Transition metal bioconjugates with an organometallic link between the metal and the biomolecular scaffold

Coordination Chemistry Reviews

Volumn 257, Issue 17-18, 2013, Pages 2420-2433

  Monney, Angèle ^a   Albrecht, Martin ^a  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

Author keywords

Bioconjugates; Bioorganometallics; N heterocyclic carbenes; Organometallics; Peptides

Indexed keywords

EID: 84881544856     PISSN: 00108545     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ccr.2012.12.015     Document Type: Review

References (171)

1. Bioorganometallics: Biomolecules, Labeling, Medicine 2006, Wiley-VCH, Weinheim, Germany. G. Jaouen (Ed.).
2. Jaouen G., Vessières A. Pure Appl. Chem. 1985, 57:1865.
3. Fish R.H., Jaouen G. Organometallics 2003, 22:2166.
4. A recent book compiles the bioorganometallic chemistry in Nature, see: A. Sigel, H. Sigel, R.K.O. Sigel, Metal Ions in Life Science, Vol. 6: Metal Carbon Bonds in Enyzmes and Cofactors, RSC, London, 2009.
5. Hodgkin D.C. Proc. R. Soc. London, Ser. A 1965, 288:294.
6. Hodgkin D.C., Pickworth J., Robertson J.H., Prosen R.J., Sparks R.A., Trueblood K.N., Vos A. Proc. R. Soc. London, Ser. A 1959, 251:306.
7. Hodgkin D.C., Kamper J., Lindsey J., MacKay M., Pickworth J., Robertson J.H., Shoemaker C.B., White J.G., Prosen R.J., Trueblood K.N. Proc. R. Soc. London, Ser. A 1957, 242:228.
8. 12 1982, vols. 1 and 2. John Wiley & Sons, New York, USA.
9. Adams M.W.W., Stiefel E.I. Curr. Opin. Chem. Biol. 2000, 4:214.
10. Volbeda A., Charon M.-H., Piras C., Hatchikian E.C., Frey M., Fontecilla-Camps J.C. Nature 1995, 373:580.
11. Jaouen G., Vessières A., Top S. J. Am. Chem. Soc. 1985, 107:4778.
12. Hillard E.A., Jaouen G. Organometallics 2011, 30:20.
13. Riordan C.G. Dalton Trans. 2009, 4273. (thematic issue).
14. Peacock A.F.A., Sadler P.J. Chem. Asian J. 2008, 3:1890.
15. Dyson P.J. Aust. J. Chem. 2010, 63:1503. (thematic issue).
16. Hartinger C.G., Metzler-Nolte N., Dyson P. Organometallics 2012, 31:5677.
17. Mercs L., Albrecht M. Chem. Soc. Rev. 2010, 39:1912.
18. Melaimi M., Soleilhavoup M., Bertrand G. Angew. Chem. Int. Ed. 2010, 49:8810.
19. Arduengo A.J., Bertrand G. Chem. Rev. 2009, 109:3209. (thematic issue).
20. Hahn F.E., Jahnke M.C. Angew. Chem. Int. Ed. 2008, 47:3122.
21. Herrmann W.A. Angew. Chem. Int. Ed. 2002, 41:1290.
22. Patra M., Gasser G., Metzler-Nolte N. Dalton Trans. 2012, 41:6350. For recent reviews see:.
23. Gasser G., Metzler-Nolte N. Curr. Opin. Chem. Biol. 2012, 16:84.
24. Gasser G., Ott I., Metzler-Nolte N. J. Med. Chem. 2011, 54:3.
25. Ang W.H., Casini A., Sava G., Dyson P.J. J. Organomet. Chem. 2011, 696:989.
26. Hartinger C.G., Dyson P.J. Chem. Soc. Rev. 2009, 38:391.
27. Bruijnincx P.C.A., Sadler P.J. Curr. Opin. Chem. Biol. 2008, 12:197.
28. Ronconi L., Sadler P.J. Coord. Chem. Rev. 2007, 251:1633.
29. Heinisch T., Ward T.R. Curr. Opin. Chem. Biol. 2010, 14:184. For recent reviews, see:.
30. Abe S., Ueno T., Watanabe Y. Top. Organomet. Chem. 2009, 25:25.
31. Pordea A., Ward T.R. Synlett 2009, 20:3225.
32. Bartlett P.N., Whitaker R.G., Green M.J., Frew J. J. Chem. Soc., Chem. Commun. 1987, 1603.
33. Degani Y., Heller A. J. Am. Chem. Soc. 1988, 110:2615.
34. Schuhmann W., Ohara T.J., Schmidt H.-L., Heller A. J. Am. Chem. Soc. 1991, 113:1394.
35. Heller A., Feldman B. Acc. Chem. Res. 2010, 43:973.
36. Martic S., Labib M., Shipman P.O., Kraatz H.-B. Dalton Trans. 2011, 40:7264.
37. Qi D., Tann C.-M., Haring D., Distefano M.D. Chem. Rev. 2001, 101:3081.
38. Hwang H.J., Carey K.R., Brower E.T., Gengenback A.J., Abramite J.A., Lu Y. J. Am. Chem. Soc. 2005, 127:15356.
39. Mayer C., Gillingham D.G., Ward T.R., Hilvert D. Chem. Commun. 2011, 47:12068.
40. Kruithof C.A., Casado M.A., Guillena G., Egmond M.R., van der Kerk-van Hoof A., Heck A.J.R., Klein Gebbink R.J.M., van Koten G. Chem. Eur. J. 2005, 11:6869.
41. Rutten L., Wieczorek B., Mannie J.-P.B.A., Kruithof C.A., Dijkstra H.P., Egmond M.R., Lutz M., Klein Gebbink R.J.M., Gros P., van Koten G. Chem. Eur. J. 2009, 15:4270.
42. Wieczorek B., Lemcke B., Dijkstra H.P., Egmond M.R., Klein Gebbink R.J.M., van Koten G. Eur. J. Inorg. Chem. 2010, 1929.
43. Wieczorek B., Snelders D.J.M., Dijkstra H.P., Versluis K., Lutz M., Spek A.L., Egmond M.R., Klein Gebbink R.J.M., van Koten G. Organometallics 2012, 31:2810.
44. Wieczorek B., Träff A., Krumlinde P., Dijkstra H.P., Egmond M.R., van Koten G., Bäckvall J.-E., Klein Gebbink R.J.M. Tetrahedron Lett. 2011, 52:1601.
45. Wilson M.E., Whitesides G.M. J. Am. Chem. Soc. 1978, 100:306.
46. Ward T.R. Acc. Chem. Res. 2011, 44:47.
47. Klein G., Humbert N., Gradinaru J., Ivanova A., Gilardoni F., Rusbandi U.E., Ward T.R. Angew. Chem. Int. Ed. 2005, 44:7764.
48. Letondor C., Humbert N., Ward T.R. Proc. Natl. Acad. Sci. U.S.A. 2005, 102:4683.
49. Lo C., Ringenberg M.R., Gnandt D., Wilson Y., Ward T.R. Chem. Commun. 2011, 47:12065.
50. Brustad E.M., Arnold F.H. Curr. Opin. Chem. Biol. 2011, 15:201. For recent reviews, see.
51. Reetz M.T. Top. Organomet. Chem. 2009, 25:63.
52. Boersma A.J., Megens R.P., Feringa B.L., Roelfes G. Chem. Soc. Rev. 2010, 39:2083. For examples, see:.
53. Myers C.P., Williams M.E. Coord. Chem. Rev. 2010, 254:2416.
54. Husken N., Gebala M., Schuhmann W., Metzler-Nolte N. Chembiochem 2010, 11:1754.
55. Martic S., Gabriel M., Turowec J.P., W: Litchfield D., Kraatz H.-B. J. Am. Chem. Soc. 2012, 134:17036.
56. Xuan F., Luo X., Hsing I.-M. Biosens. Bioelectron. 2012, 35:230.
57. Gross A., Husken N., Schur J., Raszeja L., Ott I., Metzler-Nolte N. Bioconjugate Chem. 2012, 23:1764.
58. Fournier P., Fiammengo R., Jäschke A. Angew. Chem. Int. Ed. 2009, 48:4426.
59. Jaouen G., Vessières A. Pure Appl. Chem. 1985, 57:1865.
60. Top S., Jaouen G., Vessières A., Abjean J.-P., Davoust D., Rodger C.A., Sayer B.G., McGlinchey M.J. Organometallics 1985, 4:2143.
61. Osella D., Gambino O., Fiedler J., Pospisil L., Amouri H.E., Le Bras J., Vichard D., Gruselle M., Jaouen G. Inorg. Chim. Acta 1996, 250:379.
62. Schobert R., Seibt S., Effenberger-Neidnicht K., Underhill C., Biersack B., Hammond G.L. Steroids 2011, 76:393.
63. Ruiz J., Rodríguez V., Cutillas N., Espinosa A., Hannon M.J. Inorg. Chem. 2011, 50:9164.
64. G.D. Batema, Korstanje, G. Guillena, G. Rodriguez, M. Lutz, Kooijman, A.L. Spek, G.P.M. van Klink, G. van Koten, manuscript in preparation.
65. Hessler F., Cisarova I., Sedlak D., Bartunek P., Kotora M. Chem. Eur. J. 2012, 18:5515.
66. Clarke M.J., Taube H. J. Am. Chem. Soc. 1975, 97:1397.
67. Krentzien H.J., Clarke M.J., Taube H. Bioinorg. Chem. 1975, 4:143.
68. Price C., Elsegood M.R.J., Clegg W., Rees N.H., Houlton A. Angew. Chem. Int. Ed. Engl. 1997, 36:1762.
69. Price C., Shipman M.A., Gummerson S.L., Houlton A., Clegg W., Elsegood M.R.J. J. Chem. Soc. Dalton Trans. 2001, 353.
70. Kascatan-Nebioglu A., Panzner M.J., Garrison J.C., Tessier C.A., Youngs W.J. Organometallics 2004, 23:1928.
71. Schütz J., Herrmann W.A. J. Organomet. Chem. 2004, 689:2995.
72. Panzner M.J., Hindi K.M., Wright B.D., Taylor J.B., Han D.S., Youngs W.J., Cannon C.L. Dalton Trans. 2009, 7308.
73. Kascatan-Nebioglu A., Melaiye A., Hindi K., Durmus S., Panzner M.J., Hogue L.A., Mallett R.J., Hovis C.E., Coughenour M., Crosby S.D., Milsted A., Ely D.L., Tessier C.A., Cannon C.L., Youngs W.J. J. Med. Chem. 2006, 49:6811.
74. Luo F.-T., Lo H.-K. J. Organomet. Chem. 2011, 696:1262.
75. Hu J.J., Bai S.-Q., Yeh H.H., Young D.J., Chi Y., Hor T.S.A. Dalton Trans. 2011, 40:4402.
76. Schlawe D., Majdalani A., Vecicky J., Hessler E., Wieder T., Prokop A., Schmalz H.-G. Angew. Chem. Int. Ed. 2004, 43:1731.
77. James P., Neudörfl J., Eissmann M., Jesse P., Prokop A., Schmalz H.-G. Org. Lett. 2006, 8:2763.
78. De Champdore M., Di Fabio G., Messere A., Montesarchio D., Piccialli G., Loddo R., La Colla M., La Colla P. Tetrahedron 2004, 60:6555.
79. Kowalski K., Koceva-Chyla A., Pleniazek A., Bernasinska J., Skiba J., Rybarczyk-Pirek A.J., Jozwiak Z. J. Organomet. Chem. 2012, 700:58.
80. Patra M., Gasser G., Wenzel M., Merz K., Bandow J.E., Metzler-Nolte N. Organometallics 2012, 31:5760.
81. Lehnert T., Özüduru G., Grugel H., Albrecht F., Telligmann S.M., Boysen M.M.K. Synthesis 2011, 17:2685. For reviews, see:.
82. Woodward S., Dieguez M., Pamiez O. Coord. Chem. Rev. 2010, 254:2007.
83. Benessere V., Del Litto R., De Roma A., Ruffo F. Coord. Chem. Rev. 2010, 254:390.
84. Diéguez M., Claver C., Pamies O. Eur. J. Org. Chem. 2007, 4621.
85. Castillon S., Claver C., Díaz Y. Chem. Soc. Rev. 2005, 34:702.
86. Dieguez M., Pamies O., Claver C. Chem. Rev. 2004, 104:3189.
87. Dieguez M., Pamiez O., Ruiz A., Diaz Y., Castillon S., Claver C. Coord. Chem. Rev. 2004, 248:2165.
88. Steinborn D., Junicke H. Chem. Rev. 2000, 100:4283.
89. Förster C., Kovacevic M., Barisic L., Rapic V., Heinze K. Organometallics 2012, 31:3683. For recent examples, see:.
90. Hottin A., Dubar F., Steenackers A., Delannoy P., Biot C., Behr J.-B. Org. Biomol. Chem. 2012, 10:5592.
91. Trivedi R., Deepthi S.B., Giribabu L., Sridhar B., Sujitha P., Kumar C.G., Ramaskrishna K.V.S. Eur. J. Inorg. Chem. 2012, 2267.
92. Dive D., Biot C. Chem. Med. Chem. 2007, 3:383.
93. Ferreira C.L., Ewart C.B., Barta C.A., Little S., Yardley V., Martins C., Polishchuk E., Smith P.J., Moss J.R., Merkel M., Adam M.J., Orvig C. Inorg. Chem. 2006, 45:8414.
94. Biot C., Castro W., Botte C.Y., Navarro M. Dalton Trans. 2012, 41:6335. For recent examples, see:.
95. Navarro M., Castro W., Biot C. Organometallics 2012, 31:5715.
96. Haase W.-C., Nieger M., Dötz K.H. Chem. Eur. J. 1999, 5:2014.
97. Dötz K.H., Ehlenz R. Chem. Eur. J. 1997, 3:1751.
98. Dötz K.H., Ehlenz R., Straub W., Weber J.C., Airola K., Nieger M. J. Organomet. Chem. 1997, 548:91.
99. Bühler G., Feiters M.C., Nolte R.J.M., Dötz K.H. Angew. Chem. Int. Ed. 2003, 42:2494.
100. Beccati D., Halkes K.M., Batema G.D., Guillena G., Carvalho de Souza A., van Koten G., Kamerling J.P. ChemBioChem 2005, 6:1196.
101. Nishioka T., Shibata T., Kinoshita I. Organometallics 2007, 26:1126.
102. Tewes F., Schlecker A., Harms K., Glorius F. J. Organomet. Chem. 2007, 692:4593.
103. Shi J.-c., Lei N., Tong Q., Peng Y., Wei J., Jia L. Eur. J. Inorg. Chem. 2007, 2221.
104. Keitz B.K., Grubbs R.H. Organometallics 2010, 29:403.
105. Shibata T., Ito S., Doe M., Tanaka R., Hashimoto H., Kinoshita I., Yano S., Nishioka T. Dalton Trans. 2011, 40:6778.
106. Shibata T., Hashimoto H., Kinoshita I., Yano S., Nishioka T. Dalton Trans. 2011, 40:4826.
107. Yang C.-C., Lin P.-S., Liu F.-C., Lin I.J.B. Organometallics 2010, 29:5959.
108. Severin K., Bergs R., Beck W. Angew. Chem. Int. Ed. 1998, 37:1634.
109. Gaviglio L., Gross A., Metzler-Nolte N., Ravera M. Metallomics 2012, 4:260. For selected recent examples see:.
110. Abramkin S., Valiahdi S.M., Jakupec M.A., Galanski M., Metzler-Nolte N., Keppler B.K. Dalton Trans. 2012, 41:3001.
111. van Rijt S.H., Kostrhunova H., Brabec B., Sadler P.J. Bioconjugate Chem. 2011, 22:218.
112. Laungani A.C., Slattery J.M., Krossing I., Breit B. Chem. Eur. J. 2008, 14:4488.
113. Christensen C.A., Meldal M. J. Comb. Chem. 2007, 9:79.
114. Herrick R.S., Dupont J., Wrona I., Pilloni J., Beaver M., Benotti M., Powers F., Ziegler C.J. J. Organomet. Chem. 2007, 692:1226.
115. Agarkov A., Greenfield S., Xie D., Pawlick R., Starkey G., Gilbertson S.R. Biopolymers 2006, 84:48.
116. Kirin S.I., Dübon P., Weyhermüller T., Bill E., Metzler-Nolte N. Inorg. Chem. 2005, 44:5405.
117. Benito J.M., Christensen C.A., Meldal M. Org. Lett. 2005, 7:581.
118. Christensen C.A., Meldal M. Chem. Eur. J. 2005, 11:4121.
119. Pastor I.M., Västilä P., Adolfsson H. Chem. Eur. J. 2003, 9:4031.
120. Osgerby J.M., Pauson P.L. J. Chem. Soc. 1958, 656.
121. Hauser C.R., Lindsay J.K. J. Org. Chem. 1957, 22:1246.
122. Schlögl K. Monatsh. Chem. 1957, 88:601.
123. van Staveren D.R., Metzler-Nolte N. Chem. Rev. 2004, 104:5931.
124. Kirin S.I., Kraatz H.-B., Metzler-Nolte N. Chem. Soc. Rev. 2006, 35:348.
125. Neuse E.W. J. Inorg. Organomet. Polym. Mater. 2005, 15:3.
126. Toshiyuki M., Hirao T. Chem. Soc. Rev. 2004, 33:294.
127. Moriuchi T., Hirao T. Acc. Chem. Res. 2010, 43:1040.
128. Lal B., Badshah A., Altaf A.A., Khan N., Ullah S. Appl. Organomet. Chem. 2011, 25:843.
129. Beheshti S., Martic S., Kraatz H.-B. Chem. Eur. J. 2012, 18:9099. For a recent example, see:.
130. Corry A.J., Goel A., Kenny P.T.M. Inorg. Chim. Acta 2012, 384:293.
131. Anne A., Chovin A., Demaille C. Langmuir 2012, 28:8804.
132. Beheshti S., Martic S., Kraatz H.-B. ChemPhysChem 2012, 13:542.
133. Zhou B., Li J., Feng B.-J., Ouyang Y., Liu Y.-N., Zhou F. J. Inorg. Biochem. 2012, 116:19.
134. Grotjahn D.B. Coord. Chem. Rev. 1999, 190-192:1125. For an early review, see:.
135. Moriarty R.M., Ku Y.-Y., Gill U.S. J. Chem. Soc., Chem. Commun. 1987, 1837.
136. Wolff J.M., Sheldrick W.S. J. Organomet. Chem. 1997, 531:141.
137. Grotjahn D.B., Joubran C., Combs D., Brune D.C. J. Am. Chem. Soc. 1998, 120:11814.
138. Perekalin D.S., Karslyan E.E., Petrovskii P.V., Nelyubina Y.V., Lyssenko K.A., Kononikhin A.S., Nikolaev E.N., Kudinov A.R. Chem. Eur. J. 2010, 16:8466.
139. West C.W., Rich D.H. Org. Lett. 1999, 1:1819.
140. Janetka J.W., Rich D.H. J. Am. Chem. Soc. 1997, 119:6488.
141. Janetka J.W., Rich D.H. J. Am. Chem. Soc. 1995, 117:10585.
142. Pearson A.J., Lee K. J. Org. Chem. 1995, 60:7153.
143. Pearson A.J., Lee K. J. Org. Chem. 1994, 59:2304.
144. Hu W., Splith K., Neundorf I., Merz K., Schatzschneider U. J. Biol. Inorg. Chem. 2012, 17:175.
145. Splith K., Neundorf I., Hu W., N'Dongo H.W.P., Vasylyeva V., Merz K., Schatzschneider U. Dalton Trans. 2010, 39:2536.
146. Splith K., Hu W., Schatzschneider U., Gust R., Ott I., Onambele L.A., Prokop A., Neundorf I. Bioconjugate Chem. 2010, 21:1288.
147. Lalrempuia R., McDaniel N.D., Müller-Bunz H., Bernhard S., Albrecht M. Angew. Chem. Int. Ed. 2010, 49:9765. For examples, see:.
148. Bernet L., Lalrempuia R., Ghattas W., Mueller-Bunz H., Vigara L., Llobet A., Albrecht M. Chem. Commun. 2011, 47:8058.
149. Dialer H., Polborn K., Beck W. J. Organomet. Chem. 1999, 589:21.
150. Salmain M., Blais J.-C., Tran-Huy H., Compain C., Jaouen G. Eur. J. Biochem. 2001, 269:5479.
151. Salmain M., Licandro E., Baldoli C., Maiorana S., Tran-Huy H., Jaouen G. J. Organomet. Chem. 2001, 617-618:376.
152. Kernbach U., Mühl M., Polborn K., Fehlhammer W.P., Jaouen G. Inorg. Chim. Acta 2002, 334:45.
153. Xu G., Gilbertson S.R. Org. Lett. 2005, 7:4605.
154. Jensen J.F., Worm-Leonhard K., Meldal M. Eur. J. Org. Chem. 2008, 3785.
155. Worm-Leonhard K., Meldal M. Eur. J. Org. Chem. 2008, 5244.
156. Lemke J., Metzler-Nolte N. Eur. J. Inorg. Chem. 2008, 3359.
157. Lemke J., Pinto A., Niehoff P., Vasylyeva V., Metzler-Nolte N. Dalton Trans. 2009, 7063.
158. Lemke J., Metzler-Nolte N. J. Organomet. Chem. 2011, 696:1018.
159. Hannig F., Kehr G., Fröhlich R., Erker G. J. Organomet. Chem. 2005, 690:5959.
160. Monney A., Venkatachalam G., Albrecht M. Dalton Trans. 2011, 40:2716.
161. Monney A., Alberico E., Ortin Y., Müller-Bunz H., Gladiali S., Albrecht M. Dalton Trans. 2012, 41:8813.
162. Monney A., Albrecht M. Chem. Commun. 2012, 49:10960.
163. Albrecht M., Rodríguez G., Schoenmaker J., van Koten G. Org. Lett. 2000, 2:3461.
164. Guillena G., Halkes K.M., Rodríguez G., Batema G.D., van Koten G., Kamerling J.P. Org. Lett. 2003, 5:2021.
165. Guillena G., Rodríguez G., van Koten G. Tetrahedron Lett. 2002, 43:3895.
166. Curran T.P., Yoon R.S.H., Volk B.R. J. Organomet. Chem. 2004, 689:4837.
167. Curran T.P., Marques K.A., Silva M.V. Org. Biomol. Chem. 2005, 3:4134.
168. Gasser G., Neukamm M.A., Ewers A., Brosch O., Weyhermüller T., Metzler-Nolte N. Inorg. Chem. 2009, 48:3157.
169. Neukamm M.A., Pinto A., Metzler-Nolte N. Chem. Commun. 2008, 232.
170. Gross A., Neukamm M., Metzler-Nolte N. Dalton Trans. 2011, 40:1382.
171. Köster S.D., Alborzinia H., Can S., Kitanovic I., Wölfl S., Rubbiani R., Ott I., Riesterer P., Prokop A., Merz K., Metzler-Nolte N. Chem. Sci. 2012, 3:2062.