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. 2019 Jan 4;24(1):172. doi: 10.3390/molecules24010172

Table 4.

The application of copper-free click chemistry for tumor targeting delivery and imaging.

Reaction Type Tumor Labeling Targeting Agent Tumor Model Purpose Reference
Labeling Method Labeling Agent Administration Route Targeting Agent Administration Route
SPAAC MGE Ac4ManNAz it DBCO-liposome iv A549 subcutaneous tumor Imaging [40]
(2012)
SPAAC MGE RR-S-Ac3ManNAz it DBCO-Cy5.5 iv HT-29 subcutaneous tumor Imaging [84]
(2016)
SPAAC MGE DCL-AAM iv DBCO-Cy5 iv LS174T subcutaneous tumor Imaging [41]
(2017)
DBCO-VC-Dox LS174T and MDA-MB-231 subcutaneous tumor and4T1 lung metastatic tumor Therapy
SPAAC MGE Ac4ManNAz-loaded CNPs iv BCN-Ce6-CNPs iv A549 subcutaneous tumor Imaging and therapy [83]
(2014)
SPAAC MGE Ac4ManNAz-liposome iv DBCO-ZnPc-liposome iv A549 subcutaneous tumor Imaging andtherapy [43]
(2017)
SPAAC MGE Nano-MPs iv Cy5.5 labeled BCN-liposome iv U87 and MCF7 subcutaneous tumor Imaging [37]
(2017)
SPAAC MGE Ac4ManNAz loaded microbubble iv DBCO-Cy5 iv 4T1 subcutaneous tumor Imaging [85]
(2016)
SPAAC Azide-labeling cells Azide-labeling MSCs it NIR-dye containing DBCO-NPs iv A549-Luc subcutaneous tumor Imaging [33]
(2016)
ip Paclitaxel-loaded DBCO-NPs ip MA148 metastatic ovarian tumor Therapy
SPAAC Nanoparticles DBCO-PEG-MSNs iv 18F-azide iv U87 MG subcutaneous tumor Imaging [86]
(2013)
SPAAC, Staudinger ligation and iEDDA MGE Ac4GalNAz ip Tz-DyLight iv LL2 subcutaneous tumor Imaging [87]
(2013)
TMDIBO-TCO and PHOS-TCO iv
iEDDA Antigen-antibody reaction CD49-TCO iv 111 In-Tz iv Colon carcinoma xenograft Imaging [88]
(2010)
iEDDA Antigen-antibody reaction A33-TCO iv 64Cu-Tz-Bn-NOTA iv SW1222 subcutaneous tumor Imaging [89]
(2013)
iEDDA Antigen-antibody reaction mAb-TCO iv 18F-Tz iv A431 and BT-474 subcutaneous tumor Imaging [90]
(2017)
iEDDA Antigen-antibody reaction A33-TCO iv Polymer-modified Tz iv LS174 subcutaneous tumor Imaging [91]
(2012)
iEDDA Antigen-antibody reaction CC49-TCO iv 177Lu-Tz iv LS174T subcutaneous tumor Imaging [92]
(2013)
iEDDA Antigen-antibody reaction CC49-TCO iv 111In-Tz iv LS174T subcutaneous tumor Imaging [93]
(2013)
iEDDA Antigen-antibody reaction TCO-oxymethylacetamide-tagged CC49 iv 111In-Tz iv LS174T subcutaneous tumor Imaging [94]
(2014)
iEDDA Antigen-antibody reaction A33-TCO iv 68Ga-Tz-DTPA dextran iv LS174T subcutaneous tumor Imaging [95]
(2014)
iEDDA Antigen-antibody reaction TCO-antiVEGFR2 iv MBTZ iv SKOV-3 subcutaneous tumor Imaging [96]
(2014)
iEDDA Antigen-antibody reaction 5B1-TCO iv 64Cu-NOTA-PEG7-TCO iv Capan-2 and BxPC3 subcutaneous tumor Imaging [97]
(2016)
iEDDA Antigen-antibody reaction 5B1-TCO iv 177Lu-DOTA-PEG7-Tz iv BxPC3 subcutaneous tumor Therapy [98]
(2017)
89Zr-Tz Imaging
iEDDA Antigen-antibody reaction Ts29.2-PEG-TCO iv Tz-Cy5 iv HT29 subcutaneous tumor Imaging [99]
(2017)
35A7-PEG-TCO iv Tz-Cy5 ip A431-CEA-Luc peritoneal carcinomatosis tumor
iEDDA Membrane inserted peptide pHLIP-Tz it 18F-TCO-liposome iv SKOV-3 subcutaneous tumor Imaging [100]
(2013)
iEDDA Aptamer (peptide) GEBP11-TCO iv Cy5.5-Tz iv SGC-7901 subcutaneous tumor Imaging [45]
(2017)
iEDDA Antigen-antibody reaction CC49-TCO-DOX iv Radio-labeled Tz iv and ip LS174T subcutaneous tumor Therapy [101]
(2016)
iEDDA Antigen-antibody reaction TAG72-TCO-MMAE iv Tz-DOTA iv LS174T and OVCAR 3 subcutaneous tumor Therapy [102]
(2018)

MGE, metabolic glycoengineering; it, intratumoral injection; DBCO-liposome, DBCO conjugated PEGylated liposome (PEG = poly[ethylene glycol]); iv, intravenous injection; LST174T, human colon cancer cell line; DBCO-ZnPc-LP, DBCO-modified zinc (II)-phthalocyanine-loaded liposome; U87, human glioblastoma cell line; MCF7, human breast cancer cell line; ip, intraperitoneal injection; DBCO-PEG-MSNs, DBCO-functionalized PEGylated mesoporous silica nanoparticles; Ac4GalNAz, tetraacetylated N-Azidoacetyl-galactosamine; TMDIBO-TCO, tetramethoxydibenzocyclooctyne-TCO; PHOS-TCO, bifunctional TCO-phosphine; Tz-DyLight, fluorescently labeled Tz; LL2, murine small cell lung cancer cell line; SW1222, human colorectal cancer cell line; A431, human epidermoid carcinoma cell line; BT-474, human breast carcinoma cell line; TCO-anti-VEGFR2, TCO-conjugated anti-vascular endothelial growth factor receptor 2; MBtz, Tz-labeled gas-filled microbubbles; SKOV-3, human ovarian carcinoma cell line; 5B1-TCO, TCO-modified a human anti-CA19.9 monoclonal antibody 5B1; Capan-2, human pancreas adenocarcinoma cell line Cpan-2; BxPC3, human pancreatic cancer cell line; Ts29.2-PEG-TCO, anti-TSPAN8 monoclonal antibody (Ts29.2)-PEG-TCO; 35A7-PEG-TCO, anti-CEA monoclonal antibody (35A7)-PEG-TCO; A431-CEA-Luc, colon carcinoma transfected with constructs encoding both carcinoembryonic antigen and luciferase; pHLIP-Tz, Tz-conjugated pH (low) insertion peptide; GEBP11-TCO, a vascular-homing peptide (GEBP11)-TCO conjugate; SGC-7901, human gastric carcinoma cell line SGC-7901; MMAE, monomethyl auristatin E.