Interactions between boric acid derivatives and saccharides in aqueous media: Structures and stabilities of resulting esters

Coordination Chemistry Reviews

Volumn 268, Issue , 2014, Pages 1-22

  Peters, Joop A ^a  

^a DELFT UNIVERSITY OF TECHNOLOGY   (Netherlands)

Author keywords

Glucose; Glycated proteins; Polyols; Preorganization; Sialic acid; Targeting vectors

Indexed keywords

EID: 84893610515     PISSN: 00108545     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ccr.2014.01.016     Document Type: Review

References (226)

1. Schubert D. Borates in Industrial Use. Group 13 Chemistry III 2003, 1. Springer Berlin, Heidelberg. H. Roesky, D. Atwood (Eds.).
2. Scorei R. Orig. Life Evol. Biosph. 2012, 42:3.
3. Benner S.A., Kim H.-J., Carrigan M.A. Acc. Chem. Res. 2012, 45:2025.
4. Magnanini G. Gazz. Chim. Ital. 1890, 20(i):428.
5. van't Hoff J.H. Die Lagerung der Atome im Raume 1894, F. Vieweg, Braunschweig.
6. Böeseken J. Adv. Carbohydr. Chem. 1949, 4:189.
7. Gupta V.A., Nooka A.K., Lonial S., Boise L.H. Blood Lymphatic Cancer 2013, 3:41.
8. Bull S.D., Davidson M.G., van den Elsen J.M.H., Fossey J.S., Jenkins A.T.A., Jiang Y.-B., Kubo Y., Marken F., Sakurai K., Zhao J., James T.D. Acc. Chem. Res. 2013, 46:312.
9. Hansen J.S., Christensen J.B., Petersen J.F., Hoeg-Jensen T., Norrild J.C. Sens. Actuators B 2012, 161:45.
10. Merbach A.E., Helm L., Tóth É. The Chemistry of Contrast Agents in Medical Resonance Imaging 2013, John Wiley & Sons, Chichester. 2nd ed.
11. Edwards J.O., Morrison G.C., Ross V.F., Schultz J.W. J. Am. Chem. Soc. 1955, 77:266.
12. Lorand J.P., Edwards J.O. J. Org. Chem. 1959, 24:769.
13. Owen B.B. J. Am. Chem. Soc. 1935, 57:1526.
14. Bosch L.I., Fyles T.M., James T.D. Tetrahedron 2004, 60:11175.
15. Yan J., Springsteen G., Deeter S., Wang B. Tetrahedron 2004, 60:11205.
16. Torssell K. Ark. Kemi. 1957, 10:507.
17. Snyder H.R., Reedy A.J., Lennarz W.J. J. Am. Chem. Soc. 1958, 80:835.
18. Dowlut M., Hall D.G. J. Am. Chem. Soc. 2006, 128:4226.
19. Tomsho J.W., Pal A., Hall D.G., Benkovic S.J. ACS Med. Chem. Lett. 2012, 3:48.
20. Norrild J.C., Søtofte I. J. Chem. Soc. Perkin Trans. 2002, 2:303.
21. Burgemeister T., Grobe-Einsler R., Grotstollen R., Mannschreck A., Wulff G. Chem. Ber. 1981, 114:3403.
22. Zhu L., Shabbir S.H., Gray M., Lynch V.M., Sorey S., Anslyn E.V. J. Am. Chem. Soc. 2006, 128:1222.
23. Franzen S., Ni W., Wang B. J. Phys. Chem. B 2003, 107:12942.
24. Larkin J.D., Fossey J.S., James T.D., Brooks B.R., Bock C.W. J. Phys. Chem. A 2010, 114:12531.
25. Wiskur S.L., Lavigne J.J., Ait-Haddou H., Lynch V., Chiu Y.H., Canary J.W., Anslyn E.V. Org. Lett. 2001, 3:1311.
26. Wulff G. Pure Appl. Chem. 1982, 54:2093.
27. Mesmer R.E., Palen K.M., Baes C.F. Inorg. Chem. 1973, 12:89.
28. Mesmer R.E., Rutenberg A.C. Inorg. Chem. 1973, 12:699.
29. Maya L. Inorg. Chem. 1976, 15:2179.
30. Cooper C.R., Spencer N., James T.D. Chem. Commun. 1998, 1365.
31. Ward C.J., Patel P., James T.D. Chem. Lett. 2001, 406.
32. Galbraith E., James T.D. Chem. Soc. Rev. 2010, 39:3831.
33. DiCesare N., Lakowicz J.R. Anal. Biochem. 2002, 301:111.
34. Arimori S., Davidson M.G., Fyles T.M., Hibbert T.G., James T.D., Kociok-Köhn G.I. Chem. Commun. 2004, 1640.
35. Badugu R., Lakowicz J.R., Geddes C.D. Anal. Chim. Acta 2004, 522:9.
36. Badugu R., Lakowicz J.R., Geddes C.D. Curr. Anal. Chem. 2005, 1:157.
37. Badugu R., Lakowicz J.R., Geddes C.D. J. Am. Chem. Soc. 2005, 127:3635.
38. Badugu R., Lakowicz J.R., Geddes C.D. Dyes Pigm. 2005, 64:49.
39. Koskela S.J.M., Fyles T.M., James T.D. Chem. Commun. 2005, 945.
40. Swamy K.M.K., Lee Y.J., Lee H.N., Chun J., Kim Y., Kim S.-J., Yoon J. J. Org. Chem. 2006, 71:8626.
41. Oehlke A., Auer A.A., Jahre I., Walfort B., Rüffer T., Zoufalá P., Lang H., Spange S. J. Org. Chem. 2007, 72:4328.
42. Xu Z., Kim S.K., Han S.J., Lee C., Kociok-Kohn G., James T.D., Yoon J. Eur. J. Org. Chem. 2009, 2009:3058.
43. Huang Y.-J., Jiang Y.-B., Bull S.D., Fossey J.S., James T.D. Chem. Commun. 2010, 46:8180.
44. Yang X., Cheng Y., Jin S., Wang B. Artificial Receptors for Chemical Sensors 2011, 169. Wiley-VCH Verlag GmbH & Co., Weinheim. V.M. Mirsky, Yatsimirsky (Eds.).
45. Ingri N., Lagerström G., Frydman M., Sillén L.G. Acta Chem. Scand. 1957, 11:1034.
46. Smith H.D., Wiersema R.J. Inorg. Chem. 1972, 11:1152.
47. Coddington J.M., Taylor M.J. J. Coord. Chem. 1989, 20:27.
48. Gaspar A., Schmitt-Kopplin P. Eur. J. Mass Spectrom. 2010, 16:237.
49. Momii R.K., Nachtrieb N.H. Inorg. Chem. 1967, 6:1189.
50. Salentine C.G. Inorg. Chem. 1983, 22:3920.
51. Schubert D.M., Visi M.Z., Knobler C.B. Inorg. Chem. 2008, 47:2017.
52. Tokunaga Y., Ueno H., Shimomura Y., Seo T. Heterocycles 2002, 57:787.
53. Carr J.M., Duggan P.J., Humphrey D.G., Tyndall E.M., White J.M. Aust. J. Chem. 2011, 64:1417.
54. Edwards J.O. J. Am. Chem. Soc. 1953, 75:6151.
55. Antikainen P.J. Acta Chem. Scand. 1956, 10:756.
56. Pizer R., Tihal C. Inorg. Chem. 1987, 26:3639.
57. Chernyshov B.N., Shchetinina G.P., Brovkina O.V., Ippolitov E.G. Koord. Khim. 1985, 11:31.
58. Flanagan J., Griffith W.P., Powell R.D., West A.P. J. Chem. Soc. Dalton Trans. 1989, 1651.
59. Adams C.J., Clark I.E. Polyhedron 1983, 2:673.
60. Flanagan J., Griffith W.P., Powell R.D., West A.P. Spectrochim. Acta A 1989, 45A:951.
61. Hansson A. Acta Chem. Scand. 1961, 15:934.
62. de M.A.A.F., Carrondo C.T., Skapski A.C. Acta Crystallogr. Sect. B 1978, B34:3551.
63. Ainley A.D., Challenger F. J. Chem. Soc. 1930, 2171.
64. Kuivila H.G., Armour A.G. J. Am. Chem. Soc. 1957, 79:5659.
65. Miyazaki Y., Fujimori T., Okita H., Hirano T., Yoshimura K. Dalton Trans. 2013, 42:10473.
66. van Duin M., Peters J.A., Kieboom A.P.G., van Bekkum H. Tetrahedron 1984, 40:2901.
67. Woolley E.M., Tomkins J., Hepler L.G. J. Solution Chem. 1972, 1:341.
68. Bishop M., Shahid N., Yang J., Barron A.R. Dalton Trans. 2004, 2621.
69. Rietjens M., Steenbergen P.A. Eur. J. Inorg. Chem. 2005, 1162.
70. Iwatsuki S., Nakajima S., Inamo M., Takagi H.D., Ishihara K. Inorg. Chem. 2007, 46:354.
71. Miyamoto C., Suzuki K., Iwatsuki S., Inamo M., Takagi H.D., Ishihara K. Inorg. Chem. 2008, 47:1417.
72. Tomsho J.W., Benkovic S.J. J. Org. Chem. 2012, 77:2098.
73. Hubert A.J., Hargitay B., Dale J. J. Chem. Soc. 1961, 931.
74. Springsteen G., Wang B. Tetrahedron 2002, 58:5291.
75. Norrild J.C., Eggert H. J. Am. Chem. Soc. 1995, 117:1479.
76. Draffin S.P., Duggan P.J., Fallon G.D., Tyndall E.M. Acta Crystallogr. Sect. E: Struct. Rep. Online 2005, 61:o1733.
77. Draffin S.P., Duggan P.J., Fallon G.D. Acta Crystallogr. Sect. E: Struct. Rep. Online 2004, 60:o1520.
78. Hermans P.H., Anorg Z. Allg. Chem. 1925, 142:83.
79. Paál T.L. Acta Chim. Acad. Sci. Hung. 1980, 103:181.
80. van Haveren J., Peters J.A., Batelaan J.G., Kieboom A.P.G., van Bekkum H. Recl. Trav. Chim. Pays-Bas 1989, 108:179.
81. Bachelier N., Verchère J.-F. Polyhedron 1995, 14:2009.
82. Martínez-Aguirre M.A., Villamil-Ramos R., Guerrero-Alvarez J.A., Yatsimirsky A.K. J. Org. Chem. 2013, 78:4674.
83. Bérubé M., Dowlut M., Hall D.G. J. Org. Chem. 2008, 73:6471.
84. Fang X.M., Gong F.Y., Ye J.N., Fang Y.Z. Chromatographia 1997, 46:137.
85. Dawber J.G., Green S.I.E., Dawber J.C., Gabrail S. J. Chem. Soc. Faraday Trans. 1988, 1(84):41.
86. Evans W.J., McCourtney E.J., Carney W.B. Anal. Biochem. 1979, 95:383.
87. van den Berg R., Peters J.A., van Bekkum H. Carbohydr. Res. 1994, 253:1.
88. Chapelle S., Verchère J.F. Tetrahedron 1988, 44:4469.
89. de Bruyn A., Anteunis M. Acta Cienc. Indica 1976, 2:1.
90. Shiomi Y., Saisho M., Tsukagoshi K., Shinkai S. J. Chem. Soc. Perkin Trans. 1993, 1:2111.
91. Dale J. J. Chem. Soc. 1961, 922.
92. Makkee M., Kieboom A.P.G., van Bekkum H. Recl. Trav. Chim. Pays-Bas 1985, 104:230.
93. van Duin M., Peters J.A., Kieboom A.P.G., van Bekkum H. Tetrahedron 1985, 41:3411.
94. Norrild J.C. J. Chem. Soc. Perkin Trans. 2001, 2:719.
95. Caldeira M.M., Ramos M.L., Gil V.M.S., van Bekkum H., Peters J.A. Inorg. Chim. Acta 1994, 221:69.
96. Djanashvili K., Frullano L., Peters J.A. Chem. Eur. J. 2005, 11:4010.
97. Bromba C., Carrie P., Chui J.K.W., Fyles T.M. Supramol. Chem. 2009, 21:81.
98. van Duin M., Peters J.A., Kieboom A.P.G., van Bekkum H. J Chem. Soc. Perkin Trans. 1987, 2:473.
99. van Duin M., Peters J.A., Kieboom A.P.G., van Bekkum H. Carbohydr. Res. 1987, 162:65.
100. van Duin M., Peters J.A., Kieboom A.P.G., van Bekkum H. J. Chem. Soc. Dalton Trans. 1987, 2051.
101. van Duin M., Peters J.A., Kieboom A.P.G., van Bekkum H. Recl. Trav. Chim. Pays-Bas 1989, 108:57.
102. Mehltretter C.L., Alexander B.H., Rist C.E. Ind. Eng. Chem. 1953, 45:2782.
103. Sawyer D.T. Chem. Rev. 1964, 64:633.
104. Pizer R., Ricatto P.J. Inorg. Chem. 1994, 33:4985.
105. van Haveren J., Peters J.A., Batelaan J.G., Kieboom A.P.G., van Bekkum H. J. Chem. Soc. Dalton Trans. 1991, 2649.
106. van Haveren J., Lammers H., Peters J.A., Batelaan J.G., van Bekkum H. Carbohydr. Res. 1993, 243:259.
107. van Haveren J., van Bekkum H., Peters J.A. Inorg. Chim. Acta 1993, 205:1.
108. van Haveren J., Peters J.A., Batelaan J.G., van Bekkum H. Inorg. Chim. Acta 1992, 192:261.
109. Guo Z., Shin I., Yoon J. Chem. Commun. 2012, 48:5956.
110. Kitamura M., Suzuki T., Abe R., Ueno T., Aoki S. Inorg. Chem. 2011, 50:11568.
111. C. Platas Iglesias, personal communication.
112. Pizer R., Babcock L. Inorg. Chem. 1977, 16:1677.
113. Paál T.L. Acta Chim. Acad. Sci. Hung. 1981, 106:71.
114. James T.D., Sandanayake K.R.A.S., Iguchi R., Shinkai S. J. Am. Chem. Soc. 1995, 117:8982.
115. Bielecki M., Eggert H., Norrild J.Chr. J. Chem. Soc. Perkin Trans. 1999, 2:449.
116. CRC Handbook of Chemistry and Physics, 93rd edition, Internet version 201, 7.
117. Rohovec J., Maschmeyer T., Aime S., Peters J.A. Chem. Eur. J. 2003, 9:2193.
118. Werz D.B., Ranzinger R., Herget S., Adibekian A., von der Lieth C.-W., Seeberger P.H. ACS Chem. Biol. 2007, 2:685.
119. Frullano L., Rohovec J., Aime S., Maschmeyer T., Prata M.I., Pedroso de Lima J.J., Geraldes C.F.G.C., Peters J.A. Chem. Eur. J. 2004, 10:5205.
120. Nagai Y., Kobayashi K., Toi H., Aoyama Y. Bull. Chem. Soc. Jpn. 1993, 66:2965.
121. Geninatti C.S., Alberti D., Szabo I., Aime S., Djanashvili K. Angew. Chem. Int. Ed. 2013, 52:1161.
122. Maple S.R., Allerhand A. J. Am. Chem. Soc. 1987, 109:3168.
123. Davis H.B., Mott C.J.B. J. Chem. Soc. Faraday Trans. 1980, 1(76):1991.
124. Norrild J.C., Eggert H. J. Chem. Soc. Perkin Trans. 1996, 2:2583.
125. James T.D., Sandanayake K.R.A.S., Shinkai S. J. Chem. Soc. Chem. Commun. 1994, 477.
126. Sandanayake K.R.A., Shinkai S. J. Chem. Soc. Chem. Commun. 1994, 1083.
127. Adamczyk-Woźniak A., Brzózka Z., Cyrański M.K., Filipowicz-Szymańska A., Klimentowska P., Zubrowska A., Zukowski K., Sporzyński A. Appl. Organomet. Chem. 2008, 22:427.
128. Adamczyk-Woźniak A., Borys K.M., Madura I.D., Pawełko A., Tomecka E., Zukowski K. New J. Chem. 2013, 37:188.
129. Hansen J.S., Christensen J.B., Solling T.I., Jakobsen P., Hoeg-Jensen T. Tetrahedron 2011, 67:1334.
130. James T.D., Sandanayake K.R.A.S., Shinkai S. Angew. Chem. 1994, 106:2287.
131. Sandanayake K.R.A.S., James T.D., Shinkai S. Chem. Lett. 1995, 503.
132. James T.D., Sandanayake K.R.A.S., Shinkai S. Angew. Chem. Int. Ed. Engl. 1996, 35:1910.
133. James T.D., Shinkai S. Top. Curr. Chem. 2002, 218:159.
134. James T.D., Shinkai S. J. Chem. Soc. Chem. Commun. 1995, 1483.
135. Arimori S., Bell M.L., Oh C.S., James T.D. Org. Lett. 2002, 4:4249.
136. Arimori S., Bell M.L., Oh C.S., Frimat K.A., James T.D. J. Chem. Soc. Perkin Trans. 2002, 1:803.
137. Karnati V.V., Gao X., Gao S., Yang W., Ni W., Sankar S., Wang B. Bioorg. Med. Chem. Lett. 2002, 12:3373.
138. Fang H., Kaur G., Wang B. J. Fluoresc. 2004, 14:481.
139. Kaur G., Fang H., Gao X., Li H., Wang B. Tetrahedron 2006, 62:2583.
140. Gamsey S., Miller A., Olmstead M.M., Beavers C.M., Hirayama L.C., Pradhan S., Wessling R.A., Singaram B. J. Am. Chem. Soc. 2007, 129:1278.
141. Sharrett Z., Gamsey S., Fat J., Cunningham-Bryant D., Wessling R.A., Singaram B. Tetrahedron Lett. 2007, 48:5125.
142. Hoeg-Jensen T. QSAR Comb. Sci. 2004, 23:344.
143. Phillips M.D., James T.D. J. Fluoresc. 2004, 14:549.
144. Eggert H., Frederiksen J., Morin C., Norrild J.C. J. Org. Chem. 1999, 64:3846.
145. Gamsey S., Suri J.T., Wessling R.A., Singaram B. Langmuir 2006, 22:9067.
146. James T.D., Sandanayake K.R.A.S., Shinkai S. Nature 1995, 374:345.
147. Heinrichs G., Schellenträger M., Kubik S. Eur. J. Org. Chem. 2006, 4177.
148. Duggan P.J., Offermann D.A. Tetrahedron 2009, 65:109.
149. Zhang S., Trokowski R., Sherry A.D. J. Am. Chem. Soc. 2003, 125:15288.
150. Trokowski R., Zhang S., Sherry A.D. Bioconjugate Chem. 2004, 15:1431.
151. Ren J., Trokowski R., Zhang S., Malloy C.R., Sherry A.D. Magn. Reson. Med. 2008, 60:1047.
152. Kumai M., Kozuka S., Samizo M., Hashimoto T., Suzuki I., Hayashita T. Anal. Sci. 2012, 28:121.
153. Shimpuku C., Ozawa R., Sasaki A., Sato F., Hashimoto T., Yamauchi A., Suzuki I., Hayashita T. Chem. Commun. 2009, 1709.
154. Tsukagoshi K., Shinkai S. J. Org. Chem. 1991, 56:4089.
155. Kondo K., Shiomi Y., Saisho M., Harada T., Shinkai S. Tetrahedron 1992, 48:8239.
156. Appleton B., Gibson T.D. Sens. Actuators B 2000, 65:302.
157. Sandanayake K.R.A.S., Nakashima K., Shinkai S. J. Chem. Soc. Chem. Commun. 1994, 1621.
158. Angew. Chem. Int. 2001, 40:1714.
159. Cao H., McGill T., Heagy M.D. J. Org. Chem. 2004, 69:2959.
160. Kanekiyo Y., Tao H. Chem. Lett. 2005, 34:196.
161. Huang Y.-J., Ouyang W.-J., Wu X., Li Z., Fossey J.S., James T.D., Jiang Y.-B. J. Am. Chem. Soc. 2013, 135:1700.
162. Duggan P.J. Aust. J. Chem. 2004, 57:291.
163. Duggan P.J., Houston T.A., Kiefel M.J., Levonis S.M., Smith B.D., Szydzik M.L. Tetrahedron 2008, 64:7122.
164. Das S., Alexeev V.L., Sharma A.C., Geib S.J., Asher S.A. Tetrahedron Lett. 2003, 44:7719.
165. Schumacher S., Katterle M., Hettrich C., Paulke B.-R., Pal A., Hall D.G., Scheller F.W., Gajovic-Eichelmann N. Chem. Senses 2011, 1:1/1/7.
166. James T.D., Shinmori H., Takeuchi M., Shinkai S. Chem. Commun. 1996, 705.
167. Lee J.W., Lee J.-S., Chang Y.-T. Angew. Chem. Int. Ed. 2006, 45:6485.
168. Edwards N.Y., Sager T.W., McDevitt J.T., Anslyn E.V. J. Am. Chem. Soc. 2007, 129:13575.
169. Schiller A., Wessling R.A., Singaram B. Angew. Chem. Int. Ed. 2007, 46:6457.
170. Diabetes Care 2005, 28:S1. American Diabetes Association.
171. Shima K., Ito N., Abe F., Hirota M., Yano M., Yamamoto Y., Uchida T., Noguchi K. Diabetologia 1988, 31:627.
172. Kricka L.J., Gregoire T., Dumont L., Wilding P. Clin. Chem. 1991, 37:1520.
173. Silver A.C., Lamb E., Cattell W.R., Dawnay A.B.S.J. Clin. Chim. Acta 1991, 202:11.
174. Ikeda K., Sakamoto Y., Kawasaki Y., Miyake T., Tanaka K., Urata T., Katayama Y., Ueda S., Horiuchi S. Clin. Chem. 1998, 44:256.
175. Liu J.-T., Chen L.-Y., Shih M.-C., Chang Y., Chen W.-Y. Anal. Biochem. 2008, 375:90.
176. Wang X., Xia N., Liu L. Int. J. Mol. Sci. 2013, 14:20890.
177. Song S.Y., Yoon H.C. Sens. Actuators B 2009, B140:233.
178. Aime S., Botta M., Dastru W., Fasano M., Panero M., Arnelli A. Inorg. Chem. 1993, 32:2068.
179. Battistini E., Mortillaro A., Aime S., Peters J.A. Imaging 2007, 2:163.
180. Aime S., Digilio G., Fasano M., Paoletti S., Arnelli A., Ascenzi P. Biophys. J. 1999, 76:2735.
181. Schauer R. Glycoconj. J. 2000, 17:485.
182. Dall'Olio F., Chiricolo M. Glycoconj. J. 2001, 18:841.
183. Cazet A., Julien S., Bobowski M., Krzewinski-Recchi M.-A., Harduin-Lepers A., Groux-Degroote S., Delannoy P. Carbohydr. Res. 2010, 345:1377.
184. Fernández-Briera A., García-Parceiro I., Cuevas E., Gil-Martín E. Oncology 2010, 78:196.
185. Martinez-Duncker I., Salinas-Marin R., Martinez-Duncker C. Int. J. Mol. Imaging 2011, 283497. 10pp.
186. Carter A., Martin N.H. J. Clin. Pathol. 1962, 15:69.
187. Krolikowski F.J., Reuter K., Waalkes T.P., Sieber S.M., Adamson R.H. Pharmacology 1976, 14:47.
188. Laganà A., Pardo-Martínez B., Marino A., Fago G., Bizzarri M. Clin. Chim. Acta 1995, 243:165.
189. Raval G.N., Parekh L.J., Patel D.D., Jha F.P., Sainger R.N., Patel P.S. Indian J. Clin. Biochem. 2004, 19:60.
190. Crook M.A., Tutt P., Simpson H., Pickup J.C. Clin. Chim. Acta 1993, 219:131.
191. Chrostek L., Cylwik B., Korcz W., Krawiec A., Koput A., Supronowicz Z., Szmitkowski M. Alcohol. Clin. Exp. Res. 2007, 31:996.
192. Klepach T., Carmichael I., Serianni A.S. J. Am. Chem. Soc. 2008, 130:11892.
193. Angata T., Varki A. Chem. Rev. 2002, 102:439.
194. Otsuka H., Uchimura E., Koshino H., Okano T., Kataoka K. J. Am. Chem. Soc. 2003, 125:3493.
195. Matsumoto A., Sato N., Kataoka K., Miyahara Y. J. Am. Chem. Soc. 2009, 131:12022.
196. Yang Y., Lewis P.T., Escobedo J.O., Luce N.N.S., Treleaven W.D., Cook R.L., Strongin R.M. Collect. Czech. Chem. Commun. 2004, 69:1282.
197. Meng J., Yu S., Wan S., Ren S., Jiang T. Chem. Biol. Drug Des. 2011, 78:816.
198. Han E., Ding L., Ju H. Anal. Chem. 2011, 83:7006.
199. Duan S.-J., He X.-W., Chen L.-X., Zhang Y.-K. Gaodeng Xuexiao Huaxue Xuebao 2012, 33:464.
200. Kwak B.S., Kim H.O., Kim J.H., Lee S., Jung H.-I. Biosens. Bioelectron. 2012, 35:484.
201. Chen Y., Ding L., Ju H. Chem. Commun. 2013, 49:862.
202. Diltemiz S.E., Ersoz A., Hur D., Kecili R., Say R. Mater. Sci. Eng. C 2013, 33:824.
203. Matsumoto A., Cabral H., Sato N., Kataoka K., Miyahara Y. Angew. Chem. Int. Ed. 2010, 49:5494.
204. Matsumoto A., Sato N., Cabral H., Kataoka K., Miyahara Y. Procedia Eng. 2010, 5:926.
205. Deshayes S., Cabral H., Ishii T., Miura Y., Kobayashi S., Yamashita T., Matsumoto A., Miyahara Y., Nishiyama N., Kataoka K. J. Am. Chem. Soc. 2013, 135:15501.
206. Dai C., Sagwal A., Cheng Y., Peng H., Chen W., Wang B. Pure Appl. Chem. 2012, 84:2479.
207. Uchimura E., Otsuka H., Okano T., Sakurai Y., Kataoka K. Biotechnol. Bioeng. 2001, 72:307.
208. Wang J., Zhang Z., Wang X., Wu W., Jiang X. J. Controlled Release 2013, 168:1.
209. Liu H., Li Y., Sun K., Fan J., Zhang P., Meng J., Wang S., Jiang L. J. Am. Chem. Soc. 2013, 135:7603.
210. Levonis S.M., Kiefel M.J., Houston T.A. Chem. Commun. 2009, 2278.
211. Levonis S.M., Kiefel M.J., Houston T.A. Aust. J. Chem. 2011, 64:1454.
212. Yang W., Fan H., Gao X., Gao S., Karnati V.V.R., Ni W., Hooks W.B., Carson J., Weston B., Wang B. Chem. Biol. 2004, 11:439.
213. Yang W., Gao S., Gao X., Karnati V.V.R., Ni W., Wang B., Hooks W.B., Carson J., Weston B. Bioorg. Med. Chem. Lett. 2002, 12:2175.
214. Yamamoto M., Takeuchi M., Shinkai S. Tetrahedron 1998, 54:3125.
215. Takeuchi M., Yamamoto M., Shinkai S. Chem. Commun. 1997, 1731.
216. Regueiro-Figueroa M., Djanashvili K., Esteban-Gómez D., Chauvin T., Tóth É., de B.A., Rodríguez-Blas T., Platas-Iglesias C. Inorg. Chem. 2010, 49:4212.
217. Regueiro-Figueroa M., Djanashvili K., Esteban-Gomez D., de Blas A., Platas-Iglesias C., Rodriguez-Blas T. Eur. J. Org. Chem. 2010, 3237.
218. Patterson S., Smith B.D., Taylor R.E. Tetrahedron Lett. 1998, 39:3111.
219. Liu A., Peng S., Soo J.C., Kuang M., Chen P., Duan H. Anal. Chem. 2010, 83:1124.
220. Djanashvili K., Koning G.A., van der Meer A.J.G.M., Wolterbeek H.T., Peters J.A. Imaging 2007, 2:35.
221. Ellis G.A., Palte M.J., Raines R.T. J. Am. Chem. Soc. 2012, 134:3631.
222. Lammers T., Kiessling F., Hennink W.E., Storm G. Mol. Pharm. 2010, 7:1899.
223. Smith B.D., Gardiner S.J. Adv. Supramol. Chem. 1999, 5:157.
224. Shinbo T., Nishimura K., Yamaguchi T., Sugiura M. J. Chem. Soc. Chem. Commun. 1986, 349.
225. Mohler L.K., Czarnik A.W. J. Am. Chem. Soc. 1993, 115:2998.
226. Martin A.R., Vasseur J.-J., Smietana M. Chem. Soc. Rev. 2013, 42:5684.