Synthesis of bombesin-functionalized iron oxide nanoparticles and their specific uptake in prostate cancer cells

Journal of Nanoparticle Research

Volumn 12, Issue 5, 2010, Pages 1599-1608

  Martin, Amanda L ^a   Hickey, Jennifer L ^a   Ablack, Amber L ^a   Lewis, John D ^a   Luyt, Leonard G ^a   Gillies, Elizabeth R ^a  

^a UNIVERSITY OF WESTERN ONTARIO   (Canada)

Author keywords

Bombesin; Iron oxide; Magnetic resonance imaging; Nanomedicine; Nanoparticles; Prostate cancer

Indexed keywords

BOMBESIN; CLICK CHEMISTRY; FUNCTIONALIZED; FUNCTIONALIZED NANOPARTICLES; IRON OXIDE NANOPARTICLE; MOLECULAR MARKER; NANOMEDICINES; PROSTATE CANCER CELLS; PROSTATE CANCERS; SUPERPARAMAGNETIC IRON OXIDE NANOPARTICLES; TREATMENT MONITORING;

CELLS; DISEASES; IRON OXIDES; MAGNETIC MATERIALS; MAGNETIC RESONANCE; MEDICAL NANOTECHNOLOGY; NANOMAGNETICS; NANOPARTICLES; PEPTIDES; PROBES; SUPERPARAMAGNETISM;

MAGNETIC RESONANCE IMAGING;

BOMBESIN DERIVATIVE; BOMBESIN[7-14][11 BETA ALANINE 13 PHENYLALANINE 14 NORLEUCINE]; MOLECULAR MARKER; SUPERPARAMAGNETIC IRON OXIDE NANOPARTICLE; TETRADECAPEPTIDE; UNCLASSIFIED DRUG;

ARTICLE; CANCER CELL; CANCER DIAGNOSIS; CONJUGATION; CONTROLLED STUDY; CYCLOADDITION; DRUG STRUCTURE; DRUG SYNTHESIS; EARLY DIAGNOSIS; GENE OVEREXPRESSION; HUMAN; HUMAN CELL; MOLECULAR IMAGING; NANOMEDICINE; NUCLEAR MAGNETIC RESONANCE IMAGING; PRIORITY JOURNAL; PROSTATE CANCER; QUANTITATIVE ANALYSIS;

EID: 77955086735     PISSN: 13880764     EISSN: 1572896X     Source Type: Journal    
DOI: 10.1007/s11051-009-9681-3     Document Type: Article

References (50)

1. Alonzi R, Padhani AR, Allen C (2007) Dynamic contrast enhanced MRI in prostate cancer. Eur J Radiol 63:335-350
2. American Cancer Society (2007) Cancer facts and figures 2007. American Cancer Society, Atlanta, p 54
3. Ametamey SM, Honer M, Schubiger PA (2008) Molecular imaging with PET. Chem Rev 108:1501-1516
4. Baidoo KE, Lin KS, Zhan Y, Finley P, Scheffel U, Wagner HN Jr (1998) Design, synthesis, and initial evaluation of highaffinity technetium bombesin analogues. Bioconjug Chem 9:218-225
5. Basilion JP, Yeon S, Botnar R (2005) Magnetic resonance imaging: utility as a molecular imaging modality. Curr Top Dev Biol 70:1-33 (Pubitemid 43588878)
6. Broccardo M, Falconieri Erspamer G, Melchiorri P, Negri L (1975) Relative potency of bombesin-like peptides. Br J Pharmacol 5:221-227
7. Cai W, Chen X (2008) Multimodality molecular imaging oftumor angiogenesis. J Nucl Med 49:113S-128S
8. Caravan P, Ellison JJ, McMurry TJ, Lauffer RB (1999) Gadolinium (III) chelates as MRI contrast agents: structure, dynamics, and applications. Chem Rev 99:2293-2352
9. Chodak GW, Keller P, Schoenberg HW (1989) Assessment of screening for prostate cancer using the digital rectal exam. J Urol 141:1136-1138
10. Girard F, Bachelard H, St-Pierre S, Rioux F (1984) The contractile effect of bombesin, gastrin releasing peptide and various fragments in the rat stomach strip. Eur Pharmacol 102:489-497
11. Heijmink SW, Futterer JJ, Hambrock T, Takahashi S, Scheenen TWJ, Huisman HJ, Hulsbergen-Van de Kaa CA, Knipscheer BC, Kiemeney LAL, Witjes JA, Barentsz JO (2007) Prostate cancer: Body-array versus endorectal coil MR imaging at 3 T-comparison of image quality, localization, and staging performance. Radiology 244:184-195
12. Hoffman TJ, Gali H, Smith CJ, Sieckman GL, Hayes DL, Owen NK, Volkert WA (2003) Novel series of 111Inlabeled bombesin analogs as potential radiopharmaceuticals for specific targeting of gastrin-releasing peptide receptors expressed on human prostate cancer cells. J Nuc Med 44:823-831
13. Hosseinkhani H, Hosseinkhani M (2009) Biodegradable polymer- metal complexes for gene and drug delivery. Curr Drug Safety 4:79-83
14. Huzjan R, Sala E, Hricak H (2005) Magnetic resonance imaging and magnetic resonance spectroscopic imaging of prostate cancer. Nat Clin Prac Urol 2:434-442 (Pubitemid 41486125)
15. Ikonen S, Karkkainen P, Kivisaari L, Salo JO, Taari K, Vehmas T, Tervahartiala P, Rannikko S (2001) Endorectal magnetic resonance imaging of prostatic cancer: Comparison between fat-suppressed T2-weighted fast spin echo and three-dimensional dual-echo, steady-state sequences. Eur Radiol 11:236-241
16. Jobsis FF (1977) Noninvasive, infrared monitoring of cerebral and myocardial oxygen sufficiency and circulatory parameters. Science 198:1264-1267
17. Josephson L, Tung C, Moore A, Weissleder R (1999) High-efficiency intracellular magnetic labeling with novel superparamagnetic- Tat peptide conjugates. Bioconjug Chem 10:186-191
18. Jun Y, Lee J, Cheon J (2008) Chemical design of nanoparticle probes for high-performance magnetic resonance imaging. Angew Chem Int Ed Engl 47:5122-5135
19. Kelly KA, Setlur S, Ross R, Anbazhagan R, Waterman P, Rubin MA, Weissleder R (2008) Detection of early prostate cancer using a hepsin-targeted imaging agent. Cancer Res 68:2286-2291
20. Kirkham AP, Emberton M, Allen C (2006) How good is MRI at detecting and characterising cancer within the prostate? Eur Urol 50:1163-1174
21. Kolb HC, Sharpless KB (2003) The growing impact of click chemistry on drug discovery. Drug Disc Today 8:1128-1137
22. La Bella R, Garcia-Garayoa E, Bahler M, Blauenstein P, Schibli R, Conrath P, Tourwe D, Schibiger PA (2002) A 99mTc(I)-postlabeled high affinity bombesin analogue as a potential tumor imaging agent. Bioconjug Chem 13:599-604
23. Laurent S, Forge D, Port M, Roch A, Robic C, Vander Elst L, Muller RN (2008) Magnetic iron oxide nanoparticles: synthesis, stabilization, vectorization, physicochemical characterizations, and biological applications. Chem Rev108:2064-2110
24. Lewis JD, Destito G, Zijlstra A, Gonzalez MJ, Quigley JP, Manchester M, Stuhlmann H (2006) Viral nanoparticles as tools for intravital vascular imaging. Nat Med 12:354-360
25. Lutz J, Zarafshani Z (2008) Efficient construction of therapeutics, bioconjugates, biomaterials and bioactive surfaces using azide-alkyne "click" chemistry. Adv Drug Deliv Rev 60:958-970
26. Mantey SA, Weber HC, Sainz E, Akeson M, Ryan RR, Pradhan TK, Searles RP, Spindel ER, Battey JF, Coy DH, Jensen RT (1997) Discovery of a high affinity radioligand for the human orphan receptor, bombesin receptor subtype 3, which deomonstrates that it has a unique pharmacology compared with other mammalian bombesin receptors. J Biol Chem 272:26062-26071
27. Martin AL, Bernas L, Foster PF, Rutt BK, Gillies ER (2008) Enhanced cell uptake of superparamagnetic iron oxide nanoparticles functionalized with dendritic guanidines. Bioconjug Chem 19:2375-2384
28. Molday RS, MacKenzie D (1982) Immunospecific ferromagnetic iron-dextran reagents for the labeling and magnetic separation of cells. J Immunol Methods 52:353-367
29. Montet X, Weissleder R, Josephson L (2006) Imaging pancreatic cancer with a peptide-nanoparticle conjugate targeted to normal pancreas. Bioconjug Chem 17:905-911
30. Nam RK, Toi A, Klotz LH, Trachtenberg J, Jewett MAS, Appu S, Loblaw AD, Sugar L, Narod SA, Kattan MW (2007) Assessing individual risk for prostate cancer. J Clin Oncol 25:3582-3588
31. Padhani AR, Gapinski CJ, Macvicar DA, Parker GJ, Suckling J, Revell PB, Leach MO, Dearnaley DP, Husband JE (2000) Dynamic contrast enhanced MRI of prostate cancer: correlation with morphology and tumour stage, histological grade and PSA. Clin Radiol 55:99-109
32. Patel O, Shulkes A, Baldwin GS (2006) Gastrin releasing peptide and cancer. Biochim Biophys Acta 1766:23-41
33. Pittet MJ, Swirski PK, Reynolds F, Josephson L, Weissleder R (2006) Labeling of immune cells for in vivo imaging using magnetofluorescent nanoparticles. Nat Protoc 1:73-78
34. Pradhan TK, Katsuno T, Taylor JE, Kim SH, Ryan RR, Mantey SA, Donohue PJ, Weber HC, Sainz E, Battey JF, Coy DH, Jensen RT (1998) Identification of a unique ligand which has high affinity for all four bombesin receptor subtypes. Eur J Pharm 343:275-287
35. Reubi JC, Wenger S, Schmuckli-Maurer J, Schaer JC, Gigger M (2002) Bombesin receptor subtypes in human cancers: Detection with the universal radioligand I-125-[D-TYR6, beta-ALA(11), PHE13, NLE14] bombesin(6-14). Clin Cancer Res 8:1139-1146
36. Reynolds F, Weissleder R, Josephson L (2005) Protamine as an efficient membrane-translocating peptide. Bioconjug Chem 16:1240-1245
37. Rogers BE, Bigott HM, McCarthy DW, Della Manna D, Kim J, Sharp TL, Welch MJ (2003) MicroPET imaging of a gastrin-releasing peptide receptor-positive tumor in a mouse model of human prostate cancer using a 64Culabeled bombesin analogue. Bioconjug Chem 14:756-763
38. Serada RE, Adolphi NL, Bisoffi M, Sillerud LO (2007) Targeting and cellular trafficking of magnetic nanoparticles for prostate cancer imaging. Mol Imaging 6:277-288
39. Smith CJ, Sieckman GL, Owen NK, Hayes DL, Mazuru DG, Kannan R, Volkert WA, Hoffman TJ (2003) Radiochemical investigations of gastrin-releasing peptide receptor-specific [99mTc(X)(CO)3-Dpr-Ser-Ser-Ser-Gln- Trp-Ala-Val-Gly-His-Leu- Met-NH2] in PC-3, tumorbearing rodent models; syntheses, radiolabeling, and in vitro/in vivo studies where Dpr = 2, 3-diaminopropionic acid and X = H2O or P(CH2OH)3. Cancer Res 63:4082-4088
40. Song HT, Choi JS, Huh YM, Kim S, Jun YW, Suh JS, Cheon J (2005) Surface modulation of magnetic nanocrystals in the development of highly efficient magnetic resonance probes for intracellular labeling. J Am Chem Soc 127:9992-9993
41. Sun B, Schally AV, Halmos G (2000) The presence of receptors for bombesin/GRP and mRNA for three receptor subtypes in human ovarian epithelial Cancers. Regul Pept 90:77-84 (Pubitemid 30331013)
42. Sun EY, Josephson L, Weissleder R (2006) "Clickable" nanoparticles for targeted imaging. Mol Imaging 5:122-128
43. Tanimoto A, Nakashima J, Kohno H, Shinmoto H, Kuribayashi S (2007) Prostate cancer screening: The clinical value of diffusion-weighted imaging and dynamic MR imaging in combination with T2-weighted imaging. J Magn Reson Imaging 25:146-152
44. Van de Wiele C, Dumont F, Vanden Broecke R, Oosterlinck W, Cocquyt V, Serreyn R, Peers S, Thronback J, Slegers G, Dierckx RA (2000) Technetium-99m RP527, a GRP analogue for visualization of GRP receptor-expressing malignancies: a feasibility study. Eur J Nuc Med 27:1694-1699
45. Van de Wiele CV, Dumont F, Dierckx RA, Peers SH, Thornback JR, Slegers G (2001) Biodistribution and dosimetry of 99mTc-RP527, a gastrin-releasing peptide (GRP) agonist for the visualization of GRP receptor-expressing malignancies. J Nucl Med 42:1722-1727
46. Wang AZ, Bagalkot V, Vasilliou CC, Gu F, Alexis F, Zhang L, Shaikh M, Yuet K, Cima MJ, Langer R, Kantoff PW, Bander NH, Jon S, Farokhzad OC (2008) Superparamagnetic iron oxide nanoparticle-aptamer bioconjugates for combined prostate cancer imaging and therapy. ChemMedChem 3:1131-1315
47. Weissleder R, Pittet MJ (2008) Imaging in the era of molecular oncology. Nature 452:580-589
48. White MA, Johnson JA, Koberstein JT, Turro NJ (2006) Toward the syntheses of universal ligands for metal oxide surfaces: controlling surface functionality through click chemistry. J Am Chem Soc 128:11356-11357
49. Willmann JK, van Bruggen N, Dinkelborg LM, Gambhir SS (2008) Molecular imaging in drug development. Nat Rev Drug Discov 7:591-607
50. Zapotoczna A, Sasso G, Simpson J, Roach M (2007) Current role and future perspectives of magnetic resonance spectroscopy in radiation oncology for prostate cancer. Neoplasia 9:455-463