Tin(IV) cyanoximates: Synthesis, characterization, and cytotoxicity

Inorganic Chemistry

Volumn 46, Issue 18, 2007, Pages 7268-7284

  Gerasimchuk, Nikolay ^a   Maher, Tiffany ^a   Durham, Paul ^a   Domasevitch, Konstantin V ^b   Wilking, Janet ^c   Mokhir, Andrew ^d  

^a MISSOURI STATE UNIVERSITY   (United States)

^b TARAS SHEVCHENKO NATIONAL UNIVERSITY OF KYIV   (Ukraine)

^c UNIVERSITY OF MISSOURI ST LOUIS   (United States)

^d UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALI METAL; ANION; CYANIDE; LIGAND; ORGANOTIN COMPOUND; OXIME; SILVER; THALLIUM; TIN DERIVATIVE;

ARTICLE; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; HUMAN; SPECTROSCOPY; SYNTHESIS; TEMPERATURE; TUMOR CELL LINE; X RAY CRYSTALLOGRAPHY;

ANIONS; CELL LINE, TUMOR; CELL SURVIVAL; CRYSTALLOGRAPHY, X-RAY; CYANIDES; HUMANS; LIGANDS; METALS, ALKALI; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOTIN COMPOUNDS; OXIMES; SILVER; SPECTRUM ANALYSIS; TEMPERATURE; THALLIUM; TIN COMPOUNDS;

EID: 34548606719     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic061354f     Document Type: Article

References (163)

1. (a) Medicinal Inorganic Chemistry. Special Thematic Issue. Chem. Rev. 1999, 99 (9).
2. (b) Blower, P. B. Inorganic Pharmaceuticals. Annu. Rep. Prog. Chem., Sect. A 2001, 97, 587-603.
3. Medicinal Inorganic Chemistry; Sessler, J. L., Doctrow, S. R., McMurry, J., Lippard, S. J., Eds.; American Chemical Society Symposium Series 903; American Chemical Society: Washington, DC, 2005.
4. (a) Wong, E.; Giandomenico, C. M. Chem. Rev. 1999, 99 (9), 2451.
5. (b) Alderdeen, R. A.; Hall, M. D.; Hambley, T. W. J. Chem. Educ. 2006, 83 (5), 728-734.
6. (a) Platinum and Other Coordination Compounds in Cancer Chemotherapy; Nikolini, M., Ed.; Martinus-Nijhoff Publishing: Boston, MA, 1988.
7. (b) Köpf-Maier, P. Eur. J. Clin. Pharm. 1994, 47 (1), 1-16.
8. (c) Kranz, F.; Shutte, M. T. Cancer J. 1998, 11 (4), 176-182.
9. (a) Martin, Y. C. Quantitative Drug Design; Dekker: New York, 1978.
10. (b) Quantitative Structure-Activity Relationships of Drugs; Topliss, G. G., Ed.; Academic Press: New York, 1983.
11. (a) Nagy, L.; Szorcsik, A.; Kovacs, K. Pharm. Hungarica 2000, 70 (2), 53-71.
12. (b) Nath, M.; Pokharia, S.; Yadav, R. Coord. Chem. Rev. 2001, 215, 99-149.
13. (c) Gielen, M. Cytotoxic, Mutagenic and Carcinogenic Potential of Heavy Metals Related to Human Environment. In Tin-Based Antitumor Drugs; NATO ASI Ser., Ser. 2, 1997, 26, 445-455.
14. (d) De Vos, D.; Willem, R.; Gielen, M.; Van Wingerden, K. E.; Nooter, K. Metal-Based Drugs. 1998, 5 (4), 179-188.
15. (e) Pettinari, C. Main Group Met. Chem. 1999, 22 (11), 661-692.
16. (f) Crowe, A. J. Antitumor activity of tin compounds. In Metal Compounds in Cancer Therapy; Flicker, S. P., Ed.; Chapman & Hall: London, UK, 1994; 147-179.
17. (a) Li, Q.; Liu, R.-L.; Huang, J.-J.; Yang, P. Gaodeng Xuexiao Huaxue Xuebao 2000, 21 (4), 513-516.
18. (b) Li, Q.; Jin, N.; Yang, P.; Wan, J.; Wu, W.; Wan, J. Synt. React. Inorg. Met.-Org. Chem. 1997, 27 (6), 811-823.
19. (c) Li, Q.; Yang, P.; Hua, E.; Tian, C. J. Coord. Chem. 1996, 40 (3), 227-236.
20. (d) Casas, J. S.; Castellano, E. E.; Couce, M. D.; Ellena, J.; Sanchez, A.; Sanchez, J. L.; Sordo, J.; Taboada, C. Inorg. Chem. 2004, 43 (6), 1957-1963.
21. (e) Li, Q.; Yang, P.; Wang, H.; Guo, M. J. Inorg. Biochem. 1996, 64 (3), 181-195.
22. (a) Arakawa, Y. Biomed. Res. Trace Elem. 1993, 4 (2), 129-130.
23. (b) Arakawa, Y. Biomed. Res. Trace Elem. 2000, 11 (3), 259-286.
24. Song, X.; Zapata, A.; Eng, G. J. Organomet. Chem. 2006, 691, 1756-1760.
25. (a) Gielen, M. Appl. Organomet. Chem. 2002, 16, 481-494.
26. (b) Bulten, E. J.; Budding, H. A. British Patent 2077266, 1981.
27. (c) Meinema, H. A.; Liebregts, A. M. J.; Budding, H. A.; Bulten, E. J. Rev. Silicon, Germanium, Tin, Lead Compd. 1985, 8, 157.
28. (d) Gielen, M.; El Khloufi, M.; Biesemans, M.; Willem, R. Appl. Organomet. Chem. 1993, 7, 119-125.
29. (e) Gielen, M.; Biesemans, M.; El Khloufi, A.; Meunier-Piret, J.; Kayser, F.; Willem, R. J. Fluorine Chem. 1993, 64, 279-291.
30. (f) Gielen, M.; El Khloufi, A.; De Vos, D.; Kolker, H. J.; Schellens, J. H. M.; Willem, R. Bull. Soc. Chim. Belg. 1993, 102, 761-764.
31. (g) Camacho, C. C.; De Vos, D.; Mahieu, R.; Gielen, M.; Kemmer, M.; Biesemans, M.; Willem, R. Main Group Metal Chem. 2000, 23 (7), 381-386.
32. (h) Willem, R.; Bouhdid, A.; Mahieu, B.; Ghys, L.; Biesemans, M.; Tiekink, E. R.; De Vos, D.; Gielen, M. J. Organomet. Chem. 1997, 531 (1-2), 151-158.
33. (a) Lascourreges, J.-F.; Caumette, P.; Donard, O. F. X. Appl. Organomet. Chem. 2000, 14, 98-107.
34. (b) Smith, P. J. In Toxicological Data On Organotin Compounds; Publication #538, International Tin Research Institute: UK, 1978.
35. (c) Browning, F. Toxicity of Industrial Metals, 2nd ed.; Butterworths: London, 1969.
36. (d) Ishiwata, H.; Inone, T.; Yoshira, K. Bull Environ. Contam. Toxicol. 1986, 37, 638.
37. (e) Schaeppi, U.; Heyman, I. A.; Fleischman, R. W.; Rosenkrantz, H.; Ilievski, V.; Phelan, R.; Cooney, D. A.; Davis, R. D. Toxicol. Appl. Pharmacol. 1973, 25, 230-241.
38. (f) Milne, D. B. Biochemical Elements 1984, 3, 309-318.
39. (a) De Vos, D.; Willem, R.; Gielen, M.; Van Wingerden, K. E.; Nooter, K. Metal-Based Drugs 1998, 5 (4), 179-188.
40. (b) Syng-Ai, C.; Basu, B. T. S.; Chatterjee, A. Mutat. Res. 2002, 513 (1-2), 49-59.
41. (c) Syng-Ai, Basu, B.; Chatterjee, A. J. Environ. Pathol., Toxic. Oncol. 2001, 20 (4), 333-342.
42. (d) Gielen, M.; El Khloufi, A.; Biesemans, M.; Willem, R. Meunier-Piret, J. Polyhedron 1992, 11 (15), 1861-1868.
43. (e) Kovala-Demertzi, D.; Tauridou, P.; Russo, U.; Gielen, M. Inorg. Chim. Acta 1995, 239 (1-2), 177-183.
44. (f) Pettinari, C. Main Group Met. Chem. 1999, 22 (11), 661-692.
45. (g) Boo, P. A.; Caas, J. S.; Couce, M. D.; Freijanes, E.; Furlani, A.; Scarcia, V.; Sordo, J.; Russo, U.; Varela, M. Appl. Organomet. Chem. 1997, 11 (12), 963-968.
46. (a) Cagnoli, M.; Alama, A.; Barbieri, F.; Novelli, F.; Bruzzo, C.; Sparatore, F. Anti-Cancer Drugs 1998, 9 (7), pp. 603-610.
47. (b) Kemmer, M.; Gielen, M.; Biesemans, M.; De Vos, D.; Willem, R. Metal-Based Drugs 1998, 5 (4), 189-196.
48. (c) Colvin, M. In Pharmacologic Principles of Cancer Treatments; Chabner, B., Ed.; W. B. Saunders: Philadelphia, PA, 1982.
49. (a) Sakakibara, H.; Naganawa, H.; Ohno, M.; Maeda, K.; Umezawa, H. J. Antibiot. 1974, 27 (11), 897-899.
50. (b) Mongin, F.; Trecourt, F.; Gervais, B.; Mongin, O.; Queguiner, G. J. Org. Chem. 2002, 67, 3272-3276 (and references therein).
51. (a) Domasevitch, K. V.; Gerasimchuk, N. N. Ukr. Khim. Zh. 1992, 58 (8), 603-607.
52. (b) Gerasimchuk, N. N.; Domasevitch, K. V. Russ. J. Inorg. Chem. 1992, 37 (10), 1163-1167.
53. (c) Gerasimchuk, N. N.; Kuzmann, E.; Buki, A.; Vertes, A.; Nagy, L.; Burger, K. Inorg. Chim. Acta 1991, 188 (11), 45-50.
54. (a) Eddings, D.; Barnes, C.; Gerasimchuk, N.; Durham, P.; Domasevich, K. V. Inorg. Chem. 2004, 43 (13), 3894-3909.
55. (b) Soga, S.; Neckers, L. M.; Schulte, T. W.; Shiotsu, Y.; Akasaka, K.; Narumi, H.; Agatsuma, T.; Ikuina, Y.; Murakata, C.; Tamaoki, T.; Akinaga, S. Cancer Res. 1999, 59, 2931-2938.
56. (a) Davidson, S. H. 2-Cyano-2-hydroximinoacetamides as Plant Disease Control Agents. U.S. Patent 3957847, 1978.
57. (b) Skopenko, V. V.; Palii, G. K.; Gerasimchuk, N. N.; Makats, E. F.; Domashevskaya, O. A.; Rakovskaya, R. V. Nitrosothiocarbamylcyanmethanide of Potassium or Sodium which Show Antimicrobial Activity. USSR Patent 1405281, 1988.
58. (c) Palii, G. K.; Skopenko, V. V.; Gerasimchuk, N. N.; Makats, E. F.; Domashevskaya, O. A.; Rakovskaya, R. V. Bis-(Nitrosothiocarbamylcyanmethanide) Copper-(II) or Nickel(II) which Exhibit Antimicrobial Activity. USSR Patent 1405282, 1988.
59. (d) Skopenko, V. V.; Palii, G. K.; Gerasimchuk, N. N.; Domashevskaya, O. A.; Makats, E. F. Di-(Nitrosothiocarbamylcyanmethanide)-di-(pyridine)-copper which Shows Bacteriostatic Activity Towards Staphilococcus Aureus, and Method of Preparation of the Complex. USSR Patent 1487422, 1989.
60. (a) Lin, K. Process for making 2-cyano-2-hydroximino acetamide salts. U.S. Patent 3919284, 1976.
61. (b) Kuhne, A.; Hubele, A. Method for the Cultivation of Plants Employing α-Cyanohydroximinoacetamide Derivatives. U.S. Patent 4063921, 1978.
62. (a) Wang, P.; Wang, R.; Dai, J.; Wu, X.; Xu, J. Yaoxue Xuebao 1996, 31, 918-924.
63. (b) Wang, P.; Xu, J.; Yin, W.; Wu, R.; Wang, R. Nongyao 1998, 37, 14-15.
64. (a) Ciba Geigy AG. Srodek Ochrony Roslin Przed Dzialaniem Agresywnych Chemikalii Rolniczych. Poland Patent 127786, 1985.
65. (b) Ciba Geigy AG. Mittel zum Schutz von Kulturphflanzen von Agressiven Herbizidden. Austria Patent 367268, 1982.
66. Tirapazamine: Radiation sensitizer and chemotherapy anticancer drug in combination with cisplatin in Phase I and Phase II clinical trials by National Cancer Institute, 2005.
67. Carmustine and Lomustine: Anticancer drugs by Bristol-Myers Squibb; Physician Desk Reference, 51st Ed., 1997, pp 696, 699.
68. Mokhir, A. A.; Gerasimchuk, N. N.; Pol'shin, E. V.; Domasevich, K. V. Russ. J. Inorg. Chem. 1994, 39 (2), 289-293.
69. (a) Gielen, M.; Willem, R. Anticancer Res. 1992, 12 (4), 1323-1325.
70. (b) Boualam, M.; Willem, R.; Biesemans, M.; Mahieu, B.; Meunier-Piret, J.; Gielen, M. Main Group Met. Chem. 1991, 14 (1), 41-56.
71. (c) Gielen, M.; El Khloufi, A.; Biesemans, M.; Kayser, F.; Willem, R. Appl. Organomet. Chem. 1993, 7 (3), 201-206.
72. (d) Gielen, M.; De Vos, D.; Meriem, A.; Bouâlam, M.; El Khloufi, A.; Willem, R. In Vivo 1993, 7 (2), 171-174.
73. (e) Gielen, M.; Willem, R. Anticancer Res. 1992, 12 (1), 257-268.
74. (f) Zuo, D.-S.; Jiang, T.; Guan, H.-S.; Qi, X.; Wang, K.-Q.; Shi, Z. Chin. J. Chem. 2001, 19 (11), 1141-1145.
75. (g) Casini, A.; Messori, L.; Orioli, P.; Gielen, M.; Kemmer, M; Willem, R. J. Inorg. Biochem. 2001, 85 (4), 297-300.
76. (h) Mancilla, T.; Carrillo, L.; Rivera, L. S. Z.; Camacho, C. C.; De Vos, D.; Kiss, R.; Darro, F.; Mahieu, B.; Tiekink, E. R. T.; Rahier, H.; Gielen, M.; Kemmer, M.; Biesemans, M.; Willem, R. Appl. Organomet. Chem. 2001, 15 (7), 593-603.
77. Meyer, V. Ber. Dtsch. Chem. Ges. 1873, 6, s.1492.
78. Mokhir, A. A.; Domasevich, K. V.; Dalley, N. K.; Kou, X.; Gerasimchuk, N. N.; Gerasimchuk, O. A. Inorg. Chim. Acta 1999, 284, 85-98.
79. The Chemistry of the Nitro-and Nitroso-Groups; Feuer, H., Ed.; R. Krieger Publishing Co.: Huntington, NY, 1981; part 1.
80. Reichardt, C. Solvents and solvent effects in organic chemistry, 3rd ed.; Wiley-VCH: New York, 2003.
81. (a) Zamudio-Rivera, L. S.; George-Tellez, R.; Lopez-Mendoza, G.; Morales-Pacheco, A.; Flores, E.; Hopfl, H.; Barba, V.; Fernandez, F.; Cabirol, N.; Beltran, H. Inorg. Chem. 2005, 44 (15), 5370-5378.
82. (b) Di Nicola, C.; Galindo, A.; Hanna, J. V.; Marchetti, F.; Pettinari, C.; Pettinari, R.; Rivarola, E.; Skelton, B.; White, A. H. Inorg. Chem. 2005, 44 (9), 3094-3102.
83. (c) Jing, H.; Edulji, S. K.; Gibbs, J. M.; Stern, C. L.; Zhou, H.; Nguyen, S. T. Inorg. Chem. 2004, 43 (14), 4315-4327.
84. Domasevitch, K. V.; Gerasimchuk, N. N.; Mokhir, A. A. Inorg. Chem. 2000, 39 (6), 1227-1237.
85. (a) Longo, G. Gazz. Chim. Ital. 1931, 61, 575-583.
86. (b) Chou, Y. M.; Britton, D. Acta Cryst. 1974, B30, 1117-1118.
87. (c) Skopenko, V. V.; Ponomareva, V. V.; Simonov, Y. A.; Domasevich, K. V.; Dvorkin, A. A. Russ. J. Inorg. Chem. 1994, 39 (8), 1270-1277.
88. (a) Gerasimchuk, N. N.; Tchernega, A. N.; Kapshuk, A. A. Russ. J. Inorg. Chem. 1993, 38 (9), 1530-1534.
89. (b) Gerasimchuk, N. N.; Nagy, L.; Schmidt, H.-G.; Noltemeyer, M.; Bohra, R.; Roesky, H. W. Z. Naturforsch. 1992, 47b, 1741-1745.
90. Zhmurko, O. A.; Skopenko, V. V.; Gerasimchuk, N. N. Dokl. Akad. Nauk Ukr. RSR 1989, B (4), 37-41.
91. (a) Domasevitch, K. V. Russ. J. Gen. Chem. 1997, 67 (12), 1937-1943.
92. (b) Skopenko, V. V.; Lampeka, R. D. Russ. J. Inorg. Chem. 1982, 27 (12), 3117-3119.
93. (c) Köhler, H.; Seifert, B. Z. Z. Anorg. Allg. Chem. 1970, 379 (1), 1-8.
94. Parish, R. V. NMR, NQR EPR and Mössbauer Spectroscopy in Inorganic Chemistry; Ellis Horwood: New York, London, Toronto, Sydney, Tokyo, Singapore, 1990.
95. (a) Kaur, A.; Sandhu, G. K. J. Chem. Sci. 1986, 12, 1-17.
96. (b) Schlemper, E. O. Inorg. Chem. 1967, 6 (11), 2012-2017.
97. The Mössbauer Effect and Its Application in Chemistry; Siedel, C. W., Ed.; American Chemical Society Series, Vol. 68, American Chemical Society: Washington DC, 1967.
98. Ruddick, J. N. R.; Sams, J. R. J. Chem. Soc., Dalton Trans. 1974, 470-474.
99. King, T. J.; Harrison, P. G. J. Chem. Soc, Chem. Comm. 1972, 815.
100. (a) Goldanskii, V. I.; Gorodinski, G. M.; Karyagin, S. V. Dokl. AN USSR, Phizika. 1962, 147 (1), 127-130.
101. (b) Karyagin, S. V. Dokl. AN USSR, Phizika. 1963, 148 (5), 1102-1105.
102. (a) Kayser, F.; Biesemans, M.; Boualam, M.; Tiekink, E. R. T.; El Khloufi, A.; Meunier-Piret, J.; Bouhdid, A.; Jurkschat, K.; Gielen, M.; Willem, R. Organometallics 1994, 13, 1098-1113.
103. (b) Meddour, A.; Bouhdid, A.; Gielen, M.; Biesemans, M.; Mercier, F.; Tiekink, E. R. T.; Willem, R. Eur. J. Inorg. Chem. 1998, 1467-1472.
104. (a) Mercier, F. A. G.; Meddour, A.; Gielen, M.; Biesemans, M.; Willem, R. Organometallics 1998, 17, 5933-5936.
105. (b) Willem, R.; Bouhdid, A.; Meddour, A.; Camacho-Camacho, C.; Mercier, F.; Gielen, M.; Biesemans, M.; Ribot, F.; Sanchez, C.; Tiekink, E. R. T. Organometallics 1997, 16, 4377-4385.
106. (c) Willem, R.; Bouhdid, A.; Kayser, F.; Delmotte, A.; Gielen, M.; Martins, J. C.; Biesemans, M.; Mahieu, B.; Tiekink, E. R. T. Organometallics 1996, 15, 1920-1929.
107. (a) Lockhart, T. P.; Manders, W. F. Inorg. Chem. 1986, 25, 892-897.
108. (b) Lockhart, T. P.; Manders, W. F.; Zuckerman, J. J. J. Am. Chem. Soc. 1985, 107, 4546-4550.
109. Davies, A. G. Organotin Chemistry; Wiley-VCH: Weinheim, Germany, 2004.
110. (a) Puff, H.; Bung, I.; Friedrichs, E.; Jansen, A. J. Organomet. Chem. 1983, 254, 23.
111. (b) Harrison, P. G.; Begley, M. J.; Molloy, K. C. J. Organomet. Chem. 1980, 186, 213.
112. (c) Vollano, J. F.; Day, R. O.; Holmes, R. R. Organometallics 1984, 3, 745-750.
113. (d) Okawara, R.; Wada, M. J. Organomet. Chem. 1963, 1, 81.
114. (a) Barbieri, R.; Silvestri, A. Inorg. Chim. Acta 1991, 188, 95-98.
115. (b) Jankovics, H.; Nagy, L.; Buzas, N.; Pellerito, L.; Barbieri, R. J. Inorg. Biochem. 2002, 92, 55-64.
116. (c) Abd-Alla, E. M. Monatsh. Chem. 2003, 134, 1177-1184.
117. (d) Guli, G.; Gennaro, G.; Pellerito, L.; Stocco, G. C. Appl. Organomet. Chem. 1993, 7, 407-412.
118. (e) Pellerito, L.; Maggio, F.; Fiore, T.; Pellerito, A. Appl. Organomet. Chem. 1996, 10, 393-404.
119. Domingos, A. M.; Sheldrick, G. M. J. Chem. Soc, Dalton Trans. 1974, 475-477.
120. Mitzel, N. W.; Lustig, C.; Scharfe, S. Z. Naturforsch. 2001, 56b, 440-442.
121. (a) Ma, C.-L.; Li, F. Chin. J. Chem. 2003, 21, 146-152.
122. (b) Kresinski, R. A.; Staples, R. J.; Fackler, J. P. Acta Crystallogr. 1994, C50, 40-41.
123. (c) Alcock, N. W.; Pennington, M.; Willey, G. R. J. Chem. Soc., Dalton Trans. 1985, 2683-2686.
124. Holmes, R. R.; Schmid, C. G.; Chandrasekhar, V.; Day, R. O.; Holmes, J. M. J. Am. Chem. Soc. 1987, 109, 1408-1414.
125. Swamy, K. K. C.; Day, R. O.; Holmes, R. R. J. Am. Chem. Soc. 1987, 109, 5546-5548.
126. Chandrasekhar, V.; Schmid, C. G.; Burton, S. D.; Holmes, J. M.; Day, R. O.; Holmes, R. R. Inorg. Chem. 1987, 26 (7), 1050-1056.
127. Mehring, M.; Giuseppina, G.; Hadjikakou, S.; Schurmann, M.; Dakternieks, D.; Jurkschat, C. Chem. Comm. 2002, 834-835.
128. Gerasimchuk, N. N.; Skopenko, V. V.; Ponomareva, V. V.; Domasevitch, K. V. Russ. J. Inorg. Chem. 1993, 38 (6), 964-970.
129. Domasevitch, K. V.; Skopenko, V. V.; Rusanov, E. B. Z. Naturforsch. 1996, 51b, 832-837.
130. Domasevitch, K. V.; Skopenko, V. V.; Sieler, J. Inorg. Chim. Acta 1996, 249 (2), 151-155.
131. (a) Emsley, J. The Elements; Clarendon Press: Oxford, UK, 1991.
132. (b) Gordon, A. J.; Ford, R. A. The Chemist Companion (Handbook); John Wiley & Sons: New York, Chichester, Brisbane, Toronto, 1972.
133. Dean, J. A. Lange's Handbook of Chemistry, 14th ed.; McGraw-Hill: New York, 1992; p 4.11.
134. Lloyd, N. C.; Morgan, H. W.; Nicholson, B. K.; Ronimus, R. S. Angew. Chem., Int. Ed. 2005, 44, 941.
135. (a) Gielen, M.; Willem, R.; Biesemans, M.; Kemmer, M.; De Vos, D. Patent of Holland by Pharmachemie B. V. US: 6,407,265 (June, 18/2002); Europe: EP (1100804) (September, 10/2002).
136. (b) Gielen, M.; Willem, R.; Bouhdid, A.; De Vos, D. Patent of Holland by Pharmachemie B. V. US: 5,583,157 (December, 10/ 2002); Europe: EP 0677528 (March, 29/2002).
137. (c) Gielen, M.; Willem, R.; Bouhdid, A.; De Vos, D. Patent of Holland by Pharmachemie B. V. US: 5,559,147 (September, 24/1996); Europe: EP 0700291 (February, 2/2000).
138. (d) Boualam, M.; Gielen, M.; El Khloufi, A.; De Vos, D.; Willem, R. Patent of Holland by Pharmachemie B. V. US: 5,382,597 (January, 17/1995); Europe: EP 0538517 (January, 17/1996).
139. (e) Pellerito, C.; Nagy, L.; Pellerito, L.; Szorcsik, A. J. Organomet. Chem. 2006, 691, 1733-1747.
140. (f) Tabassum, S.; Pettinari, C. J. Organomet. Chem. 2006, 691, 1761-1766.
141. (a) Yang, P.; Wang, L.; Wang, L.; Li, Q.; Ding, J. Chinese patent CN 1238338 (June 2, 1999).
142. (b) Yin, H.; Ma, C. Huaxue Yanjiu 1999, 10 (4), 54-60.
143. (c) Yang, P.; Wang, L.; Wang, L.; Ding, J. Chinese patent CN 1238335 (June 2, 1999).
144. (d) Yang, P.; Wang, L.; Ding, J. Chinese patent CN 1238336 (June 2, 1999).
145. Teva Pharmaceuticals: http://www.tevapharm.com/research and its subsidiary Pharmachemie: http://www.pharmachemie.com/pharmachemie/index.cfm.
146. Kreshkov, A. P. Fundamentals of Analytical Chemistry. Vol. 2; Khimia: Moscow, 1970; p 390.
147. Sheldrick, G. M. SADABS Area-Detector Absorption Correction, version 2.03; University of Göttingen, Göttingen, Germany, 1999.
148. Sheldrick, G. M. SHELXS-97: Computer programs for the solution and refinement of X-ray crystal structures. University of Göttingen, Göttingen, Germany, 1997.
149. Spek, A. L. J. Appl. Crystallogr. 2003, 36, 7.
150. (a) Farrugia, L. J. Appl. Crystallogr. 1997, 30, 565.
151. (b) Burnett, M. N.; Johnson, C. K. ORTEP III: Report ORNL-6895; Oak Ridge National Laboratory: Oak Ridge, TN, 1996.
152. Gerasimchuk, N. N.; Dalley, N. K. J. Coord. Chem. 2004, 57 (16), 1431-1445.
153. Lukaszczyk, A.; Martin, H.; Diel, P.; Fory, W.; Gatzi, C.; Kristinson, H.; Muller, B.; Muntwyler, R.; Pachlatko, J. P. Oxime derivatives and their use in the protection of cultivated plants. (Ciba-Geigy A. G., Switzerland), European Patent 12158 A2, 1980.
154. Robertson, D.; Cannon, J. F.; Gerasimchuk, N. Inorg. Chem. 2005, 44 (23), 8326-8342.
155. Noyes, W. A. Organic Syntheses; Wiley & Sons: New York, 1943; Vol. 2, p 108.
156. Domashevskaya, O. A.; Mazus, M. D.; Gerasimchuk, N. N.; Dvorkin, A. A.; Simonov, Y. A. Russ. J. Inorg. Chem. 1989, 34 (7), 1656-1660.
157. Gerasimchuk, N. N.; Zhmurko, O. A.; Tyukhtenko, S. I. Russ. J. Inorg. Chem. 1993, 38 (2), 282-287.
158. Domasevich, K. V.; Gerasimchuk, N. N.; Rusanov, E. B.; Gerasimchuk, O. A. Russ. J. Gen. Chem. 1996, 66 (4), 635-640.
159. Fedorenko, D. A.; Gerasimchuk, N. N.; Domasevich, K. V. Russ. J. Inorg. Chem. 1993, 38 (9), 1433-1436.
160. Culture of Animal Cells: A Manual of basic technique, 4th ed.; Freshney, R. I., Ed., Wiley-Liss Inc.: New York, 2000.
161. Matter, T. Synthesis, Characterization and Anti-Cancer Properties of Organotin(IV) Cyanoximates. M.S. Thesis (132 pp, 24 tables, 52 figures), Department of Chemistry, Southwest Missouri State University, Springfield, MO, 2004.
162. (a) Glaser, J. In Advances in Inorganic Chemistry; Sykes, A. J., Ed.; Academic Press: San Diego, 1995; Vol. 43, p 1.
163. (b) Heydlauf, H. Eur. J. Pharmacol. 1969, 6, 340.