Complementary strategies for developing Gd-free high-field T1 MRI contrast agents based on MnIII porphyrins

Journal of Medicinal Chemistry

Volumn 57, Issue 2, 2014, Pages 516-520

  Cheng, Weiran ^a   Haedicke, Inga E ^a   Nofiele, Joris ^b,c   Martinez, Francisco ^d   Beera, Kiran ^a   Scholl, Timothy J ^d,e   Cheng, Hai Ling Margaret ^b,c   Zhang, Xiao An ^a  

^a UNIVERSITY OF TORONTO   (Canada)

^b UNIVERSITY OF TORONTO   (Canada)

^c HOSPITAL FOR SICK CHILDREN RESEARCH INSTITUTE   (Canada)

^d ROBARTS RESEARCH INSTITUTE   (Canada)

^e UNIVERSITY OF WESTERN ONTARIO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

4,4 ' BIS(MANGANESE(III) 5,10,15 TRIS(4 SULFONATOPHENYL)PORPHIN 20 YL)BIPHENYL; 4,4 BIS(5,10,15 TRIPHENYLPORPHIN 20 YL)BIPHENYL; 4,4' BIS(5,10,15 TRIS(4 SULFONATOPHENYL)PORPHIN 20 YL)BIPHENYL; CONTRAST MEDIUM; GADOLINIUM; MANGANESE DERIVATIVE; MANGANESE(III)PORPHYRIN; PORPHYRIN DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; AQUEOUS SOLUTION; ARTICLE; ATOMIC ABSORPTION SPECTROMETRY; BIOCOMPATIBILITY; CONFORMATION; CONTRAST ENHANCEMENT; CONTROLLED STUDY; DRUG CLEARANCE; DRUG METABOLISM; HYDROLYSIS; KIDNEY CLEARANCE; MAGNETIC FIELD; MOLECULAR SIZE; MOLECULAR WEIGHT; NONHUMAN; NUCLEAR MAGNETIC RESONANCE IMAGING; RAT; SULFONATION; TISSUE DISTRIBUTION;

ANIMALS; BIPHENYL COMPOUNDS; CONTRAST MEDIA; COORDINATION COMPLEXES; GADOLINIUM; MAGNETIC RESONANCE IMAGING; MANGANESE; METALLOPORPHYRINS; PORPHYRINS; RATS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84893092345     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm401124b     Document Type: Article

References (40)

1. Merbach, A. E.; Tóth, E. The Chemistry of Contrast Agents in Medical Magnetic Resonance Imaging; John Wiley & Sons: Chichester, U.K., 2001; p 471.
2. Lauffer, R. B. Paramagnetic metal complexes as water proton relaxation agents for NMR imaging: theory and design Chem. Rev. 1987, 87, 901-927
3. Terreno, E.; Castelli, D. D.; Viale, A.; Aime, S. Challenges for molecular magnetic resonance imaging Chem. Rev. 2010, 110, 3019-3042
4. Carr, D. H.; Brown, J.; Bydder, G. M.; Weinmann, H. J.; Speck, U.; Thomas, D. J.; Young, I. R. Intravenous chelated gadolinium as a contrast agent in NMR imaging of cerbral tumours Lancet 1984, 323, 484-486 (Pubitemid 14193142)
5. Weinmann, H. J.; Brasch, R. C.; Press, W. R.; Wesbey, G. E. Characteristics of gadolinium-DTPA complex: a potential NMR contrast agent AJR, Am. J. Roentgenol. 1984, 142, 619-624 (Pubitemid 14199123)
6. Caravan, P.; Ellison, J. J.; McMurry, T. J.; Lauffer, R. B. Gadolinium(III) chelates as MRI contrast agents: structure, dynamics, and applications Chem. Rev. 1999, 99, 2293-2352 (Pubitemid 30498114)
7. Werner, E. J.; Datta, A.; Jocher, C. J.; Raymond, K. N. High-relaxivity MRI contrast agents: where coordination chemistry meets medical imaging Angew. Chem., Int. Ed. 2008, 47, 8568-8580
8. Major, J. L.; Meade, T. J. Bioresponsive, cell-penetrating, and multimeric MR contrast agents Acc. Chem. Res. 2009, 42, 893-903
9. Cowper, S. E.; Robin, H. S.; Steinberg, S. M.; Su, L. D.; Gupta, S.; LeBoit, P. E. Scleromyxoedema-like cutaneous diseases in renal-dialysis patients Lancet 2000, 356, 1000-1001
10. Idée, J.-M.; Port, M.; Robic, C.; Medina, C.; Sabatou, M.; Corot, C. Role of thermodynamic and kinetic parameters in gadolinium chelate stability J. Magn. Reson. Imaging 2009, 30, 1249-1258
11. Datta, A.; Raymond, K. N. Gd-hydroxy-pyridinone (HOPO)-based high-relaxivity magnetic resonance imaging (MRI) contrast agents Acc. Chem. Res. 2009, 42, 938-947
12. Helm, L. Optimization of gadolinium-based MRI contrast agents for high magnetic-field applications Future Med. Chem. 2010, 2, 385-396
13. Aime, S.; Castelli, D. D.; Crich, S. G.; Gianolio, E.; Terreno, E. Pushing the sensitivity envelope of lanthanide-based magnetic resonance imaging (MRI) contrast agents for molecular imaging applications Acc. Chem. Res. 2009, 42, 822-831
14. Caravan, P. Strategies for increasing the sensitivity of gadolinium based MRI contrast agents Chem. Soc. Rev. 2006, 35, 512-523 (Pubitemid 43815285)
15. Chen, C.-w.; Cohen, J. S.; Myers, C. E.; Sohn, M. Paramagnetic metalloporphyrins as potential contrast agents in NMR imaging FEBS Lett. 1984, 168, 70-74 (Pubitemid 14159504)
16. 4) Magn. Reson. Med. 1987, 4, 252-260
17. Lyon, R. C.; Faustino, P. J.; Cohen, J. S.; Katz, A.; Mornex, F.; Colcher, D.; Baglin, C.; Koenig, S. H.; Hambright, P. Tissue distribution and stability of metalloporphyrin MRI contrast agents Magn. Reson. Med. 1987, 4, 24-33 (Pubitemid 17004469)
18. Hambright, P. An acid solvolysis kinetic study of manganese(II)-tetra(2- N -methylpyridyl)porphine J. Inorg. Nucl. Chem. 1977, 39, 1102-1103
19. Shmilovits, M.; Vinodu, M.; Goldberg, I. Self-ass-embly patterns of porphyrins in crystals. Structures of hydrogen-bonding and coordination polymers of manganese tetra(carboxyphenyl)porphyrin New J. Chem. 2004, 28, 223-227 (Pubitemid 38297274)
20. Zhang, X.-a.; Lovejoy, K. S.; Jasanoff, A.; Lippard, S. J. Water-soluble porphyrins as a dual-function molecular imaging platform for MRI and fluorescence zinc sensing Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 10780-10785 (Pubitemid 47175178)
21. Aime, S.; Botta, M.; Gianolio, E.; Terreno, E. A p(O-2)-responsive MRI contrast agent based on the redox switch of manganese(II/III)-porphyrin complexes Angew. Chem., Int. Ed. 2000, 39, 747-750 (Pubitemid 30216739)
22. Bryant, L. H., Jr.; Hodges, M. W.; Bryant, R. G. Test of electron delocalization effects on water-proton spin-lattice relaxation by bromination of [tetrakis(4-sulfonatopheny)porphine]manganese Inorg. Chem. 1999, 38, 1002-1005
23. Zhang, Z.; He, R.; Yan, K.; Guo, Q. N.; Lu, Y. G.; Wang, X. X.; Lei, H.; Li, Z. Y. Synthesis and in vitro and in vivo evaluation of manganese(III) porphyrin-dextran as a novel MRI contrast agent Bioorg. Med. Chem. Lett. 2009, 19, 6675-6678
24. 4. A comparative magnetic resonance imaging study in rats Invest. Radiol. 1992, 27, 536-542
25. Solomon, I. Relaxation processes in a system of 2 spins Phys. Rev. 1955, 99, 559-565
26. Bloembergen, N.; Morgan, L. O. Proton relaxation times in paramagnetic solutions effects of electron spin relaxation J. Chem. Phys. 1961, 34, 842-850
27. Bloembergen, N. Proton relaxation times in paramagnetic solutions J. Chem. Phys. 1957, 27, 572-573
28. IIITSPP: a unique mechanism J. Phys. Chem. A 2005, 109, 3267-3275 (Pubitemid 40625942)
29. Punna, S.; Díaz, D. D.; Finn, M. G. Palladium-catalyzed homocoupling of arylboronic acids and esters using fluoride in aqueous solvents Synlett 2004, 13, 2351-2354 (Pubitemid 39506039)
30. Srivastava, T. S.; Tsutsui, M. Unusual metalloporphyrins. XVI. Preparation and purification of tetrasodium meso-tetra(p-sulfophenyl)porphine. Easy procedure J. Org. Chem. 1973, 38, 2103-2103
31. Trova, M. P.; Gauuan, P. J. F.; Pechulis, A. D.; Bubb, S. M.; Bocckino, S. B.; Crapo, J. D.; Day, B. J. Superoxide dismutase mimetics. Part 2: Synthesis and structure-activity relationship of glyoxylate- and glyoxamide-derived metalloporphyrins Bioorg. Med. Chem. 2003, 11, 2695-2707 (Pubitemid 36682993)
32. Kimmich, R.; Anoardo, E. Field-cycling NMR relaxometry Prog. Nucl. Magn. Reson. Spectrosc. 2004, 44, 257-320
33. Anoardo, E.; Galli, G.; Ferrante, G. Fast-field-cycling NMR: applications and instrumentation Appl. Magn. Reson. 2001, 20, 365-404
34. Pierre, V. C.; Botta, M.; Raymond, K. N. Dendrimeric gadolinium chelate with fast water exchange and high relaxivity at high magnetic field strength J. Am. Chem. Soc. 2004, 127, 504-505 (Pubitemid 40174359)
35. Kotkova, Z.; Helm, L.; Kotek, J.; Hermann, P.; Lukes, I. Gadolinium complexes of monophosphinic acid DOTA derivatives conjugated to cyclodextrin scaffolds: efficient MRI contrast agents for higher magnetic fields Dalton Trans. 2012, 41, 13509-13519
36. de Sousa, P. L.; Livramento, J. B.; Helm, L.; Merbach, A. E.; Meîme, W.; Doan, B.-T.; Beloeil, J.-C.; Prata, M. I. M.; Santos, A. C.; Geraldes, C. F.; Tóth, é. In vivo MRI assessment of a novel GdIII-based contrast agent designed for high magnetic field applications Contrast Media Mol. Imaging 2008, 3, 78-85 (Pubitemid 351722196)
37. Boros, E.; Polasek, M.; Zhang, Z.; Caravan, P. Gd(DOTAla): a single amino acid Gd-complex as a modular tool for high relaxivity MR contrast agent development J. Am. Chem. Soc. 2012, 134, 19858-19868
38. Place, D. A.; Faustino, P. J.; Berghmans, K. K.; van Zijl, P. C. M.; Chesnick, A. S.; Cohen, J. S. MRI contrast-dose relationship of manganese(III)tetra(4-sulfonatophenyl) porphyrin with human xenograft tumors in nude mice at 2.0 T Magn. Reson. Imaging 1992, 10, 919-928 (Pubitemid 23082025)
39. Schwert, D. D.; Davies, J. A.; Richardson, N. Non-gadolinium-based MRI contrast agents Top. Curr. Chem. 2002, 221, 165-199
40. Holmes, A. E.; Das, D.; Canary, J. W. Chelation-enhanced circular dichroism of tripodal bisporphyrin ligands J. Am. Chem. Soc. 2007, 129, 1506-1507