99mTcO(MAG2-3G3-dimer): A new integrin αvβ3-targeted SPECT radiotracer with high tumor uptake and favorable pharmacokinetics

European Journal of Nuclear Medicine and Molecular Imaging

Volumn 36, Issue 11, 2009, Pages 1874-1884

  Shi, Jiyun ^a,b   Wang, Lijun ^a   Kim, Young Seung ^a   Zhai, Shizhen ^a   Jia, Bing ^b   Wang, Fan ^b   Liu, Shuang ^a  

^a PURDUE UNIVERSITY   (United States)

^b PEKING UNIVERSITY   (China)

Author keywords

99mTc labeled cyclic RGD peptides; Integrin v 3; Tumor imaging

Indexed keywords

RADIOPHARMACEUTICAL AGENT; S BENZOYLMERCAPTOACETYLGLYCYLGLYCYLGLYCYLGLYCYLGLYCYLGLUTAMYL[GLYCYLGLYCYLGLYCYL CYCLO(ARGINYLGLYCYLASPARTYLPHENYLALANYLLYSYL)] O TC 99M; UNCLASSIFIED DRUG; VITRONECTIN RECEPTOR; 99MTCO(MAG2 3G3 DIMER); 99MTCO(MAG2-3G3-DIMER); ARGINYL-GLYCYL-ASPARTIC ACID; ARGINYLGLYCYLASPARTIC ACID; CHELATING AGENT; DIAGNOSTIC AGENT; OLIGOPEPTIDE; TECHNETIUM COMPLEX; TRACER;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DRUG CLEARANCE; DRUG DISTRIBUTION; DRUG METABOLISM; DRUG SYNTHESIS; FEMALE; GLIOMA CELL; HUMAN; HUMAN CELL; MOUSE; NONHUMAN; PROTEIN EXPRESSION; RADIOACTIVITY; RADIOCHEMISTRY; SINGLE PHOTON EMISSION COMPUTER TOMOGRAPHY; TUMOR VOLUME; ANIMAL; CHEMISTRY; DRUG EFFECT; ENZYME SPECIFICITY; METABOLISM; NEOPLASM; PATHOLOGY; SCINTISCANNING; TISSUE DISTRIBUTION; TUMOR CELL LINE;

ANIMALS; CELL LINE, TUMOR; CHELATING AGENTS; FEMALE; HUMANS; INTEGRIN ALPHAVBETA3; MICE; NEOPLASMS; OLIGOPEPTIDES; ORGANOTECHNETIUM COMPOUNDS; RADIOACTIVE TRACERS; RADIOCHEMISTRY; SUBSTRATE SPECIFICITY; TISSUE DISTRIBUTION; TOMOGRAPHY, EMISSION-COMPUTED, SINGLE-PHOTON; TUMOR BURDEN;

EID: 72149084635     PISSN: 16197070     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00259-009-1166-1     Document Type: Article

References (57)

1. WA Weber R Haubner E Vabuliene B Kuhnast HJ Wester M Schwaiger 2001 Tumor angiogenesis targeting using imaging agents Q J Nucl Med 45 179 182 1:STN:280:DC%2BD3MvivVGgsg%3D%3D 11476168
2. NG Costouros FE Diehn SK Libutti 2002 Molecular imaging of tumor angiogenesis J Cell Biochem Suppl 39 72 78 10.1002/jcb.10426 12552605
3. S Liu DS Edwards 2002 Fundamentals of receptor-based diagnostic metalloradiopharmaceuticals Top Curr Chem 222 259 278 10.1007/3-540-46009-8-8 1:CAS:528:DC%2BD38XotVSit7k%3D
4. C Van de Wiele R Oltenfreiter O De Winter A Signore G Slegers RA Dierckx 2002 Tumor angiogenesis pathways: related clinical issues and implications for nuclear medicine imaging Eur J Nucl Med 29 699 709 10.1007/s00259-002-0783-8 (Pubitemid 34439332)
5. S Liu SP Robinson DS Edwards 2003 Integrin αvβ3 directed radiopharmaceuticals for tumor imaging Drugs Future 28 551 564 10.1358/dof.2003.028.06.740860 1:CAS:528:DC%2BD3sXot1Cgtr8%3D (Pubitemid 37168833)
6. DM McDonald PL Choyke 2003 Imaging of angiogenesis: from microscope to clinic Nature Med 9 713 725 10.1038/nm0603-713 1:CAS:528:DC%2BD3sXktFOnurs%3D 12778170 (Pubitemid 36749220)
7. R Haubner HJ Wester 2004 Radiolabeled tracers for imaging of tumor angiogenesis and evaluation of anti-angiogenic therapies Curr Pharm Des 10 1439 1455 10.2174/1381612043384745 1:CAS:528:DC%2BD2cXjsVykurg%3D 15134568 (Pubitemid 38559759)
8. S Liu 2006 Radiolabeled multimeric cyclic RGD peptides as integrin alphavbeta3 targeted radiotracers for tumor imaging Mol Pharm 3 472 487 10.1021/mp060049x 1:CAS:528:DC%2BD28XntVKgtr8%3D 17009846 (Pubitemid 44639125)
9. X Chen 2006 Multimodality imaging of tumor integrin alphavbeta3 expression Mini Rev Med Chem 6 227 234 10.2174/138955706775475975 1:CAS:528:DC%2BD28XitVagtbk%3D 16472190
10. W Cai X Chen 2008 Multimodality molecular imaging of tumor angiogenesis J Nucl Med 49 113S 128S 10.2967/jnumed.107.045922 1:CAS:528:DC%2BD1cXotFahu74%3D 18523069 (Pubitemid 351948040)
11. W Cai G Niu X Chen 2008 Imaging of integrins as biomarkers for tumor angiogenesis Curr Pharm Des 14 2943 2973 10.2174/138161208786404308 1:CAS:528:DC%2BD1MXmt1ehsQ%3D%3D 18991712
12. AR Hsu X Chen 2008 Advances in anatomic, functional, and molecular imaging of angiogenesis J Nucl Med 49 511 514 10.2967/jnumed.107.050179 18375921
13. PM van Hagen WAP Breeman HF Bernard M Schaar CM Mooij A Srinivasan 2000 Evaluation of a radiolabeled cyclic DTPA-RGD analogue for tumour imaging and radionuclide therapy Int J Cancer 90 186 198 10.1002/1097-0215(20000820)90: 4<186::AID-IJC2>3.0.CO;2-P 10993959 (Pubitemid 30679434)
14. GB Sivolapenko D Skarlos D Pectasides E Stathopoulou A Milonakis G Sirmalis, et al. 1998 Imaging of metastatic melanoma utilising a technetium-99m labelled RGD-containing synthetic peptide Eur J Nucl Med 25 1383 1389 10.1007/s002590050312 1:CAS:528:DyaK1cXmtFegt78%3D 9818277 (Pubitemid 28464112)
15. R Haubner HJ Wester R Senekowitsch-Schmidtke B Diefenbach H Kessler G Stöcklin, et al. 1997 RGD-peptides for tumor targeting: biological evaluation of radioiodinated analogs and introduction of a novel glycosylated peptide with improved biokinetics J Labelled Comp Radiopharm 40 383 385
16. R Haubner HJ Wester U Reuning R Senekowisch-Schmidtke B Diefenbach H Kessler, et al. 1999 Radiolabeled alpha(v)beta3 integrin antagonists: a new class of tracers for tumor imaging J Nucl Med 40 1061 1071 1:CAS:528: DyaK1MXktVaqsLg%3D 10452325
17. R Haubner HJ Wester WA Weber C Mang SI Ziegler SL Goodman, et al. 2001 Noninvasive imaging of alpha(v)beta3 integrin expression using 18F-labeled RGD-containing glycopeptide and positron emission tomography Cancer Res 61 1781 1785 1:CAS:528:DC%2BD3MXit1Ohtbk%3D 11280722
18. R Haubner HJ Wester F Burkhart R Senekowisch-Schmidtke W Weber SL Goodman, et al. 2001 Glycolated RGD-containing peptides: tracer for tumor targeting and angiogenesis imaging with improved biokinetics J Nucl Med 42 326 336 1:CAS:528:DC%2BD3MXhtlKmt7w%3D 11216533
19. R Haubner F Bruchertseifer M Bock M Schwaiger HJ Wester 2004 Synthesis and biological evaluation of (99m)Tc-labeled cyclic RGD peptide for imaging the alphavbeta3 expression Nuklearmedizin 43 26 32 1:CAS:528:DC%2BD2cXjslyrt7s%3D 14978538
20. G Thumshirn U Hersel SL Goodman H Kessler 2003 Multimeric cyclic RGD peptides as potential tools for tumor targeting: solid-phase peptide synthesis and chemoselective oxime ligation Chemistry 9 2717 2725 10.1002/chem.200204304 1:CAS:528:DC%2BD3sXltVSiurw%3D 12772286
21. T Poethko M Schottelius G Thumshirn M Herz R Haubner G Henriksen, et al. 2004 Chemoselective pre-conjugate radiohalogenation of unprotected mono-and multimeric peptides via oxime formation Radiochim Acta 92 317 327 10.1524/ract.92.4.317.35591 1:CAS:528:DC%2BD2cXmvVKlsbc%3D
22. T Poethko M Schottelius G Thumshirn U Hersel M Herz G Henriksen, et al. 2004 Two-step methodology for high yield routine radiohalogenation of peptides: 18F-labeled RGD and octreotide analogs J Nucl Med 45 892 902 1:CAS:528:DC%2BD2cXnsFygtLc%3D 15136641
23. S Alves JDG Correia L Gano TL Rold A Prasanphanich R Haubner, et al. 2007 In vitro and in vivo evaluation of a novel 99mTc(CO)3-pyrazolyl conjugate of cyclo-(Arg-Gly-Asp-d-Tyr-Lys) Bioconjug Chem 18 530 537 10.1021/bc060234t 1:CAS:528:DC%2BD2sXkvV2itg%3D%3D 17373771 (Pubitemid 46493526)
24. M Fani D Psimadas C Zikos S Xanthopoulos GK Loudos P Bouziotis, et al. 2006 Comparative evaluation of linear and cyclic 99mTc-RGD peptides for targeting of integrins in tumor angiogenesis Anticancer Res 26 431 434 1:CAS:528:DC%2BD28Xhs1ahtbk%3D 16475729
25. C Decristoforo B Faintuch-Linkowski A Rey E von Guggenberg M Rupprich I Hernandez-Gonzales, et al. 2006 [99mTc]HYNIC-RGD for imaging integrin alphavbeta3 expression Nucl Med Biol 33 945 952 10.1016/j.nucmedbio.2006.09.001 1:CAS:528:DC%2BD28Xht1Cls7%2FJ 17127166 (Pubitemid 44802994)
26. X Chen R Park M Tohme AH Shahinian JR Bading PS Conti 2004 MicroPET and autoradiographic imaging of breast cancer alpha v-integrin expression using 18F-and 64Cu-labeled RGD peptide Bioconjug Chem 15 41 49 10.1021/bc0300403 14733582 (Pubitemid 38165979)
27. X Chen R Park AH Shahinian M Tohme V Khankaldyyan MH Bozorgzadeh, et al. 2004 18F-labeled RGD peptide: initial evaluation for imaging brain tumor angiogenesis Nucl Med Biol 31 179 189 10.1016/j.nucmedbio.2003.10.002 1:CAS:528:DC%2BD2cXhvVyht7g%3D 15013483 (Pubitemid 38315112)
28. X Chen S Liu Y Hou M Tohme R Park JR Bading, et al. 2004 MicroPET imaging of breast cancer alphav-integrin expression with 64Cu-labeled dimeric RGD peptides Mol Imaging Biol 6 350 359 10.1016/j.mibio.2004.06.004 15380745 (Pubitemid 39243068)
29. X Chen M Tohme R Park Y Hou JR Bading PS Conti 2004 Micro-PET imaging of alphavbeta3-integrin expression with 18F-labeled dimeric RGD peptide Mol Imaging 3 96 104 10.1162/1535350041464892 1:CAS:528:DC%2BD2cXlvFCiu7s%3D 15296674
30. Y Wu X Zhang Z Xiong Z Cheng DR Fisher S Liu, et al. 2005 MicroPET imaging of glioma integrin {alpha}v{beta}3 expression using (64)Cu-labeled tetrameric RGD peptide J Nucl Med 46 1707 1718 1:CAS:528:DC%2BD28XitVGlt7o%3D 16204722
31. X Zhang Z Xiong Y Wu W Cai JR Tseng SS Gambhir, et al. 2006 Quantitative PET imaging of tumor integrin alphavbeta3 expression with 18F-FRGD2 J Nucl Med 47 113 121 1:CAS:528:DC%2BD28XhsFeisL4%3D 16391195
32. Z Wu Z Li K Chen W Cai L He FT Chin, et al. 2007 Micro-PET of tumor integrin alphavbeta3 expression using 18F-labeled PEGylated tetrameric RGD peptide (18F-FPRGD4) J Nucl Med 48 1536 1544 10.2967/jnumed.107.040816 1:CAS:528:DC%2BD2sXhtFGgsLnI 17704249 (Pubitemid 47397404)
33. X Zhang X Chen 2007 Preparation and characterization of 99mTc(CO)3-BPy-RGD complex as alphav beta3 integrin receptor-targeted imaging agent Appl Radiat Isot 65 70 78 10.1016/j.apradiso.2006.07.013 1:CAS:528:DC%2BD28XhtF2ht7fI 17011200 (Pubitemid 46053811)
34. S Liu E Cheung M Rajopadyhe MC Ziegler DS Edwards 2001 (90)Y-and (177)Lu-labeling of a DOTA-conjugated vitronectin receptor antagonist useful for tumor therapy Bioconjug Chem 12 559 568 10.1021/bc000146n 1:CAS:528: DC%2BD3MXkt1Wktr8%3D 11459461 (Pubitemid 32696230)
35. M Janssen WJG Oyen LFAG Massuger C Frielink I Dijkgraaf DS Edwards, et al. 2002 Comparison of a monomeric and dimeric radiolabeled RGD-peptide for tumor targeting Cancer Biother Radiopharm 17 641 646 10.1089/108497802320970244 1:CAS:528:DC%2BD3sXovVWmug%3D%3D 12537667
36. M Janssen WJG Oyen I Dijkgraaf LFAG Massuger C Frielink DS Edwards, et al. 2002 Tumor targeting with radiolabeled integrin alpha(v)beta(3) binding peptides in a nude mice model Cancer Res 62 6146 6151 1:CAS:528: DC%2BD38XosF2ms7w%3D 12414640
37. S Liu WY Hsieh YS Kim SI Mohammed 2005 Effect of coligands on biodistribution characteristics of ternary ligand 99mTc complexes of a HYNIC-conjugated cyclic RGDfK dimer Bioconjug Chem 16 1580 1588 10.1021/bc0501653 1:CAS:528:DC%2BD2MXhtFertLrF 16287258 (Pubitemid 41681526)
38. B Jia J Shi Z Yang B Xu Z Liu H Zhao, et al. 2006 99mTc-labeled cyclic RGDfK dimer: initial evaluation for SPECT imaging of glioma integrin alphavbeta3 expression Bioconjug Chem 17 1069 1076 10.1021/bc060055b 1:CAS:528: DC%2BD28Xmt1Khsrg%3D 16848417 (Pubitemid 44162628)
39. S Liu ZJ He WY Hsieh YS Kim Y Jiang 2006 Impact of PKM linkers on biodistribution characteristics of the 99mTc-labeled cyclic RGDfK dimer Bioconjug Chem 17 1499 1507 10.1021/bc060235l 1:CAS:528:DC%2BD28XhtFCqt77I 17105229 (Pubitemid 44851495)
40. S Liu WY Hsieh Y Jiang YS Kim SG Sreerama X Chen, et al. 2007 Evaluation of a (99m)Tc-labeled cyclic RGD tetramer for noninvasive imaging integrin alpha(v)beta3-positive breast cancer Bioconjug Chem 18 438 446 10.1021/bc0603081 17341108 (Pubitemid 46493515)
41. I Dijkgraaf JAW Kruijtzer S Liu A Soede WJG Oyen FHM Corstens, et al. 2007 Improved targeting of the alpha(v)beta (3) integrin by multimerisation of RGD peptides Eur J Nucl Med Mol Imaging 34 267 273 10.1007/s00259-006-0180-9 1:CAS:528:DC%2BD2sXnvVSgsA%3D%3D 16909226 (Pubitemid 46147510)
42. I Dijkgraaf S Liu JAW Kruijtzer AC Soede WJG Oyen RMJ Liskamp, et al. 2007 Effect of linker variation on the in vitro and in vivo characteristics of an 111In-labeled RGD peptide Nucl Med Biol 34 29 35 10.1016/j.nucmedbio.2006.10. 006 1:CAS:528:DC%2BD2sXisVajsw%3D%3D 17210459 (Pubitemid 46038156)
43. JJ Wang YS Kim ZJ He S Liu 2008 99mTc-labeling of HYNIC-conjugated cyclic RGDfK dimer and tetramer using EDDA as coligand Bioconjug Chem 19 634 642 10.1021/bc7004208 18281926
44. B Jia Z Liu J Shi ZL Yu Z Yang HY Zhao, et al. 2008 Linker effects on biological properties of 111In-labeled DTPA conjugates of a cyclic RGDfK dimer Bioconjug Chem 19 201 210 10.1021/bc7002988 1:CAS:528:DC%2BD2sXhsVWqsLnM 18069778 (Pubitemid 351213852)
45. S Liu YS Kim WY Hsieh SG Sreerama 2008 Coligand effects on solution stability, biodistribution and metabolism of 99mTc-labeled cyclic RGDfK tetramer Nucl Med Biol 35 111 121 10.1016/j.nucmedbio.2007.08.006 1:CAS:528: DC%2BD2sXhsVOlt7zM 18158950 (Pubitemid 350298246)
46. MS Morrison SA Ricketts J Barnett A Cuthbertson J Tessier SR Wedge 2009 Use of a novel Arg-Gly-Asp radioligand, 18F-AH111585, to determine changes in tumor vascularity after antitumor therapy J Nucl Med 50 116 122 10.2967/jnumed.108.056077 1:CAS:528:DC%2BD1MXhvFCjt7s%3D 19091899
47. LM Kenny RC Coombes I Oulie KB Contractor M Miller TJ Spinks, et al. 2008 Phase I trial of the positron-emitting Arg-Gly-Asp (RGD) peptide radioligand 18F-AH111585 in breast cancer patients J Nucl Med 49 879 886 10.2967/jnumed.107.049452 18483090 (Pubitemid 351793427)
48. AJ Beer R Haubner M Goebel S Luderschmidt ME Spilker HJ Webster, et al. 2005 Biodistribution and pharmacokineticss of the alphavbeta3-selective tracer 18F-galacto-RGD in cancer patients J Nucl Med 46 1333 1341 1:CAS:528: DC%2BD28XitVGlsb8%3D 16085591
49. R Haubner WA Weber AJ Beer E Vabulience D Reim M Sarbia, et al. 2005 Noninvasive visualization of the activated alphavbeta3 integrin in cancer patients by positron emission tomography and [18F]galacto-RGD PLoS Med 2 3 e70 10.1371/journal.pmed.0020070 15783258 (Pubitemid 40629471)
50. AJ Beer AL Grosu J Carlsen A Kolk M Sarbia I Stangier, et al. 2007 [18F]galacto-RGD positron emission tomography for imaging of alphavbeta3 expression on the neovasculature in patients with squamous cell carcinoma of the head and neck Clin Cancer Res 13 6610 6616 10.1158/1078-0432.CCR-07-0528 1:CAS:528:DC%2BD2sXhtlSmu7nO 18006761 (Pubitemid 350206795)
51. J Shi L Wang YS Kim S Zhai Z Liu X Chen, et al. 2008 Improving tumor uptake and excretion kinetics of 99mTc-labeled cyclic arginine-glycine-aspartic (RGD) dimers with triglycine linkers J Med Chem 51 7980 7990 10.1021/jm801134k 1:CAS:528:DC%2BD1cXhsVKlu73K 19049428
52. Shi J, Wang L, Kim YS, Zhai S, Liu Z, Chen X, Liu S. Improving tumor uptake and pharmacokinetics of 64Cu-labeled cyclic RGD dimers with triglycine and PEG4 Linkers. Bioconjug Chem Accepted.
53. Shi J, Kim YS, Chakraborty S, Zhou Y, Wang F, Liu, S. Improving tumor uptake and excretion kinetics of 111In-labeled cyclic RGD peptide dimers with PEG4 and G3 Linkers. Bioconjug Chem Submitted.
54. L Wang YS Kim J Shi S Zhai B Jia Z Liu, et al. 2009 Improving tumor-targeting capability and pharmacokinetics of (99m)Tc-labeled cyclic RGD dimers with PEG(4) linkers Mol Pharm 6 231 245 10.1021/mp800150r 1:CAS:528:DC%2BD1cXhsVOmt77I 19067525
55. S Liu DS Edwards RJ Looby AR Harris MJ Poirier M Rajopadhye, et al. 1996 Labeling cyclic glycoprotein IIb/IIIa receptor antagonists with 99mTc by the preformed chelate approach: effects of chelators on properties of [99mTc]chelator-peptide conjugates Bioconjug Chem 7 196 202 10.1021/bc9500958 1:CAS:528:DyaK28XhsVGhsbs%3D 8983341 (Pubitemid 3043437)
56. W Cai J Rao SS Gambhir X Chen 2006 How molecular imaging is speeding up antiangiogenic drug development Mol Cancer Ther 5 2624 2633 10.1158/1535-7163. MCT-06-0395 1:CAS:528:DC%2BD28Xht1els7jE 17121909 (Pubitemid 44848989)
57. G Niu X Chen 2008 Has molecular and cellular imaging enhanced drug discovery and drug development? Drugs R D 9 351 368 10.2165/0126839-200809060- 00002 1:CAS:528:DC%2BD1MXmsVaktw%3D%3D 18989988