Synthesis and investigation of a radioiodinated F3 peptide analog as a SPECT tumor imaging radioligand

PLoS ONE

Volumn 6, Issue 7, 2011, Pages

  Bhojani, Mahaveer S ^a   Ranga, Rajesh ^a   Luker, Gary D ^a,b   Rehemtulla, Alnawaz ^a,b   Ross, Brian D ^a,b   van Dort, Marcian E ^a,b  

^a UNIVERSITY OF MICHIGAN   (United States)

^b UNIVERSITY OF MICHIGAN MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALEXAFLUOR 532; ALEXAFLUOR 647; FLUORESCENT DYE; N [2 (3 IODOBENZOYL)AMINOETHYL]MALEIMIDE F3 CYSTEINE PEPTIDE I 125; RADIOLIGAND; UNCLASSIFIED DRUG; DIAGNOSTIC AGENT; IBMF3 PEPTIDE; IODOBENZENE; LIGAND; PEPTIDE; RADIOACTIVE IODINE; RADIOPHARMACEUTICAL AGENT;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CANCER CELL CULTURE; CARBOXY TERMINAL SEQUENCE; CHEMICAL MODIFICATION; CONTROLLED STUDY; DRUG DISTRIBUTION; DRUG SYNTHESIS; DRUG UPTAKE; EX VIVO STUDY; FEMALE; FLUORESCENCE ANALYSIS; HISTOPATHOLOGY; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; LUNG CANCER; MELANOMA; MOUSE; NONHUMAN; NUDE MOUSE; POSITRON EMISSION TOMOGRAPHY; RADIOIODODESTANNYLATION; SINGLE PHOTON EMISSION COMPUTER TOMOGRAPHY; TUMOR XENOGRAFT; AMINO ACID SEQUENCE; ANIMAL; CHEMISTRY; METABOLISM; MOLECULAR GENETICS; NEOPLASM; SCINTISCANNING; SYNTHESIS; TISSUE DISTRIBUTION; TUMOR CELL LINE;

MUS MUSCULUS;

AMINO ACID SEQUENCE; ANIMALS; CELL LINE, TUMOR; FLUORESCENT DYES; HUMANS; IODINE RADIOISOTOPES; IODOBENZENES; LIGANDS; MICE; MOLECULAR SEQUENCE DATA; NEOPLASMS; PEPTIDES; RADIOPHARMACEUTICALS; TISSUE DISTRIBUTION; TOMOGRAPHY, EMISSION-COMPUTED, SINGLE-PHOTON;

EID: 79960473224     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0022418     Document Type: Article

References (31)

1. Hicks RJ, Wahl RL, (2010) PET diagnosis and response monitoring in oncology. In: Weissleder R, Ross BD, Rehemtulla A, Gambhir SS, editors. Molecular Imaging-Principles and Practice Shelton, CT People's Medical Publishing House pp. 875-895.
2. Kelloff GJ, Hoffman JM, Johnson B, Scher HI, Siegel BA, et al. (2005) Progress and promise of FDG-PET imaging for cancer patient management and oncologic drug development. Clin Cancer Res 11: 2785-2808.
3. Porkka K, Laakkonen P, Hoffman JA, Bernasconi M, Ruoslahti E, (2002) A fragment of the HMGN2 protein homes to the nuclei of tumor cells and tumor endothelial cells in vivo. Proc Natl Acad Sci U S A 99: 7444-7449.
4. Christian S, Pilch J, Akerman ME, Porkka K, Laakkonen P, et al. (2003) Nucleolin expressed at the cell surface is a marker of endothelial cells in angiogenic blood vessels. J Cell Biol 163: 871-878.
5. Ginisty H, Sicard H, Roger B, Bouvet P, (1999) Structure and functions of nucleolin. J Cell Sci 112 (Pt 6): 761-772.
6. Srivastava M, Pollard HB, (1999) Molecular dissection of nucleolin's role in growth and cell proliferation: new insights. Faseb J 13: 1911-1922.
7. Borer RA, Lehner CF, Eppenberger HM, Nigg EA, (1989) Major nucleolar proteins shuttle between nucleus and cytoplasm. Cell 56: 379-390.
8. Yu D, Schwartz MZ, Petryshyn R, (1998) Effect of laminin on the nuclear localization of nucleolin in rat intestinal epithelial IEC-6 cells. Biochem Biophys Res Commun 247: 186-192.
9. Shibata Y, Muramatsu T, Hirai M, Inui T, Kimura T, et al. (2002) Nuclear targeting by the growth factor midkine. Mol Cell Biol 22: 6788-6796.
10. Said EA, Krust B, Nisole S, Svab J, Briand JP, et al. (2002) The anti-HIV cytokine midkine binds the cell surface-expressed nucleolin as a low affinity receptor. J Biol Chem 277: 37492-37502.
11. Destouches D, El Khoury D, Hamma-Kourbali Y, Krust B, Albanese P, et al. (2008) Suppression of tumor growth and angiogenesis by a specific antagonist of the cell-surface expressed nucleolin. PLoS One 3: e2518.
12. Bhojani MS, Van Dort M, Rehemtulla A, Ross BD, (2010) Targeted Imaging and Therapy of Brain Cancer Using Theranostic Nanoparticles. Mol Pharm.
13. Reddy GR, Bhojani MS, McConville P, Moody J, Moffat BA, et al. (2006) Vascular targeted nanoparticles for imaging and treatment of brain tumors. Clin Cancer Res 12: 6677-6686.
14. Wilbur DS, (1992) Radiohalogenation of proteins: an overview of radionuclides, labeling methods, and reagents for conjugate labeling. Bioconjug Chem 3: 433-470.
15. Brinkley M, (1992) A brief survey of methods for preparing protein conjugates with dyes, haptens, and cross-linking reagents. Bioconjug Chem 3: 2-13.
16. Boeckler C, Frisch B, Schuber F, (1998) Design and synthesis of thiol-reactive lipopeptides. Bioorganic & Medicinal Chemistry Letters 8: 2055-2058.
17. Al-Jammaz I, Al-Otaibi B, Amartey JK, (2002) A novel route to radioiodinated [123I]-N-succinimidyl-3-iodobenzoate, a reagent for radioiodination of bioactive peptides. Appl Radiat Isot 57: 743-747.
18. Garg PK, Slade SK, Harrison CL, Zalutsky MR, (1989) Labeling proteins using aryl iodide acylation agents: influence of meta vs para substitution on in vivo stability. Int J Rad Appl Instrum B 16: 669-673.
19. Park JH, von Maltzahn G, Zhang L, Derfus AM, Simberg D, et al. (2009) Systematic surface engineering of magnetic nanoworms for in vivo tumor targeting. Small 5: 694-700.
20. Derfus AM, Chen AA, Min DH, Ruoslahti E, Bhatia SN, (2007) Targeted quantum dot conjugates for siRNA delivery. Bioconjug Chem 18: 1391-1396.
21. Hah HJ, Kim G, Lee YE, Orringer DA, Sagher O, et al. (2010) Methylene Blue-Conjugated Hydrogel Nanoparticles and Tumor-Cell Targeted Photodynamic Therapy. Macromol Biosci.
22. Orringer DA, Koo YE, Chen T, Kim G, Hah HJ, et al. (2009) In vitro characterization of a targeted, dye-loaded nanodevice for intraoperative tumor delineation. Neurosurgery 64: 965-971; discussion 971-962.
23. Winer I, Wang S, Lee YE, Fan W, Gong Y, et al. (2010) F3-Targeted Cisplatin-Hydrogel Nanoparticles as an Effective Therapeutic That Targets Both Murine and Human Ovarian Tumor Endothelial Cells In vivo. Cancer Res 70: 8674-8683.
24. Makela AR, Matilainen H, White DJ, Ruoslahti E, Oker-Blom C, (2006) Enhanced baculovirus-mediated transduction of human cancer cells by tumor-homing peptides. J Virol 80: 6603-6611.
25. Drecoll E, Gaertner FC, Miederer M, Blechert B, Vallon M, et al. (2009) Treatment of peritoneal carcinomatosis by targeted delivery of the radio-labeled tumor homing peptide bi-DTPA-[F3]2 into the nucleus of tumor cells. PLoS One 4: e5715.
26. Haubner R, (2006) Alphavbeta3-integrin imaging: a new approach to characterise angiogenesis? Eur J Nucl Med Mol Imaging 33 (Suppl 1): 54-63.
27. van Schaijk FG, Broekema M, Oosterwijk E, van Eerd JE, McBride BJ, et al. (2005) Residualizing iodine markedly improved tumor targeting using bispecific antibody-based pretargeting. J Nucl Med 46: 1016-1022.
28. Haubner R, Wester HJ, Burkhart F, Senekowitsch-Schmidtke R, Weber W, et al. (2001) Glycosylated RGD-containing peptides: tracer for tumor targeting and angiogenesis imaging with improved biokinetics. J Nucl Med 42: 326-336.
29. Koziorowski J, Henssen C, Weinreich R, (1998) A new convenient route to radioiodinated N-succinimidyl 3- and 4-iodobenzoate, two reagents for radioiodination of proteins. Applied Radiation and Isotopes 49: 955-959.
30. Dekker B, Keen H, Lyons S, Disley L, Hastings D, et al. (2005) MBP-annexin V radiolabeled directly with iodine-124 can be used to image apoptosis in vivo using PET. Nucl Med Biol 32: 241-252.
31. Miao Z, Luker KE, Summers BC, Berahovich R, Bhojani MS, et al. (2007) CXCR7 (RDC1) promotes breast and lung tumor growth in vivo and is expressed on tumor-associated vasculature. Proc Natl Acad Sci U S A 104: 15735-15740.