Synthesis and hybridization studies of a new cpp-pna conjugate as a potential therapeutic agent in atherosclerosis treatment

Protein and Peptide Letters

Volumn 21, Issue 7, 2014, Pages 672-678

  Wojciechowska, Monika ^a   Ruczyński, Jaroslaw ^a   Rekowski, Piotr ^a   Alenowicz, Magdalena ^a   Mucha, Piotr ^a   Pieszko, Malgorzata ^a   Miszka, Anna ^a   Dobkowski, Michal ^a   Bluijssen, Hans ^b  

^a UNIVERSITY OF GDA SK   (Poland)

^b ADAM MICKIEWICZ UNIVERSITY   (Poland)

Author keywords

Capillary electrophoresis; Cell penetrating peptides; Click reaction; CPP PNA conjugate; Peptide nucleic acids

Indexed keywords

1,2,3 TRIAZOLE DERIVATIVE; CELL PENETRATING PEPTIDE; CELL PENETRATING PEPTIDE PEPTIDE NUCLEIC ACID CONJUGATE; DNA FRAGMENT; MESSENGER RNA; PEPTIDE NUCLEIC ACID; SINGLE STRANDED DNA; STAT1 PROTEIN; UNCLASSIFIED DRUG; RHODAMINE; STAT1 PROTEIN, HUMAN;

ARTICLE; ATHEROSCLEROSIS; BINDING AFFINITY; CAPILLARY ELECTROPHORESIS; CYCLOADDITION; DRUG SYNTHESIS; ENDOTHELIUM CELL; FLUORESCENCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HYBRIDIZATION; INFLAMMATION; NUCLEIC ACID SYNTHESIS; PROTEIN EXPRESSION; PURIFICATION; SEQUENCE ALIGNMENT; CHEMISTRY; CLICK CHEMISTRY; GENETICS; ISOLATION AND PURIFICATION; SYNTHESIS;

CELL-PENETRATING PEPTIDES; CLICK CHEMISTRY; HUMANS; PEPTIDE NUCLEIC ACIDS; RHODAMINES; RNA, MESSENGER; STAT1 TRANSCRIPTION FACTOR;

EID: 84901953353     PISSN: 09298665     EISSN: 18755305     Source Type: Journal    
DOI: 10.2174/0929866521666140320102034     Document Type: Article

References (40)

1. Nielsen, P.E.; Egholm, M.; Berg, R.H.; Buchardt, O. Sequenceselective recognition of DNA by strand displacement with a thymine-substituted polyamide. Science, 1991, 254, 14971500.
2. Nielsen, P.E. Peptide Nucleic Acids. A molecule with two identities. Acc. Chem. Res., 1999, 32, 624630.
3. Nielsen, P.E. Peptide nucleic acids (PNA) in chemical biology and drug discovery, Chem. Biodivers., 2010, 7, 786804
4. Uhlmann, E.; Peyman, A.; Breipohl, G.; Will, D.W. PNA: synthesis polyamide nucleic acids with unusual binding properties. Angew. Chem., Int. Ed. Engl., 1998, 37, 27962823.
5. Egholm, M.; Buchardt, O.; Christensen, L.; Behrens, C.; Freier, S.M.; Driver, D.A.; Berg, R.H.; Kim, S.K.; Norden, B.; Nielsen, P.E. PNA hybridizes to complementary oligonucleotides obeying the Watson-Crick hydrogen-bonding rules. Nature, 1993, 365, 566-568.
6. Wang, G.; Xu, X.S. Peptide nucleic acid (PNA) binding-mediated gene regulation. Cell Res., 2004, 14, 111116.
7. Knudsen, H.; Nielsen, P.E. Antisense properties of duplex-And triplex-forming PNAs. Nucleic Acids Res., 1996, 24, 494500.
8. Good, L.; Nielsen, P.E. Progress in developing PNA as a genetargeted drug. Antisense Nucleic Acid Drug Dev., 1997, 7, 431437.
9. Hultdin, M.; Grönlund, E.; Norrback, K.; Eriksson-Lindström, E.; Just, T.; Roos, G. Telomere analysis by fluorescence in situ hybridization and flow cytometry. Nucleic Acids Res., 1998, 26, 36513656.
10. Thiede, C.; Bayerdörffer, E.; Blasczyk, R.; Wittig, B.; Neubauer, A. Simple and sensitive detection of mutations in the ras protooncogenes using PNA-mediated PCR clamping. Nucleic Acids Res., 1996, 24, 983984.
11. Perry-O'Keefe, H.; Yao, XW.; Coull, J.M.; Fuchs, M.; Egholm, M. Peptide nucleic acid pre-gel hybridization: an alternative to southern hybridization. Proc. Natl. Acad. Sci. USA, 1996, 93, 14670-14675.
12. Manoharan, M. Oligonucleotide conjugates as potential antisense drugs with improved uptake, biodistribution, targeted delivery, and mechanism of action. Antisense Nucleic Acid Drug Dev., 2002, 12, 103128.
13. Venkatesan, N.; Hydean Kim, B. Peptide conjugates of oligonucleotides: synthesis and applications. Chem. Rev., 2006, 106, 3712-3761.
14. Albertshofer, K.; Siwkowski, A.M.; Wancewicz, E.V.; Esau, C.C.; Watanabe, T.; Nishihara, K.C.; Kinberger, G.A.; Malik, L.; Eldrup, A.B.; Manoharan, M.; Geary, R.S.; Monia, B.P.; Swayze, E.E.; Griffey, R.H.; Bennett, C.F.; Maier, M.A. Structure-Activity relationship study on a simple cationic peptide motif for cellular delivery of antisense peptide nucleic acid. J. Med. Chem., 2005, 48, 67416749.
15. Bendifallah, N.; Rasmussen, F.W.; Zachar, V.; Ebbesen, P.; Nielsen, P.E.; Koppelhus, U. Evaluation of cellpenetrating peptides (CPPs) as vehicles for intracellular delivery of antisense peptide nucleic acid (PNA). Bioconjugate Chem., 2006, 17, 750758.
16. Maier, M.A.; Esau, C.C.; Siwkowski, A.M.; Wancewicz, E.V.; Albertshofer, K.; Kinberger, G.A.; Kadaba, N.S.; Watanabe, T.; Manoharan, M.; Bennett, C.F.; Griffey, R.H.; Swayze, E.E. Evaluation of basic amphipathic peptides for cellular delivery of antisense peptide nucleic acids. J. Med. Chem., 2006, 49, 25342542.
17. Veldhoen, S.; Laufer, S.D.; Restle, T. Recent developments in peptide-based nucleic acid delivery. Int. J. Mol. Sci., 2008, 9, 1276-1320.
18. Fonseca, S.B.; Pereira, M.P.; Kelley, S.O. Recent advances in the use of cell-penetrating peptides for medicinal and biological applications. Adv. Drug Deiver. Rev., 2009, 61, 953964.
19. Joshi, T.; Gasser, G.; Martin, L.L.; Spiccia, L. Specific uptake and interactions of peptide nucleic acid derivatives with biomimetic membranes. RSC Advances., 2012, 2, 47034712.
20. Majumdar, S.; Siahaan, T.J. Peptide-mediated targeted drug delivery. Med. Res. Rev., 2010, 3, 637658.
21. Gallazzi, F.; Wang, Y.; Jia, F.; Shenoy, N.; Landon, L.A.; Hannink, M.; Lever, S.Z.; Lewis, M.R. Synthesis of radiometal-labeled and fluorescent cell-permeating peptide-PNA conjugates for targeting the bcl2 proto-oncogene. Bioconjugate Chem., 2003, 14, 1083-1095.
22. van den Berg, A.; Dowdy, S.F. Protein transduction domain delivery of therapeutic macromolecules. Curr. Opin. Biotechnol., 2011, 22, 88893.
23. Ho, A.; Schwarze, S.R.; Mermelstain, S.J.; Waksman, G.; Dowdy, S.F. Synthetic Protein Transduction Domains: Enhanced Transduction Potential in vitro and in vivo. Cancer Res., 2001, 61, 474477.
24. Mayfield, L.D.; Corey, D.R. Automated synthesis of peptide nucleic acids and peptide nucleic acids-PNA conjugates. Anal. Biochem., 1999, 268, 401404.
25. Turner, J.J.; Arzumanov, A.A.; Gait, M.J. Synthesis, cellular uptake and HIV1 Tat-dependent trans-Activation inhibition activity of oligonucleotide analogues disulphide-conjugated to cellpenetrating peptides. Nucleic Acids Res., 2005, 33, 2742.
26. Turner, J.J; Ivanova, G.D.; Verbeure, B.; Williams, D.D.; Arzumanov, D.; Abes; S.; Lebleu, B.; Gait, M.J. Cell-penetrating peptide conjugate of peptide nucleic acids (PNA) as inhibitors of HIV1 Tat-dependent trans-Activation in cells. Nucleic Acids Res., 2005, 33, 68376849.
27. Huisgen, R. 1,3-dipolar cycloaddtion chemistry. In Padwa, A. Ed.; Wiley, New York, 1984.
28. Tornøe, C.W.; Christensen, C.; Meldal, M. Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes and azides. J. Org. Chem., 2002, 67, 3057303064.
29. Narayan, S.; Muldoon, J.; Finn, M.G.; Fokin V.V.; Kolb, H.C.; Sharpless, K.B. "On Water": Unique reactivity of organic compounds in aqueous suspension. Angew. Chem. Int. Ed., 2005, 44, 32753279.
30. Khirud, G.; Meenakshi, V.; Sunita, S.K.; Vaijayanti A.K. A versatile method for the preparation of conjugates of peptide with DNA/PNA/analog by employing chemo-selective click reactions in water. Nucleic Acids Res., 2007, 35, 139139.
31. Hein, C.D.; Liu, X.; Wang, D. Click Chemistry, A Powerful Tool for Pharm Sciences. Pharm Res., 2008, 10, 22162230.
32. Kumar, R.; El-Sagheer, A.; Tumpane, J.; Lincoln, P.; Wilhelmsson, L.M.; Brown, T. Template directed oligonucleotide strand ligation, covalent intramolecular DNA circularization and catenation using click chemistry. J. Am. Chem. Soc., 2007, 129, 68596864.
33. Li, H.; Aneja, R.; Chaiken, I. Click chemistry in peptide-based drug design. Molecules, 2013, 18, 97979817.
34. Boren, B.C.; Narayan, S.; Rasmussen, L.K.; Zhang, L.; Zhao, H.; Lin, Z.; Jia, G.; Fokin, V.V. Ruthenium-catalyzed azide-Alkyne cycloaddition: scope and mechanism. J. Am. Chem. Soc., 2008, 130, 89238930.
35. Jewett, J.C.; Bertozzi, C.R. Cu-free click cycloaddition reactions in chemical biology. Cehm. Soc. Rev., 2010, 39, 12721279.
36. Nakane, M.; Ichikawa, S.; Matsuda, A. Synthesis of crosslinked circular DNAs using Huisgen reaction. Nucleic Acids Symp Ser., 2005, 49, 189190.
37. Leon, M.L.; Zuckerman, S.H. Gamma interferon: a central mediator in atherosclerosis. Inflamm Res., 2005, 54, 395411.
38. Basile, A.; Giuliani, A.; Pirri, G.; Chiari, M. Use of peptide nucleic acid probes for detecting DNA single-base mutations by capillary electrophoresis. Electrophoresis, 2002, 23, 926929.
39. Nielsen, P.E.; Egholm, M. Peptide nucleic acids (PNA). In Nielsen, P.E. and Egholm, M., Ed.; Protocols and Applications., Horizon Scientific, Norfolk, CT. 1999.
40. Chan, W.C.; White, P.D. In Fmoc solid phase peptide synthesis: a practical approach. Oxford University Press: Oxford, 2000.