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EP-2104R: A Fibrin-Specific Gadolinium-Based MRI Contrast Agent for Detection of Thrombus
Abstract
Thrombus (blood clot) is implicated in a number of life threatening diseases, e.g., heart attack, stroke, pulmonary embolism. EP-2104R is an MRI contrast agent designed to detect thrombus by binding to the protein fibrin, present in all thrombi. EP-2104R comprises an 11 amino acid peptide derivatized with 2 GdDOTA-like moieties at both the C- and N-terminus of the peptide (4 Gd in total). EP-2104R was synthesized by a mixture of solid phase and solution techniques. The La(III) analogue was characterized by and 1D and 2D NMR spectroscopy and was found to have the expected structure. EP-2104R was found to be significantly more inert to Gd(III) loss than commercial contrast agents. At the most extreme conditions tested (pH 3, 60 degrees C, 96 hrs), less than 10% of Gd was removed from EP-2104R by a challenge with a DTPA based ligand, while the commercial contrast agents equilibrated within minutes to hours. EP-2104R binds equally to two sites on human fibrin (Kd = 1.7 +/- 0.5 microM) and has a similar affinity to mouse, rat, rabbit, pig, and dog fibrin. EP-2104R has excellent specificity for fibrin over fibrinogen (over 100-fold) and for fibrin over serum albumin (over 1000-fold). The relaxivity of EP-2104R bound to fibrin at 37 degrees C and 1.4 T was 71.4 mM(-1) s(-1) per molecule of EP-2104R (17.4 per Gd), about 25 times higher than that of GdDOTA measured under the same conditions. Strong fibrin binding, fibrin selectivity, and high molecular relaxivity enable EP-2104R to detect blood clots in vivo.
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Flacke, S., Fischer, S., Scott, M. J., Fuhrhop, R. J., Allen, J. S., McLean, M., Winter, P., Sicard, G. A., Gaffney, P. J., Wickline, S. A., et al. (2001) · Circulation · doi:10.1161/hc3601.094303 · Cited by 515
A Novel Site-Targeted Ultrasonic Contrast Agent With Broad Biomedical Application
Lanza, G. M., Wallace, K. D., Scott, M. J., Cacheris, W. P., Abendschein, D. R., Christy, D. H., Sharkey, A. M., Miller, J. G., Gaffney, P. J., & Wickline, S. A. (1996) · Circulation · doi:10.1161/01.cir.94.12.3334 · Cited by 406
Cited by
Villaraza, A. J. L., Bumb, A., & Brechbiel, M. W. (2010) · Chemical Reviews · doi:10.1021/cr900232t · Cited by 632
Fibrinogen in neurological diseases: mechanisms, imaging and therapeutics
Petersen, M. A., Ryu, J. K., & Akassoglou, K. (2018) · Nature reviews. Neuroscience · doi:10.1038/nrn.2018.13 · Cited by 527
25 Years of Contrast-Enhanced MRI: Developments, Current Challenges and Future Perspectives
Lohrke, J., Frenzel, T., Endrikat, J., Alves, F. C., Grist, T. M., Law, M., Lee, J. M., Leiner, T., Li, K.-C., Nikolaou, K., et al. (2016) · Advances in Therapy · doi:10.1007/s12325-015-0275-4 · Cited by 420
Rossignoli, F., Spano, C., Grisendi, G., Foppiani, E. M., Golinelli, G., Mastrolia, I., Bestagno, M., Candini, O., Petrachi, T., Recchia, A., et al. (2019) · Theranostics · doi:10.7150/thno.27576 · Cited by 55
Metadata
- Authors
- Overoye-Chan, K., Koerner, S., Looby, R. J., Kolodziej, A. F., Zech, S. G., Deng, Q., Chasse, J. M., McMurry, T. J., & Caravan, P.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2008-04-08
- Volume
- 130
- Issue
- 18
- Pages
- 6025-6039
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2049559137
- Cited by
- 226
- References
- 2
- FWCI
- 6.23
- Type
- journal article
- Language
- en
- Open access
- closed
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- Overoye-Chan, K., Koerner, S., Looby, R. J., Kolodziej, A. F., Zech, S. G., Deng, Q., Chasse, J. M., McMurry, T. J., & Caravan, P. (2008). EP-2104R: A Fibrin-Specific Gadolinium-Based MRI Contrast Agent for Detection of Thrombus. Journal of the American Chemical Society. https://doi.org/10.1021/ja800834y
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