Intracellular oxygen-sensitive phosphorescent probes based on cell-penetrating peptides

Analytical Biochemistry

Volumn 398, Issue 1, 2010, Pages 24-33

  Dmitriev, Ruslan I ^a   Zhdanov, Alexander V ^a   Ponomarev, Gelii V ^b   Yashunski, Dmitri V ^b   Papkovsky, Dmitri B ^a  

^a UNIVERSITY COLLEGE CORK   (Ireland)

^b INSTITUTE OF BIOMEDICAL CHEMISTRY   (Russian Federation)

Author keywords

Cell penetrating peptides; Cellular oxygen; Hypoxia; Intracellular oxygen sensitive probe; Mitochondrial function; Pt porphyrins

Indexed keywords

CYTOLOGY; MAMMALS; MITOCHONDRIA; MOLECULAR OXYGEN; PEPTIDES; PHOSPHORESCENCE; PLATINUM COMPOUNDS; PORPHYRINS; PROBES; WELL STIMULATION;

CELL-PENETRATING PEPTIDE; CELLULAR OXYGEN; HYPOXIA; MITOCHONDRIAL FUNCTION; SENSITIVE PROBE;

MOLECULAR BIOLOGY;

CELL PENETRATING PEPTIDE; COPROPORPHYRIN; OXYGEN; PEPTIDE; PORPHYRIN; REAGENT;

ANIMAL CELL; ARTICLE; CELL ENERGY; CELL METABOLISM; CELL STIMULATION; CELL TRANSPORT; CELL TYPE; CELLULAR DISTRIBUTION; CONTROLLED STUDY; COVALENT BOND; HUMAN; HUMAN CELL; MAMMAL CELL; MITOCHONDRION; MOLECULAR PROBE; NONHUMAN; PHOSPHORESCENCE; PRIORITY JOURNAL;

MAMMALIA;

EID: 73549124772     PISSN: 00032697     EISSN: 10960309     Source Type: Journal    
DOI: 10.1016/j.ab.2009.10.048     Document Type: Article

References (33)

1. Giulivi C., Kato K., and Cooper C.E. Nitric oxide regulation of mitochondrial oxygen consumption I: cellular physiology. Am. J. Physiol. Cell Physiol. 291 (2006) C1225-C1231
2. Duchen M.R. Mitochondria in health and disease: perspectives on a new mitochondrial biology. Mol. Aspects Med. 25 (2004) 365-451
3. Taylor C.T. Mitochondria and cellular oxygen sensing in the HIF pathway. Biochem. J. 409 (2008) 19-26
4. Robinson J.M. Phagocytic leukocytes and reactive oxygen species. Histochem. Cell Biol. 131 (2009) 465-469
5. Takahashi E., and Asano K. Mitochondrial respiratory control can compensate for intracellular O(2) gradients in cardiomyocytes at low PO(2). Am. J. Physiol. Heart Circ. Physiol. 283 (2002) H871-H878
6. 2 supply to mitochondria in actively respiring single cardiomyocyte of rats. Am. J. Physiol. 276 (1999) H718-H724
7. Hagen T., Taylor C.T., Lam F., and Moncada S. Redistribution of intracellular oxygen in hypoxia by nitric oxide: effect on HIF1alpha. Science 302 (2003) 1975-1978
8. Koo Y.E., Cao Y., Kopelman R., Koo S.M., Brasuel M., and Philbert M.A. Real-time measurements of dissolved oxygen inside live cells by organically modified silicate fluorescent nanosensors. Anal. Chem. 76 (2004) 2498-2505
9. Buck S.M., Koo Y.E., Park E., Xu H., Philbert M.A., Brasuel M.A., and Kopelman R. Optochemical nanosensor PEBBLEs: photonic explorers for bioanalysis with biologically localized embedding. Curr. Opin. Chem. Biol. 8 (2004) 540-546
10. Brinas R.P., Troxler T., Hochstrasser R.M., and Vinogradov S.A. Phosphorescent oxygen sensor with dendritic protection and two-photon absorbing antenna. J. Am. Chem. Soc. 127 (2005) 11851-11862
11. O'Riordan T.C., Soini A.E., and Papkovsky D.B. Monofunctional derivatives of coproporphyrins for phosphorescent labeling of proteins and binding assays. Anal. Biochem. 290 (2001) 366-375
12. Hynes J., Floyd S., Soini A.E., O'Connor R., and Papkovsky D.B. Fluorescence-based cell viability screening assays using water-soluble oxygen probes. J. Biomol. Screen. 8 (2003) 264-272
13. O'Riordan T.C., Zhdanov A.V., Ponomarev G.V., and Papkovsky D.B. Analysis of intracellular oxygen and metabolic responses of mammalian cells by time-resolved fluorometry. Anal. Chem. 79 (2007) 9414-9419
14. Guice K.B., Caldorera M.E., and McShane M.J. Nanoscale internally referenced oxygen sensors produced from self-assembled nanofilms on fluorescent nanoparticles. J. Biomed. Opt. 10 (2005) 064031
15. Foerg C., and Merkle H.P. On the biomedical promise of cell penetrating peptides: limits versus prospects. J. Pharm. Sci. 97 (2008) 144-162
16. Gupta B., Levchenko T.S., and Torchilin V.P. Intracellular delivery of large molecules and small particles by cell-penetrating proteins and peptides. Adv. Drug Deliv. Rev. 57 (2005) 637-651
17. Pujals S., and Giralt E. Proline-rich, amphipathic cell-penetrating peptides. Adv. Drug Deliv. Rev. 60 (2008) 473-484
18. Sibrian-Vazquez M., Jensen T.J., Fronczek F.R., Hammer R.P., and Vicente M.G. Synthesis and characterization of positively charged porphyrin-peptide conjugates. Bioconjug. Chem. 16 (2005) 852-863
19. Sibrian-Vazquez M., Hao E., Jensen T.J., and Vicente M.G. Enhanced cellular uptake with a cobaltacarborane-porphyrin-HIV-1 Tat 48-60 conjugate. Bioconjug. Chem. 17 (2006) 928-934
20. Sibrian-Vazquez M., Ortiz J., Nesterova I.V., Fernandez-Lazaro F., Sastre-Santos A., Soper S.A., and Vicente M.G. Synthesis and properties of cell-targeted Zn(II)-phthalocyanine-peptide conjugates. Bioconjug. Chem. 18 (2007) 410-420
21. Choi Y., McCarthy J.R., Weissleder R., and Tung C.H. Conjugation of a photosensitizer to an oligoarginine-based cell-penetrating peptide increases the efficacy of photodynamic therapy. ChemMedChem 1 (2006) 458-463
22. Schwarze S.R., Ho A., Vocero-Akbani A., and Dowdy S.F. In vivo protein transduction: delivery of a biologically active protein into the mouse. Science 285 (1999) 1569-1572
23. Wender P.A., Mitchell D.J., Pattabiraman K., Pelkey E.T., Steinman L., and Rothbard J.B. The design, synthesis, and evaluation of molecules that enable or enhance cellular uptake: peptoid molecular transporters. Proc. Natl. Acad. Sci. USA 97 (2000) 13003-13008
24. Nakase I., Takeuchi T., Tanaka G., and Futaki S. Methodological and cellular aspects that govern the internalization mechanisms of arginine-rich cell-penetrating peptides. Adv. Drug Deliv. Rev. 60 (2008) 598-607
25. Futaki S., Nakase I., Tadokoro A., Takeuchi T., and Jones A.T. Arginine-rich peptides and their internalization mechanisms. Biochem. Soc. Trans. 35 (2007) 784-787
26. Duchardt F., Fotin-Mleczek M., Schwarz H., Fischer R., and Brock R. A comprehensive model for the cellular uptake of cationic cell-penetrating peptides. Traffic 8 (2007) 848-866
27. U. Neugebauer, Y. Pellegrin, M. Devocelle, R.J. Forster, W. Signac, N. Moran, T.E. Keyes, Ruthenium polypyridyl peptide conjugates: membrane permeable probes for cellular imaging, Chem. Commun. (Camb) (2008) 5307-5309.
28. Zhdanov A.V., Ward M.W., Prehn J.H., and Papkovsky D.B. Dynamics of intracellular oxygen in PC12 Cells upon stimulation of neurotransmission. J. Biol. Chem. 283 (2008) 5650-5661
29. Sadler K., Eom K.D., Yang J.L., Dimitrova Y., and Tam J.P. Translocating proline-rich peptides from the antimicrobial peptide bactenecin 7. Biochemistry 41 (2002) 14150-14157
30. Spicer Z., and Millhorn D.E. Oxygen sensing in neuroendocrine cells and other cell types: pheochromocytoma (PC12) cells as an experimental model. Endocr. Pathol. 14 (2003) 277-291
31. Vives E., Richard J.P., Rispal C., and Lebleu B. TAT peptide internalization: seeking the mechanism of entry. Curr. Protein Pept. Sci. 4 (2003) 125-132
32. Kaplan I.M., Wadia J.S., and Dowdy S.F. Cationic TAT peptide transduction domain enters cells by macropinocytosis. J. Control. Release 102 (2005) 247-253
33. van Nostrum C.F. Delivery of photosensitizers in photodynamic therapy. Adv. Drug Deliv. Rev. 56 (2004) 5-6