Schiff Base of Gossypol with 3,6,9-Trioxa-decylamine Complexes, with Monovalent Cations Studied by Mass Spectrometry, 1H-NMR, FTIR, and PM5 Semiempirical Methods

Biopolymers

Volumn 73, Issue 4, 2004, Pages 470-483

  Przybylski, Piotr ^a   Ilkevych, Nataliya ^a   Schroeder, Grzegorz ^a   Brzezinski, Bogumil ^a   Bartl, Franz ^b  

^a ADAM MICKIEWICZ UNIVERSITY   (Poland)

^b CHARITÉ UNIVERSITÄTSMEDIZIN BERLIN   (Germany)

Author keywords

3,6,9 trioxa decylamine; 1H NMR; Correlation spectroscopy; Electrospray ionization; Far FTIR; FTIR; Gossypol; Gossypol Schiff base; Gossypol Schiff base complexes; Metal cation fluctuation; Monovalent cations; PM5 calculation; Polyoxaalkylamines

Indexed keywords

AMINES; FOURIER TRANSFORM INFRARED SPECTROSCOPY; IONIZATION; MASS SPECTROMETRY; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTONS;

SCHIFF BASES; TAUTOMERS;

COMPLEXATION;

3,6,9 TRIOXADECYLAMINE; CESIUM; DECYLAMINE; ENAMINE; GOSSYPOL; KRYPTON; LITHIUM ION; PROTON; RUBIDIUM; SCHIFF BASE; SODIUM ION; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CALCULATION; COMPLEX FORMATION; DRUG MECHANISM; ELECTROSPRAY MASS SPECTROMETRY; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; PARAMETRIC METHOD 5; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS;

AMINES; CATIONS, MONOVALENT; GOSSYPOL; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MATHEMATICAL COMPUTING; MODELS, MOLECULAR; MOLECULAR STRUCTURE; SCHIFF BASES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; STEREOISOMERISM; THERMODYNAMICS;

EID: 1542619628     PISSN: 00063525     EISSN: None     Source Type: Journal    
DOI: 10.1002/bip.10553     Document Type: Article

References (52)

1. Adams, R.; Morris, R. C.; Geissman, T. A.; Butterbaugh, D. J.; Kirkpatrick, K. C. J Am Chem Soc 1938, 60, 2193.
2. Dechary, J. M.; Pradel, P. J Am Oil Chem Soc 1971, 48, 563.
3. Kulkarni, V. N.; Khadi, B. M.; Sangam, V. S. Curr Sci 2002, 82, 434.
4. Tan, X. P.; Liang, W. Q.; Liu, C. J.; Luo, P.; Heinstein, P.; Chen, X. Y. Planta 2000, 210, 644.
5. National Coordination Group on Male Antifertility Agents. J Chin Med 1978, 91, 417.
6. Leung, W. N.; Tso, W. W. Abstr Chin Med 1988, 2, 233.
7. Vyas, R. K.; Kalla, N. R. Contraception 1990, 39, 687.
8. Abraham, R. T.; Wiederrecht, G. J. Annu Rev Immunol 1996, 14, 483.
9. Reidenberg, M. M. Toxicology 2000, 144, 107.
10. Couthino, E. M.; Athayde, C.; Atta, G.; Gu, Z. P.; Chen, Z. W.; Sang, G. W.; Emuveyan, E.; Adekunle, A. O.; Mati, J.; Otubu, J.; Reidenberg, M. M.; Segal, S. J. Contraception 2000, 61, 61.
11. Jan, C. R.; Lin, M. C.; Chou, K. J.; Huang, J. K. Biochim Biophys Acta Mol Cell Res 2000, 1496, 270.
12. Dabrowski, K.; Lee, K. J.; Rinchard, J.; Ciereszko, A.; Blom, J. H.; Ottobre, J. S. Biochim Biophys Acta Gen Subject 2001, 1525, 37.
13. Chenoweth, P. J.; Chase, C. C.; Risco, C. A.; Larsen, R. E. Theriogenology 2000, 53, 1193.
14. Waller, D. P.; Bunyaprahastsara, N.; Martin, A.; Vournazos, C. J.; Ahmed, M. S.; Soejarto, D. D.; Cordell, G. A.; Fong, H. H. S.; Russell, L. D.; Malone, J. P. J. Andrology 1983, 4, 276.
15. Matlin, S.; Zhou, R. Contraception 1985, 31, 141.
16. Chang, W. Y.; Sugimoto, Y.; Shidaifat, F.; Kulp, S. K.; Canatan, H.; Lin, Y. C. Biochem Biophys Res Commun 1997, 231, 383.
17. Baumgrass, R.; Weiwad, M.; Erdmann, F.; Liu, J. O.; Wunderlich, D.; Grabley, S.; Fischer, G. J Biol Chem 2001, 276, 47914.
18. Yu, Y.; Deck, J. A.; Hunsaker, L. A.; Deck, L. M.; Royer, R. E.; Goldberg, E.; Vander Jagt, D. L. Biochem Pharmacol 2001, 62, 81.
19. Polsky, B.; Segal, S. J.; Baron, P. A.; Gold, J. W. M.; Ueno, H.; Armstrong, D. Contraception 1989, 39, 579.
20. Deck, L. M.; Van der Jagt, D. L.; Royer, R. E. J Med Chem 1991, 34, 3001.
21. Fish, R. G.; Groundwater, P. W.; Morgan, J. J. G. Tetrahedron Assym 1995, 6, 873.
22. Vlietinck, A. J.; De Bruyne, T.; Apers, S.; Pieters, L. A. Planta Med 1998, 64, 97.
23. Gilbert, E. N.; O'Reilly, J. E.; Chang, C. J. G.; Lin, Y. C.; Brueggemeier, R. W. Life Sci 1995, 57, 61.
24. Stein, R. C.; Joseph, A. F. A.; Matlin, S. A.; Cunningham, D. C.; Ford, H. T.; Coombes, C. R. Cancer Chem Pharmacol 1992, 30, 480.
25. Tuszynski, G. P.; Cossu, G. Cancer Res 1984, 44, 768.
26. Blackstaffe, L.; Shelley, M. D.; Fish, R. G. Melanoma Res 1997, 7, 364.
27. Quintana, P. J. E.; de Peyster, A.; Klatzke, S.; Park, H. J. Toxicol Lett 2000, 117, 85.
28. Matsuo, M. J Nutr Sci Vitaminol 2000, 46, 210.
29. Shelley, M. D.; Hartley, L.; Groundwater, P. W.; Fish, R. G. Anti-Cancer Drugs 2000, 11, 209.
30. Razakantoanina, V.; Phung, N. K. P.; Jaureguiberry, G. Parasitol Res 2000, 86, 665.
31. Dao, V. T.; Gaspard C.; Mayer, M.; Werner, G. H.; Nguyen, S. N.; Michelot, R. J. Eur J Med Chem 2000, 35, 805.
32. Royer, R. E.; Deck, L. M.; Vander Jagt, T. J.; Martinez, F. J.; Mills, R. G.; Young, S. A.; Vander Jagt, D. L. J Med Chem 1995, 38, 2427.
33. Przybylski, P.; Brzezinski, B. Biopolym Biospectrosc 2002, 67, 61.
34. Przybylski, P.; Jasiński, K.; Brzezinski, B.; Bartl, F. J Mol Struct 2002, 611, 193.
35. Przybylski, P.; Bartl, F.; Brzezinski, B. Biopolym Biospectrosc 2002, 65, 111.
36. Fish, R. G.; Groundwater, P. W.; Morgan, J. J. G. Tetrahedron Asym 1995, 6, 873.
37. Brzezinski, B.; Paszyc, S.; Zundel, G. J Mol Struct 1991, 246, 45.
38. Brzezinski, B.; Marciniak, B.; Paszyc, S.; Zundel, G. J Mol Struct 1992, 268, 61.
39. Brzezinski, B.; Rozwadowski, J.; Marciniak, B.; Paszyc, S. J Mol Struct 1997, 435, 275.
40. Przybylski, P.; Wojciechowski, G.; Brzezinski, B.; Kozubek, H.; Marciniak, B.; Paszyc, S. J Mol Struct 2001, 569, 147.
41. Przybylski, P.; Schroeder, G.; Brzezinski, B. Phys Chem Chem Phys 2002, 4, 6137.
42. Przybylski, P.; Schroeder, G.; Brzezinski, B.; Bartl, F. J Phys Org Chem, 2003, 16, 289.
43. Chaput, G.; Jeminet, G.; Juillard, J. Can J Chem 1975, 53, 2240.
44. Heimann, U.; Herzhoff, M.; Vogtle, F. Chem Ber 1979, 112, 1392.
45. Ghu, I. H.; Zhang, H.; Dearden, D. V. J Am Chem Soc 1993, 115, 5736.
46. Stewart, J. J. P. Method J Comput Chem 1989, 10, 209.
47. Stewart, J. J. P. J Comput Chem 1991, 12, 320.
48. Brzezinski, B.; Gierczyk, B.; Różalski, B.; Wojciechowski, G.; Schroeder, G.; Zundel, G. J Mol Struct 2000, 519, 119.
49. Schroeder, G.; Gierczyk, B.; Łȩska, B.; Wojciechowski, G.; Pankiewicz, R.; Brzezinski, B.; Bartl, F. J Mol Struct 2002, 607, 9.
50. Bełtowska-Brzezinska, M.; Łuczak, T.; Gierczyk, B.; Eitner, K.; Brzezinski, B.; Pankiewicz, R.; Schroeder, G. J Mol Struct 2002, 607, 77.
51. Pankiewicz, R.; Schroeder, G.; Gierczyk, B.; Brzezinski, B. Biopolym Biospectrosc 2002, 65, 95.
52. Pankiewicz, R.; Wojciechowski, G.; Schroeder, G.; Brzezinski, B.; Bartl, F.; Zundel, G. J Mol Struct 2001, 565, 213.