Synthesis and evaluation of a peptide targeted small molecular Gd-DOTA monoamide conjugate for MR molecular imaging of prostate cancer

Bioconjugate Chemistry

Volumn 23, Issue 8, 2012, Pages 1548-1556

  Wu, Xueming ^a   Burden Gulley, Susan M ^b   Yu, Guan Ping ^a   Tan, Mingqian ^a   Lindner, Daniel ^c   Brady Kalnay, Susann M ^b   Lu, Zheng Rong ^a  

^a Case Western Reserve University   (United States)

^b CASE WESTERN RESERVE UNIVERSITY SCHOOL OF MEDICINE   (United States)

^c LERNER RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; BIOMARKERS; BIOSYNTHESIS; CHELATION; DISEASES; FLUORESCENCE IMAGING; GADOLINIUM COMPOUNDS; MAMMALS; MOLECULAR IMAGING; TUMORS; UROLOGY;

DESIGN AND DEVELOPMENT; EXTRACELLULAR MATRICES; GD-DOTA; HIGH SPATIAL RESOLUTION; INNOVATIVE DESIGN; ORTHOTOPIC; PROSTATE CANCERS; PROSTATE TUMOR; SYNTHESISED; TARGETED CONTRAST AGENTS;

PEPTIDES;

CTL1 DL PEPTIDE TETRAXETAN GADOLINIUM; DENDRIMER; NUCLEAR MAGNETIC RESONANCE IMAGING AGENT; PEPTIDE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CONTRAST ENHANCEMENT; DRUG DISTRIBUTION; DRUG MUSCLE LEVEL; DRUG SYNTHESIS; DRUG TISSUE LEVEL; FEMUR; FLUORESCENCE; HEART; HISTOLOGY; KIDNEY; LIVER; LUNG; MALE; MOLECULAR IMAGING; MOUSE; MUSCLE; NONHUMAN; PROSTATE CANCER; SPLEEN; TUMOR XENOGRAFT;

EID: 84865124429     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc300009t     Document Type: Article

References (51)

1. Vlastos, G. and Verkooijen, H. M. (2007) Minimally invasive approaches for diagnosis and treatment of early-stage breast cancer Oncologist 12, 1-10 (Pubitemid 46143498)
2. Gelovani, J. G. (2008) Molecular imaging of epidermal growth factor receptor expression-activity at the kinase level in tumors with positron emission tomography Cancer Metastasis Rev. 27, 645-53
3. Piwnica-Worms, D, Kesarwala, A. H., Pichler, A., Prior, J. L., and Sharma, V. (2006) Single photon emission computed tomography and positron emission tomography imaging of multi-drug resistant P-glycoprotein - monitoring a transport activity important in cancer, blood-brain barrier function and Alzheimers disease Neuroimaging Clin. N. Am. 16, 575-89 (Pubitemid 44828756)
4. Hayashi, M., Murakami, K., Oyama, T., Domeki, Y., Hagiwara, S., Katsumata, D., and Sunagawa, M. (2008) PET/CT supports breast cancer diagnosis and treatment Breast Cancer. 15, 224-230
5. Saga, T., Koizumi, M., Furukawa, T., Yoshikawa, K., and Fujibayashi, Y. (2009) Molecular imaging of cancer: evaluating characters of individual cancer by PET/SPECT imaging Cancer Sci. 100, 375-81
6. Oude Munnink, T. H., Nagengast, W. B., Brouwers, A. H., Schroder, C. P., Hospers, G. A., Lub-de Hooge, M. N., van der Wall, E., van Diest, P. J., and de Vries, E. G. (2009) Molecular imaging of breast cancer Breast 18 (SUPPL. 3) S66-73
7. Pan, T. and Mawlawi, O. (2008) PET/CT in radiation oncology Med. Phys. 35, 4955-4966
8. Lucignani, G. (2008) PET-MRI synergy in molecular, functional and anatomical cancer imaging Eur. J. Nucl. Med. Mol. Imaging 35, 1550-1553
9. Maurer, A. H. (2008) Combined imaging modalities: PET/CT and SPECT/CT Health Phys. 95, 571-576
10. Lijowski, M., Caruthers, S., Hu, G., Zhang, H., Scott, M. J., Williams, T., Erpelding, T., Schmieder, A. H., Kiefer, G., Gulyas, G., Athey, P. S., Gaffney, P. J., Wickline, S. A., and Lanza, G. M. (2009) High sensitivity: high-resolution SPECT-CT/MR molecular imaging of angiogenesis in the Vx2 model Invest. Radiol. 44, 15-22
11. Haacke, E. M., Brown, R. W., Thompson, M. R., and Venkatesan, R. (1999) Magnetic Resonance Imaging Physical Principles and Sequence Design, John Wiley & Sons, Inc., New York.
12. Brown, M. A. and Semelka, R. C. (2003) MRI Basic Principles and Applications, 3 rd ed., John Wiley & Sons, Inc., Hoboken, NJ.
13. Artemov, D. (2003) Molecular magnetic resonance imaging with targeted contrast agents J. Cell. Biochem. 90, 518-524 (Pubitemid 37243699)
14. Kalber, T. L., Kamaly, N., So, P. W., Pugh, J. A., Bunch, J., McLeod, C. W., Jorgensen, M. R., Miller, A. D., and Bell, J. D. (2011) A low molecular weight folate receptor targeted contrast agent for magnetic resonance tumor imaging Mol. Imaging Biol. 13, 653-562
15. Unger, E. C., Totty, W. G., Neufeld, D. M., Otsuka, F. L., Muephy, W. A., Welch, M. S., Connett, J. M., and Philpott, G. W. (1985) Magnetic resonance imaging using gadolinium labeled monoclonal antibody Invest. Radiol. 20, 693-700 (Pubitemid 16242109)
16. Schmieder, A. H., Winter, P. M., Caruthers, S. D., Harris, T. D., Williams, T. A., Allen, J. S., Lacy, E. K., Zhang, H., Scott, M. J., Hu, G., Robertson, J. D., Wickline, S. A., and Lanza, G. M. (2005) Molecular MR imaging of melanoma angiogenesis with alphanubeta3-targeted paramagnetic nanoparticles Magn. Reson. Med. 53, 621-7 (Pubitemid 40332283)
17. Mulder, W. J., Strilkers, G. J., Griffioen, A. W., van Bloois, L., Molema, G., Storm, G., Koning, G. A., and Nicolay, K. (2004) A liposomal system for contrast-enhanced magnetic resonance imaging of molecular targets Bioconjugate Chem. 15, 799-806 (Pubitemid 38981954)
18. Lipinski, M. J., Amirbekian, V., Frias, J. C., Aguinaldo, J. G., Mani, V., Briley-Saebo, K. C., Fuster, V., Fallon, J. T., Fisher, E. A., and Fayad, Z. A. (2006) MRI to detect atherosclerosis with gadolinium-containing immunomicelles targeting the macrophage scavenger receptor Magn. Reson. Med. 56, 601-10 (Pubitemid 44338879)
19. Lanza, G. M., Winter, P. M., Caruthers, S. D., Morawski, A. M., Schmieder, A. H., Crowder, K. C., and Wickline, S. A. (2004) Magnetic resonance molecular imaging with nanoparticles J. Nucl. Cardiol. 11, 733-743 (Pubitemid 40012045)
20. Anderson, S. A., Rader, R. K., Westlin, W. F., Null, C., Jackson, D., Lanza, G. M., Wickline, S. A., and Kotyk, J. J. (2000) Magnetic resonance contrast enhancement of neovasculature with alpha(v)beta(3)-targeted nanoparticles Magn. Reson. Med. 44, 433-439
21. Amirbekian, V., Lipinski, M. J., Briley-Saebo, K. C., Amirbekian, S., Aguinaldo, J. G., Weinreb, D. B., Vucic, E., Frias, J. C., Hyafil, F., Mani, V., Fisher, E. A., and Fayad, Z. A. (2007) Detecting and assessing macrophages in vivo to evaluate atherosclerosis noninvasively using molecular MRI Proc. Natl. Acad. Sci. U.S.A. 104, 961-966 (Pubitemid 46154719)
22. Mulder, W. J., Strijkers, G. J., Habets, J. W., Bleeker, E. J., van der Schaft, D. W., Storm, G., Koning, G. A., Griffioen, A. W., and Nicolay, K. (2005) MR molecular imaging and fluorescence microscopy for identification of activated tumor endothelium using a bimodal lipidic nanoparticle FASEB J. 19, 2008-10 (Pubitemid 41759747)
23. Franano, F. N., Edwards, W. B., Welch, M. J., Brechbiel, M. W., Gansow, O. A., and Duncan, J. R. (1995) Biodistribution and metabolism of targeted and nontargeted protein-chelate-gadolinium complexes: evidence for gadolinium dissociation in vitro and in vivo Magn. Reson. Imaging 13, 201-214
24. Wang, S. J., Brechbiel, M., and Wiener, E. C. (2003) Characteristics of a new MRI contrast agent prepared from polypropyleneimine dendrimers, generation 2 Invest. Radiol. 38, 662-668 (Pubitemid 37140289)
25. Bryant, L. H., Jr, Jordan, E. K., Bulte, J. W., Herynek, V., and Frank, J. A. (2002) Pharmacokinetics of a high-generation dendrimer-Gd-DOTA Acad. Radiol. 9 (S1) S29-33
26. Helbich, T. H., Gossman, A., Mareski, P. A., Raduchel, B., Roberts, T. P., Shames, D. M., Muhler, M., Turetschek, K., and Brasch, R. C. (2000) A new polysaccharide macromolecular contrast agent for MR imaging: biodistribution and imaging characteristics J. Magn. Reson. Imaging 11, 694-701 (Pubitemid 30350314)
27. 3 integrin expression in atherosclerotic plaques with a mimetic of RGD peptide grafted to Gd-DTPA Cardiovasc. Res. 78, 148-157 (Pubitemid 351430956)
28. Botnar, R. M., Buecker, A., Wiethoff, A. J., Parsons, E. C., Katoh, M., Jr, Katsimaglis, G., Weisskoff, R. M., Lauffer, R. B., Graham, P. B., Gunther, R. W., Manning, W. J., and Spuentrup, E. (2004) In vivo magnetic resonance imaging of coronary thrombosis using a fibrin-binding molecular magnetic resonance contrast agent Circulation 110, 1463-1466 (Pubitemid 39238024)
29. Spuentrup, E., Katoh, M., Wiethoff, A. J., Parsons, E. C., Jr, Botnar, R. M, Mahnken, A. H., Gunther, R. W., and Buecker, A. (2005) Molecular magnetic resonance imaging of pulmonary emboli with a fibrin-specific contrast agent Am. J. Respir. Crit. Care Med. 172, 494-500 (Pubitemid 41117396)
30. Overoye-Chan, K., Koerner, S., Looby, R. J., Kolodziej, A. F., Zech, S. G., Deng, Q., Chasse, J. M., McMurry, T. J., and Caravan, P. (2008) EP-2104R: a fibrin-specific gadolinium-Based MRI contrast agent for detection of thrombus J. Am. Chem. Soc. 130, 6025-6039 (Pubitemid 351620850)
31. Spuentrup, E., Botnar, R. M., Wiethoff, A. J., Ibrahim, T., Kelle, S., Katoh, M., Ozgun, M., Nagel, E., Vymazal, J., Graham, P. B., Gunther, R. W., and Maintz, D. (2008) MR imaging of thrombi using EP-2104R, a fibrin-specific contrast agent: initial results in patients Eur. Radiol. 18, 1995-2005
32. Spuentrup, E., Ruhl, K. M., Botnar, R. M., Wiethoff, A. J., Buhl, A., Jacques, V., Greenfield, M. T., Krombach, G. A., Gunther, R. W., Vangel, M. G., and Caravan, P. (2009) Molecular magnetic resonance imaging of myocardial perfusion with EP-3600, a collagen-specific contrast agent: initial feasibility study in a swine model Circulation 119, 1768-1775
33. Caravan, P., Das, B., Dumas, S., Epstein, F. H., Helm, P. A., Jacques, V., Koerner, S., Kolodziej, A., Shen, L., Sun, W. C., and Zhang, Z. (2007) Collagen-targeted MRI contrast agent for molecular imaging of fibrosis Angew. Chem., Int. Ed. Engl. 46, 8171-8173 (Pubitemid 350096590)
34. Amirbekian, V., Aguinaldo, J. G., Amirbekian, S., Hyafil, F., Vucic, E., Sirol, M., Weinreb, D. B., Le Greneur, S., Lancelot, E., Corot, C., Fisher, E. A., Galis, Z. S., and Fayad, Z. A. (2009) Atherosclerosis and matrix metalloproteinases: experimental molecular MR imaging in vivo Radiology 251, 429-438
35. Boutry, S., Burtea, C., Laurent, S., Toubeau, G., Vander Elst, L., and Muller, R. N. (2005) Magnetic resonance imaging of inflammation with a specific selectin-targeted contrast agent Magn. Reson. Med. 53, 800-807 (Pubitemid 40478427)
36. Abe, K., Shoji, M., Chen, J., Bierhaus, A., Danave, I., Micko, C., Casper, K., Dillhay, D. L., Nawroth, P. P., and Rickles, F. R. (1999) Regulation of vascular endothelial growth factor production and angiogenesis by the cytoplasmic tail of tissue factor Proc. Natl. Acad. Sci. U.S.A. 96, 8663-8668 (Pubitemid 29354848)
37. Zhang, J., Ding, J., Zhang, X., Shao, X., and Hao, Z. (2005) Regulation of vascular endothelial growth factor (VEGF) production and angiogenesis by tissue Factor (TF) in SGC-7901 gastric cancer cells Cancer Biol. Ther. 4, 769-772 (Pubitemid 41351178)
38. Ruoslahti, E. (2002) Specialization of tumour vasculature Nat. Rev. Cancer. 2, 83-90 (Pubitemid 37328795)
39. Pilch, J., Brown, D. M., Komatsu, M., Jarvinen, T. A., Yang, M., Peters, D., Hoffman, R. M., and Ruoslahti, E. (2006) Peptides selected for binding to clotted plasma accumulate in tumor stroma and wounds Proc. Natl. Acad. Sci. U.S.A. 103, 2800-2804
40. Simberg, D., Duza, T., Park, J. H., Essler, M., Pilch, J., Zhang, L., Derfus, A. M., Yang, M., Hoffman, R. M., Bhatia, S., Sailor, M. J., and Ruoslahti, E. (2007) Biomimetic amplification of nanoparticle homing to tumors Proc. Natl. Acad. Sci. U.S.A. 104, 932-936 (Pubitemid 46154714)
41. Ye, F., Wu, X., Jeong, E. K., Jia, Z., Yang, T., Parker, D., and Lu, Z.-R. (2008) A peptide targeted contrast agent specific to fibrin-fibronectin complexes for cancer molecular imaging with MRI Bioconjugate Chem. 19, 2300-2303
42. Ye, F., Jeong, E. K., Parker, D., and Lu, Z.-R. (2011) Evaluation of CLT1-(Gd-DTPA) for MR molecular imaging in a mouse breast cancer model Chin. J. Magn. Reson. Imaging 2, 325-330
43. Idée, J. M., Port, M., Metdina, C., Lancelot, E., Fayoux, E., Ballet, S., and Corot, C. (2008) Possible involvement of gadolinium chelates in the pathophysiology of nephrogenic systemic fibrosis: a critical review Toxicology 248, 77-88
44. Idée, J. M., Port, M., Raynal, I., Schaefer, M., Le Greneur, S., and Corot, C. (2006) Clinical and biological consequences of transmetallation induced by contrast agents for magnetic resonance imaging: a review Fundam. Clin. Pharmacol. 20, 563-576 (Pubitemid 44760175)
45. White, G. W., Gibby, W. A., and Tweedle, M. F. (2006) Comparison of Gd(DTPA-BMA) (Omniscan) versus Gd(HP-DO3A) (ProHance) relative to gadolinium retention in human bone tissue by inductively coupled plasma mass spectroscopy Invest. Radiol. 41, 272-8 (Pubitemid 44406188)
46. Wu, X., Zong, Y., Ye, Z., and Lu, Z.-R. (2010) Stability and biodistribution of a biodegradable macromolecular MRI contrast agent Gd-DTPA cystamine copolymers (GDCC) in rats Pharm. Res. 27, 1390-1397
47. Burden-Gulley, S. M., Gates, T. J., Burgoyn, A. M., Cutte,r, J. L., Lodowski, D. T., Robinson, S., Sloan, A. E., Miller, R. H., Basilion, J. P., and Brady-Kalnay, S. M. (2010) A novel molecular diagnostic of glioblastomas: detection of an extracellular fragment of protein tyrosine phosphatase mu Neoplasia 12, 305-316
48. Rohrer, M., Bauer, H., Mintorovitch, J., Requardt, M., and Weinmann, H. J. (2005) Comparison of magnetic properties of MRI contrast media solutions at different magnetic field strengths Invest. Radiol. 40, 715-724 (Pubitemid 41546838)
49. Tan, M., Wu, X., Jeong, E. K., Chen, Q., and Lu, Z.-R. (2010) Peptide-targeted Nanoglobular Gd-DOTA monoamide conjugates for magnetic resonance cancer molecular imaging Biomacromolecules 11, 754-761
50. Tan, M., Burden-Gulley, S., Li, W., Wu, X., Lindner, D., Brady-Kalnay, S., and Lu, Z.-R. (2012) MR molecular imaging of prostate cancer with a peptide-targeted contrast agent in a mouse orthotopic prostate cancer model Pharm. Res. 29, 953-60
51. DeNardo, S. J., ODonnell, R. T., and DeNardo, G. L. (1996) Potential use of amino acid cocktails to reduce renal tubular reabsorption of radioconjugates J. Nucl. Med. 37, 837-8