4-[3,5-bis(2-hydroxyphenyl)-1,2,4-triazol-1-yl]-benzoic acid: A novel efficient and selective iron(III) complexing agent

Angewandte Chemie - International Edition

Volumn 38, Issue 17, 1999, Pages 2568-2570

  Heinz, Uwe ^a   Hegetschweiler, Kaspar ^a   Acklin, Pierre ^b   Faller, Bernard ^b   Lattmann, René ^b   Schnebli, Hans Peter ^b  

^a SAARLAND UNIVERSITY   (Germany)

^b NOVARTIS PHARMA AG   (Switzerland)

Author keywords

Aluminum; Chelates; Iron

Indexed keywords

4 [3,5 BIS(2 HYDROXYPHENYL) 1,2,4 TRIAZOL 1 YL]BENZOIC ACID; CHELATING AGENT; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; COMPLEX FORMATION; DECOMPOSITION; DRUG STRUCTURE; IRON CHELATION; IRON METABOLISM; IRON OVERLOAD; LIGAND BINDING; METAL BINDING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH; PROTON TRANSPORT; REACTION TIME; SOLUBILITY; STRUCTURE ACTIVITY RELATION;

EID: 0033520468     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990903)38:17<2568::AID-ANIE2568>3.0.CO;2-C     Document Type: Article

References (27)

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7. Yu. I. Ryabukhin, N. V. Shibaeva, A. S. Kuzharov, V. G. Korobkova, A. V. Khokhlov, A. D. Garnovskii, Koord. Khim. 1987, 13, 869-874; Yu. I. Ryabukhin, N. V. Shibaeva, A. S. Kuzharov, V. G. Korobkova. A. V. Khokhlov, A. D. Garnovskii, Sov. J. Coord. Chem. (Engl. Transl.) 1987, 13, 493-499.
8. 4.
9. H. P. Schnebli, Brit. J. Haematol. 1998, 102, 280 (Abstr. Pap. ISHEHA Combined Haematology Congress, Amsterdam); a comprehensive report of the biochemical investigations is in preparation.
10. 2O: C 47.63, H 4.33, N 7.93, O 28.32, Na 6.51, Fe 5.27; found: C 47.79, H 4.25, N 7.84, O 28.38, Na 6.34, Fe 5.31.
11. III complexes.
12. III complexes.
13. III complexes.
14. -3 for Al.
15. -3.
16. +). The equipment has already been described previously (K. Hegetschweiler, T. Kradolfer, V. Gramlich, R. D. Hancock, Chem. Eur. J. 1995, 1, 74-88). The computer programs SUPERQUAD (P. Gans, A. Sabatini, A. Vacca, J. Chem. Soc. Dalton Trans. 1985, 1195) and BEST (R. J. Motekaitis, A. E. Martell, Can. J. Chem. 1982, 60, 2403) were used for evaluation. The complex formation generally took place at such low pH values that hydrolysis of the aqua ions could be neglected.
17. +). The equipment has already been described previously (K. Hegetschweiler, T. Kradolfer, V. Gramlich, R. D. Hancock, Chem. Eur. J. 1995, 1, 74-88). The computer programs SUPERQUAD (P. Gans, A. Sabatini, A. Vacca, J. Chem. Soc. Dalton Trans. 1985, 1195) and BEST (R. J. Motekaitis, A. E. Martell, Can. J. Chem. 1982, 60, 2403) were used for evaluation. The complex formation generally took place at such low pH values that hydrolysis of the aqua ions could be neglected.
18. +). The equipment has already been described previously (K. Hegetschweiler, T. Kradolfer, V. Gramlich, R. D. Hancock, Chem. Eur. J. 1995, 1, 74-88). The computer programs SUPERQUAD (P. Gans, A. Sabatini, A. Vacca, J. Chem. Soc. Dalton Trans. 1985, 1195) and BEST (R. J. Motekaitis, A. E. Martell, Can. J. Chem. 1982, 60, 2403) were used for evaluation. The complex formation generally took place at such low pH values that hydrolysis of the aqua ions could be neglected.
19. a values from Table 1 were used for the calculations.
20. pH=0.0023 for [FeL]).
21. 3) using a diode array spectrophotometer TIDAS-UVNIR/100-1 from J&M with a HELLMA immersion probe and least squares calculations for evaluation (R. A. Binstead, A. D. Zuberbühler, SPECFIT version 2.10, Spectrum Software Associates, Chapel Hill, NC 27515-4494 (USA); see also H. Gampp, M. Maeder, C. J. Meyer, A. D. Zuberbühler, Talanta 1985, 32, 257-264).
22. 3) using a diode array spectrophotometer TIDAS-UVNIR/100-1 from J&M with a HELLMA immersion probe and least squares calculations for evaluation (R. A. Binstead, A. D. Zuberbühler, SPECFIT version 2.10, Spectrum Software Associates, Chapel Hill, NC 27515- 4494 (USA); see also H. Gampp, M. Maeder, C. J. Meyer, A. D. Zuberbühler, Talanta 1985, 32, 257-264).
23. The measurements were performed at 25°C on a DX17MV instrument (Applied Photophysics).
24. 3+ (D. T. Richens, The Chemistry of Aqua Ions, Wiley, Chichester, 1997).
25. 2O/DMSO system were determined separately.
26. R. D. Hancock, J. Chem. Educ. 1992, 69, 615-621.
27. M. Ghisletta, L. Hausherr-Primo, K. Gajda-Schrantz, G. Machula, L. Nagy, H. W. Schmalle, G. Rihs, F. Endres, K. Hegetschweiler, Inorg. Chem. 1998, 37, 997-1008.