BIOMEDICINAL ASPECTS OF GROUP-15 ELEMENTS (As,Sb,Bi)

PREETI RANI¹, PRAMILA GUPTA², RAVI KANT³*
¹Department of Chemistry, Mewar University, Chittorgarh, Rajasthan, India
²Department of Chemistry, Mewar University, Chittorgarh, Rajasthan, India
³Department of Chemistry, Mewar University, Chittorgarh, Rajasthan, India
* Corresponding Author : drravikant78@gmail.com

Received : 14-07-2017     Accepted : 12-08-2017     Published : 28-08-2017
Volume : 9     Issue : 1       Pages : 201 - 208
Int J Chem Res 9.1 (2017):201-208

Keywords : Biomedicinal Perspective, Organometallic, Antimicrobial, Entomological, Toxicological, Antitumor, and Gastroprotective activity
Conflict of Interest : None declared
Acknowledgements/Funding : Author are thankful to Department of Chemistry, Mewar University, Chittorgarh, Rajasthan, India
Author Contribution : All author equally contributed

The present review article deals the advancement in bioorganometallic and Metalopharmaceuticals applications and perspectives of group-15 elements in recent past. It is well known that organometallics of group-15 elements shows vast potentiality in biomedical research in past few years and used in the treatment of various chronic and acute diseases. The authors tried to compile literature regarding this area of research in the manuscript up to date along with brief out lines of medicinal importance of metals.

1. G.O. Doak and L.D. Freedman: Arsenicals, Antimonials and Bismuthicals in medicinal chemistry, Wiley Interscience, New York, 1973.
2. Charles E. Carraher Jr, and Charles U. Pittman Jr. "Organometallic compounds in Biomedical application", Macromolecules containing metal and metal like elements Vol. 3, 2004.
3. J.S. Thayer, J. Organometallic Chem., 76, 265, 1974.
4. W.G. Christiansen, "Organic derivatives of antimony", Chem. Catalog. Co., New York, 101, 1925.
5. A.K. Sijpesteyn, J.G.A. Luijten and G.J.M. Vander Kerk in D.C. Toregeson (Ed.), Fungicides: An advanced treatise, Academic Press, New York, 331, 1969.
6. J.M. Bernes and L. Magos, Organometal. Chem. Rev., 3, 137, 1968.
7. H.G. Langer, U.S. 3, 442, 922 (l. 260-429, 7; CO 7 F, A Qlm, A 61K), 06 May 1969, Appl. 09, Apr. 1964, 4 pp. Chem. Abstract; 72, 12880, 1970.
8. D. Varsanyl, A. Margot and F. Sohwinn, S. African 7006, 908, 04 June 1971, Swiss Appl. 15, 234/69, 10 Oct., 1969, 35 pp., Chem. Abstr., 76, 141928, 1972.
9. Mala Nath, Rakesh Yadav, G. Eng., Thanh-True-Nguyen, Ashok Kumar, J. Organomet. Chem. 577(1), 1-8, 1999
10. Mazahir Kidwai, Bhavesh Dave, P. Misra, R.K. Saxena, M. Singh, Inorg. Chem. Communications; 3, 465-468, 2000
11. Jr. C.E. Charles, Jr. P.U. Charles, Macromolecules, containing metal and metal like elements, 3, 1-19, 2004.
12. K.K. Soni, Alok Kumar, R. Kant, Inter. Jour. of Chem. Resear, 7(1), 159-163, 2015.; P.J. Sadler, H. Li, H. Sun; Coord. Chem. Rev., (185-186), 689-709, 1991
13. K.K. Soni, Alok Kumar, R. Kant, Inter. Jour. of Chem. Resear, 8(1),168-172, 2016.; H. Sun, H. Li, P.J. Sadler, Chem. Ber/Recucil, 130, 669-681, 1997.
14. G.G. Briand, N. Barlord, Chem. Rev., 99, 2601-2657, 1999.
15. D.W. Bierer, Rev. Infect. Dise., (12-1), 53-58, 1990.
16. B.J. Marshall, Am. J. Gastroenterol, 86, 16-25, 1991.
17. J.R. Rambert, Rev. Infect. Dis., (13-8), S 691-S695, 1991.
18. S.L. Gorbach, Gastroenterology, 99, 863-875, 1990.
19. G.F. Baxter, Chem. Brit., 445-448, 1992.
20. V.Z. Veldhuyzen, S.J.O., P.M. Sherman, Can. Med. Asso. J., 150, 189-198, 1994
21. V.Z. Veldhuyzen, S.J.O., P.M. Sherman, Can. Med. Asso. J., 150, 177-185, 1994.
22. H.L. DuPont, C.D. Ericsson, P.C. Johnson, F.J. delacabada, Rev. Infect. Dis., (12-1), S64-S67, 1990.
23. R. Steffen, Rev. Infect. Dis. (12-1), S80-S86, 1990.
24. S. Brücher, H.E, P. Avendano, M. O Ryan, H.A. Soriano, Rev. Infect. Dis., (12-1), S51-S56, 1990.
25. J.D. Gryboski, S. Kocoshis, Rev. Infect. Dis., (12-1), S36-S40, 1990.
26. J.R. Lambert, P. Midolo, Aliment. Pharmacol. Ther., (11-1), 27-33, 1997.
27. N. Chiba, Can. J. Gastroenterol, 14, 885-889, 2000.
28. U. Dittes, E. Vogel, B.K. Keppler, Coord. Chem. Rev., 163, 345-364, 1997.
29. Toshihiro Murafuji, Y. Miyoshi, M. Ishibashi, A.F.M. Mustafizur Rahman, Y. Sugihara, I. Miyakawa, H. Uno, J. Inorg. Biochem., 98, 547-552, 2004.
30. A.Dahlgren, C. Glogard, M. Gammelsacher, A.J. Aasen, J. Klevenss, B.P. Bardal, T. Bergan, Scand. J. Gastroenterol, 135-137, 1999.
31. W.A. Hermann, E. Herdtweek, L. Pajdla, Inorg. Chem., 30, 2579-2581, 1991.
32. E. Asato, K. Kamamuta, Y. Akamine, T. Fukami, R. Nukada, M. Mikuriya, S.Deguchi, Y. Yoikata, Bull. Chem. Soc. Japan, 70, 639-648, 1997.
33. M.A. Ghannoum, L.B. Rice, Clin. Microbiol. Rev. 12, 501-517, 1999.
34. I. Turel, L. Golic, P. Bukovec, M. Gubina, J. Inorg. Biochem., 71, 53-60, 1998.
35. P. Dominico, R.J. Salo, S.G. Novick, P.E. Schoch, K.V. Horn, B.A. Cunha, Antimicrobial agent Chemother, 41, 1697-1703, 1997.
36. C.W. Stratton, R.R.Warner, P.E. Coudron, N.A. Lilly, J. Antimicrobi. Chemother, 43, 659-666, 1999.
37. L. Agoes, G.G. Briand, N. Burford, T.S. Cameron, W.W. Kwiatkowski, K.N. Robertson, Inorg. Chem. 36, 2855-2860, 1997.
38. L. Agoes, N. Buford, T.S. Cameron J.M. Curtis, J.F. Richardson, K.M. Robertson, G.B. Yhard. J. Am. Chem. Soc., 118, 3225-3232, 1996.
39. T. Murafuji, M. Nagasue, Y. Tashiro, Y. Sugihara, N. Azuma, Organometallics, 19, 1003-1007, 2000.
40. D.E. Mahony, S.L. Morrison, L. Bryden, G. Faulkner, P.S. Hoftman, L. Agoes, G.G. Briand, N. Burford, H. Maguire, Antimicrobial. Agents and Chemother. 43(3), 582-588, 1999.
41. R. Asato, K. Kamamuta, Y. Akamine, T. Fukami, R. Nukada, M. Mikuriya, S. Deguchi, Y. Yokota. Bull. Chem. Soci. Japan, 70, 639-648, 1997.
42. R. Diemer, B., K. Keppler, U. Dittes, B. Nuber, V. Seifried, W. Opferkuch, Chem. Ber., 128, 335-342, 1995.
43. U. Dittes, E. Vogel, B.K. Keppler, Coord. Chem. Rev., 163, 345-364, 1997.
44. P. Pergo, G.S. Jimenez, L. Gatti, S.B. Howell, F. Zunnino, Pharmacol. Rev., 52, 4770491, 2000.
45. S.P. Summers, K.A. Abboud,S.R. Farrah, G.J. Palinik, Inorg. Chem., 33, 88-92, 1994.
46. T. Klapötke, J. Organomet. Chem., 331, 299, 1987.
47. T. Klapötke, Monatsh. Chem. 119, 1317, 1988.
48. H.J. Bieling, G. Lützel, A. Reidus, Chem. Ber. 89, 775, 1956.
49. P. Gowich, T. Klapötke, Z. Natureforsch, 42b, 940, 1987.
50. p. Köpf-maier, T. Klapötke, Inorg. Chem. Acta., 152, 49, 1988.
51. T. Klapötke, Biol. Metal., 1, 69-76, 1988.
52. E. Walker, J. Biochem., 22, 292, 1928.
53. K.A. Smith, G.B. Deacon, W.R. Jackson, E.R.T. Tiekink, S. Rainone, L.K. Webster, Metal-Based Drugs, 5, 295-304, 1998.
54. H. Suzuki, T Ogawa, N Komatsu, Y. Motano, T. Murafuji, T. Ikegami, Organombismuth Chem., 247-278, 2001.
55. J.L. Domingo, J. Toxicolog. Environ. Health, 42, 123-141, 1994.
56. B. Rosenberg, L. Vamcamp, T. Krigas, Nature, 205, 698-699, 1965.
57. L.R. Kelland, G. Abel, M.J. Mckeage, et al. Cancer. Res., 53, 2581-2586, 1993.
58. P.J. O'Dwyer, J.P. Sterenson, S.W. Johnson; Drugs; 59, 19-27, 2000.
59. R.S. Go, A.A. Adjei, J. Clin. Oncol., 17, 409-422, 1999.
60. D. Lebwohl, R. Canetta, Eur. J. Cancer., 34, 1522-1534, 1998.
61. J. Lokich, N. Anderson, Ann. Oncol., 9, 13-21, 1998.
62. E. Raymond, S.G. Chaney, A. Taamma et al. Ann. Oncol., 9, 1053-1071, 1998.
63. E. Cvitkovie, Br. J. Cancer, 77(4), 8-11, 1998.
64. F. Levi, G. Metzger, C.Massari, et al. Clin Pharmacokinet, 38, 1-21, 2000.
65. M.A. Graham, G.F. Lockwood, D. Greenslade, et al. Clin. Cancer. Res., 6, 1205-1218, 2000.
66. J.L. Miset, Br. J. Cancer, 77(4), 4-7, 1998.
67. J.P. Caussanel, F.Levi, S. Brienza, et al. J. Natl. Cancer. Inst., 82, 1046-1050, 1990.
68. Y. Sasaki, T. Tamura, K. Eguchi, et al. Cancer, Chemother. Pharmacol, 23, 243-246, 1989.
69. Y. Sasaki, T. Amano, M. Morita, et al. Cancer. Res. 51, 1472-1477, 1991.
70. A.M. Fichtinger-Schepman, F.J. Dijit, W.H. DeJong, A.T. Van Oosterom, F.Brends, In: M. Nicolini (Ed.), Platinum and other metal coordination compounds in cancer chemotherapy. Boston: Martinum Nijhoff, 32-46, 1998.
71. E. Elizabeth, Trimmer and John, M. Essigmann, cisplatin, an essay in Biochemistry, 34, 191-211, 1999.
72. D.E. Szymkowski, K. Yarema, J.M. Essigmann, et al. Proc. Natl. Acad. Sci. USA, 89, 10772-20776, 1992.
73. B.K. Keppler, C. Friesen, H.G. Moritz, H. Vongerichtem, E. Vogel, Struct. Bonding, 78, 97-127, 1991.
74. M.J. Clarke, F.Zhu, D.R. Frasca, Chem. Rev., 99, 2511, 1999.
75. T. Schilling, B.K. Keppler, M.E. Heim, Invest. New Drugs, 13, 327, 1996.
76. H. Köpf, P. Köpf-maier, Angew. Chem. Int. Ed. Engl., 18, 477, 1979.
77. P. Köpf-maier, Eur. J. Clin. Pharmacol., 47, 1, 1994.
78. P. Köpf-maier, H. Köpf, Struct. Bonding, 70, 103, 1998.
79. P. Köpf-maier, H. Köpf, Chem. Rev., 87, 1137, 1987.
80. W.E. Berdel, H.J. Schmoll, M.E. Scheulen, et al., J. Cancer. Res. Clin. Oncol., 120(R), 172, 1994.
81. A. Korfel, M.E. Scheulen, H.J. Schmoll, et al. Clin Cancer. Res., 4, 2701, 1998.
82. G.Luemmen, H. Sperling, H. Luboldt, T. Otto, H. Ruebben, Cancer. Chemother. Pharmacol., 42, 415, 1998.
83. C.V. Christodoulou, D.R. Ferry, D.W. Fyfe, et al. J. Clin Oncol., 16, 2761, 1998.
84. N. Kröger, U.R. Kllenberg, K. Mross, G. Saars, D.K. Hossfeld, Onkologie, 23, 60, 2000.
85. P. Köpf-maier. In: B.K. Keppler (Ed.), Metal complexes in cancer chemotherapy; Weinhein, VCH, 259-296, 1993.
86. A. Harstrick, H.J. Schmoll, G. Sass, H. Paliwoda, Y. Rustum, Eur. J. Cancer, 29A, 1000, 1993.
87. C.M. Kurbacher, P. Mallmann, J.A. Kurbacher, et al. Anti. Cancer Res., 14, 1961, 1994.
88. C.M. Kurbacher, H.W. Bruckner, P.E. Androotti, J.A. Kurbacher, G. Sass, D. Krebs, Anti. Cancer Drugs, 6, 697, 1995.
89. C.V. Christodoulu, A.G. Eliopoulos, L.S. Young, L. Hodgkins, D.R. Ferry, D.J. Kerr, Br. J. Cancer, 77, 2088, 1988.
90. C.V. Haisen, M. Friedrick, A.K. Ertan, C. Farnhammer, W. Schmidt, Anti. Cancer Drugs, 9, 557, 1998.
91. M. FRiedrick, C.V. Haisen, C. Farnhammer, W. Schmidt, Eur. J. Gynaecol. Oncol, 19(4), 333, 1998.
92. E.Melendez, M. Marero, C. Rivera, E. Hernandez, A. Segal, Inorg. Chem. Acta, 298, 178, 2000.
93. F. Gonzalez, E. Melendez, Unpublished Results.
94. P. Köpf-maier, H. Köpf, Naturwissenschaften, 67, 415, 1980.
95. P. Köpf-maier, W. Wagner, H. Köpf, Naturwissenschaften, 68, 272, 1981.
96. L.Y. Kuo, A.H. Liu, T.J. Marks, In: A. Segal, H. Segal, (Eds.) Metallocene Interactions with DNA and DNA-processing enzymes, 33, 53-85, 1996.
97. P. Yang, M. Guo, Coord. Chem. Rev., 189, 185-186, 1999.
98. C. Rivera, E. Melendez, Metal ions in biology and medicine, 6, 580, 2000.
99. P. Yang, M. Guo, Metal. Based Drugs, 5(1)< 41, 1998.
100. M.L. McLaughlin, J.M. Cronam, T.R. Schaller, R.D. Snelling, J. Am. Chem. Soc., 112, 8949, 1990.
101. J.H. Murray, M.M. Harding, J. Med. Chem., 37, 1936, 1994.
102. M.M. Harding, G. Mokdsi, Curr. Med. Chem., 7, 1289, 2000.
103. M. Guo, P.J. Sadler, J. Chem. Soc., Dalton. Trans., 7, 2000.
104. M. Guo, H. Sun, S. Bihari, et al., Inorg. Chem., 39, 206, 2000.
105. C. Djordjevitz, G.L. Wampler, J. Inorg. Biochem. 25, 51-55, 1985.
106. A. Morinville, D. Maysinger, A. Shaver, TIPS, 19, 4520460, 1998.
107. P. Köpf-maier, Eur. J. Clin. Pharmacol., 47, 1-16, 1994.
108. J. Aubrecht, R.K. Narula, P. Ghosh, J. Stanek, F.M. Uckum, Toxicol. Appl. Pharmacol., 154, 228-235, 1999.
109. M.M. Harding, G. Moksdi, Curr. Medi. Chem., 7, 1289-1293, 2000.
110. O.J. D'Cruz, F.M. Uckum, Toxicol. Appl. Pharmacol., 166, 186-195, 2000.
111. P. Ghosh, O.J. D'Cruz, R.K. Narula, F.M. Uckum, Clin. Cancer Res., 6, 1536-1543, 2000.
112. P. Köpf-maier, W.Wagner, H. Köpft, Cancer Chemother. Pharmacol., 5, 237-241, 1981.
113. P. Köpf-maier, D. Krahl, Chem. Biol. Interactions, 44, 317-328, 1983.
114. P. Köpf-maier, H. Köpf, Chem. Rev., 87, 1137-1152, 1987.
115. M.S. Murthy, L.N. Rao, L.Y. Kuo, J.H. Toneig, T.J. Marks, Inorg. Chem. Acta., 152, 117-124, 1988.
116. E. Sabbioni, G. Pozzi, S. Devos, A. Pintar, L. Gasella, M. Fischbach, Carcinogensis, 14, 2565-2568, 1993.
117. X.L. Shi, N.S. Dalal, Free. Radic. Res. Commun. 17, 369-376, 1992.
118. X.L. Shi, N.S. Dalal, Arch. Bioch. Biophys., 289, 355-361, 1991.
119. H.J. Thompson, D.N. Chasteen, L. Neeker, Carcinogenesis, 5, 849-851, 1984.
120. A. Bishayee, S. Quinam, M. Basu, M. Chaterjee, Br. J. Cancer, 71, 1214-1220, 1995.
121. A. Bishayee, R. Karmaker, A., Mandal, S.N. Kundu, M. Chaterjee, Eur. J. Cancer. Prev. 6, 58-70, 1997.
122. A. Chakraborty, M. Chaterjee, Neoplasma, 41, 291-296, 1994.
123. T.F. Cruz, A. Morgon, W. Min, Mol. Biochem., 153, 161-166, 1995.
124. R. Faure, M. Vincent, M. Dufour, A. Shaver, B. I. Posner, J. Cell. Biochem., 389-401, 1995.
125. Y.L. Kuo, A.H. Liu, T.J. Marks, In: H. Siegel, A. Siegel, (Eds.) Metal ions in biological systems, New York, Maral, Deckker, 53-85, 1995.
126. M.M. Hart, R.H. Adamson, Proc. Natl. Acad. Sci. USA, 68, 1623-1626, 1971.
127. M.M. Hart, C.F. Smith, S.T. Yancey, et al., J. Natl. Cancer Inst., 47, 1121-1127, 1971.
128. C.L. Edwards, R.L. Hayes, J. Nucl. Med., 10, 103-105, 1969.
129. C.R. Chitamber, P. Boon, J.P. Wereley, Clin. Cancer Res., 2, 1009-1015, 1996.
130. F. Wang, X. Jiang, D.C. Yang, et al., Anti Cancer Res., 20, 799-808, 2000.
131. B. Desoize, B.K. Keppler, M.G. Akeli, J.C. Etienne, P. Collery, In: J.A. Centeno, P. Collery, et al. (Eds.), Metal ions in biology and medicine, 6, 573-576, 2000.
132. P. Collery, F. Lechinault, A. Cazabat, et al. Anti. Cancer. Res. 20, 955-958, 2000.
133. C.R. Chitamber, J.P. Wereley, J. Biol. Chem., 272, 12151-12157, 1997.
134. Y. Hata, A sandler, P.J. Lochrer, et al., Oncol. Res., 6, 19024, 1994.
135. P. Collery, H. Millart, M. Pluot, L.J. Anghileri, Anticancer. Res., 6, 1085-1088, 1986.
136. P. Collery, L.J. Anghileri, M. Morel, G. Tran, P. Rinjard, J.C. Etienne, In: J. Anastossopoulou, P. Collery, J.C. Etienne, T. Theophanides, (Eds.), Metal ions in biology and medicine, 2, 176-177, 1992.
137. H.A. Tajmir-Riahi, M. Naovi, R. Ahmad, Toxicol. Appl. Pharmacol; 106, 462-468, 1990.
138. M. Manfait, P. Collery, Gallium. Magnesium Bull., 4, 153-155, 1984.
139. D.W. Hedley, E.H. Tripp, P. Slowiaczek, et al., Cancer Res., 48, 3014-3018, 1988.
140. I. Haiduc, C. Cilvestru, M. Gielen, Bull. Soc. Chem. Belg., 91, 187, 1982.
141. M. Gielen, K. Jurkschat, G. Atassi, Bull. Soc. Chem. Belg, 93, 153, 1984.
142. M. Gielen, C. Vanbellinghen, J. Gelan, R. Willem, Bull. Soc. Chem. Belg., 97, 873, 1985.
143. A.H. Penninks, M.B. Schoenmakers, M. Gielen, W. Seinen, Main group Met. Chem., 12, 1, 1989.
144. M. Ross, M. Gielen, P. Lelieveld, D.deVos, Anticancer. Res., 11, 1089, 1991.
145. M. Ross, M. Gielen, P. Lelieveld, D. deVos, Anti Cancer Res., 10(5B), 1379, 1990.
146. Z. Zhang, H. Pan, C. Hu, F. Fu, Y. Sun, R. Willem, M. Gielen, Appl. Organomet. Chem., 5, 183, 1991.
147. C. Silvestru, I. Haiduc, E.R.T.Tiekink, D. deVos, M. Biesemans, R. Willem, D. Kovala-Demertzi, P. Touridou, U. Russo, M. Gielen, Inorg. Chem. Acta, 239, 177, 1995.
148. M. Gielen, R.Willem, J. Holicek, A. Lycka, Main Group Met. Chem., 16, 29, 1993.
149. H. Preut, F. Huber, M. Gielen, Acta. Crystallography. Sect. C, 46, 2071, 1990.
150. M. Gielen, R. Willem, Anti Cancer Res., 12, 257, 1992.
151. M. Gielen, M. Boualam, M. Biesemans, B. Mahieu, R. Willem, Heterocycles, 34, 549, 1992.
152. M. Gielen, In: N.F. Cardarelli (Ed.), CRC Press, 169, 1986.
153. M. Gielen, R. Willem, T. Mancilla, J. Ramharter, E. Joosen, Si, Ge, Sn, Pb Compounds, 9, 349, 1986.
154. M. Gielen, A. Meriem, M. Boualam, A. Delmotte, R. Willem, D. DeVos, In: V.G.K. Das, S.W. Ng, M. Gielen (Eds.), Oxford Uni. Press, 1991.
155. M. Gielen, In: Proceedings of the tenth world meeting on organotin. Environment Programme, Association, 107, 1992.
156. M. Gielen,D.deVos, A. Mariem, M. Boualam, A. Elkhaloufi, R. Willem; In Vitro, 7, 171, 1993.
157. Y. Arakawa, In: Chemistry of fin; P. Smith (Ed.), 2nd edn. Blackie. Academic and Professional, 1998.
158. M. Gielen, A. Elkhloufi, M. Biesemans, B. Mahieu, R. Willem, Bull. Soc. Chem. Belg., 101, 243, 1992.
159. M. Boualam, R. Willem, M. Biesemans, M. Gielenz. Appl. Organomet. Chem. 5, 497, 1991.
160. M. Gielen, L. Declercq, R. Willem, E. Joosen, In: J.J. Zuckerman (Ed.), CRC, Press, 39, 1988.
161. M. Gielen, M. Melotte, G. Attassi, R. Willem, Tetrahedron, 45, 1219, 1989.
162. A. Meriem, M. Gielen, R. Willem, J. Organomet. Chem., 91, 365, 1989.
163. M. Gielen, P. Lelicveld, D. deVos, R. Willem, In: Metal based antitumor drugs, M. Gielen (Ed.), 2, 29, 1992.
164. M. Gielen, E.Joosen, T. Mancilla, K. Jurkschat, R. Willem, C. Roobol, J. Bernheim, G. Atassi, F. Huber, E. Hoftmann, H. Preut, B. Mahieu, Main Group Met. Chem., 10, 147, 1987.
165. F. Kayser, M. Biesemans, M. Gielen, R. Willem, Magn. Reson. Chem., 32, 358, 1994.
166. J.C. Martins, R. Willems, F.G.A. Mercier, M. Gielen, M. Biesemans, E.R.T.Tiekink, D. deVos, M. Gielin, J. Organomet. Chem., 531, 151, 1997.
167. R. Willem, A. Bouhadid, B. Mahieu, L. Ghys, M. Biessemans, J. Am. Chem. Soci., 121, 3284, 1999.
168. M. Gielen, A. Elkhaloufi, M. Biessemans, A. Bouhdid, D. deVos, B. Mahieu, R. Willeum, Metal Based Drugs, 4, 123, 1997.
169. N. Cardarelli, S.V. Kanakkantt, U.S. Patent, Publ. US4634693, 1987.
170. E.J. Bulten, H.A. Budding, U.S. Patent Publ. 4547320, 1985.
171. M. Gielen, P. Lelieveld, D. deVos, H. Pan, R. Willeum, M. Biessemans, H.H. Fiebig, Inorg. Chem. Acta. 196, 115, 1992.
172. R. Willem, H. Dalil, P. Broekaert, M. Biessemans, L. Ghys, K. Nooter,D. deVos, F. Ribot, M. Gielen, Main Group Met Chem., 20, 535, 1997.
173. G. Attassi, Rev. Si, Ge, Sn, Pb compounds, 8, 219, 1985.
174. M. Gielen, H. Ma, A. Bouhdid, H. Dalil, M. Biessemans, R. Willem, Metal Based Drugs, 4, 193, 1997.
175. A.J. Crowe, In: M. Gielen, (Ed.), Metal Based Antitumor Drugs, 1, 103, 1989.
176. L. Declercq, R. Willem, M. Gielen, Bull. Soc. Chem. Belg., 93, 1089, 1984.
177. J.C. Riess, M. LeBlant, Angew. Chem., 90, 654, 1978, Angew. Chem., 90, 654, 1978.
178. M. Gielen, A. Elkhloufi, M. Biessemans, R. Willem, Appl. Organomet. Chem., 7, 119, 1993.
179. M. Gielen, M. Biessemans, A. Elkhloufi, F. Kayser, R. Willem, Appl. Organomet. Chem., 7, 201, 1993.
180. M. Gielen, M. Biessemans, A. Elkhloufi, J.M. Piret, R.Willem, J. Fluorine Chemistry, 64, 279, 1993.
181. M. Gielen, A. Elkhloufi, D. deVos, H.J. Kolker, J.H.M. Schellens, R. Willem, Bull. Soc. Chem. Belg, 102, 761, 1993.
182. M. Gielen, E.R.T. Tiekink, A. Bouhid, D. deVos, M. Biessemans, I. Vebruggen, R. Willem, Appl. Organomet. Chem., 9, 639, 1995.
183. S.W. Ng, V.G.K. Das, M. Gielen, E.R.T. Tiekink, Appl. Organomet. Chem., 6, 19, 1992.
184. R. Willem, M. Biessemans, F. Kayser, M. Boualam, M. Gielen, Inorg. Chem. Acta, 197, 25, 1992.
185. S.W. Ng, V.G.K. Das, M. Gielen, Appl. Organomet. Chem., 6, 489, 1992.
186. R. Willem, M. Biessemans, M. Bualam, A. Delmotte, A. Elkhloufi, M. Gielen, Appl. Organomet. Chem. 7, 311, 1993.
187. S.W. Ng, V.G.K. Das, J. Haliak, A.Lyeka, M. Gielen, M.G.B.-Drew, Appl. Organomet. Chem., 11, 39, 1997.
188. M. Kemmer, M. Gielen, M. Biessemans, D. deVos, R. Willem, Metal Based Drugs, 5, 189, 1998.
189. M. Kemmer, L. Ghys, M. Gielen, M. Biessemans, E.R.T. Tiekiak, R. Willem, J. Organomet. Chem., 582, 195, 1999.
190. L. Ghys, M. Biessemans, M. Gielen, A. Garoufis, N. Hodjiliadis, R. Willem, J.C. Martins, Eur. J. Inorg. Chem., 513, 2000.
191. G. Casisi, L. Messori, P. Orioli, M. Gielen, M. Kemmer, R. Willem, J. Inorg. Biochem., 85, 297, 2001.
192. Q.Li, P. Yang, H. Wang, M. Guo, J. Inorg. Biochem., 41, 31, 1991.
193. Z. Yang, T. Bakas, A.S. Diaz, C. Charalambopoulos, J. Tsangaris, N. Hadjiliadis, J. Inorg. Biochem., 72, 133, 1998.
194. A. Jancso, L. Nagy, E. Moldrhiem, E. Slitten, J. Chem. Soc. Dalton. Trans., 1587, 1999.
195. R. Barbieri, A. Silvestru, J. Inorg. Biochem., 41, 31, 1991.
196. V. Piro, F.D. Simone, G. Madonia, A. Silvestru, A.M. Giuliani, G. Ruisi, R. Barbieri, Appl. Organomet. Chem., 6, 537, 1992.
197. R. Barbieri, A. Silvestru, A.M. Giuliani, V. Piro, F.D. Simone, G. Madonia, J. Chem. Soc. Dalton. Trans, 585, 1992.
198. G.Barone, M.C. Ramusino, R. Barbieri, G.L. Manna, J. Mol. Struct, 469, 143, 1999.
199. R. Barbieri, F. Huber, A. Silvestru, G. Ruisi, M. Roosi, G. Barone, R. Barbieri, A. Paulsen, Appl. Organomet. Chem., 13, 595, 1999.
200. Bode, Dong, Critical Review in Oncology and Hematology, 42, 1-3, 2002.
201. E.R.T. Tiekink, Critical Review in Oncology and Haematology, 42, 217-24, 2002.
202. B.A. Chapner, C.J. Allegra, G.A. Curt, P. Calabreshi, Antineoplastic agents. In: J.G. Hardman, L.E. Limberd, P.B. Molinoft, R.W. Ruddon, A.G. Gilman (Eds.), The pharmaceutical basis of therapeutics, 9, 1233-1287, 1995.
203. M.D. Joesten, R. Najjar, G. Hebrank, Polyhedron, 1, 637-639, 1982.
204. S.Z. Hu, L-D. Tu, Y-Q. Huang, Z-X. Li, Inorg. Chem. Acta., 232, 161-165, 1995.
205. S-Z. Hu, Y-M. Fu, B. Xu, W-D. Tang, W-J. Yu, Main Group Met Chem., 20, 169-180, 1997.
206. C. Silvestru, C. Socaciu, A. Bara, I. Haiduc; Anticancer Res., 10, 803-804, 1990.
207. A. Bara, C. Socaciu, C. Silvestru, I. Haidue, Anticancer Res., 11, 1651-1656, 1991.
208. C. Sacaciu, A. Bara, C. Silvestru, I. Haiduc, In vivo, 5, 425-428, 1991.
209. B.K. Keppler, C. Silvestru, I. Haiduc, Metal Based Drugs, 1, 73-77, 1994.
210. C. Socaciu, I. Pasca, C. Silvestru, A. Bara, I. Haiduc, Metal. Based Drugs., 1, 291-297, 1994.
211. C. Jasmin, J.C. Charman, G. Herve et al., J. Natl. Cancer. Inst., 53, 469-474, 1974.
212. N. Lorincol, Y. Augery, C.L.B. Kerdilis, et al., J. Gen. Virol. 55, 17-23, 1981.
213. K. Ono, H. Nakane, F.B. Sinoussi, J.C. Charman, Eur. J. Biochem., 176, 305-310, 1988.
214. S. Müller, Jr. W.H. Miller, A. Dejean, Blood , 92, 4308-4316, 1998.
215. Z-X. Shen, G-Q. Chen, J-H. Ni, et al. Blood, 89, 3354-3360, 1997.
216. P. Naredi, D.D. Heath, R.E. Enns, S.B. Howell, Cancer Res, 54, 6464-6468, 1994.
217. P. Naredi, D.D. Heath, R.E. Enns, S.B. Howell, J. Clin. Invest., 95, 1193-1198, 1995.
218. M. Haber, S.B. Bordow, J. Gilbert et al., Oncogene, 18, 2777-2782, 1999.
219. L. Vernhet, A. Coutois, N. Alain, et al., FEBS Lett., 443, 321-325, 1999.
220. C.E. Carraher, Jr., C.U. Pittman, Jr. Macromolecules containing metal and metal like elements, 3, 1-17, 2004.
221. Ravi Kant, G. Amresh, K. Chandrashekar, Anil.K.K.S, Phosphorus, Sulfur, Silicon, 183, 1410-1419,2008.; C. Silvestru, I. Haiduc, E.R.T. Tiekink et al. Appl. Organomet. Chem. 9, 597, 1995.
222. Ravi Kant, S.K.Shukla, K.Singhal, K.Chandrashekar, A.K.Saxena, A.Ranjan, P.Raj, Phosphorus, Sulfur, Silicon, 183, 2029-2039, 2008.; D. Siegmann-Louda, C. Carraher, Q. Quinones, G. McBride, Polym. Mater. Sci. Eng., 88, 390, 2003.
223. H. Sun, H Li, P.J. Sadler, Chem. Ber, Racacil, 130, 669-681, 1997.
224. P.J. Sadler, H. Li, H. Sun, Coord. Chem. Rev., 185-186, 689-709, 1999.
225. W.A. Hermann, E. Herdtweek, L. Pajdla, Z. Kristallografiya, 198, 257-264, 1992.
226. W.A. Hermann, E. Herdtweek, L. Pajdla, Inorg. Chem., 30, 2579-2581, 1991.
227. E. Asato, W.L. Driessen, R.A.G.De Graaff, F.B. Hulsbergen, J. Reedejk, Inorg. Chem., 30, 4210-4218, 1991.
228. E. Asato, K. Katsura, M. Mikuriya, T. Fujii, J. Reedifik, Chem. Lett., 1967-1970, 1992.
229. E. Asato, K. Katsura, M. Mikuriya, T. Fugii, J. Rudijk, Inorg. Chem., 32, 5322-5329, 1993.
230. E. Asato, C.M. Hol, F.B. Hulsbergen, N.T.M. Klooster, J. Rudijk, Inorg. Chem. Acta., 214, 159-167, 1993.
231. E. Asato, K. Katsura, M. Mikuriya, U.Turpeinen, I. Mutjkainen, J. Rudijk, Inorg. Chem., 34, 2447-2454, 1995.
232. S.M. Skinner, J.M. Swatzell, R.W. Lewis, Res. Commun. Chem. Pathol. Pharmacol., 17, 165-168, 1978.
233. G. Alongo, N. Bertazzi, M. Consiglio, Inorg. Chem. Acta, 85, L35-37, 1984.
234. P. Köpf-maiker, T. Klapötke, Inorg. Chem. Acta, 152, 49-52, 1988.
235. K.A. Smith, G.B. Deacon, W.R. Jackson, E.R.T. Tiekink, S. Rainone, L.K. Webster, Metal. Based Drugs, 5, 295-304, 1998.
236. A. Naganuma, M. Satoh, N. Imura, Cancer. Dis., 47, 983-987, 1987.
237. E.R. Oatman, J.A. McMurthy, V. Voth, J. Eco. Entomol. 60, 1344, 1958; R.L. Metcalf, Organic insecticides, Interscience London and New York, 1955
238. B.T. Brooks chlorinated insecticides, Vol. 1, 7, 1974; F. Moriarty (Ed.) Organochlorine insecticides, Academic Press, London and New York, 1975.
239. D.F. Heath, Organophosphorus Poisons, Pergamon Press, Oxford, 1961, M. Eto, Organphosphorous pestitices; organic and biological chemistry, CRC Press Cleveland, Olio, 1974, R.D.O.' Brien, Toxic phosphorus esters, Academic Press, London and New York, 1960.
240. G Schrader, The modification of biological activity by structural changes in organophosphores compounds, World Rev. Pest. Control, 4, 1965.
241. A.R. Main, P.E. Braid, Braid. J. Biochem; 84, 255, 1962, P.R. Chen, W.P. Tucker, W.C. Dauterman, J. Agri. Food. Chem. 17, 86, 1969; H.R. Kruieger, R.D. O' Brien, J. Eco. Entomol. 52, 1063, 1959.
242. N.E. Willis; (Monsanto Chem. Co.): A.P. 2.523.243 (1948/50); R.A. McIvor, G.D. McCarthy, G.A. Grant. Can. J. Chem. 34, 1819, 1956.
243. W.J. Zhou, K.H. Wang, J.X. Wang, D.F. Huang, Eur. J. Org. Chem., 416-419, 2010.
244. M.L.N. Rao, D.N. Jadhav, V. Venkatesh, Eur. J. Org. Chem., 4300-4306, 2009.
245. M.L.N. Rao, D. Banerjee, S. Giri, J. Organometal. Chem., 695, 1518-1525, 2010.
246. A.P. Brogan, J. Verghese, W.R. Widger, H. Kohn, J. Inorg. Biochem. 99, 841-851, 2005.
247. T. Kotani, D. Nagai, K. Asahi, H. Suzuki, F. Yamao, N. Kataoka, T. Yagura, Antimicrob. Agents Chemother. 49, 2729-2734, 2005.
248. R. Chen, M.H. So, J. Yang, F. Deng, C.M. Che, H. Sun, Chem. Comm., 2265-2267,2006.
249. I.L.P.Beales, J. M.C. Gastroenterology, 1, 7, 2001.; D.M.Tripathi, Amresh G., Ravi Kant, Inter. Jour. of Chem. Resear, 4(1), 110-113, 2012.
250. D. Panatarotto, C.D. Prtidos, J. Hoebeke, F. Brown, E. Kramer, J.P. Briand, S. Muller, M. Prato, A. Bianco, Chem. Biol. 10, 961-966, 2003. V. K. Tiwari, Shailendra K. Shukla, V. S. Chauhan, Ravi Kant, Sushma Rani, I.C. Tewari, Inter. Jour. of Pharma. Analy., 2(1), 09-14, 2010.