed as well.

Key words: NIR-Ⅱ fluorescence imaging, Small molecule fluorescent probe, Activatable probe, Bioimaging

CLC Number:

O656

Xin-Yu ZHAO, Zuo-Jia QIN, Xiao-Bing ZHANG, Lin YUAN. Research Progress in Activatable NIR-Ⅱ Small Molecule Fluorescent Probes[J]. Chinese Journal of Applied Chemistry, 2024, 41(1): 39-59.

Figures/Tables 14

Fig.1 Representative probe for liver inflammation imaging. （A） Structure and response mechanism of Hydro-1080［23］. （B） Absorption and fluorescence spectra of Hydro-1080 and Et-1080 in DMSO［23］. （C） NIR-Ⅱ fluorescence images of mice liver injury［23］. （D） Structure and response mechanism of probe TC-H2O2［24］. （E） MOST and fluorescence imaging of mice liver injury model［24］. （F） Structure and response mechanism of IR-990［26］. （G） NIR-Ⅱ fluorescence imaging of H2O2 in HepG2 cells and APAP-induced mice liver injury models［26］

Fig.2 Representative probes for liver inflammation imaging. （A） Structure and response mechanism of NIRII-HD5-ONOO－［30］. （B） NIR-Ⅱ fluorescence spectra of NIRII-HD5-ONOO－（5 μmol/L） after reaction with various concentrations of ONOO－. （C） NIR-Ⅱ fluorescence response of NIRII-HD5-ONOO－（5 μmol/L） toward different analytes［30］. （D） NIR-Ⅱ fluorescence imaging of liver injury after APAP treatment［30］. （E） Structure and response mechanism of IRBTP-B［31］. （F） Response mechanism of probe NIR-Ⅱ Cy3-988［33］. （G） Fluorescence intensity changes of NIR-Ⅱ Cy3-988 （5 μmol/L） after reaction with various concentrations of HClO （0~15 μmol/L） and H2S （0~3.5 μmol/L）［33］. （H） NIR-Ⅱ fluorescence imaging of mice liver injury and repair［33］. （I） Structure of probe NIRII-RT-ATP［34］. （J） NIR-Ⅱ fluorescence spectra of NIRII-RT-ATP （5 μmol/L） after reaction with various concentrations of ATP［34］. （K） Fluorescence imaging of liver injury after APAP treatment［34］. （L） Structure and response mechanism of TTX-P［35］. （M） NIR-Ⅱ fluorescence imaging of liver injury［35］. （N） Structure and response mechanism of NIR-Ⅱ-LAP［36］. （O） Fluorescence imaging of liver injury after APAP treatment［36］

Fig.3 Representative probes for imaging kidney inflammation. （A） Structure and response mechanism of BOD-Ⅱ-NAG［39］. （B） NIR-Ⅱ fluorescence images of living mice after injection of BOD-Ⅱ-NAG-NP （16 μmol/kg） at different time［39］. （C） The fluorescence intensity in different groups after intravenous injection of BOD-Ⅱ-NAG-NP［39］. （D） Changes in KIM-1， NGAL， NAG， Cyst C， sCr and BUN in living mice after different treatment［39］. （E） Structure and design strategy of HP-N dyes and HP-H2O2［40］（F） NIR-Ⅱ fluorescence spectra of HP-H2O2 after reaction with various concentrations of H2O2（10 μmol/L）［40］. （G） Fluorescence intensities of the probe HP-H2O2 at different time［40］. （H） NIR-Ⅱ fluorescence images of control mice and AKI mice［40］

Fig.4 Representative probe for imaging cystitis. （A） Structure and photophysical properties of Chrodol［42］. （B） Response mechanism of dual-activatable probe PN910［42］. （C） Absorption and fluorescence spectra of PN910 and Chrodol-3［42］. （D） Fluorescence intensity upon addition of H2O2 （left） and ONOO－（right）［42］. （E） Structure and response mechanism of BTPE-NO2@F127 probe［43］. （F） MOST images （left） and NIR-Ⅱ fluorescence images （right） of the control and the interstitial cystitis model［43］

Fig.5 Representative probes for imaging joint inflammation. （A） Structure and response mechanism of probe PTA［46］. （B） Fluorescence images of exogenous and endogenous HClO in HeLa cell［46］. （C） Fluorescence imaging of HClO in RA mouse model［46］. （D） Structure and response mechanism of DNCP@SeTT［47］. （E） Structure and response mechanism of probe HC-N［48］. （F） NIR-Ⅱ fluorescence spectra （left） and fluorescence intensity at 923 nm （right） of HC-N （5 μmol/L） after reaction with various concentrations of NO［48］

Fig.6 Representative probe for imaging ulcerative colitis［50］. （A） Structure and response mechanism of probe BOD-XT-DHM. （B） NIR-Ⅱ fluorescent images of mice after oral administration of BM@EP （50 mg/kg）. （C） Changes in body mass of different groups' mice. （D） NIR-Ⅱ fluorescence images of mice （left） and average fluorescent intensities at mice′s colon region （right） after oral dosing of BM@EP （43.6 mg/kg）

Table 1 NIR-Ⅱ activatable probes for inflammation models

Disease model	Biomarker	Probe	λ_ex/λ_em（nm）	LOD	Ref.
Liver injury	?OH	Hydro-1080	980/1 044	0.5 nmol/L	［23］
	H₂O₂	TC-H₂O₂	808/920	-	［24］
		IR-990	808/990	0.59 μmol/L	［26］
		BHC-Lut	808/930	-	［29］
	ONOO^-	NIRII-HD5-ONOO^-	808/936	-	［30］
	ONOO^-	IRBTP-B	808/1 000	55.9 nmol/L	［31］
	HClO	NIR Ⅱ Cy3-988	980/1 058	-	［33］
	ATP	NIRII-RT-ATP	808/918	-	［34］
	ALP	TTX-P	808/920	0.038 U/L	［35］
	LAP	NIR-Ⅱ-F2LAP	808/940	0.063 U/L	［36］
Kidney injury	NAG	BOD-II-NAG-NP	710/1 000	0.72 mU/mL	［39］
Kidney injury	H₂O₂	HP-H₂O₂	808/937	-	［40］
Cystitis	ROS/RNS and base	PN910	808/910	1 μmol/L	［42］
Cystitis	H₂O₂	BTPE-NO₂	780/938	740 nmol/L	［43］
Joint inflammation	HClO	PTA	808/936	55 nmol/L	［46］
	HClO	DNCP@SeTT	980/1 150	0.4 μmol/L	［47］
	NO	HC-N	808/923	0.18 μmol/L	［48］
Colitis	pH/ROS	BM@EP	808/950	-	［50］

Fig.7 Representative probe for liver cancer imaging［52］. （A） Structure and response mechanism of probe BH-NO2@BSA. （B） 3D MOST imaging of mouse liver tumors （middle） and NIR-Ⅱ fluorescence image-guided resection of liver tumors （right）

Fig.8 Representative probes for breast cancer imaging. （A） Structure and response mechanism of probe LET-7［53］. （B） NIR-Ⅱ fluorescence spectra of probe LET-7 （2 μmol/L） after reaction with various concentrations of GSH （left） and corresponding linear relationships （right）［53］. （C） NIR-Ⅱ fluorescence images of mice［53］. （D） Structure and response mechanism of probe BP-A［55］. （E） Different groups′ mice′s NIR-Ⅱ fluorescence images after intratumoral injection of BP-A （200 μmol/L）［55］. （F） Design strategy of the ratiometric probe Rap-N［57］. （G） Time dependence of fluorescence spectra （left） and I1000 nm/I940 nm ratio of Rap-N （right） incubation with NTR （10 μg/mL）［57］. （H） Ratiometric fluorescence images （left） and signal intensity （right） of mice bearing breast tumors （the left tumor injected with the NTR inhibitor dicoumarol）［57］. （I） Structure of the molecular probe Q-NO2 ［59］. （J）NIR-Ⅱ images and （K） MOST images of regional and distant breast cancer metastases in mice［59］

Fig.9 Representative probes for lung cancer imaging. （A） Structure and response mechanism of enzyme-activated probes［61］. （B） Time dependence of fluorescence spectra of Rap-N （20 mg/mL） incubation with NTR［61］. （C） Different groups' mice's NIR-Ⅱ fluorescence images after injection of the probe NTR-InD （30 nmol）［61］. （D） Structure and response mechanism of probe RHC-NO2［62］. （E） NIR-Ⅱ fluorescence spectra of probe RHC-NO2 （10 μmol/L） after reaction with various concentrations of NTR［62］. （F） NIR-Ⅱ images of lung tumor-bearing mice after tail vein injection of RHC-NO2 （500 μmol/L）［62］

Fig.10 Representative probes for colon cancer imaging. （A） Structure and response mechanism of WH-X probes［64］. （B） Fluorescence spectra of WH-X probe［64］. （C） Fluorescence images of different treated cells with probe WH-3 ［64］. （D） NIR-Ⅱ fluorescence images of mice. after injection of probe WH-3 （20 μL， 1 mmol/L）［64］. （E） Structure and response mechanism of NIRII@Si［65］. （F） The structure of FRET donor NAB and acceptor NRh［67］. （G） Fluorescence intensity at 940 and 1026 nm of probe pTAS as a function of pH［67］

Fig.11 Representative probes for imaging ovarian cancer. （A） Structure and response mechanism of BOD-M-βGal［70］. （B） NIR-Ⅱ fluorescence images of mice after injection of probe WH-3 （30 nmol）［70］. （C） Structure of Flavchromenes［71］. （D） Response mechanism of Flavchrom-4 probe［71］. （E） Absorption and fluorescence spectra of Flavchrom-4 after incubation with β-Gal［71］. （F） MOST images （left） and NIR-Ⅱ fluorescence images （right） of the ovarian cancer model after injection of Flavchrom-4［71］

Table 2 NIR-Ⅱ activatable probes for cancer models

Disease model	Biomarker	Probe	λ_ex/λ_em（nm）	LOD	Ref.
Liver cancer	NTR	BH-NO₂	808/923	53 ng/mL	［52］
Breast cancer	GSH	LET-7	808/928	85 nmol/L	［53］
	H₂S	BP-A	808/1 032	15 nmol/L	［55］
	NTR	Rap-N	808/1 000	-	［57］
	NTR	NP-Q-NO₂	808/922	52 ng/mL	［58］
Lung cancer	NTR	NTR-InD	730/900	-	［61］
Lung cancer	NTR	RHC-NO₂	808/921	5.9 ng/mL	［62］
Colorectal cancer	H₂S	WH-3	925/1 140	51 nmol/L	［64］
	H₂S	NIR-Ⅱ@Si	780/900	37 nmol/L	［65］
	pH	pTAS	808/1 026	6.11~7.22	［67］
Ovarian cancers	βGal	BOD-M-βGal	723/853	40.16 μmol/L	［70］
Ovarian cancers	βGal	Flavchrom-4	830/900	0.037 U/mL	［71］

Fig.12 Representative probes for imaging Alzheimer′s disease［73］. （A） Structure and response mechanism of DMP2. （B） Fluorescence spectra of DMP2 in different solvents. （C） NIR-Ⅱ fluorescence imaging of the brain of healthy mice （left） and AD-model mice （right） after injection of probe DMP2 （2 mg/kg）

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Research Progress in Activatable NIR-Ⅱ Small Molecule Fluorescent Probes

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