Development of a new thiol site-specific prosthetic group and its conjugation with [Cys40]-exendin-4 for in vivo targeting of insulinomas

Bioconjugate Chemistry

Volumn 24, Issue 7, 2013, Pages 1191-1200

  Yue, Xuyi ^a,b   Kiesewetter, Dale O ^a   Guo, Jinxia ^a,b   Sun, Zhongchan ^a   Zhang, Xiaoxiang ^a   Zhu, Lei ^a,b   Niu, Gang ^a   Ma, Ying ^a   Lang, Lixin ^a   Chen, Xiaoyuan ^a  

^a NATIONAL INSTITUTE OF BIOMEDICAL IMAGING AND BIOENGINEERING   (United States)

^b XIAMEN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING ENERGY; POSITRON EMISSION TOMOGRAPHY; SULFUR COMPOUNDS; TUMORS;

FREE AMINES; FREE THIOL GROUP; IN-VIVO; INSULINOMA; LABELINGS; MALEIMIDES; PROSTHETIC GROUPS; SITE-SPECIFIC; SYNTHESISED; VIVO TARGETING;

PEPTIDES;

1 (3 FLUOROPROPYL) 1H PYRROLE 2,5 DIONE; 2 [BIS(TERT BUTOXYCARBONYL)AMINO]ETHOXY(4 METHYLPHENYL) DIOXO SULFANE; 3 [BIS(TERT BUTOXYCARBONYL)AMINO]PROPOXY(4 METHYLPHENYL) DIOXO SULFANE; 5 BIS(TERT BUTOXYCARBONYL)AMINO]PENTOXY(4 METHYLPHENYL) DIOXO SULFANE; AMINE; CYSTEINE DERIVATIVE; EXENDIN 4; GLUCAGON LIKE PEPTIDE 1; MALEIMIDE DERIVATIVE; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CANCER CELL CULTURE; CELL UPTAKE; CELLULAR PARAMETERS; CONTROLLED STUDY; DRUG CONJUGATION; DRUG SYNTHESIS; DRUG TARGETING; IN VIVO STUDY; INSULINOMA; ISOTOPE LABELING; KIDNEY CLEARANCE; LIVER CLEARANCE; MASS SPECTROMETRY; MOUSE; NONHUMAN; RADIOCHEMISTRY;

EID: 84880343467     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc400084u     Document Type: Article

References (49)

1. Reubi, J. C. (2003) Peptide receptors as molecular targets for cancer diagnosis and therapy Endocr. Rev. 24, 389-427
2. Sideris, L., Dube, P., and Rinke, A. (2012) Antitumor effects of somatostatin analogs in neuroendocrine tumors Oncologist 17, 747-55
3. Wilbur, D. S. (1992) Radiohalogenation of proteins: an overview of radionuclides, labeling methods, and reagents for conjugate labeling Bioconjugate Chem. 3, 433-70
4. Couturier, O., Luxen, A., Chatal, J. F., Vuillez, J. P., Rigo, P., and Hustinx, R. (2004) Fluorinated tracers for imaging cancer with positron emission tomography Eur. J. Nucl. Med. Mol. Imaging 31, 1182-206
5. 13N radiolabels for positron emission tomography Angew. Chem. Int. Ed. 47, 8998-9033
6. Chen, K. and Conti, P. S. (2010) Target-specific delivery of peptide-based probes for PET imaging Adv. Drug Delivery Rev. 62, 1005-22
7. 18F-labeling J. Am. Chem. Soc. 127, 13094-5
8. 18F-labeling of peptides by means of an organosilicon-based fluoride acceptor Angew. Chem., Int. Ed. 45, 6047-50
9. 18F-radiolabeling of peptides for PET imaging Angew. Chem., Int. Ed. 47, 4922-5
10. 18F-labeling of peptides via nucleophilic aromatic substitution Bioconjugate Chem. 20, 2254-61
11. Jacobson, O., Zhu, L., Ma, Y., Weiss, I. D., Sun, X., Niu, G., Kiesewetter, D. O., and Chen, X. (2011) Rapid and simple one-step F-18 labeling of peptides Bioconjugate Chem. 22, 422-8
12. 18F]SFB) Appl. Radiat. Isot. 63, 329-32
13. 18F Nat. Protoc. 1, 1655-61
14. Jacobson, O. and Chen, X. (2010) PET designated flouride-18 production and chemistry Curr. Top. Med. Chem. 10, 1048-59
15. 18F]SFB in solution and on solid phase: a comparative study Amino Acids 43, 1431-43
16. 18F]fluorobenzoate and preliminary examination by postmortem whole-hemisphere human brain autoradiography Nucl. Med. Biol. 39, 315-23
17. 18F-T140 J. Nucl. Med. 51, 1796-804
18. Yang, C. Y., Gu, Z. W., Yang, M., Lin, S. N., Garcia-Prats, A. J., Rogers, L. K., Welty, S. E., and Smith, C. V. (1999) Selective modification of apoB-100 in the oxidation of low density lipoproteins by myeloperoxidase in vitro J. Lipid Res. 40, 686-98
19. Fu, X., Mueller, D. M., and Heinecke, J. W. (2002) Generation of intramolecular and intermolecular sulfenamides, sulfinamides, and sulfonamides by hypochlorous acid: a potential pathway for oxidative cross-linking of low-density lipoprotein by myeloperoxidase Biochemistry 41, 1293-301
20. Beilan, H. S., Kenyon, G. L., and Browne, D. T. (1983) Incorporation of specifically labeled cysteine into Escherichia coli protein Anal. Biochem. 128, 169-74
21. Kolmar, H. (2008) Alternative binding proteins: biological activity and therapeutic potential of cystine-knot miniproteins FEBS J. 275, 2684-90
22. 18F J. Labelled Compd. Radiopharm. 26, 287-289
23. 18F-labeling agent Bioconjugate chem 14, 1253-9
24. 18F]fluorobenzylidene)aminooxyhexyl]maleimide Nucl. Med. Biol. 34, 5-15
25. 18F]SFB) Amino Acids 36, 283-95
26. 18F-labeling of peptides and proteins Bioconjugate Chem. 19, 1202-10
27. 18F]fluoropyridine-based maleimide reagent for the labeling of peptides and proteins Bioconjugate Chem. 16, 406-20
28. 18F-fluorobenzamido)ethyl] maleimide, and synthesis of RGD peptide-based tracer for PET imaging of alpha v beta 3 integrin expression J. Nucl. Med. 47, 1172-80
29. Wang, H., Gao, H., Guo, N., Niu, G., Ma, Y., Kiesewetter, D. O., and Chen, X. (2012) Site-specific labeling of scVEGF with fluorine-18 for positron emission tomography imaging Theranostics 2, 607-17
30. 18F]fluorobenzylamine: A versatile building block for the preparation of PET radiotracers Org. Biomol. Chem. 8, 4730-5
31. 18F labelling agents Chem.-Eur. J. 18, 11079-87
32. 18F]AlF method Appl. Radiat. Isot. 70, 200-4
33. Dolle, F. (2005) Fluorine-18-labelled fluoropyridines: advances in radiopharmaceutical design Curr. Pharm. Des. 11, 3221-35
34. 18F-radiolabeled analogs of exendin-4 for PET imaging of GLP-1 in insulinoma Eur. J. Nucl. Med. Mol. Imaging 39, 463-73
35. 18F]AlF-NOTA analog of exendin-4 for imaging of GLP-1 receptor in insulinoma Theranostics 2, 999-1009
36. Keller, O. and Rudinger, J. (1975) Preparation and some properties of maleimido acids and maleoyl derivatives of peptides Helv. Chim. Acta 58, 531-41
37. Mohler, D. L. and Shen, G. (2006) The synthesis of tethered ligand dimers for PPARgamma-RXR protein heterodimers Org. Biomol. Chem. 4, 2082-7
38. Bell, T. W., Choi, H. J., Harte, W., and Drew, M. G. (2003) Syntheses, conformations, and basicities of bicyclic triamines J. Am. Chem. Soc. 125, 12196-210
39. Walczak, R. M., Cowart, J. S., and Reynolds, J. R. (2007) Tethered PProDOTs: conformationally restricted 3,4-propylenedioxythiophene based electroactive polymers J. Mater. Chem. 17, 254-260
40. Kiesewetter, D. O., Sassaman, M. B., Robbins, J., Jagoda, E. M., Carson, R. E., Appel, N. M., Sutkowski, E., Herscovitch, P., Braun, A., and Eckelman, W. C. (2000) Synthesis and evaluation of an F-18 analog of forskolin for imaging adenylyl cyclase J. Fluorine Chem. 101, 297-304
41. Zhang, Y. and Chen, W. (2012) Radiolabeled glucagon-like peptide-1 analogues: a new pancreatic beta-cell imaging agent Nucl. Med. Commun. 33, 223-7
42. 68Ga-labelled exendin-3, a new agent for the detection of insulinomas with PET Eur. J. Nucl. Med. Mol. Imaging 37, 1345-55
43. Wild, D., Wicki, A., Mansi, R., Behe, M., Keil, B., Bernhardt, P., Christofori, G., Ell, P. J., and Macke, H. R. (2010) Exendin-4-based radiopharmaceuticals for glucagonlike peptide-1 receptor PET/CT and SPECT/CT J. Nucl. Med. 51, 1059-67
44. 2]exendin-4, a very promising ligand for glucagon-like peptide-1 (GLP-1) receptor targeting J. Nucl. Med. 47, 2025-33
45. 2]-Exendin-4 is a highly efficient radiotherapeutic for glucagon-like peptide-1 receptor-targeted therapy for insulinoma Clin. Cancer Res. 13, 3696-705
46. Brom, M., Joosten, L., Oyen, W. J., Gotthardt, M., and Boerman, O. C. (2012) Radiolabelled GLP-1 analogues for in vivo targeting of insulinomas Contrast Media Mol. Imaging 7, 160-6
47. Baggio, L. L. and Drucker, D. J. (2007) Biology of incretins: GLP-1 and GIP Gastroenterology 132, 2131-57
48. Sahu, S., Tosh, D., and Hardikar, A. A. (2009) New sources of beta-cells for treating diabetes J. Endocrinol. 202, 13-6
49. Robertson, R. P. (2004) Islet transplantation as a treatment for diabetes-a work in progress N. Engl. J. Med. 350, 694-705