The cellular uptake and localization of non-emissive iridium(III) complexes as cellular reaction-based luminescence probes

Biomaterials

Volumn 34, Issue 4, 2013, Pages 1223-1234

  Li, Chunyan ^a   Liu, Yi ^a   Wu, Yongquan ^a   Sun, Yun ^a   Li, Fuyou ^a  

^a FUDAN UNIVERSITY   (China)

Author keywords

Fluorescent bioimaging; Iridium(III) complex; Nucleus stain; Structure activity relationship

Indexed keywords

2-PHENYLPYRIDINE; BIO-IMAGING; BROAD APPLICATION; CARBON CHAINS; CELL PERIPHERY; CELLULAR IMAGING; CELLULAR STRUCTURE; CELLULAR UPTAKE; COUNTER ANIONS; COUNTERIONS; DESIGN AND OPTIMIZATION; ENERGY DEPENDENT; IRIDIUM COMPLEX; LIVE-CELL IMAGING; LIVING CELL; LOW TEMPERATURES; METHYL GROUP; N LIGANDS; NUCLEAR MEMBRANES; NUCLEAR PORE COMPLEXES; NUCLEUS STAIN; OPTICAL PROBE; PERINUCLEAR REGION; SIDE-CHAINS; STRUCTURE ACTIVITY RELATIONSHIPS; SUBCELLULAR RESOLUTION; TRANSPORT PATHWAYS; UPTAKE MECHANISM;

CELL MEMBRANES; CYTOLOGY; FUNCTIONAL GROUPS; IRIDIUM; LIGANDS; PROBES; SOLVENTS; STRUCTURAL DESIGN; SYNTHESIS (CHEMICAL);

IRIDIUM COMPOUNDS;

CHLORPROMAZINE; FILIPIN; IRIDIUM COMPLEX; PHENYLPYRIDINE DERIVATIVE; PYRIDINE; UNCLASSIFIED DRUG;

ARTICLE; CELL STRUCTURE; CELL TRANSPORT; CELLULAR DISTRIBUTION; CYTOTOXICITY; FEMALE; HELA CELL; HUMAN; HUMAN CELL; LUMINESCENCE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION;

CONTRAST MEDIA; HELA CELLS; HUMANS; IRIDIUM; LUMINESCENT MEASUREMENTS; MICROSCOPY, FLUORESCENCE; MOLECULAR IMAGING; MOLECULAR PROBES; SUBCELLULAR FRACTIONS;

EID: 84870345517     PISSN: 01429612     EISSN: 18785905     Source Type: Journal    
DOI: 10.1016/j.biomaterials.2012.09.014     Document Type: Article

References (43)

1. Lodish H., Berk A., Matsudaira P., Kaiser C.A., Krieger M., Scott M.P., et al. Molecular cell biology 2004, WH Freeman, New York. 5th ed.
2. Harris H. The birth of the cell 1999, Yale University Press, New Haven.
3. Stephens D.J., Allan V.J. Light microscopy techniques for live cell imaging. Science 2003, 300:82-86.
4. Haugland R.P. A guide to fluorescent probes and labelling technologies 2005, Molecular Probes, Eugene, Oregon, p. 397. http://www.invitrogen.com, 10th ed.
5. Pfeifer G.P., You Y.H., Besaratinia A. Mutations induced by ultraviolet light. Mutat Res Fund Mol M 2005, 571:19-31.
6. Hanaoka K., Kikuchi K., Kobayashi S., Nagano T. Time-resolved long-lived luminescence imaging method employing luminescent lanthanide probes with a new microscopy system. J Am Chem Soc 2007, 129:13502-13509.
7. Botchway S.W., Charnley M., Haycock J.W., Parker A.W., Rochester D.L., Weinstein J.A., et al. Time-resolved and two-photon emission imaging microscopy of live cells with inert platinum complexes. Proc Natl Acad Sci U S A 2008, 105:16071-16076.
8. Murphy L., Congreve A., Palsson L.O., Williams J.A.G. The time domain in co-stained cell imaging: time-resolved emission imaging microscopy using a protonatable luminescent iridium complex. Chem Commun 2010, 46:8743-8745.
9. 2 nanostructures: time-gated bioprobes with single particle sensitivity and negligible background. Adv Mater 2011, 23:4649-4654.
10. Montgomery C.P., Murray B.S., New E.J., Pal R., Parker D. Cell-penetrating metal complex optical probes: targeted and responsive systems based on lanthanide luminescence. Acc Chem Res 2009, 42:925-937.
11. New E.J., Congreve A., Parker D. Definition of the uptake mechanism and sub-cellular localisation profile of emissive lanthanide complexes as cellular optical probes. Chem Sci 2010, 1:111-118.
12. Zhao Q., Huang C.H., Li F.Y. Phosphorescent heavy-metal complexes for bioimaging. Chem Soc Rev 2011, 40:2508-2524.
13. Lo K.K.W., Choi A.W.T., Law W.H.T. Applications of luminescent inorganic and organometallic transition metal complexes as biomolecular and cellular probes. Dalton Trans 2012, 41:6021-6047.
14. Lo K.K.W., Li S.P.Y., Zhang K.Y. Development of luminescent iridium(III) polypyridine complexes as chemical and biological probes. New J Chem 2011, 35:265-287.
15. Baggaley E., Weinstein J.A., Williams J.A.G. Lighting the way to see inside the live cell with luminescent transition metal complexes. Coordin Chem Rev 2012, 256:1762-1785.
16. Leung S.K., Liu H.W., Lo K.K.W. Functionalization of luminescent cyclometalated iridium(III) polypyridine complexes with a fluorous moiety: photophysics, protein-binding, bioconjugation, and cellular uptake properties. Chem Commun 2011, 47:10548-10550.
17. Steunenberg P., Ruggi A., van den Berg N.S., Buckle T., Kuil J., van Leeuwen F.W.B., et al. Phosphorescence imaging of living cells with amino acid-functionalized tris(2-phenylpyridine)iridium(III) complexes. Inorg Chem 2012, 51:2105-2114.
18. Wu P., Wong E.L.M., Ma D.L., Tong G.S.M., Ng K.M., Che C.M. Cyclometalated platinum(II) complexes as highly sensitive luminescent switch-on probes for practical application in protein staining and cell imaging. Chem Eur J 2009, 15:3652-3656.
19. Kumar R., Ohulchanskyy T., Turowski S., Thompson M., Seshadri M., Prasad P. Combined magnetic resonance and optical imaging of head and neck tumor xenografts using gadolinium-labelled phosphorescent polymeric nanomicelles. Head Neck Oncol 2010, 2(1):35.
20. Koo C.K., So L.K.Y., Wong K.L., Ho Y.M., Lam Y.W., Lam M.H.W., et al. A triphenylphosphonium-functionalised cyclometalated platinum(II) complex as a nucleolus-specific two-photon molecular dye. Chem Eur J 2010, 16:3942-3950.
21. Zhao Q., Yu M.X., Shi L.X., Liu S.J., Li C.Y., Shi M., et al. Cationic iridium(III) complexes with tunable emission color as phosphorescent dyes for live cell imaging. Organometallics 2010, 29:1085-1091.
22. Yang T.S., Liu Q., Pu S.Z., Dong Z.S., Huang C.H., Li F.Y. Fluorophore-photochrome co-embedded polymer nanoparticles for photoswitchable fluorescence bioimaging. Nano Res 2012, 5:494-503.
23. Tan W.J., Zhou J., Li F.Y., Yi T., Tian H. Visible light-triggered photoswitchable diarylethene-based iridium(III) complexes for imaging living cells. Chem Asian J 2011, 6:1263-1268.
24. Fan Y.B., Li C.Y., Cao H., Li F.Y., Chen D.Y. The intranuclear release of a potential anticancer drug from small nanoparticles that are derived from intracellular dissociation of large nanoparticles. Biomaterials 2012, 33:4220-4228.
25. Yang H., Ding L., An L., Xiang Z.Y., Chen M., Zhou J., et al. A d-f heteronuclear complex for dual-mode phosphorescence and magnetic resonance imaging. Biomaterials 2012, 33:8591-8599.
26. Yu M.X., Zhou C., Liu J.B., Hankins J.D., Zheng J. Luminescent gold nanoparticles with pH-dependent membrane adsorption. J Am Chem Soc 2011, 133:11014-11017.
27. Law G.L., Man C., Parker D., Walton J.W. Observation of the selective staining of chromosomal DNA in dividing cells using a luminescent terbium(III) complex. Chem Commun 2010, 46:2391-2393.
28. Yu J.H., Parker D., Pal R., Poole R.A., Cann M.J. A europium complex that selectively stains nucleoli of cells. J Am Chem Soc 2006, 128:2294-2299.
29. Zhang K.Y., Li S.P.Y., Zhu N.Y., Or I.W.S., Cheung M.S.H., Lam Y.W., et al. Structure, photophysical and electrochemical properties, biomolecular interactions, and intracellular uptake of luminescent cyclometalated iridium(III) dipyridoquinoxaline complexes. Inorg Chem 2010, 49:2530-2540.
30. Brunner J., Barton J.K. Targeting DNA mismatches with rhodium intercalators functionalized with a cell-penetrating peptide. Biochemistry 2006, 45:12295-12302.
31. Gill M.R., Garcia-Lara J., Foster S.J., Smythe C., Battaglia G., Thomas J.A. A ruthenium(II) polypyridyl complex for direct imaging of DNA structure in living cells. Nat Chem 2009, 1:662-667.
32. Li C.Y., Yu M.X., Sun Y., Wu Y.Q., Huang C.H., Li F.Y. A nonemissive iridium(III) complex that specifically lights-up the nuclei of living cells. J Am Chem Soc 2011, 133:11231-11239.
33. Ma D.L., Wong W.L., Chung W.H., Chan F.Y., So P.K., Lai T.S., et al. A highly selective luminescent switch-on probe for histidine/histidine-rich proteins and its application in protein staining. Angew Chem Int Ed 2008, 47:3735-3739.
34. Nonoyama M. Benzo[H]quinolin-10-Yl-N iridium (III) complexes. B Chem Soc Jpn 1974, 47:767-768.
35. Schmid B., Garces F.O., Watts R.J. Synthesis and characterizations of cyclometalated iridium(III) solvent complexes. Inorg Chem 1994, 33(1):9-14.
36. Puckett C.A., Barton J.K. Mechanism of cellular uptake of a ruthenium polypyridyl complex. Biochemistry 2008, 47:11711-11716.
37. Zhang K.Y., Lo K.K.W. Synthesis, properties, and live-cell imaging studies of luminescent cyclometalated iridium(III) polypyridine complexes containing two or three biotin pendants. Inorg Chem 2009, 48:6011-6025.
38. Zhang K.Y., Liu H.W., Fong T.T.H., Chen X.G., Lo K.K.W. Luminescent dendritic cyclometalated iridium(III) polypyridine complexes: synthesis, emission behavior, and biological properties. Inorg Chem 2010, 49:5432-5443.
39. Gratton S.E.A., Ropp P.A., Pohlhaus P.D., Luft J.C., Madden V.J., Napier M.E., et al. The effect of particle design on cellular internalization pathways. Proc Natl Acad Sci U S A 2008, 105:11613-11618.
40. Burgess S.A., Walker M.L., Sakakibara H., Knight P.J., Oiwa K. Dynein structure and power stroke. Nature 2003, 421:715-718.
41. Gross S.P., Welte M.A., Block S.M., Wieschaus E.F. Dynein-mediated cargo transport in vivo: a switch controls travel distance. J Cell Biol 2000, 148:945-955.
42. Zhao M., Weissleder R. Intracellular cargo delivery using tat peptide and derivatives. Med Res Rev 2004, 24:1-12.
43. Rout M.P., Aitchison J.D., Suprapto A., Hjertaas K., Zhao Y.M., Chait B.T. The yeast nuclear pore complex: composition, architecture, and transport mechanism. J Cell Biol 2000, 148:635-651.