Applications of azo-based probes for imaging retinal hypoxia

ACS Medicinal Chemistry Letters

Volumn 6, Issue 4, 2015, Pages 445-449

  Uddin, Md Imam ^a   Evans, Stephanie M ^a   Craft, Jason R ^a   Marnett, Lawrence J ^b   Uddin, Md Jashim ^b   Jayagopal, Ashwath ^a,b  

^a VANDERBILT UNIVERSITY MEDICAL CENTER   (United States)

^b VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Hypoxia; imaging agents; molecular imaging; retina; retinal hypoxia; retinal imaging

Indexed keywords

CASPASE 3;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; ENZYME ACTIVITY; FEMALE; FLUORESCENCE; HUMAN; HUMAN CELL; HYPOXIA; IN VITRO STUDY; MOLECULAR IMAGING; MOUSE; NONHUMAN; OXYGEN CONCENTRATION; PRIORITY JOURNAL; RETINA; RETINA CELL; RETINA DISEASE; RETINA HYPOXIA; SIGNAL NOISE RATIO;

ANIMALIA;

EID: 84927628565     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml5005206     Document Type: Article

References (28)

1. Kaur, C.; Foulds, W. S.; Ling, E. A. Hypoxia-ischemia and retinal ganglion cell damage Clin. Ophthalmol. 2008, 2, 879-889
2. Li, S. Y.; Fu, Z. J.; Lo, A. C. Hypoxia-induced oxidative stress in ischemic retinopathy Oxid. Med. Cell. Longevity 2012, 2012, 426769
3. Hardarson, S. H.; Harris, A.; Karlsson, R. A.; Halldorsson, G. H.; Kagemann, L.; Rechtman, E.; Zoega, G. M.; Eysteinsson, T.; Benediktsson, J. A.; Thorsteinsson, A.; Jensen, P. K.; Beach, J.; Stefansson, E. Automatic retinal oximetry Invest. Ophthalmol. Vis. Sci. 2006, 47, 5011-5016
4. Shahidi, M.; Shakoor, A.; Blair, N. P.; Mori, M.; Shonat, R. D. A method for chorioretinal oxygen tension measurement Curr. Eye Res. 2006, 31, 357-366
5. Dai, C.; Liu, X.; Zhang, H. F.; Puliafito, C. A.; Jiao, S. Absolute retinal blood flow measurement with a dual-beam Doppler optical coherence tomography Invest. Ophthalmol. Vis. Sci. 2013, 54, 7998-8003
6. Busk, M.; Jakobsen, S.; Horsman, M. R.; Mortensen, L. S.; Iversen, A. B.; Overgaard, J.; Nordsmark, M.; Ji, X.; Lee, D. Y.; Raleigh, J. R. PET imaging of tumor hypoxia using 18F-labeled Pimonidazole Acta Oncol. 2013, 52, 1300-1307
7. Kizaka-Kondoh, S.; Konse-Nagasawa, H. Significance of nitroimidazole compounds and hypoxia-inducible factor-1 for imaging tumor hypoxia Cancer Sci. 2009, 100, 1366-1373
8. Yang, Y.; Zhu, X. R.; Xu, Q. G.; Metcalfe, H.; Wang, Z. C.; Yang, J. K. Magnetic resonance imaging retinal oximetry: a quantitative physiological biomarker for early diabetic retinopathy? Diabetic Med. 2012, 29, 501-505
9. Scott, A.; Fruttiger, M. Oxygen-induced retinopathy: a model for vascular pathology in the retina Eye 2010, 24, 416-421
10. Mowat, F. M.; Luhmann, U. F.; Smith, A. J.; Lange, C.; Duran, Y.; Harten, S.; Shukla, D.; Maxwell, P. H.; Ali, R. R.; Bainbridge, J. W. HIF-1alpha and HIF-2alpha are differentially activated in distinct cell populations in retinal ischaemia PLoS One 2010, 5, e11103
11. Evans, S. M.; Kim, K.; Moore, C. E.; Uddin, M. I.; Capozzi, M. E.; Craft, J. R.; Sulikowski, G. A.; Jayagopal, A. Molecular probes for imaging of hypoxia in the retina Bioconjugate Chem. 2014, 25, 2030-2037
12. Ross, D.; Beall, H. D.; Siegel, D.; Traver, R. D.; Gustafson, D. L. Enzymology of bioreductive drug activation Br J. Cancer Suppl. 1996, 27, S1-8
13. Linder, K. E.; Metcalfe, E.; Nanjappan, P.; Arunachalam, T.; Ramos, K.; Skedzielewski, T. M.; Marinelli, E. R.; Tweedle, M. F.; Nunn, A. D.; Swenson, R. E. Synthesis, in vitro evaluation, and in vivo metabolism of fluor/quencher compounds containing IRDye 800CW and Black Hole Quencher-3 (BHQ-3) Bioconjugate Chem. 2011, 22, 1287-1297
14. Takahashi, S.; Piao, W.; Matsumura, Y.; Komatsu, T.; Ueno, T.; Terai, T.; Kamachi, T.; Kohno, M.; Nagano, T.; Hanaoka, K. Reversible off-on fluorescence probe for hypoxia and imaging of hypoxia-normoxia cycles in live cells J. Am. Chem. Soc. 2012, 134, 19588-19591
15. Piao, W.; Tsuda, S.; Tanaka, Y.; Maeda, S.; Liu, F.; Takahashi, S.; Kushida, Y.; Komatsu, T.; Ueno, T.; Terai, T.; Nakazawa, T.; Uchiyama, M.; Morokuma, K.; Nagano, T.; Hanaoka, K. Development of azo-based fluorescent probes to detect different levels of hypoxia Angew. Chem., Int. Ed. 2013, 52, 13028-13032
16. Myochin, T.; Hanaoka, K.; Komatsu, T.; Terai, T.; Nagano, T. Design strategy for a near-infrared fluorescence probe for matrix metalloproteinase utilizing highly cell permeable boron dipyrromethene J. Am. Chem. Soc. 2012, 134, 13730-13737
17. Kiyose, K.; Hanaoka, K.; Oushiki, D.; Nakamura, T.; Kajimura, M.; Suematsu, M.; Nishimatsu, H.; Yamane, T.; Terai, T.; Hirata, Y.; Nagano, T. Hypoxia-sensitive fluorescent probes for in vivo real-time fluorescence imaging of acute ischemia J. Am. Chem. Soc. 2010, 132, 15846-15848
18. Weissleder, R. A clearer vision for in vivo imaging Nat. Biotechnol. 2001, 19, 316-317
19. Zhang, P.; Zhang, X.; Fan, J. L.; Hao, X. F.; Wang, Y. S.; Hui, Y. N.; Hu, D.; Zhou, J. Rac1 activates HIF-1 in laser induced choroidal neovascularization Int. J. Ophthalmol. 2011, 4, 14-18
20. Dunn, K. C.; Aotaki-Keen, A. E.; Putkey, F. R.; Hjelmeland, L. M. ARPE-19, a human retinal pigment epithelial cell line with differentiated properties Exp. Eye Res. 1996, 62, 155-169
21. Seigel, G. M.; Mutchler, A. L.; Adamus, G.; Imperato-Kalmar, E. L. Recoverin expression in the R28 retinal precursor cell line In Vitro Cell Dev Biol. Anim. 1997, 33, 499-502
22. Genetos, D. C.; Cheung, W. K.; Decaris, M. L.; Leach, J. K. Oxygen tension modulates neurite outgrowth in PC12 cells through a mechanism involving HIF and VEGF J. Mol. Neurosci. 2010, 40, 360-366
23. Yanni, S. E.; McCollum, G. W.; Penn, J. S. Genetic deletion of COX-2 diminishes VEGF production in mouse retinal Muller cells Exp. Eye Res. 2010, 91, 34-41
24. Smith, L. E.; Wesolowski, E.; McLellan, A.; Kostyk, S. K.; DAmato, R.; Sullivan, R.; DAmore, P. A. Oxygen-induced retinopathy in the mouse Invest. Ophthalmol. Vis. Sci. 1994, 35, 101-111
25. Shi, X.; Semkova, I.; Muther, P. S.; Dell, S.; Kociok, N.; Joussen, A. M. Inhibition of TNF-alpha reduces laser-induced choroidal neovascularization Exp. Eye Res. 2006, 83, 1325-1334
26. Lu, H.; Lu, Q.; Gaddipati, S.; Kasetti, R. B.; Wang, W.; Pasparakis, M.; Kaplan, H. J.; Li, Q. IKK2 inhibition attenuates laser-induced choroidal neovascularization PLoS One 2014, 9, e87530
27. Yang, X. M.; Wang, Y. S.; Zhang, J.; Li, Y.; Xu, J. F.; Zhu, J.; Zhao, W.; Chu, D. K.; Wiedemann, P. Role of PI3K/Akt and MEK/ERK in mediating hypoxia-induced expression of HIF-1alpha and VEGF in laser-induced rat choroidal neovascularization Invest. Ophthalmol. Vis. Sci. 2009, 50, 1873-1879
28. Lambert, V.; Lecomte, J.; Hansen, S.; Blacher, S.; Gonzalez, M. L.; Struman, I.; Sounni, N. E.; Rozet, E.; de Tullio, P.; Foidart, J. M.; Rakic, J. M.; Noel, A. Laser-induced choroidal neovascularization model to study age-related macular degeneration in mice Nat. Protoc. 2013, 8, 2197-2211