A small-molecule dye for NIR-II imaging
Source abstract
Abstract
Fluorescent imaging of biological systems in the second near-infrared window (NIR-II) can probe tissue at centimetre depths and achieve micrometre-scale resolution at depths of millimetres. Unfortunately, all current NIR-II fluorophores are excreted slowly and are largely retained within the reticuloendothelial system, making clinical translation nearly impossible. Here, we report a rapidly excreted NIR-II fluorophore (∼90% excreted through the kidneys within 24 h) based on a synthetic 970-Da organic molecule (CH1055). The fluorophore outperformed indocyanine green (ICG)-a clinically approved NIR-I dye-in resolving mouse lymphatic vasculature and sentinel lymphatic mapping near a tumour. High levels of uptake of PEGylated-CH1055 dye were observed in brain tumours in mice, suggesting that the dye was detected at a depth of ∼4 mm. The CH1055 dye also allowed targeted molecular imaging of tumours in vivo when conjugated with anti-EGFR Affibody. Moreover, a superior tumour-to-background signal ratio allowed precise image-guided tumour-removal surgery.
Source: europepmc · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Nanoplatforms for cancer theranostics · Cancer Research and Treatments · Nanoparticle-Based Drug Delivery
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (43)
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1. Kamolz, L. P., Andel, H., Auer, T., Meissl, G. & Frey, M. Evaluation of skin perfusion by use of indocyanine green video angiography: Rational design and planning of trauma surgery. J. Trauma 61, 635–641 (2006).10.1097/01.ta.0000233910.47550.9c ↗
2. Orth, D. H., Patz, A. & Flower, R. W. Potential clinical applications of indocyanine green choroidal angiography—preliminary-report. Eye Ear Nose Throat Mon. 55, 4–11 (1976).
3. Choi, H. S. et al. Targeted zwitterionic near-infrared fluorophores for improved optical imaging. Nature Biotechnol. 31, 148–153 (2013).10.1038/nbt.2468 ↗
4. Gioux, S., Choi, H. S. & Frangioni, J. V. Image-guided surgery using invisible near-infrared light: Fundamentals of clinical translation. Mol. Imaging 9, 237–255 (2010).10.2310/7290.2010.00034 ↗
5. Hong, G. et al. Multifunctional in vivo vascular imaging using near-infrared II fluorescence. Nature Med. 18, 1841–1846 (2012).10.1038/nm.2995 ↗
6. Liu, Z. et al. In vivo biodistribution and highly efficient tumour targeting of carbon nanotubes in mice. Nature Nanotech. 2, 47–52 (2007).10.1038/nnano.2006.170 ↗
7. Vahrmeijer, A. L., Hutteman, M., van der Vorst, J. R., van de Velde, C. J. & Frangioni, J. V. Image-guided cancer surgery using near-infrared fluorescence. Nature Rev. Clin. Oncol. 10, 507–518 (2013).10.1038/nrclinonc.2013.123 ↗
8. Hong, G. et al. In vivo fluorescence imaging with Ag2S quantum dots in the second near-infrared region. Angew. Chem. Int. Ed. 124, 9956–9959 (2012).10.1002/ange.201206059 ↗
9. Hong, G. et al. Ultrafast fluorescence imaging in vivo with conjugated polymer fluorophores in the second near-infrared window. Nature Commun. 5, 4206 (2014).10.1038/ncomms5206 ↗
10. Diao, S. et al. Chirality enriched (12,1) and (11,3) single-walled carbon nanotubes for biological imaging. J. Am. Chem. Soc. 134, 16971–16974 (2012).10.1021/ja307966u ↗
11. Choi, H. S. et al. Renal clearance of quantum dots. Nature Biotechnol. 25, 1165–1170 (2007).10.1038/nbt1340 ↗
12. Liu, Z. et al. Circulation and long-term fate of functionalized, biocompatible single-walled carbon nanotubes in mice probed by Raman spectroscopy. Proc. Natl Acad. Sci. USA 105, 1410–1415 (2008).10.1073/pnas.0707654105 ↗
13. Antaris, A. L. et al. Ultra-low doses of chirality sorted (6,5) carbon nanotubes for simultaneous tumor imaging and photothermal therapy. ACS Nano 7, 3644–3652 (2013).10.1021/nn4006472 ↗
14. Welsher, K. et al. A route to brightly fluorescent carbon nanotubes for near-infrared imaging in mice. Nature Nanotech. 4, 773–780 (2009).10.1038/nnano.2009.294 ↗
15. Welsher, K., Sherlock, S. P. & Dai, H. J. Deep-tissue anatomical imaging of mice using carbon nanotube fluorophores in the second near-infrared window. Proc. Natl Acad. Sci. USA 108, 8943–8948 (2011).10.1073/pnas.1014501108 ↗
16. Fitzpatrick, J. A. J. et al. Long-term persistence and spectral blue shifting of quantum dots in vivo. Nano Lett. 9, 2736–2741 (2009).10.1021/nl901534q ↗
17. Yang, S. T. et al. Long-term accumulation and low toxicity of single-walled carbon nanotubes in intravenously exposed mice. Toxicol. Lett. 181, 182–189 (2008).10.1016/j.toxlet.2008.07.020 ↗
18. Xie, R., Chen, K., Chen, X. & Peng, X. InAs/InP/ZnSe core/shell/shell quantum dots as near-infrared emitters: Bright, narrow-band, non-cadmium containing, and biocompatible. Nano Res. 1, 457–464 (2008).10.1007/s12274-008-8048-x ↗
19. Hu, F. et al. Real-time in vivo visualization of tumor therapy by a near-infrared-II Ag2S quantum dot-based theranostic nanoplatform. Nano Res. 8, 1637–1647 (2015).10.1007/s12274-014-0653-2 ↗
20. Tao, Z. M. et al. Biological imaging using nanoparticles of small organic molecules with fluorescence emission at wavelengths longer than 1000 nm. Angew. Chem. Int. Ed. 52, 13002–13006 (2013).10.1002/anie.201307346 ↗
21. Kim, S. et al. Near-infrared fluorescent type II quantum dots for sentinel lymph node mapping. Nature Biotechnol. 22, 93–97 (2004).10.1038/nbt920 ↗
22. Maeda, H., Wu, J., Sawa, T., Matsumura, Y. & Hori, K. Tumor vascular permeability and the EPR effect in macromolecular therapeutics: A review. J. Control Release 65, 271–284 (2000).10.1016/S0168-3659(99)00248-5 ↗
23. Wishart, G. C., Loh, S. W., Jones, L. & Benson, J. R. A feasibility study (ICG-10) of indocyanine green (ICG) fluorescence mapping for sentinel lymph node detection in early breast cancer. Eur. J. Surg. Oncol. 38, 651–656 (2012).10.1016/j.ejso.2012.05.007 ↗
24. Gao, J. H. et al. Affibody-based nanoprobes for HER2-expressing cell and tumor imaging. Biomaterials 32, 2141–2148 (2011).10.1016/j.biomaterials.2010.11.053 ↗
25. Qian, G. et al. Band gap tunable, donor–acceptor–donor charge-transfer heteroquinoid-based chromophores: Near infrared photoluminescence and electroluminescence. Chem. Mater. 20, 6208–6216 (2008).10.1021/cm801911n ↗
26. Hong, G. et al. Through-skull fluorescence imaging of the brain in a new near-infrared window. Nature Photon. 8, 723–730 (2014).10.1038/nphoton.2014.166 ↗
27. Murphy, J. E. et al. PbTe colloidal nanocrystals: Synthesis, characterization, and multiple exciton generation. J. Am. Chem. Soc. 128, 3241–3247 (2006).10.1021/ja0574973 ↗
28. Williams, A. T. R., Winfield, S. A. & Miller, J. N. Relative fluorescence quantum yields using a computer-controlled luminescence spectrometer. Analyst 108, 1067–1071 (1983).10.1039/an9830801067 ↗
29. Ju, S. Y., Kopcha, W. P. & Papadimitrakopoulos, F. Brightly fluorescent single-walled carbon nanotubes via an oxygen-excluding surfactant organization. Science 323, 1319–1323 (2009).10.1126/science.1166265 ↗
30. Fox, M. E., Szoka, F. C. & Frechet, J. M. J. Soluble polymer carriers for the treatment of cancer: The importance of molecular architecture. Acc. Chem. Res. 42, 1141–1151 (2009).10.1021/ar900035f ↗
31. Troyan, S. L. et al. The FLARE intraoperative near-infrared fluorescence imaging system: A first-in-human clinical trial in breast cancer sentinel lymph node mapping. Ann. Surg. Oncol. 16, 2943–2952 (2009).10.1245/s10434-009-0594-2 ↗
32. Chi, C. W. et al. Use of indocyanine green for detecting the sentinel lymph node in breast cancer patients: From preclinical evaluation to clinical validation. PLoS ONE 8, e83927 (2013).10.1371/journal.pone.0083927 ↗
33. Tanaka, E., Choi, H. S., Fujii, H., Bawendi, M. G. & Frangioni, J. V. Image-guided oncologic surgery using invisible light: Completed pre-clinical development for sentinel lymph node mapping. Ann. Surg. Oncol. 13, 1671–1681 (2006).10.1245/s10434-006-9194-6 ↗
34. Diao, S. et al. Biological imaging without autofluorescence in the second near-infrared window. Nano Res. 8, 3027–3034 (2015).10.1007/s12274-015-0808-9 ↗
35. Zheng, M. B. et al. Robust ICG theranostic nanoparticles for folate targeted cancer imaging and highly effective photothermal therapy. ACS Appl. Mater. Interfaces 6, 6709–6716 (2014).10.1021/am5004393 ↗
36. Gurfinkel, M. et al. Pharmacokinetics of ICG and HPPH-car for the detection of normal and tumor tissue using fluorescence, near-infrared reflectance imaging: A case study. Photochem. Photobiol. 72, 94–102 (2000).10.1562/0031-8655(2000)072<0094:POIAHC>2.0.CO;2 ↗
37. Zimmermann, M., Zouhair, A., Azria, D. & Ozsahin, M. The epidermal growth factor receptor (EGFR) in head and neck cancer: Its role and treatment implications. Radiat. Oncol. 1, 11 (2006).10.1186/1748-717X-1-11 ↗
38. Miao, Z., Ren, G., Liu, H. G., Jiang, L. & Cheng, Z. Cy5.5-labeled Affibody molecule for near-infrared fluorescent optical imaging of epidermal growth factor receptor positive tumors. J. Biomed. Opt. 15, 36007 (2010).10.1117/1.3432738 ↗
39. Qi, S. B. et al. Evaluation of four affibody-based near-infrared fluorescent probes for optical imaging of epidermal growth factor receptor positive tumors. Bioconjug. Chem. 23, 1149–1156 (2012).10.1021/bc200596a ↗
40. Ekblad, T. et al. Development and preclinical characterisation of Tc-99m-labelled Affibody molecules with reduced renal uptake. Eur. J. Nucl. Med. Mol. Imaging 35, 2245–2255 (2008).10.1007/s00259-008-0845-7 ↗
41. Tolmachev, V. et al. Affibody molecules for epidermal growth factor receptor targeting in vivo: Aspects of dimerization and labeling chemistry. J. Nucl. Med. 50, 274–283 (2009).10.2967/jnumed.108.055525 ↗
42. Harris, J. M. & Chess, R. B. Effect of pegylation on pharmaceuticals. Nature Rev. Drug Discov. 2, 214–221 (2003).10.1038/nrd1033 ↗
43. He, X. X., Gao, J. H., Gambhir, S. S. & Cheng, Z. Near-infrared fluorescent nanoprobes for cancer molecular imaging: Status and challenges. Trends Mol. Med. 16, 574–583 (2010).10.1016/j.molmed.2010.08.006 ↗