Synthesis of multi-galactose-conjugated 2′-O-methyl oligoribonucleotides and their in vivo imaging with positron emission tomography

Bioorganic and Medicinal Chemistry

Volumn 22, Issue 24, 2014, Pages 6806-6813

  Mäkilä, Jussi ^a   Jadhav, Satish ^a   Kiviniemi, Anu ^a   Käkelä, Meeri ^b   Liljenbäck, Heidi ^a,b   Poijärvi Virta, Päivi ^a   Laitala Leinonen, Tiina ^a   Lönnberg, Harri ^a   Roivainen, Anne ^a,b   Virta, Pasi ^a  

^a UNIVERSITY OF TURKU   (Finland)

^b TURKU PET CENTRE   (Finland)

Author keywords

68Ga labelled oligonucleotides; Liver targeting; Oligonucleotide glyco conjugates; PET imaging; Solid phase synthesis

Indexed keywords

3 AZIDOPROPYL 2,3,4,6 TETRA O ACETYL BETA DEXTRO GALACTOPYRANOSIDE; 4 [3 (PROP 2 YN 1 YLOXY) 2,2 BIS(PROP 2 YN 1 YLOXYMETHYL)PROPOXY]BENZALDEHYDE; DIMETHYL [7 [1 [4 [4 (4,4' DIMETHOXYTRITYLOXY)BUTOXY]PHENYL] 2 METHOXY 2 OXOETHYL] 1,4,7 TRIAZACYCLONONANE 1,4 DIYL]DIACETATE; GALACTOSE CONJUGATED 2' O METHYL OLIGORIBONUCLEOTIDE DERIVATIVE; OLIGORIBONUCLEOTIDE; PHOSPHORAMIDOUS ACID; UNCLASSIFIED DRUG; 1,4,7-TRIAZACYCLONONANE; GALACTOSE; GALLIUM; HETEROCYCLIC COMPOUND; RADIOPHARMACEUTICAL AGENT;

ACETYLATION; ALDOL REACTION; ANIMAL EXPERIMENT; ANIMAL TISSUE; APOPTOSIS; ARTICLE; CONJUGATION; CONTROLLED STUDY; COUPLING FACTOR; DRUG STRUCTURE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; IMAGING; IN VIVO STUDY; ISOTOPE LABELING; LIVER CELL; LIVER METABOLISM; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; PROTEIN TARGETING; RADIOACTIVITY; RAT; SOLID PHASE SYNTHESIS; TISSUE DISTRIBUTION; ANIMAL; CHEMISTRY; DIAGNOSTIC USE; FEMALE; KIDNEY; LIVER DISEASES; MALE; METABOLISM; SPRAGUE DAWLEY RAT; SYNTHESIS; URINE;

ANIMALS; FEMALE; GALACTOSE; GALLIUM RADIOISOTOPES; HETEROCYCLIC COMPOUNDS; KIDNEY; LIVER DISEASES; MALE; OLIGORIBONUCLEOTIDES; POSITRON-EMISSION TOMOGRAPHY; RADIOPHARMACEUTICALS; RATS; RATS, SPRAGUE-DAWLEY;

EID: 84913591370     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2014.10.034     Document Type: Article

References (54)

1. J.S. Burnett, and J.J. Rossi Chem. Biol. 19 2012 60
2. R. Kole, A.R. Krainer, and S. Altman Nat. Rev. Drug Discovery 11 2012 125
3. R.L. Juliano, X. Ming, and O. Nakagawa Bioconjugate Chem. 23 2012 147
4. J. Kurreck Angew. Chem., Int. Ed. 48 2009 1378
5. D. Castanotto, and J.J. Rossi Nature 457 2009 426
6. R.L. Juliano, X. Ming, K. Carver, and B. Laing Nucleic Acid Ther. 24 2014 101
7. J. Winkler Ther. Delivery 4 2013 791
8. X. Ming Exp. Opin. Drug Delivery 8 2011 435
9. F. Marlin, P. Simon, T. Saison-Behmoares, and C. Giovannangeli ChemBioChem 11 2010 1493
10. B. Ernst, and J.L. Magnani Nat. Rev. Drug Discovery 8 2009 661
11. P.H. Seeberger, and D.B. Werz Nature 446 2007 1046
12. B.E. Collins, and J.C. Paulson Curr. Opin. Chem. Biol. 8 2004 617
13. C.R. Bertozzi, and L.L. Kiessling Science 291 2001 2357
14. H. Lis, and N. Sharon Chem. Rev. 98 1998 637
15. T.K. Dam, and C.F. Brewer Adv. Carbohydr. Chem. Biochem. 63 2010 139
16. J.L.J. Blanco, C.O. Mellet, and J.M.G. Fernández Chem. Soc. Rev. 42 2013 4518
17. V. Wittmann, and R.J. Pieters Chem. Soc. Rev. 42 2013 4492
18. Y.M. Chabre, and R. Roy Chem. Soc. Rev. 42 2013 4657
19. R.T. Lee, M.-H. Wang, W.-J. Lin, and Y.C. Lee Bioorg. Med. Chem. 19 2011 2494
20. A. Aviñó, S.M. Ocampo, R. Lucas, J.J. Reina, J.C. Morales, J.C. Perales, and R. Eritja Mol. Divers. 15 2011 751
21. A. Kiviniemi, P. Virta, and H. Lönnberg Bioconjugate Chem. 22 2011 1249
22. B. Ugarte-Uribe, S. Pérez-Rentero, R. Lukas, A. Aviñó, J.J. Reina, I. Alkorta, R. Eritja, and J.C. Morales Bioconjugate Chem. 21 2010 1280
23. M. Karskela, M. Helkearo, P. Virta, and H. Lönnberg Bioconjugate Chem. 21 2010 748
24. A. Kiviniemi, P. Virta, and H. Lönnberg Bioconjugate Chem. 21 2010 1890
25. G. Pourceau, A. Meyer, Y. Chevolot, E. Souteyrand, J.-J. Vasseur, and F. Morvan Bioconjugate Chem. 21 2010 1520
26. K.N. Jayaprakash, C.G. Peng, D. Butler, J.P. Varghese, M.A. Maier, K.G. Rajeev, and M. Manoharan Org. Lett. 12 2010 5410
27. G. Pourceau, A. Meyer, J.-J. Vasseur, and F. Morvan J. Org. Chem. 74 2009 1218
28. Y. Singh, P. Murat, and E. Defrancq Chem. Soc. Rev. 39 2010 2054
29. H. Lönnberg Bioconjugate Chem. 20 2009 1065
30. M. Karskela, P. Virta, M. Malinen, A. Urtti, and H. Lönnberg Bioconjugate Chem. 19 2008 2549
31. A. Kiviniemi, P. Virta, and H. Lönnberg Bioconjugate Chem. 19 2008 1726
32. F. Morvan, A. Meyer, A. Jochum, C. Sabin, Y. Chevolot, A. Imberty, J.-P. Praly, J.-J. Vasseur, E. Souteyrland, and S. Vidal Bioconjugate Chem. 18 2007 1637
33. R.J. Duff, S.F. Deamond, C. Roby, Y. Zhou, and P.O.P. Ts'o Methods Enzymol. 313 1999 297
34. E.A.L. Biessen, H. Vietsch, E.T. Rump, K. Fluiter, M.K. Bijsterbosch, and T.J.C. van Berkel Methods Enzymol. 314 2000 324
35. E.A.L. Biessen, H. Vietsch, E.T. Rump, K. Fluiter, J. Kuiper, M.K. Bijsterbosch, and T.J.C. van Berkel Biochem. J. 340 1999 783
36. L. Zhu, Z. Ye, K. Chemg, D.D. Miller, and R.I. Mahato Bioconjugate Chem. 19 2008 290
37. R. Hamzavi, F. Dolle, B. Tavitian, O. Dahl, and P.E. Nielsen Bioconjugate Chem. 14 2003 941
38. E.A.L. Biessen, K. Sliedregt-Bol, P.A.Chr.T. Hoen, P. Prince, E. Van der Bilt, A.R.P.M. Valentijn, N.J. Meeuwenoord, H. Princen, M.K. Bijsterbosch, G.A. Van der Marel, J.H. Van Boom, and T.J.C. Van Berkel Bioconjugate Chem. 13 2002 295
39. Rajeev, K. G.; Zimmermann, T.; Manoharan, M.; Maier, M.; Kuchimanchi, S.; Charisse, K. Patent WO 2013075035 A1, 2013.
40. T.P. Prakash, M.J. Graham, J. Yu, R. Carty, A. Low, A. Chappell, K. Schmidt, C. Zhao, M. Aghajan, H.F. Murray, S. Riney, S.L. Booten, S.F. Murray, H. Gaus, J. Crosby, W.F. Lima, S. Guo, B.P. Monia, E.E. Swayze, and P.P. Seth Nucleic Acids Res. 42 2014 8796
41. F. An, B. Gong, H. Wang, D. Yu, G. Zhao, L. Lin, W. Tang, H. Yu, S. Bao, and Q. Xie Apoptosis 17 2012 702
42. C.J. Guo, Q. Pan, D.G. Li, H. Sun, and B.W. Liu J. Hepatol. 50 2009 766
43. W. Liu, G. Hao, M.A. Long, T. Anthony, J.-T. Hsieh, and X. Sun Angew. Chem., Int. Ed. 48 2009 7346
44. G. Lendvai, I. Velikyan, M. Bergström, S. Estrada, D. Laryea, M. Välilä, S. Salomäki, B. Långström, and A. Roivainen Eur. J. Pharm. Sci. 26 2005 26
45. A. Roivainen, T. Tolvanen, S. Salomäki, G. Lendvai, I. Velikyan, P. Numminen, M. Välilä, H. Sipilä, M. Bergström, P. Härkönen, H. Lönnberg, and B. Långström J. Nucl. Med. 45 2004 347
46. J. Schlesinger, I. Koezle, R. Bergmann, S. Tamburini, C. Bolzati, F. Tisato, B. Noll, S. Klussmann, S. Vonhoff, F. Wuest, H.-J. Pietzsch, and J. Steinbach Bioconjugate Chem. 19 2008 928
47. Y. Li, P. Schaffer, and D.M. Perrin Bioorg. Med. Chem. Lett. 23 2013 6313
48. W.M. Rockey, L. Huang, K.C. Kloepping, N.J. Baumhover, P.H. Giangrande, and M.K. Schultz Bioorg. Med. Chem. 19 2011 4080
49. A. Kiviniemi, J. Mäkelä, J. Mäkilä, T. Saanijoki, H. Liljenbäck, P. Poijärvi-Virta, H. Lönnberg, T. Laitala-Leinonen, A. Roivainen, and P. Virta Bioconjugate Chem. 23 2012 1981
50. J. Katajisto, P. Virta, and H. Lönnberg Bioconjugate Chem. 15 2004 890
51. H. Salo, P. Virta, H. Hakala, T.P. Prakash, A.M. Kawasaki, M. Manoharan, and H. Lönnberg Bioconjugate Chem. 10 1999 815
52. J. Brask, and K. Jensen Bioorg. Med. Chem. Lett. 11 2001 697
53. J.A.F. Joosten, V. Loimaranta, C.C.M. Appeldoorn, S. Haataja, F.A. El Maate, R.M. Liskamp, J. Finne, and R.J. Pieters J. Med. Chem. 47 2004 6499
54. Y.C. Lee FASEB J. 6 1992 3193