Synthesis and cellular uptake of a MR contrast agent coupled to an antisense peptide nucleic acid - Cell-penetrating peptide conjugate

Contrast Media and Molecular Imaging

Volumn 2, Issue 1, 2007, Pages 42-49

  Su, W ^a   Mishra, R ^a   Pfeuffer, J ^a,b   Wiesmuller K H ^c   Ugurbil, K ^a,d   Engelmann, J ^a  

^a MAX PLANCK INSTITUTE FOR BIOLOGICAL CYBERNETICS   (Germany)

^b SIEMENS AG   (Germany)

^c EMC MICROCOLLECTIONS GMBH   (Germany)

^d UNIVERSITY OF MINNESOTA MEDICAL SCHOOL   (United States)

Author keywords

Cell penetrating peptide; Contrast agent; MR imaging; Peptide nucleic acid

Indexed keywords

CELL PENETRATING PEPTIDE; CONTRAST MEDIUM; GADOTERIC ACID; MESSENGER RNA; PEPTIDE NUCLEIC ACID; RED FLUORESCENT PROTEIN; DIAGNOSTIC AGENT; GADOLINIUM 1,4,7,10-TETRAAZACYCLODODECANE-N,N',N'',N'''-TETRAACETATE; HETEROCYCLIC COMPOUND; ORGANOMETALLIC COMPOUND; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ANIMAL CELL; ARTICLE; CELL NUCLEUS; CELL STRAIN 3T3; CELL VACUOLE; CELLULAR DISTRIBUTION; CONCENTRATION RESPONSE; CONTRAST ENHANCEMENT; ELECTROSPRAY MASS SPECTROMETRY; FLUORESCENCE ANALYSIS; IN VITRO STUDY; IN VIVO STUDY; MOLECULAR IMAGING; MOUSE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE IMAGING; PRIORITY JOURNAL; PROTEIN BINDING; RNA TRANSCRIPTION; SEQUENCE ANALYSIS; STATISTICAL SIGNIFICANCE; SYNTHESIS; ANIMAL; DOSE RESPONSE; EVALUATION; IMAGE ENHANCEMENT; METABOLIC CLEARANCE RATE; METHODOLOGY;

ANIMALS; CONTRAST MEDIA; DOSE-RESPONSE RELATIONSHIP, DRUG; HETEROCYCLIC COMPOUNDS; IMAGE ENHANCEMENT; MAGNETIC RESONANCE IMAGING; METABOLIC CLEARANCE RATE; MICE; NIH 3T3 CELLS; ORGANOMETALLIC COMPOUNDS; PEPTIDE NUCLEIC ACIDS;

EID: 34147165107     PISSN: 15554309     EISSN: 15554317     Source Type: Journal    
DOI: 10.1002/cmmi.126     Document Type: Article

References (29)

1. Weissleder R, Mahmood U. Molecular imaging. Radiology 2001; 219: 316-333.
2. Jacques V, Desreux JF. New classes of MRI contrast agents. Top. Curr. Chem. 2002; 221: 123-163.
3. Bhorade R, Weissleder R, Nakakoshi T, Moore A, Tung CH. Macrocyclic chelators with paramagnetic cations are internalized into mammalian cells via a HIV-Tat derived membrane translocation peptide. Bioconjug. Chem. 2000; 11: 301-305.
4. Woolf TM, Melton DA, Jennings CG. Specificity of antisense oligonucleotides in vivo. Proc. Natl Acad. Sci. USA 1992; 89: 7305-7309.
5. Tavitian B, Terrazzino S, Kuhnast B, Marzabal S, Stettler O, Dolle F, Deverre JR, Jobert A, Hinnen F, Bendriem B, Crouzet C, Di Giamberardino L. In vivo imaging of oligonucleotides with positron emission tomography. Nat. Med. 1998; 4: 467-471.
6. Sazani P, Gemignani F, Kang SH, Maier MA, Manoharan M, Persmark M, Bortner D, Kole R. Systemically delivered antisense oligomers upregulate gene expression in mouse tissues. Nat. Biotechnol. 2002; 20: 1228-1233.
7. Sazani P, Astriab-Fischer A, Kole R. Effects of base modifications on antisense properties of 2′-O-methoxyethyl and PNA oligonucleotides. Antisense Nucl. Acid Drug Dev. 2003; 13: 119-128.
8. Younes CK, Boisgard R, Tavitian B. Labeled oligonucleotides as radiopharmaceuticals: Pitfalls, problems and perspectives. Curr. Pharm. Des. 2002; 8: 1451-1466.
9. Nielsen PE, Egholm M, Berg RH, Buchardt O. Sequence-selective recognition of DNA by strand displacement with a thymine-substituted polyamide. Science 1991; 254: 1497-1500.
10. Larsen HJ, Bentin T, Nielsen PE. Antisense properties of peptide nucleic acid. Biochim. Biophys. Acta 1999; 1489: 159-166.
11. Paulasova P, Andreo B, Diblik J, Macek M, Pellestor F. The peptide nucleic acids as probes for chromosomal analysis: application to human oocytes, polar bodies and preimplantation embryos. Mol. Hum. Reprod. 2004; 10: 467-472.
12. Tian X, Aruva MR, Qin W, Zhu W, Sauter ER, Thakur ML, Wickstrom E. Noninvasive molecular imaging of MYC mRNA expression in human breast cancer xenografts with a [(99m)Tc] peptide-peptide nucleic acid-peptide chimera. Bioconjug. Chem. 2005; 16: 70-79.
13. McMahon BM, Stewart J, Fauq A, Younkin S, Younkin L, Richelson E. Using peptide nucleic acids as gene-expression modifiers to reduce beta-amyloid levels. J. Mol. Neurosci. 2002; 19: 71-76.
14. Lewis MR, Jia F. Antisense imaging: and miles to go before we sleep? J. Cell. Biochem. 2003; 90: 464-472.
15. Baird GS, Zacharias DA, Tsien RY. Biochemistry, mutagenesis, and oligomerization of DsRed, a red fluorescent protein from coral. Proc. Natl Acad. Sci. USA 2000; 97(22): 11984-11989.
16. Mologni L, Marchesi E, Nielsen PE, Gambacorti-Passerini C. Inhibition of promyelocytic leukemia (PML)/retinoic acid receptor-alpha and PML expression in acute promyelocytic leukemia cells by anti-PML peptide nucleic acid. Cancer Res. 2001; 61: 5468-5473.
17. Coester C, Kreuter J, von Briesen B, Langer K. Preparation of avidin-labeled gelatin nanoparticles as carriers for biotinylated peptide nucleic acid (PNA). Int. J. Pharm. 2000; 196: 147-149.
18. Shi N, Boado RJ, Pardridge WM. Antisense imaging of gene expression in the brain in vivo. Proc. Natl Acad. Sci. USA 2000; 97: 14709-14714.
19. Gait MJ. Peptide-mediated cellular delivery of antisense oligonucleotides and their analogues. Cell. Mol. Life Sci. 2003; 60: 844-853.
20. Heckl S, Pipkorn R, Waldeck W, Spring H, Jenne J, Debus J, Braun K. Intracellular visualization of prostate cancer using magnetic resonance imaging. Cancer Res. 2003; 63: 4766-4772.
21. Zhao M, Weissleder R. Intracellular cargo delivery using Tat peptide and derivatives. Med. Res. Rev. 2004; 24: 1-12.
22. Gammon ST, Villalobos VM, Prior JL, Sharma V, Piwnica-Worms D. Quantitative analysis of permeation peptide complexes labeled with Technetium-99m: chiral and sequence-specific effects on net cell uptake. Bioconjug. Chem. 2003; 14: 368-376.
23. Su W, Mishra R, Engelmann J, Pfeuffer J, Ugurbil K. Preparation, characterization and visualization of CPP-mediated MR contrast agents. Molecular Imaging. 2005; 4: 378.
24. Engelmann J, Su W, Jha D, Mishra R, Pfeuffer J, Ugurbil K. Intracellular, MR contrast agents based on cationic cell penetrating peptides: a comparative study. Proc. ISMRM. 2006; 1887.
25. Hainsworth J, Harrison P, Mather JS. Preparation and characterization of a DOTA-Lysine-Biotin conjugate as an effector molecule for pretargeted radionuclide. Bioconjug. Chem. 2005; 16: 1468-1474.
26. 3+ ions. Contrast Med. Mol. Imag. 2006; 1: 23-29.
27. Fischer R, Köhler K, Fotin-Mleczek M, Brock R. A stepwise dissection of the intracellular fate of cationic cell-penetrating peptides. J. Biol. Chem. 2004; 279: 12625-12635.
28. Sun X, Fang H, Li X, Rossin R, Welch MJ, Taylor JS. MicroPET imaging of MCF-7 tumors in mice via unr mRNA-targeted peptide nucleic acids. Bioconjug. Chem. 2005; 16: 294-305.
29. Heppeier A, Froidevaux S, Macke HR, Jermann E, Powell P, Henning M. Radiometal-labeled macrocyclic chelator-derivatised somatostatin analogue with superb tumor-targeting properties and potential for receptor-mediated internal radiotherapy. Chem. Eur. J. 1999; 5: 1974-1981.