A cyclic-RGD-bioshuttle functionalized with TMZ by DARinv "click chemistry" targeted to αvβ3 integrin for therapy

International Journal of Medical Sciences

Volumn 7, Issue 6, 2010, Pages 326-339

  Braun, Klaus ^a   Wiessler, Manfred ^a   Pipkorn, Rüdiger ^a   Ehemann, Volker ^b   Bäuerle, Tobias ^a   Fleischhacker, Heinz ^a   Müller, Gabriele ^a   Lorenz, Peter ^a   Waldeck, Waldemar ^a  

^a GERMAN CANCER RESEARCH CENTER DKFZ   (Germany)

^b UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Adaptor systems; Bioshuttle; Click chemistry; Cycloaddition; Inverse diels alder reaction; Ligation chemistry; Linker systems; RGD; Targeted therapy; Temozolomide; Tetrazines

Indexed keywords

ARGINYLGLYCYLASPARTIC ACID; BIOSHUTTLE; CYCLOPEPTIDE; DRUG CARRIER; TEMOZOLOMIDE; UNCLASSIFIED DRUG; VITRONECTIN RECEPTOR;

ARTICLE; BREAST CANCER; CANCER CELL; CELL KILLING; CELL MEMBRANE TRANSPORT; CELL STRAIN MCF 7; CONTROLLED STUDY; DIELS ALDER REACTION; DRUG DESIGN; DRUG FORMULATION; DRUG SYNTHESIS; DRUG TARGETING; HUMAN; HUMAN CELL; LIGATION; MOLECULARLY TARGETED THERAPY;

EID: 78649674605     PISSN: None     EISSN: 14491907     Source Type: Journal    
DOI: 10.7150/ijms.7.326     Document Type: Article

References (34)

1. NIH Consensus Statement. Breast cancer screening for women ages 40-49. NIH Consens Statement. 1997; 15: 1-35.
2. Harms JF, Welch DR, Samant RS, et al. A small molecule antagonist of the alpha(v)beta3 integrin suppresses MDA-MB-435 skeletal metastasis. Clin Exp Metastasis. 2004; 21: 119-28.
3. Takada Y, Ye X, Simon S. The integrins. Genome Biol. 2007; 8: 215.
4. Sakamoto S, Kyprianou N. Targeting anoikis resistance in prostate cancer metastasis. Mol Aspects Med. 2010 Apr;31(2):205-14.
5. Zanardi LA, Battistini L, Burreddu P, et al. Targeting alpha(v)beta(3) Integrin: Design and Applications of Monoand Multifunctional RGD-Based Peptides and Semipeptides. Curr Med Chem. 2010;17(13):1255-99.
6. Chen X, Sievers E, Hou Y, et al. Integrin alpha v beta 3-targeted imaging of lung cancer. Neoplasia. 2005; 7: 271-9.
7. Willmann JK, Lutz AM, Paulmurugan R, et al. Dual-targeted contrast agent for US assessment of tumor angiogenesis in vivo. Radiology. 2008; 248: 936-44.
8. Liu Z, Niu G, Wang F, et al. (68)Ga-labeled NOTA-RGD-BBN peptide for dual integrin and GRPR-targeted tumor imaging. Eur J Nucl Med Mol Imaging. 2009; 36: 1483-94.
9. Haier J, Goldmann U, Hotz B, et al. Inhibition of tumor progression and neoangiogenesis using cyclic RGD-peptides in a chemically induced colon carcinoma in rats. Clin Exp Metastasis. 2002; 19: 665-72.
10. Oba M, Fukushima S, Kanayama N, et al. Cyclic RGD peptide-conjugated polyplex micelles as a targetable gene delivery system directed to cells possessing alphavbeta3 and alphavbeta5 integrins. Bioconjug Chem. 2007; 18: 1415-23.
11. Wiessler M, Kliem C, Lorenz P, Mueller E, and Fleischhacker H. EU Patent: Ligation reaction based on the Diels Alder Reaction with invers electron demand. [EP 06 012 414.6]. 6-10-2006.
12. Wiessler M, Waldeck W, Kliem C, et al. The Diels-Alder-reaction with inverse-electron-demand, a very efficient versatile click-reaction concept for proper ligation of variable molecular partners. Int J Med Sci. 2009; 7: 19-28.
13. Arrowsmith J, Jennings SA, Clark AS, et al. Antitumor imidazotetrazines. 41. Conjugation of the antitumor agents mitozolomide and temozolomide to peptides and lexitropsins bearing DNA major and minor groove-binding structural motifs. J Med Chem. 2002; 45: 5458-70.
14. Reppe W, Schlichting O, Klager K, et al. Cyclisierende Polymerisation von Acetylen I. Justus Liebigs Annalen der Chemie. 1948; 560: 1-92.
15. Chay C, Smith DC. Adjuvant and neoadjuvant therapy in prostate cancer. Semin Oncol. 2001; 28: 3-12.
16. Hegeman RB, Liu G, Wilding G, et al. Newer therapies in advanced prostate cancer. Clin Prostate Cancer. 2004; 3: 150-6.
17. Newlands ES, Blackledge GR, Slack JA, et al. Phase I trial of temozolomide (CCRG 81045: M&B 39831: NSC 362856). Br J Cancer. 1992; 65: 287-91.
18. Chang MC, Wang BR, Huang TF. Characterization of endothelial cell differential attachment to fibrin and fibrinogen and its inhibition by Arg-Gly-Asp-containing peptides. Thromb Haemost. 1995; 74: 764-9.
19. Belin MT, Boulanger P. Involvement of cellular adhesion sequences in the attachment of adenovirus to the HeLa cell surface. J Gen Virol. 1993; 74 (Pt 8): 1485-97.
20. Wickham TJ, Mathias P, Cheresh DA, et al. Integrins alpha v beta 3 and alpha v beta 5 promote adenovirus internalization but not virus attachment. Cell. 1993; 73: 309-19.
21. Gasparini G, Brooks PC, Biganzoli E, et al. Vascular integrin alpha(v)beta3: a new prognostic indicator in breast cancer. Clin Cancer Res. 1998; 4: 2625-34.
22. Beer AJ, Haubner R, Sarbia M, et al. Positron emission tomography using [18F]Galacto-RGD identifies the level of integrin alpha(v)beta3 expression in man. Clin Cancer Res. 2006; 12: 3942-9.
23. Zitzmann S, Ehemann V, Schwab M. Arginine-glycine-aspartic acid (RGD)-peptide binds to both tumor and tumor-endothelial cells in vivo. Cancer Res. 2002; 62: 5139-43.
24. Haubner R, Weber WA, Beer AJ, et al. Noninvasive visualization of the activated alphavbeta3 integrin in cancer patients by positron emission tomography and [18F]Galacto-RGD. PLoS Med. 2005; 2: e70.
25. Zhang C, Jugold M, Woenne EC, et al. Specific targeting of tumor angiogenesis by RGD-conjugated ultrasmall superparamagnetic iron oxide particles using a clinical 1.5-T magnetic resonance scanner. Cancer Res. 2007; 67: 1555-62.
26. Muzykantov VR. Biomedical aspects of targeted delivery of drugs to pulmonary endothelium. Expert Opin Drug Deliv. 2005; 2: 909-26.
27. Braun K, Pipkorn R, Waldeck W. Development and Characterization of Drug Delivery systems for Targeting Mammalian Cells and Tissues: A Review. Curr Med Chem. 2005; 12: 1841-58.
28. Peer D, Karp JM, Hong S, et al. Nanocarriers as an emerging platform for cancer therapy. Nat Nanotechnol. 2007; 2: 751-60.
29. Lammers T, Hennink WE, Storm G. Tumour-targeted nanomedicines: principles and practice. Br J Cancer. 2008; 99: 392-7.
30. Davis ME, Chen ZG, Shin DM. Nanoparticle therapeutics: an emerging treatment modality for cancer. Nat Rev Drug Discov. 2008; 7: 771-82.
31. Burke PA, DeNardo SJ, Miers LA, et al. Cilengitide targeting of alpha(v)beta(3) integrin receptor synergizes with radioimmunotherapy to increase efficacy and apoptosis in breast cancer xenografts. Cancer Res. 2002; 62: 4263-72.
32. Cheng Y, Prusoff WH. Relationship between the inhibition constant (K1) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction. Biochem Pharmacol. 1973; 22: 3099-108.
33. Braun K, Peschke P, Pipkorn R, et al. A biological transporter for the delivery of peptide nucleic acids (PNAs) to the nuclear compartment of living cells. J Mol Biol. 2002; 318: 237-43.
34. Braun K, von Brasch L, Pipkorn R, et al. BioShuttle-mediated plasmid transfer. Int J Med Sci. 2007; 4: 267-77.