A Fluorescent Probe for Rapid, High-Contrast Visualization of Folate-Receptor-Expressing Tumors In Vivo.
cancer
chromophores
fluorescent probes
imaging
vitamins
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
06 04 2020
06 04 2020
Historique:
received:
20
11
2019
revised:
30
12
2019
pubmed:
28
1
2020
medline:
18
3
2021
entrez:
28
1
2020
Statut:
ppublish
Résumé
Folate receptors (FRs) are membrane proteins involved in folic acid uptake, and the alpha isoform (FR-α) is overexpressed in ovarian and endometrial cancer cells. For fluorescence imaging of FRs in vivo, the near-infrared (NIR) region (650-900 nm), in which tissue penetration is high and autofluorescence is low, is optimal, but existing NIR fluorescent probes targeting FR-α show high non-specific tissue adsorption, and require prolonged washout to visualize tumors. We have designed and synthesized a new NIR fluorescent probe, FolateSiR-1, utilizing a Si-rhodamine fluorophore having a carboxy group at the benzene moiety, coupled to a folate ligand moiety through a negatively charged tripeptide linker. This probe exhibits very low background fluorescence and afforded a tumor-to-background ratio (TBR) of up to 83 in FR-expressing tumor-bearing mice within 30 min. Thus, FolateSiR-1 has the potential to contribute to the research in the field of biology and the clinical medicine.
Identifiants
pubmed: 31984590
doi: 10.1002/anie.201914826
doi:
Substances chimiques
Fluorescent Dyes
0
Folate Receptors, GPI-Anchored
0
Rhodamines
0
Folic Acid
935E97BOY8
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
6015-6020Informations de copyright
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Références
W. Xia, P. S. Low, J. Med. Chem. 2010, 53, 6811-6824.
Y. G. Assaraf, C. P. Leamon, J. A. Reddy, Drug Resist. Updates 2014, 17, 89-95.
P. S. Low, S. A. Kularatne, Curr. Opin. Chem. Biol. 2009, 13, 256-262.
K. R. Kalli, A. L. Oberg, G. L. Keeney, T. J. H. Christianson, P. S. Low, K. L. Knutson, L. C. Hartmann, Gynecol. Oncol. 2008, 108, 619-626.
S. Markert, S. Lassmann, B. Gabriel, M. Klar, M. Werner, G. Gitsch, F. Kratz, A. Hasenburg, Anticancer Res. 2008, 28, 3567-3572.
A. L. Vahrmeijer, M. Hutteman, J. R. van der Vorst, C. J. H. van de Velds, J. V. Frangioni, Nat. Rev. Clin. Oncol. 2013, 10, 507-518.
G. M. van Dam, G. Themelis, L. M. A. Crane, N. J. Harlaar, R. G. Pleijhuis, W. Kelder, A. Sarantopoulos, J. S. de Jong, H. J. G. Arts, A. G. J. van der Zee, J. Bart, P. S. Low, V. Ntziachristos, Nat. Med. 2011, 17, 1315-1319.
J. V. Frangioni, Curr. Opin. Chem. Biol. 2003, 7, 626-634.
R. Weissleder, V. Ntziachristos, Nat. Med. 2003, 9, 123-128.
W. K. Moon, Y. Lin, T. O'Loughlin, Y. Tang, D. E. Kim, R. Weissleder, C. H. Tung, Bioconjugate Chem. 2003, 14, 539-545.
C. H. Tung, Y. Lin, W. K. Moon, R. Weissleder, ChemBioChem 2002, 3, 784-786.
L. E. Kelderhouse, V. Chelvam, C. Wayua, S. Mahalingam, S. Poh, S. A. Kularatne, P. S. Low, Bioconjugate Chem. 2013, 24, 1075-1080.
Y. Urano, D. Asanuma, Y. Hama, Y. Koyama, T. Barrett, M. Kamiya, T. Nagano, T. Watanabe, A. Hasegawa, P. L. Choyke, H. Kobayashi, Nat. Med. 2009, 15, 104-109.
J. Yang, H. Chen, I. R. Vlahov, J.-X. Cheng, P. S. Low, J. Pharmacol. Exp. Ther. 2007, 321, 462-468.
J. Yang, H. Chen, I. R. Vlahov, J.-X. Cheng, P. S. Low, Proc. Natl. Acad. Sci. USA 2006, 103, 13872-13877.
H. S. Choi, S. L. Gibbs, J. H. Lee, S. H. Kim, Y. Ashitate, F. Liu, H. Hyun, G. L. Park, Y. Xie, S. Bae, M. Henary, J. V. Frangioni, Nat. Biotechnol. 2013, 31, 148-153.
C. Chen, J. Ke, X. E. Zhou, W. Yi, J. S. Brunzelle, J. Li, E.-L. Yong, H. E. Xu, K. Melcher, Nature 2013, 500, 486-489.
S. Gawéda, G. Stochel, K. Szaciłowski, Chem. Asian J. 2007, 2, 580-590.
J. A. Piedrahita, B. Oetama, G. D. Bennett, J. van Waes, B. A. Kamen, J. Richardson, S. W. Lacey, R. G. W. Anderson, R. H. Finnell, Nat. Genet. 1999, 23, 228-232.
V. Ramaekers, J. M. Sequeira, E. V. Quadros, Clin. Chem. Lab. Med. 2013, 51, 497-511.
H. Saitsu, M. Ishibashi, H. Nakano, K. Shiota, Dev. Dyn. 2003, 226, 112-117.
G. Lukinavičius, K. Umezawa, N. Olivier, A. Honigmann, G. Yang, T. Plass, V. Mueller, L. Reymond, I. R. Corrêa, Jr., Z.-G. Luo, C. Schultz, E. A. Lemke, P. Heppenstall, C. Eggeling, S. Manley, K. Johnsson, Nat. Chem. 2013, 5, 132-139.
M. A. Miller, E. Kim, M. F. Cuccarese, A. L. Plotkin, M. Prytyskach, R. H. Kohler, M. J. Pittet, R. Weissleder, Chem. Commun. 2018, 54, 42-45.
E. Kim, K. S. Yang, R. H. Kohler, J. M. Dubach, H. Mikula, R. Weissleder, Bioconjugate Chem. 2015, 26, 1513-1518.
E. Kim, K. S. Yang, R. J. Giedt, R. Weissleder, Chem. Commun. 2014, 50, 4504-4507.
S. H. Alamudi, R. Satapathy, J. Kim, D. Su, H. Ren, R. Das, L. Hu, E. Alvarado-Martínez, J. Y. Lee, C. Hoppmann, E. Peña-Cabrera, H.-H. Ha, H.-S. Park, L. Wang, Y.-T. Chang, Nat. Commun. 2016, 7, 11964.
C. T. Supuran, Nat. Rev. Drug Discovery 2008, 7, 168-181.
C. E. S. Hoogstins, Q. R. J. G. Tummers, K. N. Gaarenstroom, C. D. de Kroon, J. B. M. Z. Trimbos, T. Bosse, V. T. H. B. M. Smit, J. Vuyk, C. J. H. van de Velde, A. F. Cohen, P. S. Low, J. Burggraaf, A. L. Vahrmeijer, Clin. Cancer Res. 2016, 22, 2929-2938.
E. de Jesus, J. J. Keating, S. A. Kularatne, J. Jiang, R. Judy, J. Predina, S. Nie, P. Low, S. Singhal, Int. J. Mol. Imaging 2015, 469047.
J.-Y. Winum, Expert Opin. Ther. Pat. 2016, 26, 1223-1226.
O. Ab, K. R. Whiteman, L. M. Bartle, X. Sun, R. Singh, D. Tavares, A. LaBelle, G. Payne, R. J. Lutz, J. Pinkas, V. S. Goldmacher, T. Chittenden, J. M. Lambert, Mol. Cancer Ther. 2015, 14, 1605-1613.
X. Cheng, J. Li, K. Tanaka, U. Majumder, A. Z. Milinichik, A. C. Verdi, C. J. Maddage, K. A. Rybinski, S. Fernando, D. Fernando, M. Kuc, K. Furuuchi, F. Fang, T. Uenaka, L. Grasso, E. F. Albone, Mol. Cancer Ther. 2018, 17, 2665-2675.
M. P. Deonarain, G. Yahioglu, I. Stamati, A. Pomowski, J. Clarke, B. M. Edwards, S. Diez-Posada, A. C. Stewart, Antibodies 2018, 7, 16.