Design, synthesis, and evaluation of 1,4,7,10-tetraazacyclododecane-1,4,7- triacetic acid derived, redox-sensitive contrast agents for magnetic resonance imaging

Journal of Medicinal Chemistry

Volumn 53, Issue 18, 2010, Pages 6747-6757

  Raghunand, Natarajan ^a   Guntle, Gerald P ^a   Gokhale, Vijay ^a   Nichol, Gary S ^b   Mash, Eugene A ^b   Jagadish, Bhumasamudram ^b  

^a UNIVERSITY OF ARIZONA   (United States)

^b University of Arizona   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,4,7,10 TETRAAZACYCLODODECANE 1,4,7 TRIACETIC ACID; 1,4,7,10 TETRAAZACYCLODODECANE 1,4,7,10 TETRAACETIC ACID; ACETIC ACID DERIVATIVE; CHELATE; CONTRAST MEDIUM; CYCLOALKENE; EUROPIUM; GADOLINIUM; HOMOCYSTEINE; HUMAN SERUM ALBUMIN; THIOL; UNCLASSIFIED DRUG; 1,4,7,10-TETRAAZACYCLODODECANE- 1,4,7,10-TETRAACETIC ACID; 1,4,7,10-TETRAAZACYCLODODECANE-1,4,7-TRIACETIC ACID; COORDINATION COMPOUND; PROTEIN BINDING; SERUM ALBUMIN; SINGLE HETEROCYCLIC RINGS;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; COMPETITIVE INHIBITION; COMPLEX FORMATION; CRYSTAL STRUCTURE; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; MOLECULAR DOCKING; NUCLEAR MAGNETIC RESONANCE IMAGING; OXIDATION REDUCTION POTENTIAL; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY; BINDING COMPETITION; CHEMICAL STRUCTURE; CHEMISTRY; HUMAN; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

BINDING, COMPETITIVE; CONTRAST MEDIA; COORDINATION COMPLEXES; CRYSTALLOGRAPHY, X-RAY; EUROPIUM; GADOLINIUM; HETEROCYCLIC COMPOUNDS, 1-RING; HUMANS; MAGNETIC RESONANCE IMAGING; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PROTEIN BINDING; SERUM ALBUMIN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77956721414     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm100592u     Document Type: Article

References (52)

1. Lauffer, R. B. Paramagnetic Metal Complexes as Water Proton Relaxation Agents for NMR Imaging: Theory and Design Chem. Rev. 1987, 87, 901-927
2. Tóth, É.; Helm, L.; Merbach, A. E. Relaxivity of MRI Contrast Agents Top. Curr. Chem. 2002, 221, 61-101
3. Westbrook, C.; Roth, C. K.; Talbot, J. MRI in Practice, 3 rd ed.; Blackwell: Malden, MA, 2005.
4. 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
5. Caravan, P. Strategies for Increasing the Sensitivity of Gadolinium Based MRI Contrast Agents Chem. Soc. Rev. 2006, 35, 512-523
6. Hermann, P.; Kotek, J.; Kubìcek, V.; Lukes, I. Gadolinium(III) Complexes as MRI Contrast Agents: Ligand Design and Properties of the Complexes Dalton Trans. 2008, 3027-3047
7. Aime, S.; Castelli, D. D.; Terreno, E. Novel pH-Reporter MRI Contrast Agents Angew. Chem., Int. Ed. 2002, 41, 4334-4336
8. Lowe, M. P.; Parker, D.; Reany, O.; Aime, S.; Botta, M.; Castellano, G.; Gianolio, E.; Pagliarin, R. pH-Dependent Modulation of Relaxivity and Luminescence in Macrocyclic Gadolinium and Europium Complexes Based on Reversible Intramolecular Sulfonamide Ligation J. Am. Chem. Soc. 2001, 123, 7601-7609
9. Zhang, S.; Wu, K.; Sherry, A. D. A Novel pH-Sensitive MRI Contrast Agent Angew. Chem., Int. Ed. 1999, 38, 3192-3194
10. Aime, S.; Crich, S. G.; Botta, M.; Glovenzana, G.; Palmisano, G.; Sisti, M. A Macromolecular Gd(III) Complex as pH-Responsive Relaxometric Probe for MRI Applications Chem. Commun. 1999, 1577-1578
11. 2 Responsive Macromolecular MRI Contrast Agents Chem. Commun. 2002, 2366-2367
12. 2)- Responsive MRI Contrast Agent Based on the Redox Switch of Manganese(II/III)- Porphyrin Complexes Angew. Chem., Int. Ed. 2000, 39, 747-750
13. Que, E. L.; Gianolio, E.; Baker, S. L.; Wong, A. P.; Aime, S.; Chang, C. J. Copper-Responsive Magnetic Resonance Imaging Contrast Agents J. Am. Chem. Soc. 2009, 131, 8527-8536
14. 3+ Complexes: An Attempt towards Calcium-Sensitive MRI Contrast Agents Inorg. Chem. 2008, 47, 1370-1381
15. Hanaoka, K.; Kikuchi, K.; Urano, Y.; Nagano, T. Selective Sensing of Zinc Ions with a Novel Magnetic Resonance Imaging Contrast Agent J. Chem. Soc., Perkin Trans. 2 2001, 1840-1843
16. Li, W.-H.; Fraser, S. E.; Meade, T. J. A Calcium-Sensitive Magnetic Resonance Imaging Contrast Agent J. Am. Chem. Soc. 1999, 121, 1413-1414
17. Louie, A. Y.; Huber, M. M.; Ahrens, E. T.; Rothbacher, U.; Moats, R.; Jacobs, R. E.; Fraser, S. E.; Meade, T. J. In Vivo Visualization of Gene Expression Using Magnetic Resonance Imaging Nat. Biotechnol. 2000, 18, 321-325
18. Duimstra, J. A.; Femia, F. J.; Meade, T. J. A Gadolinium Chelate for Detection of β-Glucuronidase: A Self-Immolative Approach J. Am. Chem. Soc. 2005, 127, 12847-12855
19. Moats, R. A.; Fraser, S. E.; Meade, T. J. A Smart Magnetic Resonance Imaging Agent That Reports on Specific Enzymatic Activity Angew Chem., Int. Ed. 1997, 36, 726-728
20. Tu, C.; Nagao, R.; Louie, A. Y. Multimodal Magnetic-Resonance/Optical- Imaging Contrast Agent Sensitive to NADH Angew Chem., Int. Ed. 2009, 48, 6547-6551
21. Tu, C.; Louie, A. Y. Photochromically-Controlled, Reversibly-Activated MRI and Optical Contrast Agent Chem. Commun. 2007, 1331-1333
22. Schulze, P. C.; Yoshioka, J.; Takahashi, T.; He, Z.; King, G. L.; Lee, R. T. Hyperglycemia Promotes Oxidative Stress through Inhibition of Thioredoxin Function by Thioredoxin-Interacting Protein J. Biol. Chem. 2004, 279, 30369-30374
23. Yoh, K.; Hirayama, A.; Ishizaki, K.; Yamada, A.; Takeuchi, M.; Yamagichi, S.; Morito, N.; Nakano, T.; Ojima, M.; Shimohata, H.; Itoh, K.; Takahashi, S.; Yamamoto, M. Hyperglycemia Induces Oxidative and Nitrosative Stress and Increases Renal Functional Impairment in Nrf2-Deficient Mice Genes Cells 2008, 13, 1159-1170
24. Wu, W. S. The Signaling Mechanism of ROS in Tumor Progression Cancer Metastasis Rev. 2006, 25, 695-705
25. Lau, A.; Villeneuve, N. F.; Sun, Z.; Wong, P. K.; Zhang, D. D. Dual Roles of Nrf2 in Cancer Pharmacol. Res. 2008, 58, 262-270
26. Hayes, J. D.; McMahon, M. NRF2 and KEAP1 Mutations: Permanent Activation of an Adaptive Response in Cancer Trends Biochem. Sci. 2009, 34, 176-188
27. Biaglow, J. E.; Varnes, M. E.; Clark, E. P.; Epp, E. R. The Role of Thiols in Cellular Response to Radiation and Drugs Radiat. Res. 1983, 95, 437-455
28. Fahey, R. C.; Prise, K. M.; Stratford, M. R. L.; Watfa, R. R.; Michael, B. D. Rates for Repair of pBR 322 DNA Radicals by Thiols As Measured by the Gas Explosion Technique: Evidence that Counter-Ion Condensation and Co-Ion Depletion Are Significant at Physiological Ionic Strength Int. J. Radiat. Biol. 1991, 59, 901-917
29. Pompella, A.; De Tata, V.; Paolicchi, A.; Zunino, F. Expression of γ-Glutamyltransferase in Cancer Cells and Its Significance in Drug Resistance Biochem. Pharmacol. 2006, 71, 231-238
30. Anderson, C. L.; Iyer, S. S.; Ziegler, T. R.; Jones, D. P. Control of Extracellular Cysteine/Cystine Redox State by HT-29 Cells Is Independent of Cellular Glutathione Am. J. Physiol.: Regul., Integr. Comp. Physiol. 2007, 293, R1069-R1075
31. Raghunand, N.; Jagadish, B.; Trouard, T. P.; Galons, J.-P.; Gillies, R. J.; Mash, E. A. Redox-Sensitive Contrast Agents for MRI Based on Reversible Binding of Thiols to Serum Albumin Magn. Reson. Med. 2006, 55, 1272-1280
32. Lacerda, S.; Campello, M. P.; Marques, F.; Gano, L.; Kubícek, V.; Fousková, P.; Tóth, É.; Santos, I. A Novel Tetraazamacrocycle Bearing a Thiol Pendant Arm for Labeling Biomolecules with Radiolanthanides Dalton Trans. 2009, 4509-4518
33. Marradi, M.; Alcántara, D.; de la Fuente, J. M.; García-Martín, M. L.; Cerdán, S.; Penadés, S. Paramagnetic Gd-Based Gold Glyconanoparticles as Probes for MRI: Tuning Relaxivities with Sugars Chem. Commun. 2009, 3922-3924
34. Sugio, S.; Kashima, A.; Mochizuki, S.; Noda, M.; Kobayashi, K. Crystal Structure of Human Serum Albumin at 2.5 Å Resolution Protein Eng. 1999, 12, 439-446
35. Insight II 2005L modeling software was obtained from Accelrys Inc., San Diego, CA.
36. Bugaut, A.; Jantos, K.; Wietor, J.-L.; Rodriguez, R.; Sanders, J. K. M.; Balasubramanian, S. Exploring the Differential Recognition of DNA G-Quadruplex Targets by Small Molecules Using Dynamic Combinatorial Chemistry Angew. Chem., Int. Ed. 2008, 47, 2677-2680
37. Bowen, M. E.; Monguchi, Y.; Sankaranarayanan, R.; Vagner, J.; Begay, L. J.; Xu, L.; Jagadish, B.; Hruby, V. J.; Gillies, R. J.; Mash, E. A. Design, Synthesis, and Validation of a Branched Flexible Linker for Bioactive Peptides J. Org. Chem. 2007, 72, 1675-1680
38. Appel, R. Tertiary Phosphane/Tetrachloromethane, a Versatile Reagent for Chlorination, Dehydration and P-N Linkage Angew. Chem., Int. Ed. Engl. 1975, 14, 801-811
39. Axelsson, O.; Olsson, A. Synthesis of Cyclen Derivatives. WO 2006112723 A1; CAN 145:419189, 2006.
40. Lin, Y.; Favre-Reguillon, A.; Pellet-Rostaing, S.; Lemaire, M. Synthesis of Pyridine-Based Polyaminocarboxylic Ligands Bearing a Thioalkyl Anchor Tetrahedron Lett. 2007, 48, 3463-3466
41. Yang, C.-T.; Li, Y.; Liu, S. Synthesis and Structural Characterization of Complexes of a DO3A-Conjugated Triphenylphosphonium Cation with Diagnostically Important Metal Ions Inorg. Chem. 2007, 46, 8988-8997
42. Spek, A. L. Single-Crystal Structure Validation with the Program PLATON J. Appl. Crystallogr. 2003, 36, 7-13
43. 2 > 2σ]), R1 = 0.0331 and wR2 = 0.0690 (all data).
44. Sengupta, S.; Chen, H.; Togawa, T.; DiBello, P. M.; Majors, A. K.; Büdy, B.; Ketterer, M. E.; Jacobsen, D. W. Albumin Thiolate Anion Is an Intermediate in the Formation of Albumin-S-S-Homocysteine J. Biol. Chem. 2001, 276, 30111-30117
45. Franklin, J. L.; Lumpkin, H. E. Some C-S, H-S and S-S Bond Strengths by the Electron Impact Method J. Am. Chem. Soc. 1952, 74, 1023-1026
46. 3+-Based MRI Contrast Agents: Influence of the Internal Mobility on Water Proton Relaxivity Chem. Eur. J. 2003, 9, 5468-5480
47. Aime, S.; Gianolio, E.; Terreno, E.; Giovenzana, G. B.; Pagliarin, R.; Sisti, M.; Palmisano, G.; Botta, M.; Lowe, M. P.; Parker, D. Ternary Gd(III)L-HSA Adducts: Evidence for the Replacement of Inner-Sphere Water Molecules by Coordinating Groups of the Protein. Implications for the Design of Contrast Agents for MRI J. Biol. Inorg. Chem. 2000, 5, 488-497
48. III Macrocyclic Complexes and Their Interaction with Human Serum Albumin Org. Biomol. Chem. 2004, 2, 570-577
49. III Complexes: Effect of the Basicity at the Macrocyclic Nitrogen Site Eur. J. Inorg. Chem. 2003, 3530-3533
50. Discover-3 ESFF (Extensible Systematic Force Field). Molecular Mechanics Force Fields, Insight II, 2005L; Accelrys, Inc.: San Diego, CA, 2005.
51. The General Experimental Section appears in the Supporting Information that accompanies this article. The purities of synthetic intermediates were estimated to be ≥95% based on elemental analyses and/or thin-layer chromatographic analyses. The purities of compounds 3a-5a, 3b-5b, and 24 were estimated to be ≥95% based on reversed phase thin-layer chromatographic analyses.
52. Motulsky, H.; Christopoulos, A. Fitting Models to Biological Data Using Linear and Nonlinear Regression. A Practical Guide to Curve Fitting; GraphPad Software, Inc.: San Diego, CA, 2003; pp 187-191.