Synthesis of two 3,5-disubstituted sulfonamide catechol ligands and evaluation of their iron(III) complexes for use as MRI contrast agents

Journal of Medicinal Chemistry

Volumn 48, Issue 23, 2005, Pages 7482-7485

  Schwert, Daniel D ^a,e   Richardson, Nicholas ^b   Ji, Gongjun ^a   Radüchel, Bernd ^c   Ebert, Wolfgang ^c   Heffner, Peter E ^a   Keck, Rick ^d   Davies, Julian A ^a  

^a UNIVERSITY OF TOLEDO   (United States)

^b WAGNER COLLEGE   (United States)

^c BAYER PHARMA AG   (Germany)

^d MEDICAL COLLEGE OF OHIO   (United States)

^e INDIANA UNIVERSITY SOUTHEAST   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3,5 BIS(DICHLOROSULFONYL)CATECHOL; 3,5 BIS(DIETHYLSULFONAMIDE)CATECHOL; 3,5 BIS(DIMETHYLSULFONAMIDE)CATECHOL; CATECHOL DERIVATIVE; CONTRAST MEDIUM; GADOXETIC ACID; IRON COMPLEX; LIGAND; SULFONAMIDE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; COMPLEX FORMATION; CONTRAST ENHANCEMENT; DRUG SYNTHESIS; FEMALE; KIDNEY; LIVER; NONHUMAN; NUCLEAR MAGNETIC RESONANCE IMAGING; RAT; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

ANIMALS; CATECHOLS; CONTRAST MEDIA; FEMALE; FERRIC COMPOUNDS; GADOLINIUM DTPA; IRON CHELATING AGENTS; KIDNEY; LIGANDS; LIVER; MAGNETIC RESONANCE IMAGING; RATS; RATS, INBRED F344; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES;

EID: 28544431576     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0501984     Document Type: Article

References (10)

1. Rinck, P. A. Magnetic Resonance in Medicine; 3rd ed.; Blackwell Scientific: Oxford, 1993; pp 155-174.
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. 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.
4. Schwert, D. D.; Davies, J. A.; Richardson, N. Non-gadolinium-based MRI contrast agents. In Topics in Current Chemistry; Krause, W., Ed.; Springer: New York, 2001; Vol. 221, pp 165-200.
5. Richardson, N.; Davies, J. A.; Radüchel, B. Iron(III)-based contrast agents for magnetic resonance imaging. Polyhedron 1999, 18, 2457-2482.
6. Davies, J. A.; Dutremez, S. G.; Hockensmith, C. M.; Keck, R.; Richardson, N.; Selman, S.; Smith, D. A.; Ulmer, C. W., II.; Wheatley, L. S.; Zeiss, J. Iron-based second-sphere contrast agents for magnetic resonance imaging: development of a model system and evaluation of iron(III) tris(tironate) complex in rats. Acad. Radiol. 1996, 3, 936-945.
7. Weinmann, H.-J.; Schuhmann-Giampieri, G.; Schmitt-Willich, H.; Vogler, H.; Frenzel, T.; Gries, H. A new lipophilic gadolinium chelate as a tissue-specific contrast medium for MRI. Magn. Reson. Med. 1991, 22, 233-237.
8. Schmitt-Willich, H.; Brehm, M.; Ewers, C. L. J.; Michl, G.; Müller-Fahrnow, A.; Petrov, O.; Platzek, J.; Radüchel, B.; Sülzle, D. Synthesis and physicochemical characterization of a new gadolinium chelate: The liver-specific magnetic resonance imaging contrast agent Gd-EOB-DTPA. Inorg. Chem. 1999, 38, 1134-1144.
9. Pollak, J.; Gebauer-Fulnegg, E. Über die einwirkung von clorsulfonsäre auf phenole. Monatsch. Chem. 1926, 47, 109-118.
10. Schuhmann-Giampieri, G.; Schmitt-Willich, H.; Press: W.-R.; Negishi, C.; Weinmann, H.-J.; Speck, U. Preclinical evaluation of Gd-EOB-DTPA as a contrast agent in MR imaging of the hepatobiliary system. Radiology 1992, 183, (1), 59-64.