Evaluation of triazole-chelated lanthanides as chemically stabile bioimaging agents

Journal of Pharmaceutical Sciences

Volumn 102, Issue 8, 2013, Pages 2589-2598

  Indapurkar, Amruta ^a   Henriksen, Brian ^a   Tolman, Justin ^a   Fletcher, James ^a  

^a CREIGHTON UNIVERSITY   (United States)

Author keywords

Cell culture; Chelation; Fluorescence spectroscopy; Fluorescent probes; Solubility; Thermal analysis

Indexed keywords

DYSPROSIUM; EUROPIUM; FLUORESCENT DYE; LANTHANIDE; SAMARIUM; TERBIUM; TETRAZOLIUM; TRIAZOLE;

ARTICLE; BINDING AFFINITY; BLEACHING; CANCER CELL; CELL MEDIATED CYTOTOXICITY; CELL SURFACE; CELL VIABILITY; CHELATION; DIFFERENTIAL SCANNING CALORIMETRY; ELECTROSPRAY MASS SPECTROMETRY; EVALUATION; FLUORESCENCE; HYDROPHOBICITY; IN VITRO STUDY; LUNG CANCER; MOLECULAR IMAGING; MOLECULAR STABILITY; PH; PHYSICAL CHEMISTRY; SOLUBILITY; SYNTHESIS; THERMOGRAVIMETRY; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY;

EID: 84881013774     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.23616     Document Type: Article

References (60)

1. Montgomery CP, Murray BS, New EJ, Pal R, Parker D. 2009. Cell-penetrating metal complex optical probes: Targeted and responsive systems based on lanthanide luminescence. Acc Chem Res 42:925-937.
2. Bünzli JCG. 2009. Lanthanide luminescent bioprobes (LLBs). Chem Lett 38:104-109.
3. Keefe MH, Benkstein KD, Hupp JT. 2000. Luminescent sensor molecules based on coordinated metals: A review of recent developments. Coord Chem Rev 205:201-228.
4. Selvin PR. 2002. Principles and biophysical applications of lanthanide-based probes. Annu Rev Biophys Biomol Struct 31:275-302.
5. Elbanowski M, Makowska B. 1996. The lanthanides as luminescent probes in investigations of biochemical systems. J Photochem Photobiol A 99:85-92.
6. Yuan J, Wang G. 2006. Lanthanide-based luminescence probes and time-resolved luminescence bioassays. TrAC Trend Anal Chem 25:490-500.
7. Faulkner S, Pope SJA, Burton-Pye BP. 2005. Lanthanide complexes for luminescence imaging applications. Appl Spectrosc Rev 40:1-31.
8. Buenzli J-CG. 2004. Luminescent lanthanide probes as diagnostic and therapeutic tools. In Metal complexes in tumor diagnosis and as anticancer agents. Series: Metal ions in biological systems. Vol. 42. New York: Dekker, pp 39-75.
9. Thibon A, Pierre VC. 2009. Principles of responsive lanthanide-based luminescent probes for cellular imaging. Anal Bioanal Chem 394:107-120.
10. Viguier RFH, Hulme AN. 2006. A sensitized europium complex generated by micromolar concentrations of copper (I): Toward the detection of copper (I) in biology. J Am Chem Soc 128:11370-11371.
11. Dobbs J, Susetyo W, Knight F, Castles M, Carreira LA, Azarraga L. 1989. Characterization of metal binding sites in fulvic acids by lanthanide ion probe spectroscopy. Anal Chem 61:483-488.
12. Krasnoperov LN, Marras SAE, Kozlov M, Wirpsza L, Mustaev A. 2010. Luminescent probes for ultrasensitive detection of nucleic acids. Bioconjug Chem 21:319-327.
13. Spangler CM, Spangler C, Schäerling M. 2008. Luminescent lanthanide complexes as probes for the determination of enzyme activities. Ann N Y Acad Sci 1130:138-148.
14. Gudgin Dickson EF, Pollak A, Diamandis EP. 1995. Time-resolved detection of lanthanide luminescence for ultrasensitive bioanalytical assays. J Photochem Photobiol B 27:3-19.
15. Sokolnicki J, Maruszewski K, Strek W, Legendziewicz J. 1998. Fluorescence and absorption probe of metal ion centers in silicates obtained by the sol-gel technique. J Sol Gel Sci Technol 13:611-615.
16. Avaji PG, Reddy BN, Patil SA, Badami PS. 2006. Synthesis, spectral characterization, biological and fluorescence studies of lanthanum (III) complexes with 3-substituted-4-amino-5-hydrazino-1, 2, 4-triazole Schiff bases. Transi Metal Chem 31:842-848.
17. Brunet E, Juanes O, Rodriguez-Ubis JC. 2007. Supramolecularly organized lanthanide complexes for efficient metal excitation and luminescence as sensors in organic and biological applications. Curr Chem Biol 1:11-39.
18. Liu J, Yan B. 2008. Molecular construction and photophysical properties of luminescent covalently bonded lanthanide hybrid materials obtained by grafting organic ligands containing 1, 2, 4-triazole on silica by mercapto modification. J Phys Chem C 112:14168-14178.
19. Leif R, Vallarino L. 1991. Rare-earth chelates as fluorescent markers in cell separation and analysis. 464:41-58.
20. Wu Y. 2000. Lanthanide ions inhibit the activity of dihydrofolate reductase from chicken liver. Biometals 13:195-201.
21. Rundström G, Jonsson A, Mårtensson O, Mendel-Hartvig I, Venge P. 2007. Lateral flow immunoassay using europium (III) chelate microparticles and time-resolved fluorescence for eosinophils and neutrophils in whole blood. Clin Chem 53:342-348.
22. Aime S, Fasano M, Terreno E. 1998. Lanthanide (III) chelates for NMR biomedical applications. Chem Soc Rev 27:19-29.
23. Hemmilä I, Laitala V. 2005. Progress in lanthanides as luminescent probes. J Fluoresc 15:529-542.
24. Palizban A, Sadeghi-Aliabadi H, Abdollahpour F. 2010. Effect of cerium lanthanide on HeLa and MCF-7 cancer cell growth in the presence of transferring. Res Pharmcal Sci 5:119-125.
25. Selvin PR. 2003. Lanthanide-labeled DNA. In Topics in fluorescence spectroscopy; Lakowicz JR, Ed. New York: Kluwer Academic/Plenum Publishers, pp 177-212.
26. Simpkins H, Pearlman LF, Thompson LM. 1984. Effects of adriamycin on supercoiled DNA and calf thymus nucleosomes studied with fluorescent probes. Cancer Res 44:613-618.
27. Dolatabadi JEN. 2011. Molecular aspects on the interaction of quercetin and its metal complexes with DNA. Int J Biol Macromol 48:227-233.
28. Jiang S, Gnanasammandhan MK, Zhang Y. 2010. Optical imaging-guided cancer therapy with fluorescent nanoparticles. J R Soc Interface 7:3-18.
29. Gomez-Hens A. 1991. Modern aspects of fluorimetry as applied to clinical chemistry. Pure Appl Chem 63:1083-1088.
30. Chen H, Chen J, Wang L, Zhou C, Ling B, Fu J. 2011. A sensitive method for determination of trace amounts of chromate (III) with terbium (III) sodium hexametaphosphate chelate as fluorescent probe. Luminescence 26(6):434-438.
31. Atanasijevic T, Shusteff M, Fam P, Jasanoff A. 2006. Calcium-sensitive MRI contrast agents based on superparamagnetic iron oxide nanoparticles and calmodulin. Proc Natl Acad Sci 103:14707-14712.
32. Yi G, Lu H, Zhao S, Ge Y, Yang W, Chen D, Guo LH. 2004. Synthesis, characterization, and biological application of size-controlled nanocrystalline NaYF4: Yb, Er infrared-to-visible up-conversion phosphors. Nano Lett 4:2191-2196.
33. Matsumoto K. 2010. Time-resolved luminescence microscopy and microarray using europium chelate labels. 3:2129-2136
34. Marçalo J, de Matos AP, Evans WJ. 1997. Reactivity of lanthanide, group 2, and group 3 metal and metal oxide cations with pentamethylcyclopentadiene: Gas-phase synthesis of cyclopentadienyl cations. Organometallics 16:3845-3850.
35. New EJ, Parker D, Smith DG, Walton JW. 2010. Development of responsive lanthanide probes for cellular applications. Curr Opin Chem Biol 14:238-246.
36. Law GL, Parker D, Richardson SL, Wong KL. 2009. The mechanism of quenching of the lanthanide excited state for optical probes using sensitised emission. Dalton Trans 40:8481-8484.
37. Kielar F, Montgomery CP, New EJ, Parker D, Poole RA, Richardson SL, Stenson PA. 2007. A mechanistic study of the dynamic quenching of the excited state of europium (III) and terbium (III) macrocyclic complexes by charge-or electron transfer. Org Biomol Chem 5:2975-2982.
38. Yu J, Parker D, Pal R, Poole RA, Cann MJ. 2006. A europium complex that selectively stains nucleoli of cells. J Am Chem Soc 128:2294-2299.
39. New EJ, Parker D. 2009. The mechanism of cell uptake for luminescent lanthanide optical probes: The role of macropinocytosis and the effect of enhanced membrane permeability on compartmentalisation. Org Biomol Chem 7:851-855.
40. Neugebauer U, Pellegrin Y, Devocelle M, Forster RJ, Signac W, Moran N, Keyes TE. 2008. Ruthenium polypyridyl peptide conjugates: Membrane permeable probes for cellular imaging. Chem Commun 42:5307-5309.
41. Puckett CA, Barton JK. 2009. Fluorescein redirects a ruthenium-octaarginine conjugate to the nucleus. J Am Chem Soc 131:8738-8739.
42. Fletcher JT, Bumgarner BJ, Engels ND, Skoglund DA. 2008. Multidentate 1, 2, 3-triazole-containing chelators from tandem deprotection/click reactions of (trimethylsilyl) alkynes and comparison of their Ruthenium (II) complexes. Organometallics 27:5430-5433.
43. Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. 2002. A stepwise huisgen cycloaddition process: Copper (I)-catalyzed regioselective "ligation" of azides and terminal alkynes. Angewandte Chemie 114:2708-2711.
44. Meudtner RM, Ostermeier M, Goddard R, Limberg C, Hecht S. 2007. Multifunctional "clickates" as versatile extended heteroaromatic building blocks: Efficient synthesis via click chemistry, conformational preferences, and metal coordination. Chem-A Eur J 13:9834-9840.
45. Byron PR, Kelly E, Kontny M, Lovering E, Poochikian G, Sethi S, Thiel C, Vadas E. 1994. Recommendations of the USP advisory panel on aerosols on the USP general chapters on aerosols (601) and uniformity of dosage units (905). United States Pharmacopea 20:7477-7505.
46. Mosmann T. 1983. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. J Immunol Methods 65:55-63.
47. Fotakis G, Timbrell JA. 2006. In vitro cytotoxicity assays: Comparison of LDH, neutral red, MTT and protein assay in hepatoma cell lines following exposure to cadmium chloride. Toxicol Lett 160:171-177.
48. Wang X, Xia Y, Liu L, Liu M, Gu N, Guang H, Zhang F. 2010. Comparison of MTT assay, flow cytometry, and RT-PCR in the evaluation of cytotoxicity of five prosthodontic materials. J Biomed Mater Res B Appl Biomater 95:357-364.
49. Scherliess R. 2011. The MTT assay as tool to evaluate and compare excipient toxicity in vitro on respiratory epithelial cells. Int J Pharm 411:98-105.
50. Kokko T. 2009. Lanthanide chelates as donors in fluorescence resonance energy transfer: Exciting prospects for bioaffinity assay detection. Doctoral Thesis
51. Huhtinen P, Kivelä M, Kuronen O, Hagren V, Takalo H, Tenhu H, Lövgren T, Härmä H. 2005. Synthesis, characterization, and application of Eu (III), Tb (III), Sm (III), and Dy (III) lanthanide chelate nanoparticle labels. Anal Chem 77:2643-2648.
52. Magde D, Rojas GE, Seybold PG. 2008. Solvent dependence of the fluorescence lifetimes of xanthene dyes. Photochem Photobiol 70:737-744.
53. Han J, Burgess K. 2010. Fluorescent indicators for intracellular pH. Chem Rev 110:2709-2728.
54. Salyani M, Lindner G. 2006. Fluorescent intensity of dye solutions under different pH conditions. In Pesticide formulations and delivery systems. Advances in crop protection technologies; Brazee R, Derksen R, Fox R, Krause C, Ozkan H, Zhu H, Eds. Vol 25. Pennsylvania: ASTM, pp 191-197.
55. Sigma-Aldrich. 2012. Accessed at: http://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do?country=US&language=en&productNumber=E7023&brand=SIAL&PageToGoToURL=http%3A%2F%2Fwww.sigmaaldrich.com%2Fcatalog%2F-product%2Fsial%2Fe7023%3Flang%3Den, MSDS: Ethanol 200 Proof (Absolute). Rev. 04/23/2013
56. Jacobs C, Müller RH. 2002. Production and characterization of a budesonide nanosuspension for pulmonary administration. Pharm Res 19:189-194.
57. Pu X, Sun J, Li M, He Z. 2009. Formulation of nanosuspensions as a new approach for the delivery of poorly soluble drugs. Curr Nanosci 5:417-427.
58. Yang JZ, Young AL, Chiang PC, Thurston A, Pretzer DK. 2008. Fluticasone and budesonide nanosuspensions for pulmonary delivery: Preparation, characterization, and pharmacokinetic studies. J Pharm Sci 97:4869-4878.
59. Demchenko AP. 2009. Design and properties of fluorescence reporters. In Anonymous introduction to fluorescence sensing. 1st ed. p 119. Springer, Ukraine
60. Blanco E, Kessinger CW, Sumer BD, Gao J. 2009. Multifunctional micellar nanomedicine for cancer therapy. Exp Biol Med 234:123-131.