Radiolabelled oligonucleotides for imaging of gene expression with PET

Current Medicinal Chemistry

Volumn 16, Issue 33, 2009, Pages 4445-4461

  Lendvai, G ^a,b   Estrada, S ^a   Bergstrom M ^c  

^a BIACORE AB   (Sweden)

^b UPPSALA UNIVERSITY HOSPITAL   (Sweden)

^c UPPSALA UNIVERSITY   (Sweden)

Author keywords

Antisense oligonucleotides; Gene expression; In vivo hybridisation; Pharmacokinetics; Positron emission tomography; Radiolabelling

Indexed keywords

ANTISENSE OLIGONUCLEOTIDE; LOCKED NUCLEIC ACID; MESSENGER RNA; OLIGONUCLEOTIDE; PEPTIDE NUCLEIC ACID; PHOSPHORAMIDATE MORPHOLINO; PHOSPHOROTHIOIC ACID DERIVATIVE; RADIOISOTOPE; UNCLASSIFIED DRUG;

BINDING AFFINITY; COMPUTER ASSISTED TOMOGRAPHY; DRUG ABSORPTION; DRUG DISTRIBUTION; DRUG ELIMINATION; DRUG METABOLISM; DRUG STABILITY; GENE EXPRESSION; GENE TARGETING; HUMAN; IMAGE ANALYSIS; IMAGE QUALITY; ISOTOPE LABELING; NONHUMAN; PINOCYTOSIS; POSITRON EMISSION TOMOGRAPHY; RADIOACTIVITY; REVIEW; RNA SEQUENCE; RNA STRUCTURE; RNA TRANSLATION; SINGLE DRUG DOSE;

GENE EXPRESSION; GENE EXPRESSION REGULATION; IN SITU HYBRIDIZATION; ISOTOPE LABELING; OLIGONUCLEOTIDES, ANTISENSE; POSITRON-EMISSION TOMOGRAPHY; TISSUE DISTRIBUTION;

EID: 70450193807     PISSN: 09298673     EISSN: None     Source Type: Journal    
DOI: 10.2174/092986709789712844     Document Type: Review

References (181)

1. Danese, A. A public health genetic approach for schizophrenia. Epidemiol. Psichiatr. Soc., 2006, 15, 185-193 (Pubitemid 44784460)
2. Roberts, R.; Gollob, M. Molecular cardiology and genetics in the 21st century - a primer. Curr. Probl. Cardiol., 2006, 31, 637-701. (Pubitemid 44311213)
3. Teufel, A.; Staib, F.; Kanzler, S.; Weinmann, A.; Schulze- Bergkamen, H.; Galle, P.R. Genetics of hepatocellular carcinoma. World J. Gastroenterol., 2007, 13, 2271-2282
4. Phelps, M.E. PET: the merging of biology and imaging into molecular imaging. J. Nucl. Med., 2000, 41, 661-681
5. Pharoah, P.D.; Caldas, C. Molecular genetics and the assessment of human cancers. Expert Rev. Mol. Med., 1999, 1999, 1-19.
6. Dreesen, O.; Brivanlou, A.H. Signaling pathways in cancer and embryonic stem cells. Stem. Cell Rev., 2007, 3, 7-17. (Pubitemid 47472808)
7. Grinstein, E.; Wernet, P. Cellular signaling in normal and cancerous stem cells. Cell Signal., 2007, 19, 2428-2433 (Pubitemid 47531926)
8. Sioud, M. Main approaches to target discovery and validation. Methods Mol. Biol., 2007, 360, 1-12.
9. Kim, E.E. Targeted molecular imaging. Korean J. Radiol., 2003, 4, 201-210
10. Lodish, H.; Berk, A.; Matsudaira, P.; Kaiser, C.A.; Krieger, M.; Scott, M.P.; Zipursky, S.L.; Darnell, J. Molecular cell biology. W. H. Freeman: New York, 2003.
11. Strachan, T.; Read, A.P. Human molecular genetics. Garland Science: New York, 2004.
12. Crick, F. Central dogma of molecular biology. Nature, 1970, 227, 561-563
13. Consortium, I.H.G.S. Finishing the euchromatic sequence of the human genome. Nature, 2004, 431, 931-945 (Pubitemid 39434409)
14. Alberts, B.; Johnson, A.; Lewis, J.; Raff, M.; Roberts, K.; Walter, P. Molecular biology of the cell. Garland Science: New York, 2002.
15. Blasberg, R. PET imaging of gene expression. Eur. J. Cancer, 2002, 38, 2137-2146
16. Gillies, R.J. In vivo molecular imaging. J. Cell Biochem. Suppl., 2002, 39, 231-238
17. Tavitian, B. In vivo imaging with oligonucleotides for diagnosis and drug development. Gut, 2003, 52(Suppl 4), iv40-7. (Pubitemid 36609704)
18. Phelps, M.E. Inaugural article: positron emission tomography provides molecular imaging of biological processes. Proc. Natl. Acad. Sci. U.S.A., 2000, 97, 9226-9233
19. Shah, K.; Jacobs, A.; Breakefield, X.O.; Weissleder, R. Molecular imaging of gene therapy for cancer. Gene. Ther., 2004, 11, 1175-1187 (Pubitemid 39136781)
20. Turkington, T.G. Introduction to PET instrumentation. J. Nucl. Med. Technol., 2001, 29, 4-11.
21. Bergstrom, M.; Awad, R.; Estrada, S.; Malman, J.; Lu, L.; Lendvai, G.; Bergstrom-Pettermann, E.; Langstrom, B. Autoradiography with positron emitting isotopes in positron emission tomography tracer discovery. Mol. Imaging Biol., 2003, 5, 390-396 (Pubitemid 37489829)
22. Langstrom, B.; Kihlberg, T.; Bergstrom, M.; Antoni, G.; Bjorkman, M.; Forngren, B.H.; Forngren, T.; Hartvig, P.; Markides, K.; Yngve, U.; Ogren, M. Compounds labelled with short-lived beta(+)-emitting radionuclides and some applications in life sciences. The importance of time as a parameter. Acta Chem. Scand., 1999, 53, 651-669 (Pubitemid 129611622)
23. Paans, A.M.; Vaalburg, W. Positron emission tomography in drug development and drug evaluation. Curr. Pharm. Des., 2000, 6, 1583-1591 (Pubitemid 30765412)
24. Bergstrom, M.; Langstrom, B. Pharmacokinetic studies with PET. Prog. Drug Res., 2005, 62, 279-317.
25. Weber, W.A. Positron emission tomography as an imaging biomarker. J. Clin. Oncol., 2006, 24, 3282-3292 (Pubitemid 46622068)
26. Yu, R.Z.; Geary, R.S.; Levin, A.A. Application of novel quantitative bioanalytical methods for pharmacokinetic and pharmacokinetic/ pharmacodynamic assessments of antisense oligonucleotides. Curr. Opin. Drug Discov. Devel., 2004, 7, 195-203.
27. Tavitian, B. Oligonucleotides as radiopharmaceuticals. Ernst Schering Res. Found Workshop, 2005, 1-34.
28. Bergstrom, M.; Grahnen, A.; Langstrom, B. Positron emission tomography microdosing: a new concept with application in tracer and early clinical drug development. Eur. J. Clin. Pharmacol., 2003, 59, 357-366 (Pubitemid 37214939)
29. Blodgett, T.M.; Casagranda, B.; Townsend, D.W.; Meltzer, C.C. Issues, controversies, and clinical utility of combined PET/CT imaging: what is the interpreting physician facing? AJR Am. J. Roentgenol., 2005, 184, S138-45.
30. Maldonado, A.; Gonzalez-Alenda, F.J.; Alonso, M.; Sierra, J.M. PET-CT in clinical oncology. Clin. Transl. Oncol., 2007, 9, 494-505.
31. Zaidi, H. Recent developments and future trends in nuclear medicine instrumentation. Z. Med. Phys., 2006, 16, 5-17.
32. Hnatowich, D.J. Observations on the role of nuclear medicine in molecular imaging. J. Cell Biochem. Suppl., 2002, 39, 18-24. (Pubitemid 36176551)
33. Ellington, A.D.; Szostak, J.W. In vitro selection of RNA molecules that bind specific ligands. Nature, 1990, 346, 818-822 (Pubitemid 20272100)
34. Tuerk, C.; Gold, L. Systematic evolution of ligands by exponential enrichment: RNA ligands to bacteriophage T4 DNA polymerase. Science, 1990, 249, 505-510 (Pubitemid 20248891)
35. Acton, P.D.; Zhou, R. Imaging reporter genes for cell tracking with PET and SPECT. Q J. Nucl. Med. Mol. Imaging, 2005, 49, 349-360 (Pubitemid 43246284)
36. Serganova, I.; Ponomarev, V.; Blasberg, R. Human reporter genes: potential use in clinical studies. Nucl. Med. Biol., 2007, 34, 791-807. (Pubitemid 47503822)
37. Walker, R.C.; Purnell, G.L.; Jones-Jackson, L.B.; Thomas, K.L.; Brito, J.A.; Ferris, E.J. Introduction to PET imaging with emphasis on biomedical research. Neurotoxicology, 2004, 25, 533-542 (Pubitemid 38739111)
38. Gambhir, S.S.; Barrio, J.R.; Herschman, H.R.; Phelps, M.E. Imaging gene expression: principles and assays. J. Nucl. Cardiol., 1999, 6, 219-233 (Pubitemid 29184660)
39. Kurreck, J. Antisense technologies. Improvement through novel chemical modifications. Eur. J. Biochem., 2003, 270, 1628-1644 (Pubitemid 36532522)
40. Crinelli, R.; Bianchi, M.; Gentilini, L.; Palma, L.; Sorensen, M.D.; Bryld, T.; Babu, R.B.; Arar, K.; Wengel, J.; Magnani, M. Transcription factor decoy oligonucleotides modified with locked nucleic acids: an in vitro study to reconcile biostability with binding affinity. Nucleic Acids Res., 2004, 32, 1874-1885
41. Lundin, K.E.; Good, L.; Stromberg, R.; Graslund, A.; Smith, C.I. Biological activity and biotechnological aspects of peptide nucleic acid. Adv. Genet., 2006, 56, 1-51.
42. Zamecnik, P.C.; Stephenson, M.L. Inhibition of Rous sarcoma virus replication and cell transformation by a specific oligodeoxynucleotide. Proc. Natl. Acad. Sci. U.S.A., 1978, 75, 280-284
43. Monia, B.P.; Johnston, J.F.; Ecker, D.J.; Zounes, M.A.; Lima, W.F.; Freier, S.M. Selective inhibition of mutant Ha-ras mRNA expression by antisense oligonucleotides. J. Biol. Chem., 1992, 267, 19954-19962
44. Kita, K.; Saito, S.; Morioka, C.Y.; Watanabe, A. Growth inhibition of human pancreatic cancer cell lines by anti-sense oligonucleotides specific to mutated K-ras genes. Int. J. Cancer, 1999, 80, 553-558
45. Shi, W.; Siemann, D.W. Inhibition of renal cell carcinoma angiogenesis and growth by antisense oligonucleotides targeting vascular endothelial growth factor. Br. J. Cancer, 2002, 87, 119-126
46. Yoo, B.H.; Bochkareva, E.; Bochkarev, A.; Mou, T.C.; Gray, D.M. 2′-O-methyl-modified phosphorothioate antisense oligonucleotides have reduced non-specific effects in vitro. Nucleic Acids Res., 2004, 32, 2008-2016
47. Lai, J.; Riedl, M.; Stone, L.S.; Arvidsson, U.; Bilsky, E.J.; Wilcox, G.L.; Elde, R.; Porreca, F. Immunofluorescence analysis of antisense oligodeoxynucleotide-mediated 'knock-down' of the mouse delta opioid receptor in vitro and in vivo. Neurosci. Lett., 1996, 213, 205-208
48. Lopes de Menezes, D.E.; Hudon, N.; McIntosh, N.; Mayer, L.D. Molecular and pharmacokinetic properties associated with the therapeutics of bcl-2 antisense oligonucleotide G3139 combined with free and liposomal doxorubicin. Clin. Cancer Res., 2000, 6, 2891-2902
49. Fluiter, K.; ten Asbroek, A.L.; van Groenigen, M.; Nooij, M.; Aalders, M.C.; Baas, F. Tumor genotype-specific growth inhibition in vivo by antisense oligonucleotides against a polymorphic site of the large subunit of human RNA polymerase II. Cancer Res., 2002, 62, 2024-2028
50. Sands, H.; Gorey-Feret, L.J.; Cocuzza, A.J.; Hobbs, F.W.; Chidester, D.; Trainor, G.L. Biodistribution and metabolism of internally 3H-labeled oligonucleotides. I. Comparison of a phosphodiester and a phosphorothioate. Mol. Pharmacol., 1994, 45, 932-943
51. Eckstein, F. Phosphorothioate oligodeoxynucleotides: what is their origin and what is unique about them? Antisense Nucleic Acid Drug Dev., 2000, 10, 117-121
52. Agrawal, S.; Iyer, R.P. Perspectives in antisense therapeutics. Pharmacol. Ther., 1997, 76, 151-160
53. Henry, S.P.; Templin, M.V.; Gillett, N.; Rojko, J.; Levin, A.A. Correlation of toxicity and pharmacokinetic properties of a phosphorothioate oligonucleotide designed to inhibit ICAM-1. Toxicol. Pathol., 1999, 27, 95-100.
54. Crooke, S.T. Progress in antisense technology: the end of the beginning. Methods Enzymol., 2000, 313, 3-45.
55. Grunweller, A.; Wyszko, E.; Bieber, B.; Jahnel, R.; Erdmann, V.A.; Kurreck, J. Comparison of different antisense strategies in mammalian cells using locked nucleic acids, 2′-O-methyl RNA, phosphorothioates and small interfering RNA. Nucleic Acids Res., 2003, 31, 3185-3193
56. Chan, J.H.; Lim, S.; Wong, W.S. Antisense oligonucleotides: from design to therapeutic application. Clin. Exp. Pharmacol. Physiol., 2006, 33, 533-540
57. Stein, D.; Foster, E.; Huang, S.B.; Weller, D.; Summerton, J. A specificity comparison of four antisense types: morpholino, 2′-Omethyl RNA, DNA, and phosphorothioate DNA. Antisense Nucleic Acid Drug Dev., 1997, 7, 151-157
58. Monia, B.P.; Lesnik, E.A.; Gonzalez, C.; Lima, W.F.; McGee, D.; Guinosso, C.J.; Kawasaki, A.M.; Cook, P.D.; Freier, S.M. Evaluation of 2′-modified oligonucleotides containing 2′-deoxy gaps as antisense inhibitors of gene expression. J. Biol. Chem., 1993, 268, 14514-14522 (Pubitemid 23195583)
59. Kurreck, J.; Wyszko, E.; Gillen, C.; Erdmann, V.A. Design of antisense oligonucleotides stabilized by locked nucleic acids. Nucleic Acids Res., 2002, 30, 1911-1918 (Pubitemid 34537585)
60. Crooke, S.T. Progress in antisense therapeutics discovery and development. Ciba Found Symp., 1997, 209, 158-64; discussion 64-68
61. Dias, N.; Stein, C.A. Antisense oligonucleotides: basic concepts and mechanisms. Mol. Cancer Ther., 2002, 1, 347-355
62. Roivainen, A.; Tolvanen, T.; Salomaki, S.; Lendvai, G.; Velikyan, I.; Numminen, P.; Valila, M.; Sipila, H.; Bergstrom, M.; Harkonen, P.; Lonnberg, H.; Langstrom, B. 68Ga-labeled oligonucleotides for in vivo imaging with PET. J. Nucl. Med., 2004, 45, 347-355 (Pubitemid 47618660)
63. Hnatowich, D.J. Antisense and nuclear medicine. J. Nucl. Med., 1999, 40, 693-703.
64. Aboul-Fadl, T. Antisense oligonucleotides: the state of the art. Curr. Med. Chem., 2005, 12, 2193-2214
65. Amantana, A.; Iversen, P.L. Pharmacokinetics and biodistribution of phosphorodiamidate morpholino antisense oligomers. Curr. Opin. Pharmacol., 2005, 5, 550-555
66. Karkare, S.; Bhatnagar, D. Promising nucleic acid analogs and mimics: characteristic features and applications of PNA, LNA, and morpholino. Appl. Microbiol. Biotechnol., 2006, 71, 575-586 (Pubitemid 44114786)
67. Orum, H.; Wengel, J. Locked nucleic acids: a promising molecular family for gene-function analysis and antisense drug development. Curr. Opin. Mol. Ther., 2001, 3, 239-243 (Pubitemid 32624572)
68. Elayadi, A.N.; Braasch, D.A.; Corey, D.R. Implications of high-affinity hybridization by locked nucleic acid oligomers for inhibition of human telomerase. Biochemistry, 2002, 41, 9973-9981
69. Bondensgaard, K.; Petersen, M.; Singh, S.K.; Rajwanshi, V.K.; Kumar, R.; Wengel, J.; Jacobsen, J.P. Structural studies of LNA:RNA duplexes by NMR: conformations and implications for RNase H activity. Chemistry, 2000, 6, 2687-2695
70. Jepsen, J.S.; Sorensen, M.D.; Wengel, J. Locked nucleic acid: a potent nucleic acid analog in therapeutics and biotechnology. Oligonucleotides, 2004, 14, 130-146 (Pubitemid 38987382)
71. Vester, B.; Wengel, J. LNA (locked nucleic acid): high-affinity targeting of complementary RNA and DNA. Biochemistry, 2004, 43, 13233-13241
72. Fluiter, K.; ten Asbroek, A.L.; de Wissel, M.B.; Jakobs, M.E.; Wissenbach, M.; Olsson, H.; Olsen, O.; Oerum, H.; Baas, F. In vivo tumor growth inhibition and biodistribution studies of locked nucleic acid (LNA) antisense oligonucleotides. Nucleic Acids Res., 2003, 31, 953-962
73. Jepsen, J.S.; Wengel, J. LNA-antisense rivals siRNA for gene silencing. Curr. Opin. Drug Discov. Dev., 2004, 7, 188-194 (Pubitemid 44111950)
74. Kauppinen, S.; Vester, B.; Wengel, J. Locked nucleic acid: high-affinity targeting of complementary RNA for RNomics. Handb Exp. Pharmacol., 2006, 405-422
75. Nielsen, P.E. Antisense properties of peptide nucleic acid. Methods Enzymol., 2000, 313, 156-164 (Pubitemid 129748493)
76. Braasch, D.A.; Corey, D.R. Novel antisense and peptide nucleic acid strategies for controlling gene expression. Biochemistry, 2002, 41, 4503-4510
77. Nielsen, P.E. PNA Technology. Mol. Biotechnol., 2004, 26, 233-248
78. Liu, Y.; Braasch, D.A.; Nulf, C.J.; Corey, D.R. Efficient and isoform- selective inhibition of cellular gene expression by peptide nucleic acids. Biochemistry, 2004, 43, 1921-1927 (Pubitemid 38233254)
79. Summerton, J.E. Morpholino, siRNA, and S-DNA compared: impact of structure and mechanism of action on off-target effects and sequence specificity. Curr. Top Med. Chem., 2007, 7, 651-660
80. Liu, G.; Dou, S.; He, J.; Liu, X.; Rusckowski, M.; Hnatowich, D.J. Predicting the biodistribution of radiolabeled cMORF effector in MORF-pretargeted mice. Eur. J. Nucl. Med. Mol. Imaging, 2007, 34, 237-246
81. Iversen, P.L.; Arora, V.; Acker, A.J.; Mason, D.H.; Devi, G.R. Efficacy of antisense morpholino oligomer targeted to c-myc in prostate cancer xenograft murine model and a Phase I safety study in humans. Clin. Cancer Res., 2003, 9, 2510-2519
82. Crooke. In In Handbook of experimental pharmacology (whole reference is in Crooke's article from year 2000), 1998.
83. Urbain, J.L. Oncogenes, cancer and imaging. J. Nucl. Med., 1999, 40, 498-504.
84. Loke, S.L.; Stein, C.A.; Zhang, X.H.; Mori, K.; Nakanishi, M.; Subasinghe, C.; Cohen, J.S.; Neckers, L.M. Characterization of oligonucleotide transport into living cells. Proc. Natl. Acad. Sci. U.S.A., 1989, 86, 3474-3478 (Pubitemid 19141813)
85. Cotten, M.; Wagner, E.; Birnstiel, M.L. Receptor-mediated transport of DNA into eukaryotic cells. Methods Enzymol., 1993, 217, 618-644 (Pubitemid 23173400)
86. Wu-Pong, S.; Weiss, T.L.; Hunt, C.A. Antisense c-myc oligonucleotide cellular uptake and activity. Antisense Res. Dev., 1994, 4, 155-163
87. Jaaskelainen, I.; Urtti, A. Cell membranes as barriers for the use of antisense therapeutic agents. Mini Rev. Med. Chem., 2002, 2, 307-318
88. Yakubov, L.A.; Deeva, E.A.; Zarytova, V.F.; Ivanova, E.M.; Ryte, A.S.; Yurchenko, L.V.; Vlassov, V.V. Mechanism of oligonucleotide uptake by cells: involvement of specific receptors? Proc. Natl. Acad. Sci. U.S.A., 1989, 86, 6454-6458
89. de Diesbach, P.; Berens, C.; N'Kuli, F.; Monsigny, M.; Sonveaux, E.; Wattiez, R.; Courtoy, P.J. Identification, purification and partial characterisation of an oligonucleotide receptor in membranes of HepG2 cells. Nucleic Acids Res., 2000, 28, 868-874
90. Hanss, B.; Leal-Pinto, E.; Bruggeman, L.A.; Copeland, T.D.; Klotman, P.E. Identification and characterization of a cell membrane nucleic acid channel. Proc. Natl. Acad. Sci. U.S.A., 1998, 95, 1921-1926
91. Shi, F.; Gounko, N.V.; Wang, X.; Ronken, E.; Hoekstra, D. In situ entry of oligonucleotides into brain cells can occur through a nucleic acid channel. Oligonucleotides, 2007, 17, 122-133 (Pubitemid 46651434)
92. Wu-Pong, S. Alternative interpretations of the oligonucleotide transport literature: insights from nature. Adv. Drug Deliv. Rev., 2000, 44, 59-70. (Pubitemid 30764864)
93. Bijsterbosch, M.K.; Manoharan, M.; Rump, E.T.; De Vrueh, R.L.; van Veghel, R.; Tivel, K.L.; Biessen, E.A.; Bennett, C.F.; Cook, P.D.; van Berkel, T.J. In vivo fate of phosphorothioate antisense oligodeoxynucleotides: predominant uptake by scavenger receptors on endothelial liver cells. Nucleic Acids Res., 1997, 25, 3290-3296
94. Sawai, K.; Mahato, R.I.; Oka, Y.; Takakura, Y.; Hashida, M. Disposition of oligonucleotides in isolated perfused rat kidney: involvement of scavenger receptors in their renal uptake. J. Pharmacol. Exp. Ther., 1996, 279, 284-290 (Pubitemid 27166923)
95. Steward, A.; Christian, R.A.; Hamilton, K.O.; Nicklin, P.L. Coadministration of polyanions with a phosphorothioate oligodeoxynucleotide (CGP 69846A): a role for the scavenger receptor in its in vivo disposition. Biochem. Pharmacol., 1998, 56, 509-516
96. Biessen, E.A.; Vietsch, H.; Kuiper, J.; Bijsterbosch, M.K.; Berkel, T.J. Liver uptake of phosphodiester oligodeoxynucleotides is mediated by scavenger receptors. Mol. Pharmacol., 1998, 53, 262-269
97. Suzuki, K.; Doi, T.; Imanishi, T.; Kodama, T.; Tanaka, T. Oligonucleotide aggregates bind to the macrophage scavenger receptor. Eur. J. Biochem., 1999, 260, 855-860 (Pubitemid 29148653)
98. Pearson, A.M.; Rich, A.; Krieger, M. Polynucleotide binding to macrophage scavenger receptors depends on the formation of base-quartet- stabilized four-stranded helices. J. Biol. Chem., 1993, 268, 3546-3554 (Pubitemid 23070996)
99. Bijsterbosch, M.K.; Manoharan, M.; Dorland, R.; Van Veghel, R.; Biessen, E.A.; Van Berkel, T.J. bis-Cholesteryl-conjugated phosphorothioate oligodeoxynucleotides are highly selectively taken up by the liver. J. Pharmacol. Exp. Ther., 2002, 302, 619-626
100. Cheng, K.; Ye, Z.; Guntaka, R.V.; Mahato, R.I. Biodistribution and hepatic uptake of triplex-forming oligonucleotides against type alpha1( I) collagen gene promoter in normal and fibrotic rats. Mol. Pharm., 2005, 2, 206-217
101. Crooke, R.M.; Graham, M.J.; Cooke, M.E.; Crooke, S.T. In vitro pharmacokinetics of phosphorothioate antisense oligonucleotides. J. Pharmacol. Exp. Ther., 1995, 275, 462-473
102. Temsamani, J.; Kubert, M.; Tang, J.; Padmapriya, A.; Agrawal, S. Cellular uptake of oligodeoxynucleotide phosphorothioates and their analogs. Antisense Res. Dev., 1994, 4, 35-42. (Pubitemid 24267004)
103. Gray, G.D.; Basu, S.; Wickstrom, E. Transformed and immortalized cellular uptake of oligodeoxynucleoside phosphorothioates, 3′- alkylamino oligodeoxynucleotides, 2′-O-methyl oligoribonucleotides, oligodeoxynucleoside methylphosphonates, and peptide nucleic acids. Biochem. Pharmacol., 1997, 53, 1465-1476
104. Roth, C.M. Quantitative measurements and rational materials design for intracellular delivery of oligonucleotides. Biotechnol. Prog., 2008, 24, 23-28
105. Hnatowich, D.J. Antisense imaging: where are we now? Cancer Biother. Radiopharm., 2000, 15, 447-457 (Pubitemid 30947786)
106. Butler, M.; Stecker, K.; Bennett, C.F. Cellular distribution of phosphorothioate oligodeoxynucleotides in normal rodent tissues. Lab. Invest., 1997, 77, 379-388 (Pubitemid 27465599)
107. Zhao, Q.; Matson, S.; Herrera, C.J.; Fisher, E.; Yu, H.; Krieg, A.M. Comparison of cellular binding and uptake of antisense phosphodiester, phosphorothioate, and mixed phosphorothioate and methylphosphonate oligonucleotides. Antisense Res. Dev., 1993, 3, 53-66.
108. Brannon-Peppas, L.; Ghosn, B.; Roy, K.; Cornetta, K. Encapsulation of nucleic acids and opportunities for cancer treatment. Pharm. Res., 2007, 24, 618-627 (Pubitemid 46411970)
109. Zuhorn, I.S.; Engberts, J.B.; Hoekstra, D. Gene delivery by cationic lipid vectors: overcoming cellular barriers. Eur. Biophys. J., 2007, 36, 349-362 (Pubitemid 46626209)
110. Walker, I.; Irwin, W.J.; Akhtar, S. Improved cellular delivery of antisense oligonucleotides using transferrin receptor antibody-oligonucleotide conjugates. Pharm. Res., 1995, 12, 1548-1553
111. Shi, N.; Boado, R.J.; Pardridge, W.M. Antisense imaging of gene expression in the brain in vivo. Proc. Natl. Acad. Sci. U.S.A., 2000, 97, 14709-14714 (Pubitemid 32016640)
112. Jia, F.; Figueroa, S.D.; Gallazzi, F.; Balaji, B.S.; Hannink, M.; Lever, S.Z.; Hoffman, T.J.; Lewis, M.R. Molecular Imaging of bcl- 2 Expression in Small Lymphocytic Lymphoma Using 111In- Labeled PNA-Peptide Conjugates. J. Nucl. Med., 2008, 49, 430-438
113. Liu, X.; Wang, Y.; Nakamura, K.; Liu, G.; Dou, S.; Kubo, A.; Rusckowski, M.; Hnatowich, D.J. Optical antisense imaging of tumor with fluorescent DNA duplexes. Bioconjug. Chem., 2007, 18, 1905-1911
114. Shi, F.; Hoekstra, D. Effective intracellular delivery of oligonucleotides in order to make sense of antisense. J. Control. Release, 2004, 97, 189-209. (Pubitemid 38759477)
115. Zhang, Y.M.; Rusckowski, M.; Liu, N.; Liu, C.; Hnatowich, D.J. Cationic liposomes enhance cellular/nuclear localization of 99mT-cantisense oligonucleotides in target tumor cells. Cancer Biother. Radiopharm., 2001, 16, 411-419
116. Sauer, M.; Brecht, A.; Charisse, K.; Maier, M.; Gerster, M.; Stemmler, I.; Gauglitz, G.; Bayer, E. Interaction of chemically modified antisense oligonucleotides with sense DNA: a label-free interaction study with reflectometric interference spectroscopy. Anal. Chem., 1999, 71, 2850-2857 (Pubitemid 29340477)
117. Dewanjee, M.K.; Ghafouripour, A.K.; Kapadvanjwala, M.; Samy, A.T. Kinetics of hybridization of mRNA of c-myc oncogene with 111In-labeled antisense oligodeoxynucleotide probes by high-pressure liquid chromatography. Biotechniques, 1994, 16, 844-6, 8, 50.
118. Younes, C.K.; Boisgard, R.; Tavitian, B. Labelled oligonucleotides as radiopharmaceuticals: pitfalls, problems and perspectives. Curr. Pharm. Des., 2002, 8, 1451-1466 (Pubitemid 34693063)
119. Sazani, P.; Gemignani, F.; Kang, S.H.; Maier, M.A.; Manoharan, M.; Persmark, M.; Bortner, D.; Kole, R. Systemically delivered antisense oligomers upregulate gene expression in mouse tissues. Nat. Biotechnol., 2002, 20, 1228-1233 (Pubitemid 35462487)
120. Larsen, H.J.; Bentin, T.; Nielsen, P.E. Antisense properties of peptide nucleic acid. Biochim. Biophys. Acta, 1999, 1489, 159-166
121. Tavitian, B.; Terrazzino, S.; Kuhnast, B.; Marzabal, S.; Stettler, O.; Dolle, F.; Deverre, J.R.; Jobert, A.; Hinnen, F.; Bendriem, B.; Crouzel, C.; Di Giamberardino, L. In vivo imaging of oligonucleotides with positron emission tomography. Nat. Med., 1998, 4, 467-471 (Pubitemid 28212765)
122. Wickstrom, E. Oligodeoxynucleotide stability in subcellular extracts and culture media. J. Biochem. Biophys. Methods, 1986, 13, 97-102.
123. Hoke, G.D.; Draper, K.; Freier, S.M.; Gonzalez, C.; Driver, V.B.; Zounes, M.C.; Ecker, D.J. Effects of phosphorothioate capping on antisense oligonucleotide stability, hybridization and antiviral efficacy versus herpes simplex virus infection. Nucleic Acids Res, 1991, 19, 5743-5748
124. Sands, H.; Gorey-Feret, L.J.; Ho, S.P.; Bao, Y.; Cocuzza, A.J.; Chidester, D.; Hobbs, F.W. Biodistribution and metabolism of internally 3H-labeled oligonucleotides. II. 3′,5′-blocked oligonucleotides. Mol. Pharmacol., 1995, 47, 636-646
125. Kuhnast, B.; Dolle, F.; Terrazzino, S.; Rousseau, B.; Loc'h, C.; Vaufrey, F.; Hinnen, F.; Doignon, I.; Pillon, F.; David, C.; Crouzel, C.; Tavitian, B. General method to label antisense oligonucleotides with radioactive halogens for pharmacological and imaging studies. Bioconjug. Chem., 2000, 11, 627-636
126. Tavitian, B.; Marzabal, S.; Boutet, V.; Kuhnast, B.; Terrazzino, S.; Moynier, M.; Dolle, F.; Deverre, J.R.; Thierry, A.R. Characterization of a synthetic anionic vector for oligonucleotide delivery using in vivo whole body dynamic imaging. Pharm. Res., 2002, 19, 367-376
127. Campbell, J.M.; Bacon, T.A.; Wickstrom, E. Oligodeoxynucleoside phosphorothioate stability in subcellular extracts, culture media, sera and cerebrospinal fluid. J. Biochem. Biophys. Methods, 1990, 20, 259-267 (Pubitemid 20111713)
128. Phillips, M.I.; Zhang, Y.C. Basic principles of using antisense oligonucleotides in vivo. Methods Enzymol., 2000, 313, 46-56.
129. Cossum, P.A.; Sasmor, H.; Dellinger, D.; Truong, L.; Cummins, L.; Owens, S.R.; Markham, P.M.; Shea, J.P.; Crooke, S. Disposition of the 14C-labeled phosphorothioate oligonucleotide ISIS 2105 after intravenous administration to rats. J. Pharmacol. Exp. Ther., 1993, 267, 1181-1190 (Pubitemid 24068683)
130. Geary, R.S.; Watanabe, T.A.; Truong, L.; Freier, S.; Lesnik, E.A.; Sioufi, N.B.; Sasmor, H.; Manoharan, M.; Levin, A.A. Pharmacokinetic properties of 2′-O-(2-methoxyethyl)-modified oligonucleotide analogs in rats. J. Pharmacol. Exp. Ther., 2001, 296, 890-897
131. Crooke, S.T. Progress in antisense technology. Annu. Rev. Med., 2004, 55, 61-95.
132. Phillips, J.A.; Craig, S.J.; Bayley, D.; Christian, R.A.; Geary, R.; Nicklin, P.L. Pharmacokinetics, metabolism, and elimination of a 20-mer phosphorothioate oligodeoxynucleotide (CGP 69846A) after intravenous and subcutaneous administration. Biochem. Pharmacol., 1997, 54, 657-668
133. Fluiter, K.; Frieden, M.; Vreijling, J.; Rosenbohm, C.; De Wissel, M.B.; Christensen, S.M.; Koch, T.; Orum, H.; Baas, F. On the in vitro and in vivo properties of four locked nucleic acid nucleotides incorporated into an anti-H-Ras antisense oligonucleotide. Chembiochem, 2005, 6, 1104-1109 (Pubitemid 40825353)
134. Wahlestedt, C.; Salmi, P.; Good, L.; Kela, J.; Johnsson, T.; Hokfelt, T.; Broberger, C.; Porreca, F.; Lai, J.; Ren, K.; Ossipov, M.; Koshkin, A.; Jakobsen, N.; Skouv, J.; Oerum, H.; Jacobsen, M.H.; Wengel, J. Potent and nontoxic antisense oligonucleotides containing locked nucleic acids. Proc. Natl. Acad. Sci. U.S.A., 2000, 97, 5633-5638
135. Di Giusto, D.A.; King, G.C. Strong positional preference in the interaction of LNA oligonucleotides with DNA polymerase and proofreading exonuclease activities: implications for genotyping assays. Nucleic Acids Res., 2004, 32, e32.
136. Kristensen, E. In vitro and in vivo studies on the pharmacokinetics and metabolism of PNA constructs in rodents. Methods Mol. Biol., 2002, 208, 259-269
137. Srinivasan, S.K.; Tewary, H.K.; Iversen, P.L. Characterization of binding sites, extent of binding, and drug interactions of oligonucleotides with albumin. Antisense Res. Dev., 1995, 5, 131-139
138. Hawley, P.; Gibson, I. Interaction of oligodeoxynucleotides with mammalian cells. Antisense Nucleic Acid Drug Dev., 1996, 6, 185-195
139. Lewis, M.R.; Jia, F. Antisense imaging: and miles to go before we sleep? J. Cell Biochem., 2003, 90, 464-472 (Pubitemid 37243693)
140. Tavitian, B. In vivo antisense imaging. Q. J. Nucl. Med., 2000, 44, 236-255
141. Kedzierski, W.; Porter, J.C. Quantitative study of tyrosine hydroxylase mRNA in catecholaminergic neurons and adrenals during development and aging. Brain Res. Mol. Brain Res., 1990, 7, 45-51.
142. Crooke, S.T. Molecular mechanisms of action of antisense drugs. Biochim. Biophys. Acta, 1999, 1489, 31-44.
143. Hnatowich, D.J.; Nakamura, K. Antisense targeting in cell culture with radiolabeled DNAs - a brief review of recent progress. Ann. Nucl. Med., 2004, 18, 363-368 (Pubitemid 39265056)
144. Branch, A.D. A hitchhiker's guide to antisense and nonantisense biochemical pathways. Hepatology, 1996, 24, 1517-1529
145. Lima, W.F.; Monia, B.P.; Ecker, D.J.; Freier, S.M. Implication of RNA structure on antisense oligonucleotide hybridization kinetics. Biochemistry, 1992, 31, 12055-12061
146. Stein, C.A. Keeping the biotechnology of antisense in context. Nat. Biotechnol., 1999, 17, 209.
147. Patzel, V.; Steidl, U.; Kronenwett, R.; Haas, R.; Sczakiel, G. A theoretical approach to select effective antisense oligodeoxyribonucleotides at high statistical probability. Nucleic Acids Res., 1999, 27, 4328-4334 (Pubitemid 29533171)
148. Sczakiel, G. Theoretical and experimental approaches to design effective antisense oligonucleotides. Front Biosci., 2000, 5, D194-201.
149. Agrawal, S. Antisense oligonucleotides: towards clinical trials. Trends Biotechnol., 1996, 14, 376-387 (Pubitemid 26328673)
150. Crooke, S.T. Advances in understanding the pharmacological properties of antisense oligonucleotides. Adv. Pharmacol., 1997, 40, 1-49.
151. Swayze, E.E.; Siwkowski, A.M.; Wancewicz, E.V.; Migawa, M.T.; Wyrzykiewicz, T.K.; Hung, G.; Monia, B.P.; Bennett, A.C. Antisense oligonucleotides containing locked nucleic acid improve potency but cause significant hepatotoxicity in animals. Nucleic Acids Res., 2007, 35(2), 687-700.
152. Roberts, J.; Palma, E.; Sazani, P.; Orum, H.; Cho, M.; Kole, R. Efficient and persistent splice switching by systemically delivered LNA oligonucleotides in mice. Mol. Ther., 2006, 14, 471-475
153. Dewanjee, M.K.; Ghafouripour, A.K.; Kapadvanjwala, M.; Dewanjee, S.; Serafini, A.N.; Lopez, D.M.; Sfakianakis, G.N. Noninvasive imaging of c-myc oncogene messenger RNA with indium-111- antisense probes in a mammary tumor-bearing mouse model. J. Nucl. Med., 1994, 35, 1054-1063
154. Hnatowich, D.J.; Winnard, P., Jr.; Virzi, F.; Fogarasi, M.; Sano, T.; Smith, C.L.; Cantor, C.R.; Rusckowski, M. Technetium-99m labeling of DNA oligonucleotides. J. Nucl. Med., 1995, 36, 2306-2314
155. Watanabe, N.; Sawai, H.; Endo, K.; Shinozuka, K.; Ozaki, H.; Tanada, S.; Murata, H.; Sasaki, Y. Labeling of phosphorothioate antisense oligonucleotides with yttrium-90. Nucl. Med. Biol., 1999, 26, 239-243 (Pubitemid 29125342)
156. Hedberg, E.; Langstrom, B. Synthesis of 4-([18F]fluoromethyl) phenyl isothiocyanate and its use in labelling oligonucleotides. Acta Chem. Scand., 1997, 51, 1236-1240 (Pubitemid 127547385)
157. Kobori, N.; Imahori, Y.; Mineura, K.; Ueda, S.; Fujii, R. Visualization of mRNA expression in CNS using 11C-labeled phosphorothioate oligodeoxynucleotide. Neuroreport, 1999, 10, 2971-2974 (Pubitemid 29507763)
158. 76Br]bromobenzoate and its use in conjugation labelling of macromolecules. Acta Chem. Scand., 1999, 53, 508-512
159. Velikyan, I.; Lendvai, G.; Valila, M.; Roivainen, A.; Yngve, U.; Bergstrom, M.; Langstrom, B. Microwave accelerated Ga-68- labelling of oligonucleotides. J. Labelled Comp. Radiopharmaceut., 2004, 47, 79-89. (Pubitemid 38166415)
160. Lendvai, G.; Velikyan, I.; Estrada, S.; Eriksson, B.; Langstrom, B.; Bergstrom, M. Biodistribution of (68)Ga-Labeled LNA-DNA Mixmer Antisense Oligonucleotides for Rat Chromogranin-A. Oligonucleotides, 2008, 18, 33-49.
161. Oberbauer, R.; Schreiner, G.F.; Meyer, T.W. Renal uptake of an 18-mer phosphorothioate oligonucleotide. Kidney Int., 1995, 48, 1226-1232
162. Stein, C.A.; Benimetskaya, L.; Mani, S. Antisense strategies for oncogene inactivation. Semin. Oncol., 2005, 32, 563-572
163. Zhao, Q.; Zhou, R.; Temsamani, J.; Zhang, Z.; Roskey, A.; Agrawal, S. Cellular distribution of phosphorothioate oligonucleotide following intravenous administration in mice. Antisense Nucleic Acid Drug Dev., 1998, 8, 451-458 (Pubitemid 29055873)
164. Geary, R.S.; Yu, R.Z.; Watanabe, T.; Henry, S.P.; Hardee, G.E.; Chappell, A.; Matson, J.; Sasmor, H.; Cummins, L.; Levin, A.A. Pharmacokinetics of a tumor necrosis factor-alpha phosphorothioate 2′-O-(2-methoxyethyl) modified antisense oligonucleotide: comparison across species. Drug Metab. Dispos., 2003, 31, 1419-1428
165. Sarmiento, U.M.; Perez, J.R.; Becker, J.M.; Narayanan, R. In vivo toxicological effects of rel A antisense phosphorothioates in CD-1 mice. Antisense Res. Dev., 1994, 4, 99-107. (Pubitemid 24308378)
166. Sharma, V.; Luker, G.D.; Piwnica-Worms, D. Molecular imaging of gene expression and protein function in vivo with PET and SPECT. J. Magn. Reson Imaging, 2002, 16, 336-351 (Pubitemid 35167870)
167. Wu, F.; Yngve, U.; Hedberg, E.; Honda, M.; Lu, L.; Eriksson, B.; Watanabe, Y.; Bergstrom, M.; Langstrom, B. Distribution of (76)Br-labeled antisense oligonucleotides of different length determined ex vivo in rats. Eur. J. Pharm. Sci., 2000, 10, 179-186 (Pubitemid 30190093)
168. Mardirossian, G.; Lei, K.; Rusckowski, M.; Chang, F.; Qu, T.; Egholm, M.; Hnatowich, D.J. In vivo hybridization of technetium- 99m-labeled peptide nucleic acid (PNA). J. Nucl. Med., 1997, 38, 907-913 (Pubitemid 27251983)
169. Hnatowich, D.J.; Mardirossian, G.; Fogarasi, M.; Sano, T.; Smith, C.L.; Cantor, C.R.; Rusckowski, M.; Winnard, P., Jr. Comparative properties of a technetium-99m-labeled single-stranded natural DNA and a phosphorothioate derivative in vitro and in mice. J. Pharmacol. Exp. Ther., 1996, 276, 326-334
170. Sun, X.; Fang, H.; Li, X.; Rossin, R.; Welch, M.J.; Taylor, J.S. MicroPET imaging of MCF-7 tumors in mice via unr mRNA-targeted peptide nucleic acids. Bioconjug Chem, 2005, 16, 294-305.
171. Liu, M.; Wang, R.F.; Zhang, C.L.; Yan, P.; Yu, M.M.; Di, L.J.; Liu, H.J.; Guo, F.Q. Noninvasive imaging of human telomerase reverse transcriptase (hTERT) messenger RNA with 99mTc-radiolabeled antisense probes in malignant tumors. J. Nucl. Med., 2007, 48, 2028-2036
172. Nakamura, K.; Fan, C.; Liu, G.; Gupta, S.; He, J.; Dou, S.; Kubo, A.; Rusckowski, M.; Hnatowich, D.J. Evidence of antisense tumor targeting in mice. Bioconjug. Chem., 2004, 15, 1475-1480
173. Nakamura, K.; Kubo, A.; Hnatowich, D.J. Antisense targeting of p-glycoprotein expression in tissue culture. J. Nucl. Med., 2005, 46, 509-513
174. Liu, X.; Nakamura, K.; Wang, Y.; Liu, G.; He, J.; Ding, H.; Lu, P.; Rusckowski, M.; Kubo, A.; Hnatowich, D.J. Initial Mechanistic Studies of Antisense Targeting in Cells. J. Nucl. Med., 2006, 47, 360-368
175. Tamm, I. Antisense therapy in malignant diseases: status quo and quo vadis? Clin. Sci. (Lond.), 2006, 110, 427-442
176. Kalota, A.; Dondeti, V.R.; Gewirtz, A.M. Progress in the development of nucleic acid therapeutics. Handb Exp. Pharmacol., 2006, 173-196
177. Corey, D.R. RNA learns from antisense. Nat. Chem. Biol., 2007, 3, 8-11.
178. Marwick, C. First "antisense" drug will treat CMV retinitis. JAMA, 1998, 280, 871.
179. Wang, J.; Chen, P.; Mrkobrada, M.; Hu, M.; Vallis, K.A.; Reilly, R.M. Antisense imaging of epidermal growth factor-induced p21(WAF-1/CIP-1) gene expression in MDA-MB-468 human breast cancer xenografts. Eur. J. Nucl. Med. Mol. Imaging, 2003, 30, 1273-1280
180. Conner, S.D.; Schmid, S.L. Regulated portals of entry into the cell. Nature, 2003, 422, 37-44.
181. Schmidt, K.S.; Borkowski, S.; Kurreck, J.; Stephens, A.W.; Bald, R.; Hecht, M.; Friebe, M.; Dinkelborg, L.; Erdmann, V.A. Application of locked nucleic acids to improve aptamer in vivo stability and targeting function. Nucleic Acids Res., 2004, 32, 5757-5765