Ruthenium(II) anthraquinone complexes as two-photon luminescent probes for cycling hypoxia imaging invivo

Biomaterials

Volumn 53, Issue , 2015, Pages 522-531

  Zhang, Pingyu ^a   Huang, Huaiyi ^a   Chen, Yu ^a   Wang, Jinquan ^a   Ji, Liangnian ^a   Chao, Hui ^a  

^a SUN YAT SEN UNIVERSITY   (China)

Author keywords

Anthraquinone; Cycling; Hypoxia; Ru(II) complex; Two photon

Indexed keywords

AROMATIC COMPOUNDS; CHEMOTHERAPY; KETONES; LUMINESCENCE; PHOTONS; PROBES; TUMORS;

ANTHRAQUINONE; CYCLING; HYPOXIA; RU COMPLEXES; TWO PHOTON;

RUTHENIUM COMPOUNDS;

ANTHRAQUINONE DERIVATIVE; LUMINESCENT AGENT; RUTHENIUM COMPLEX; MOLECULAR PROBE; RUTHENIUM;

A549 CELL LINE; ANIMAL CELL; ARTICLE; CANCER CELL CULTURE; CONFOCAL MICROSCOPY; HUMAN; HUMAN CELL; HYPOXIA; IN VIVO STUDY; LIGHT ABSORPTION; LIVER MICROSOME; LUMINESCENCE; NONHUMAN; PRIORITY JOURNAL; QUANTUM YIELD; RAT; TUMOR SPHEROID; CELL HYPOXIA; CHEMISTRY; MOLECULAR PROBE; PHOTON; TUMOR CELL LINE;

DANIO RERIO;

ANTHRAQUINONES; CELL HYPOXIA; CELL LINE, TUMOR; HUMANS; LUMINESCENCE; MOLECULAR PROBES; PHOTONS; RUTHENIUM;

EID: 84927946098     PISSN: 01429612     EISSN: 18785905     Source Type: Journal    
DOI: 10.1016/j.biomaterials.2015.02.126     Document Type: Article

References (48)

1. Kizaka-Kondoh S., Inoue M., Harada H., Hiraoka M. Tumor hypoxia: a target for selective cancer therapy. Cancer Sci 2003, 94:1021-1028.
2. Thambi T., Deepagan V.G., Yoon H.Y., et al. Hypoxia-responsive polymeric nanoparticles for tumor-targeted drug delivery. Biomaterials 2014, 35:1735-1743.
3. Anada T., Fukuda J., Sai Y., et al. An oxygen-permeable spheroid culture system for the prevention of central hypoxia and necrosis of spheroids. Biomaterials 2012, 33:8430-8441.
4. Brown J.M., Wilson W.R. Exploiting tumour hypoxia in cancer treatment. Nat Rev Cancer 2004, 4:437-447.
5. Son A., Kawasaki A., Hara D., Ito T., Tanabe K. Phosphorescent ruthenium complexes with a nitroimidazole unit that image oxygen fluctuation in tumor tissue. Chem Eur J 2015, 21:2527-2536.
6. Martin A., Byrne A., Burke C.S., Forster R.J., Keyes T.E. Peptide-bridged dinuclear Ru(II) complex for mitochondrial targeted monitoring of dynamic changes to oxygen concentration and ROS generation in live mammalian cells. JAm Chem Soc 2014, 136:15300-15309.
7. Varchola J., Huntosova V., Jancura D., et al. Temperature and oxygen-concentration dependence of singlet oxygen production by RuPhen as induced by quasi-continuous excitation. Photochem Photobiol Sci 2014, 13:1781-1787.
8. Wang Y., Li B., Zhang L., Song H. Multifunctional mesoporous nanocomposites with magnetic, optical, and sensing features: synthesis, characterization, and their oxygen-sensing performance. Langmuir 2013, 29:1273-1279.
9. Komatsu H., Yoshihara K., Yamada H., et al. Ruthenium complexes with hydrophobic ligands that are key factors for the optical imaging of physiological hypoxia. Chem Eur J 2013, 19:1971-1977.
10. Piao W., Tsuda S., Tanaka Y., et al. Development of azo-based fluorescent probes to detect different levels of hypoxia. Angew Chem Int Ed 2013, 52:13028-13032.
11. Komatsu H., Shindo Y., Oka K., Hill J.P., Ariga K. Ubiquinone-rhodol (UQ-Rh) for fluorescence imaging of NAD(P)H through intracellular activation. Angew Chem Int Ed 2014, 53:3993-3995.
12. Kiyose K., Hanaoka K., Oushiki D., et al. Hypoxia-sensitive fluorescent probes for invivo real-time fluorescence imaging of acute ischemia. JAm Chem Soc 2010, 132:15846-15848.
13. Kim B.J., Hambley T.W., Bryce N.S. Visualising the hypoxia selectivity of cobalt (III) prodrugs. Chem Sci 2011, 2:2135-2142.
14. Zhang S.J., Hosaka M., Yoshihara T., Negishi K., Iida Y., Tobita S., et al. Phosphorescent light-emitting iridium complexes serve as a hypoxia-sensing probe for tumor imaging in living animals. Cancer Res 2010, 70:4490-4498.
15. Goncalves M.S.T. Fluorescent labeling of biomolecules with organic probes. Chem Rev 2009, 109:190-212.
16. Kim H.M., Cho B.R. Two-photon probes for intracellular free metal ions, acidic vesicles, and lipid rafts in live tissues. Acc Chem Res 2009, 42:863-872.
17. Kim H.J., Heo C.H., Kim H.M. Benzimidazole-based ratiometric two-photon fluorescent probes for acidic pH in live cells and tissues. JAm Chem Soc 2013, 135:17969-17977.
18. Indovina P., Collini M., Chirico G., Santini M.T. Three-dimensional cell organization leads to almost immediate HRE activity as demonstrated by molecular imaging of MG-63 spheroids using two-photon excitation microscopy. FEBS Lett 2007, 581:719-726.
19. Kondrashina A.V., Dmitriev R.I., Borisov S.M., et al. Aphosphorescent nanoparticle-based probe for sensing and imaging of (intra) cellular oxygen in multiple detection modalities. Adv Funct Mater 2012, 22:4931-4939.
20. Yoshihara T., Yamaguchi Y., Hosaka M., Takeuchi T., Tobita S. Ratiometric molecular sensor for monitoring oxygen levels in living cells. Angew Chem Int Ed 2012, 51:4148-4151.
21. Lin Q., Bao C., Yang Y., Liang Q., Zhang D., Cheng S., et al. Highly discriminating photorelease of anticancer drugs based on hypoxia activatable phototrigger conjugated chitosan nanoparticles. Adv Mater 2013, 25:1981-1986.
22. Folkman J. Tumor angiogenesis: therapeutic implications. NEngl J Med 1971, 285:1182-1186.
23. Dewhirst M.W., Cao Y., Moeller B. Cycling hypoxia and free radicals regulate angiogenesis and radiotherapy response. Nat Rev Cancer 2008, 8:425-437.
24. Takahashi S., Piao W., Matsumura Y., et al. Reversible off-on fluorescence probe for hypoxia and imaging of hypoxia-normoxia cycles in live cells. JAm Chem Soc 2012, 134:19588-19591.
25. Liu J., Liu Y., Bu W., Bu J., Sun Y., Du J., et al. Ultrasensitive nanosensors based on upconversion nanoparticles for selective hypoxia imaging invivo upon near-infrared excitation. JAm Chem Soc 2014, 136:9701-9709.
26. Sullivan B.P., Salmon D.J., Meyer T.J. Mixed phosphine 2, 2'-bipyridine complexes of ruthenium. Inorg Chem 1978, 17:3334-3341.
27. Xu C., Webb W.W. Measurement of two-photon excitation cross sections of molecular fluorophores with data from 690 to 1050 nm. JOpt Soc Am B 1996, 13:481-491.
28. Friedrich J., Seidel C., Ebner R., Kunz-Schughart L.A. Spheroid-based drug screen: considerations and practical approach. Nat Protoc 2009, 4:309-324.
29. Huang H.Y., Zhang P.Y., Yu B.L., Chen Y., Wang J.Q., Ji L.N., et al. Targeting nucleus DNA with a cyclometalated dipyridophenazineruthenium(II) complex. JMed Chem 2014, 57:8971-8983.
30. 6 transition metal complexes in fluorescence cell imaging. Chem Commun 2010, 46:186-202.
31. Sun D., Liu Y., Yu Q., Qin X., Yang L., Zhou Y., et al. Inhibition of tumor growth and vasculature and fluorescence imaging using functionalized ruthenium-thiol protected selenium nanoparticles. Biomaterials 2014, 35:1572-1583.
32. 2+ detection. Chem Eur J 2013, 19:15494-15503.
33. Xu W.C., Zuo J.R., Wang L.L., Ji L.N., Chao H. Dinuclear ruthenium(II) polypyridyl complexes as single and two-photon luminescence cellular imaging probes. Chem Commun 2014, 50:2123-2125.
34. Zhang P.Y., Wang J.Q., Huang H.Y., Chen H.M., Guan R.L., Chen Y., et al. RuNH2 at AuNPs as two-photon luminescent probes for thiols in living cells and tissues. Biomaterials 2014, 35:9003-9011.
35. Nohl H., Jordan W., Youngman R.J. Quinones in biology: functions in electron transfer and oxygen activation. Adv Free Radic Biol Med 1986, 2:211-279.
36. Tanabe K., Hirata N., Harada H., Hiraoka M., Nishimoto S. Emission under hypoxia: one-electron reduction and fluorescence characteristics of an indolequinone-coumarin conjugate. ChemBioChem 2008, 9:426-432.
37. Komatsu H., Harada H., Tanabe K., Hiraoka M., Nishimoto S. Indolequinone-rhodol conjugate as a fluorescent probe for hypoxic cells: enzymatic activation and fluorescence properties. Med Chem Commun 2010, 1:50-53.
38. 2+. Inorg Chem Commun 2008, 11:1048-1050.
39. 2+ and its application in live cell imaging. Chem Eur J 2008, 14:6892-6900.
40. Liu L., Dong X., Xiao Y., Lian W., Liu Z. Two-photon excited fluorescent chemosensor for homogeneous determination of copper(II) in aqueous media and complicated biological matrix. Analyst 2011, 136:2139-2145.
41. Hamilton G. Multicellular spheroids as an invitro tumor model. Cancer Lett 1998, 131:29-34.
42. Pampaloni F., Reynaud E.G., Stelzer E.H.K. The third dimension bridges the gap between cell culture and live tissue. Nat Rev Mol Cell Biol 2007, 8:839-845.
43. Dmitrieva R.I., Zhdanova A.V., Nolanb Y.M., Papkovskya D.B. Imaging of neurosphere oxygenation with phosphorescent probes. Biomaterials 2013, 34:9307-9317.
44. Ho V.H.B., Slater N.K.H., Chen R.J. pH-responsive endosomolytic pseudo-peptides for drug delivery to multicellular spheroids tumour models. Biomaterials 2011, 32:2953-2958.
45. Wang X., Zhen X., Wang J., Zhang J.L., Wu W., Jiang X.Q. Doxorubicin delivery to 3D multicellular spheroids and tumors based on boronic acid-rich chitosan nanoparticles. Biomaterials 2013, 34:4667-4679.
46. Kim T.H., Mount C.W., Gombotz W.R., Pun S.H. The delivery of doxorubicin to 3-D multicellular spheroids and tumors in a murine xenograft model using tumor-penetrating triblock polymeric micelles. Biomaterials 2010, 31:7386-7397.
47. Filippis D.L., Delia D. Hypoxia in the regulation of neural stem cells. Cell Mol Life Sci 2011, 68:2831-2844.
48. Jou C.J., Spitzer K.W., Tristani-Firouzi M. Blebbistatin effectively uncouples the excitation-contraction process in zebrafish embryonic heart. Cell Physiol Biochem 2010, 25:419-424.