Controlled crystallization, structure, and molecular properties of iodoacetylamphotericin B

Crystal Growth and Design

Volumn 12, Issue 5, 2012, Pages 2336-2345

  Jarzembska, Katarzyna N ^a   Kamiński, Daniel ^b   Hoser, Anna A ^a   Malińska, Maura ^a   Senczyna, Bogusław ^b   Woźniak, Krzysztof ^a   Gagoś, Mariusz ^b,c  

^a UNIVERSITY OF WARSAW   (Poland)

^b UNIVERSITY OF LIFE SCIENCES IN LUBLIN   (Poland)

^c MARIA CURIE SK ODOWSKA UNIVERSITY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHOTERICIN; AMPHOTERICIN B; COHESIVE ENERGIES; COMPUTATIONAL STUDIES; CONTROLLED CRYSTALLIZATION; CRYSTAL PACKINGS; CRYSTALLIZATION PROCESS; ELECTROSTATIC POTENTIAL MAPS; INTERMOLECULAR CONTACTS; INTERMOLECULAR INTERACTIONS; LATTICE FORMATION; MOLECULAR PROPERTIES; NITROGEN ATOM; SINGLE POINT; SOLVENT MOLECULES; STRUCTURAL INFORMATION; TOTAL ENERGY; X-RAY STRUCTURE; ZWITTERION FORMATION;

HYDROGEN BONDS; SURFACE ANALYSIS;

DIMERS;

EID: 84860472606     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg2017227     Document Type: Article

References (62)

1. Omura, S. Macrolide Antibiotics, Chemistry, Biology and Practice, 2nd ed.; Omura, S., Ed.; Academic Press Inc.: New York, 2002; p 623.
2. Omura, S.; Tanaka, H. Production, structure and antifungal activity of polyene macrolides. In Macrolide Antibiotics; Omura, S, Ed.; Academic Press, Inc.: Orlando, 1984; pp 351-404
3. Hay, R. J. Recent Advances in the Chemistry of Antifungal Agents; Bentley, P. H.; Ponsdorf, R., Eds.; Royal Society of Chemistry: Cambridge, U.K., 1993; pp 163-181.
4. Woodward, R. B. Angew. Chem., Int. Ed. 1957, 69, 50-58
5. Ellis, D. J. Antimicrob. Chemother. 2002, 49, 7-10
6. Dutcher, J. D.; Gold, W.; Pagano, J. F.; Vandepatte, J. Amphotericin B, its production and its salts. Patent U.S. 2,908,611, 1959
7. Gold, W.; Stout, H. A.; Pagano, J. F.; i Donovick, R. Antibiot. Ann. 1956, 579-585
8. Lemke, A.; Kiderlen, A. F.; Kayser, O. Appl. Microbiol. Biotechnol. 2005, 68, 151-62
9. Sternberg, T. M.; Wright, E. T.; Oura, M. Antibiot. Ann. 1956, 3, 566-573
10. Trejo, W. H.; Bennett, R. E. J. Bacteriol. 1963, 85, 436-439
11. Challis, G. L.; Hopwood, D. A. Proc. Natl. Acad. Sci. U. S. A. 2003, 100, 14555-14561
12. Hartsel, S.; Bolard, J. Trends Pharmacol. Sci. 1996, 17, 445-9
13. Cereghetti, D. M.; Carreira, E. M. Synthesis-Stuttgart 2006, 6, 914-942
14. Ng, A. W. K.; Wasan, K. M.; Lopez-Berestein, G. J. Pharm. Pharm. Sci. 2003, 6, 67-83
15. Gold, W.; Stout, H. A.; Pagano, J. F.; i Donovick, R. Antibiot. Ann. 1956, 579-585
16. Gallis, H. A.; Drew, R. H.; Pickard, W. W. Amphotericin Rev. Infect. Dis. 1990, 12, 308-329
17. Gagoś, M.; Arczewska, M. Biochim. Biophys. Acta 2010, 1798 (11) 2124-30
18. 2010, 1798, 2124-2130.
19. Gagoś, M.; Arczewska, M. J. Phys. Chem. B 2011, 115, 3185-3192
20. Gagoś, M.; Arczewska, M.; Gruszecki, W. I. J. Phys. Chem. B 2011, 115, 5032-5036
21. Gagoś, M.; Hereć, M.; Arczewska, M.; Czernel, G.; Dalla Serra, M.; Gruszecki, W. I. Biophys. Chem. 2008, 136, 44-49
22. Gagoś, M.; Koper, R.; Gruszecki, W. I. Biochim. Biophys. Acta 2001, 1511, 90-98
23. De Kruijff, B.; Gerritsen, W. J.; Oerlemans, A.; Demel, R. A.; van Deenen, L. L. Biochim. Biophys. Acta 1974, 339, 30-43
24. Andreoli, T. E. Ann. N. Y. Acad. Sci. 1974, 235, 448-468
25. Czub, J.; Borowski, E.; Baginski, M. Biochim. Biophys. Acta-Biomembr. 2007, 1768, 2616-2626
26. Cohen, B. E. Biochim. Biophys. Acta 1986, 857, 117-122
27. Cohen, B. E. Biochim. Biophys. Acta 1992, 1108, 49-58
28. Nicolaou, K. C.; Daines, R. A.; Chakraborty, T. K.; Ogawa, Y. J. Am. Chem. Soc. 1987, 109, 2821-2822
29. Ganis, P.; Avitabile, G.; Mechlinski, W.; Schaffner, C. P. J. Am. Chem. Soc. 1971, 93, 4560-4564
30. Sowinski, P.; Pawlak, J.; Borowski, E.; i Gariboldi, P. Magn. Reson. Chem. 1992, 30, 275-279
31. Petersen, N. O.; Henshaw, P. F. Can. J. Chem.-Rev. Can. Chim. 1981, 59, 3376-3378
32. Wright, J. J. Derivatives of polyene macrolide antibiotics containing an amino sugar moiety, process for the preparation thereof, and pharmaceutical compositions containing them. Patent U.S. 4272525, 1980.
33. Sheldrick, G. M. Acta Crystallogr. 2008, A64, 112-122
34. APEX2, 2010.3-0; Bruker AXS Inc.: Madison, WI, USA: 2010
35. SAINT, 7.68A; Bruker AXS Inc.: Madison, WI, USA, 2010.
36. Hirshfeld, F. L. Theor. Chim. Acta 1977, 44, 129-138
37. Spackman, M. A.; Jayatilaka, D. CrystEngComm 2009, 11, 19-32
38. Dovesi, R.; Saunders, V. R.; Roetti, R.; Orlando, R.; Zicovich-Wilson, C. M.; Pascale, F.; Civalleri, B.; Doll, K.; Harrison, N. M.; Bush, I. J.; D'Arco, P.; Llunell, M. CRYSTAL09 (CRYSTAL09 User's Manual); University of Torino: Torino, 2009.
39. Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100
40. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
41. Perdew, J. P. Phys. Rev. B 1986, 33, 8822-8824
42. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650-654
43. Civalleri, B.; Zicovich-Wilson, C. M.; Valenzano, L.; Ugliengo, P. CrystEngComm 2008, 10, 405-410
44. Grimme, S. J. Comput. Chem. 2006, 27, 1787-1799
45. Allen, F. H.; Bruno, I. J. Acta Crystallogr. 2010, B66, 380-386
46. Weissbuch, I.; Addadi, L.; Berkovitchyellin, Z.; Gati, E.; Weinstein, S.; Lahav, M.; Leiserowitz, L. J. Am. Chem. Soc. 1983, 105, 6615-6621
47. Punin, Y. O.; Franke, V. D. Crystallogr. Rep. 2004, 49, 256-260
48. Hollander, F. F. A.; Kaminski, D.; Duret, D.; van Enckevort, W. J. P.; Meekes, H.; Bennema, P. Food Res. Int. 2002, 35, 909-918
49. Baginski, M.; Gariboldi, P.; Bruni, P.; Borowski, E. Biophys. Chem. 1997, 65, 91-100
50. Mazerski, J.; Borowski, E. Biophys. Chem. 1995, 54, 49-60
51. Sowinski, P.; Pawlak, J.; Borowski, E.; Gariboldi, P. Magn. Reson. Chem. 1992, 30, 275-279
52. Baginski, M.; Resat, H.; Borowski, E. Biophys. J. 1999, 76, A244-A244
53. Hirshfeld, F. L. Acta Crystallogr. 1976, A32, 239-244
54. McKinnon, J. J.; Mitchell, A. S.; Spackman, M. A. Chem.-Eur. J. 1998, 4, 2136-2141
55. Wolff, S. K.; Grimwood, D. J.; McKinnon, J. J.; Jayatilaka, D.; Spackman, M. A. CrystalExplorer, 2.1 (381); University of Western Australia: Crawley, Western Australia, 2005-2007.
56. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; J. A. Montgomery, J.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, C.02; Gaussian, Inc.: Wallingford, CT, 2004
57. Jarzembska, K. N.; Dominiak, P. M. Acta Crystallogr. 2012, A68, 139-147
58. Volkov, A.; Macchi, P.; Farrugia, L. J.; Gatti, C.; Mallinson, P.; Richter, T.; Koritsanszky, T. XD2006-a computer program package for multipole refinement, topological analysis of charge densities and evaluation of intermolecular energies from experimental and theoretical structure factors, 2006.
59. Mulliken, R. S. J. Chem. Phys. 1955, 23, 1833-1840
60. Gagoś, M.; Gabrielska, J.; Dalla Serra, M.; Gruszecki, W. I. Mol. Membr. Biol. 2005, 22, 433-42
61. Hubschle, C. B.; Dittrich, B. J. Appl. Crystallogr. 2011, 44, 238-240
62. Dominiak, P. M.; Volkov, A.; Li, X.; Messerschmidt, M.; Coppens, P. JTCT 2007, 3, 232-247