Abstract
Because of its unique electronic structure, boron has special properties useful in designing new diagnostic and therapeutic agents. Specifically, boron’s strong Lewis acidity and ability to undergo fission under neutron bombardment form the foundation for boron-containing compounds to be developed as inhibitors of hydrolytic enzymes, chemosensors and artificial receptors for carbohydrates and other Lewis bases, and boron neutron capture agents. A number of boron-containing compounds have been evaluated in animal and human studies for diagnostics and therapeutic applications. One compound in particular, Velcade, has been approved as an anticancer agent. This chapter highlights some of the most significant contributions in the field.
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References
Baker SJ, Ding CZ, Akama T, Zhang YK, Hernandez V, Xia Y (2009) Future Med Chem 1:1275
Rainey CJ, Nyquist LA, Christensen RE, Strong PL, Culver BD, Coughlin JR (1999) J Am Diet Assoc 99:335
Yan J, Fang H, Wang BH (2005) Med Res Rev 25:490
Yang WQ, Gao XM, Wang BH (2003) Med Res Rev 23:346
Das BC, Thapa P, Karki R, Schinke C, Das S, Kambhampati S, Banerjee SK, Van Veldhuizen P, Verma A, Weiss LM, Evans T (2013) Future Med Chem 5:653
Zhu Y, Hosmane NS (2013) Future Med Chem 5:705
Baker SJ, Tomsho JW, Benkovic S (2011) J Chem Soc Rev 40:4279
Touchet S, Carreaux F, Carboni B, Bouillon A, Boucher JL (2011) Chem Soc Rev 40:3895
Yang W, Gao S, Wang B (2005) In: Hall D (ed) Organoboronic acids. Wiley, New York, p 481
Dowlut M, Hall DG (2006) J Am Chem Soc 128:4226
Hiratake J, Oda J (1997) Biosci Biotech Biochem 61:211
Gallardo-Williams MT, Maronpot RR, Wine RN, Brunssen SH, Chapin RE (2003) Prostate 54:44
Adams J, Kauffman M (2004) Can Invest 22:304
Bacha U, Barrila J, Velazquez-Campoy A, Leavitt SA, Freire E (2004) Biochemistry 43:4906
Holyoak T, Wilson MA, Fenn TD, Kettner CA, Petsko GA, Fuller RS, Ringe D (2003) Biochemistry 42:6709
Snow RJ, Bachovchin WW, Barton RW, Campbell SJ, Coutts SJ, Freeman DM, Gutheil WG, Kelly TA, Kennedy CA, Krolikowski DA, Leonard SF, Pargellis CA, Tong I, Adams J (1994) J Am Chem Soc 116:10860
Geele G, Garrett E, Hageman H (1975) J Am Soc Micro 1975:391
Farr-Jones S, Smith SO, Kettner CA, Griffin RG, Bachovchin WW (1989) Proc Natl Acad Sci U S A 86:6922
Groll M, Berkers CR, Ploegh HL, Ovaa H (2006) Structure 14:451
Matthews DA, Alden RA, Birktoft JJ, Freer ST, Kraut J (1975) J Biol Chem 250:7120
Powers RA, Blazquez J, Weston GS, Morosini MI, Baquero F, Shoichet BK (1999) Protein Sci 8:2330
Powers RA, Shoichet BK (2002) J Med Chem 45:3222
Stoll VS, Eger BT, Hynes RC, Martichonok V, Jones JB, Pai EF (1998) Biochemistry 37:451
Zhong S, Jordan F, Kettner CA, Polgar L (1991) J Am Chem Soc 113:9429
Bone R, Frank D, Kettner CA, Agard DA (1989) Biochemistry 28:7600
Aharoni R, Bronstheyn M, Jabbour A, Zaks B, Srebnik M, Steinberg D (2007) Bioorg Med Chem. doi:10.1016/j.bmc.2007.11.032
Cho BT (2005) In: Hall DG (ed) Boronic acids. Wiley-VCH, Weinheim, p 411
Jabbour A, Steinberg D, Dembitsky VM, Moussaieff A, Zaks B, Srebnik M (2004) J Med Chem 47:2409
Gamsey S, Miller A, Olmstead MM, Beavers CM, Hirayama LC, Pradhan S, Wessling RA, Singaram B (2007) J Am Chem Soc 129:1278
Gray CW Jr, Houston TA (2002) J Org Chem 67:5426
Wang Z, Zhang DQ, Zhu DB (2005) J Org Chem 70:5729
Wiskur SL, Lavigne JL, Ait-Haddou H, Lynch V, Chiu YH, Canary JW, Anslyn EV (2001) Org Lett 3:1311
Mohler LK, Czarnik AW (1994) J Am Chem Soc 116:2233
Badugu R, Lakowicz JR, Geddes CD (2004) Anal Chem 327:82
Badugu R, Lakowicz JR, Geddes CD (2005) Sens Actuators B Chem 104:103
DiCesare N, Lakowicz JR (2002) Anal Biochem 301:111
Oehlke A, Auer AA, Jahre I, Walfort B, Ruffer T, Zoufala P, Lang H, Spange S (2007) J Org Chem 72:4328
Swamy KMK, Lee YJ, Lee HN, Chun J, Kim Y, Kim SJ, Yoon J (2006) J Org Chem 71:8626
Cooper CR, Spencer N, James TD (1998) Chem Commun 1998:1365
Asher SA, Alexeev VL, Goponenko AV, Sharma AC, Lednev IK, Wilcox CS, Finegold DN (2003) J Am Chem Soc 125:3322
Bielecki M, Eggert H, Norrild JC (1999) J Chem Soc, Perkin Trans 2 1999:449
Eggert H, Frederiksen J, Morin C, Norrild JC (1999) J Org Chem 64:3846
James TD, Sandanayake KRAS, Iguchi R, Shinkai S (1995) J Am Chem Soc 117:8982
Yang W, Fan H, Gao S, Gao X, Ni W, Karnati V, Hooks WB, Carson J, Weston B, Wang B (2004) Chem Biol 11:439
Yoon J, Czarnik AW (1992) J Am Chem Soc 114:5874
Badugu R, Lakowicz JR, Geddes CD (2005) Curr Anal Chem 1:157
Cao HS, Heagy MD (2004) J Fluor 14:569
James TD, Shinkai S (2002) Top Curr Chem 218:159
Narra K, Mullins SR, Lee H-O, Strzemkowski-Brun B, Magalong K, Christiansen VJ, McKee PA, Egleston B, Cohen SJ, Weiner LM, Meropol NJ, Cheng JD (2007) Cancer Biol Ther 6:1691
Mader HS, Wolfbeis OS (2008) Microchim Acta 162:1
Pickup JC, Hussain F, Evans ND, Rolinski OJ, Birch DJS (2005) Biosens Bioelectr 20:2555
Striegler S (2003) Curr Org Chem 7:81
Wang W, Gao X, Wang B (2002) Curr Org Chem 6:1285
Norrild JC, Eggert H (1995) J Am Chem Soc 117:1479
Springsteen G, Wang B (2001) Chem Commun 2001:1608
Yan J, Springsteen G, Deeter S, Wang B (2004) Tetrahedron 60:11205
Alavi A, Axford JS (eds) (1995) Glycoimmunology, vol 376. Plenum, New York
Timmer M, Stocker B, Seeberger P (2007) Curr Opin Chem Biol 11:59
Alvarez-Manilla G, Warren NL, Abney T, Atwood J, Azadi P, York WS, Pierce M, Orlando R (2007) Glycobiology 17:677
Fukuda M (1994) In: Fukuda M, Hindsgaul O (eds) Molecular glycobiology. Oxford Univeristy Press, New York, p 1
Dennis JW (1992) In: Fukuda M (ed) Cell surface carbohydrates and cell development. CRC, Boca Raton, p 161
Gabius H-J, Gabius S (eds) (1993) Lectins and glycobiology. New York, Springer
Taylor M, Drickamer K (2006) Introduction to glycobiology. Oxford University Press, New York
Fukuda M, Hindsgaul O (eds) (1994) Molecular glycobiology. Oxford Univeristy Press, New York
Fukuda M (1992) Cell surface carbohydrates and cell development. CRC, Boca Raton
Jin S, Cheng Y, Reid S, Li M, Wang B (2010) Med Res Rev 30:171
Cheng Y, Li M, Wang S, Peng H, Reid S, Ni N, Fang H, Xu W, Wang B (2010) Sci China Ser B Chem 2010:53
Andreotti AH, Kahne D (1993) J Am Chem Soc 115:3352
Bosques CJ, Tschampel SM, Woods RJ, Imperiali B (2004) J Am Chem Soc 126:8421
Brisson J-R, Uhrinova S, Woods RJ, van der Zwan M, Jarrell HC, Paoletti LC, Kasper DL, Jennings H (1997) J Biochem 36:3278
Dennis JW, Granovsky M, Warren CE (1999) BioEssays 21:412
Liu XC, Hubbard JL, Scouten WH (1995) J Organomet Chem 493:91
Springsteen G, Wang BH (2002) Tetrahedron 58:5291
Kane RC, Bross PF, Farrell AT, Pazdur R (2003) Oncologist 8:508
San Miguel J, Blade J, Boccadoroe M, Cavenagh J, Glasmacher A, Jagannath S, Lonial S, Orlowski RZ, Sonneveld P, Ludwig H (2006) Oncologist 11:51
Codony-Servat J, Tapia MA, Bosch M, Oliva C, Domingo-Domenech J, Mellado B, Rolfe M, Ross JS, Gascon P, Rovira A, Albanell J (2006) Mol Cancer Ther 5:665
Schmid P, Kuehnhardt D, Kiewe P, Lehenbauer-Dehm S, Schippinger W, Greil R, Lange W, Preiss J, Niederle N, Brossart P, Freier W, Kuemmel S, de Velde HV, Regierer A, Possinger K (2008) Ann Oncol 19:871
Schenkein DP (2005) Clin Lung Cancer 7(Suppl 2):S49
Davies AM, Lara PN Jr, Mack PC, Gandara DR (2007) Clin Cancer Res 13:4647S
Voutsadakis IA, Patrikidou A, Tsapakidis K, Karagiannaki A, Hatzidaki E, Stathakis NE, Papandreou CN (2010) Int J Color Dis 25:795
Cusack JC, Liu R, Houston M, Abendroth K, Elliott PJ, Adams J, Baldwin AS (2001) Cancer Res 61:3535
Papandreou CN, Logothetis C (2004) J Cancer Res 64:5036
Hu W, Zheng R-R, Cui H-X, Yue D, Wang Y, Jiang Y-H (2012) Asian J Androl 14:695
Nawrocki ST, Carew JS, Pino MS, Highshaw RA, Dunner K, Huang P, Abbruzzese JL, McConkey D (2005) J Cancer Res 65:11658
Adams J, Palombella VJ, Sausville EA, Johnson J, Destree A, Lazarus DD, Maas J, Pien CS, Prakash S, Elliott P (1999) J Cancer Res 59:2615
Adams J (2004) Nat Rev Cancer 4:349
Gallwitz B (2010) Pharm Unserer Zeit 39:114
Gallwitz B (2007) Drugs Today 43:13
Matsuzaki Y, Sowa Y, Hirose T, Yokota T, Sakai T (2003) Environ Health Prev Med 8:157
Suzuki N, Suzuki T, Ota Y, Nakano T, Kurihara M, Okuda H, Yamori T, Tsumoto H, Nakagawa H, Miyata N (2009) J Med Chem 52:2909
Shimizu K, Maruyama M, Yasui Y, Minegishi H, Ban HS, Nakamura H (2010) Bioorg Med Chem Lett 20:1453
Khan SRMO (2011) US 2011/0,105,431 A1
Albers HMHG, Dong A, van Meeteren LA, Egan DA, Sunkara M, van Tilburg EW, Schuurman K, van Tellingen O, Morris AJ, Smyth SS, Moolenaar WH, Ovaa H (2010) Proc Natl Acad Sci U S A 107:7257
Orlowski M (1994) J Cell Biochem 1994:120
Rose I (2005) Angew Chem Int Ed 44:5926
Hershko A (2005) Angew Chem Int Ed 44:5932
Ciechanover A (2005) Angew Chem Int Ed 44:5944
Genin E, Reboud-Ravaux M, Vidal J (2010) Curr Top Med Chem 10:232
Adams J, Behnke M, Chen SW, Cruickshank AA, Dick LR, Grenier L, Klunder JM, Ma YT, Plamondon L, Stein RL (1998) Bioorg Med Chem Lett 8:333
Richardson PG, Sonneveld P, Schuster MW, Stadtmauer EA, Facon T, Harousseau J-L, Ben-Yehuda D, Lonial S, Goldschmidt H, Reece D, Blade J, Boccadoro M, Cavenagh JD, Boral AL, Esseltine D-L, Wen PY, Amato AA, Anderson KC, San Miguel J (2009) Br J Haematol 144:895
Adams JM, Cory S (2007) Oncogene 26:1324
Kupperman E, Lee EC, Cao Y, Bannerman B, Fitzgerald M, Berger A, Yu J, Yang Y, Hales P, Bruzzese F, Liu J, Blank J, Garcia K, Tsu C, Dick L, Fleming P, Yu L, Manfredi M, Rolfe M, Bolen J (2010) Cancer Res 2010:70
Zhu Y, Yao S, Xu B, Ge Z, Cui J, Cheng T, Li R (2009) Bioorg Med Chem 17:6851
Mathew S, Scanlan MJ, Raj BKM, Murty V, Garinchesa P, Old LJ, Rettig WJ, Chaganti RSK (1995) Genomics 25:335
Scanlan MJ, Raj BKM, Calvo B, Garinchesa P, Sanzmoncasi MP, Healey JH, Old LJ, Rettig W (1994) J Proc Natl Acad Sci U S A 91:5657
O'Farrell AM, van Vliet A, Abou Farha K, Cherrington JM, Campbell DA, Li X, Hanway D, Li J, Guler H-P (2007) Clin Ther 29:1692
Adams S, Miller GT, Jesson MI, Watanabe T, Jones B, Wallner BP (2004) Cancer Res 64:5471
Sambucetti LC, Fischer DD, Zabludoff S, Kwon PO, Chamberlin H, Trogani N, Xu H, Cohen D (1999) J Biol Chem 274:34940
Burroughs SK, Kaluz S, Wang D, Wang K, Van Meir EG, Wang B (2013) Future Med Chem 5:553
Zak K, Pecak A, Rys B, Wladyka B, Doemling A, Weber L, Holak TA, Dubin G (2013) Expert Opin Ther Pat 23:425
Carry J-C, Garcia-Echeverria C (2013) Bioorg Med Chem Lett 23:2480
Miriam Shadfan VL-P (2012) Zhi-Min Yuan Transl Cancer Res 1:88
Vousden KH, Prives C (2009) Cell 137:413
Donehower LA, Lozano G (2009) Nat Rev Cancer 9:830
Haupt Y, Maya R, Kazaz A, Oren M (1997) Nature 387:296
Honda R, Tanaka H, Yasuda H (1997) FEBS Lett 420:25
Momand J, Zambetti GP, Olson DC, George D, Levine A (1992) J Cell 69:1237
Oliner JD, Pietenpol JA, Thiagalingam S, Gvuris J, Kinzler KW, Vogelstein B (1993) Nature 362:857
Umezu-Goto M, Kishi Y, Taira A, Hama K, Dohmae N, Takio K, Yamori T, Mills GB, Inoue K, Aoki J (2002) J Cell Biol 158:227
Moolenaar WH (2002) J Cell Biol 158:197
Tokumura A, Majima E, Kariya Y, Tominaga K, Kogure K, Yasuda K, Fukuzawa K (2002) J Biol Chem 277:39436
Stefan C, Jansen S, Bollen M (2005) Trends Biochem Sci 30:542
van Meeteren LA, Moolenaar WH (2007) Prog Lipid Res 46:145
Kanda H, Newton R, Klein R, Morita Y, Gunn MD, Rosen SD (2008) Nat Immunol 9:415
Pradère J-P, Klein J, Grès S, Guigné C, Neau E, Valet P, Calise D, Chun J, Bascands J-L, Saulnier-Blache J-S (2007) J Am Soc Nephrol 18:3110
Tager AM, LaCamera P, Shea BS, Campanella GS, Selman M, Zhao Z, Polosukhin V, Wain J, Karimi-Shah BA, Kim ND (2007) Nat Med 14:45
Pamuklar Z, Federico L, Liu S, Umezu-Goto M, Dong A, Panchatcharam M, Fulerson Z, Berdyshev E, Natarajan V, Fang X (2009) J Biol Chem 284:7385
Noguchi K, Herr D, Mutoh T, Chun J (2009) Curr Opin Pharmacol 9:15
Baker DL, Fujiwara Y, Pigg KR, Tsukahara R, Kobayashi S, Murofushi H, Uchiyama A, Murakami-Murofushi K, Koh E, Bandle RW (2006) J Biol Chem 281:22786
Cui P, McCalmont WF, Tomsig JL, Lynch KR, Macdonald TL (2008) Bioorg Med Chem 16:2212
Ferry G (2008) J Pharmacol Exp Ther 327:809
Van Meeteren LA, Brinkmann V, Saulnier-Blache JS, Lynch KR, Moolenaar WH (2008) Cancer Lett 266:203
Kropff M, Bisping G, Schuck E, Liebisch P, Lang N, Hentrich M, Dechow T, Kröger N, Salwender H, Metzner B (2007) Br J Haematol 138:330
Albers HM, Hendrickx LJ, van Tol RJ, Hausmann J, Perrakis A, Ovaa H (2011) J Med Chem 54:4619
Hoffmann F (1998) WO98022496
Perni RB, Almquist SJ, Byrn RA, Chandorkar G, Chaturvedi PR, Courtney LF, Decker CJ, Dinehart K, Gates CA, Harbeson SL, Heiser A, Kalkeri G, Kolaczkowski E, Lin K, Luong YP, Rao BG, Taylor WP, Thomson JA, Tung RD, Wei YY, Kwong AD, Lin C (2006) Antimicrob Agents Chemother 50:899
Venkatraman S, Bogen SL, Arasappan A, Bennett F, Chen K, Jao E, Liu Y-T, Lovey R, Hendrata S, Huang Y, Pan W, Parekh T, Pinto P, Popov V, Pike R, Ruan S, Santhanam B, Vibulbhan B, Wu W, Yang W, Kong J, Liang X, Wong J, Liu R, Butkiewicz N, Chase R, Hart A, Agrawal S, Ingravallo P, Pichardo J, Kong R, Baroudy B, Malcolm B, Guo Z, Prongay A, Madison V, Broske L, Cui X, Cheng K-C, Hsieh Y, Brisson J-M, Prelusky D, Korfmacher W, White R, Bogdanowich-Knipp S, Pavlovsky A, Bradley P, Saksena AK, Ganguly A, Piwinski J, Girijavallabhan V, Njoroge FG (2006) J Med Chem 49:6074
Boloor A, Hanway D, Joshi M, Winn DT, Mendez G, Walls M, Wei P, Qian F, Zhang X, Zhang Y, Hepperle ME, Li X, Campbell DA, Betancort JM (2009) Bioorg Med Chem Lett 19:5708
Li XF, Zhang YK, Liu Y, Ding CZ, Li Q, Zhou Y, Plattner JJ, Baker SJ, Qian XL, Fan DZ, Liao L, Ni ZJ, White GV, Mordaunt JE, Lazarides LX, Slater MJ, Jarvest RL, Thommes P, Ellis M, Edge CM, Hubbard JA, Somers D, Rowland P, Nassau P, McDowell B, Skarzynski TJ, Kazmierski WM, Grimes RM, Wright LL, Smith GK, Zou WX, Wright J, Pennicott LE (2010) Bioorg Med Chem Lett 20:3550
Llinas-Brunet M, Bailey MD, Bolger G, Brochu C, Faucher AM, Ferland JM, Garneau M, Ghiro E, Gorys V, Grand-Maitre C, Halmos T, Lapeyre-Paquette N, Liard F, Poirier M, Rheaume M, Tsantrizos YS, Lamarre D (2004) J Med Chem 47:1605
Llinas-Brunet M, Bailey MD, Goudreau N, Bhardwaj PK, Bordeleau J, Boes M, Bousquet Y, Cordingley MG, Duan J, Forgione P, Garneau M, Ghiro E, Gorys V, Goulet S, Halmos T, Kawai SH, Naud J, Poupart M-A, White PW (2010) J Med Chem 53:6466
Venkatraman S, Wu WL, Prongay A, Girijavallabhan V, Njoroge FG (2009) Bioorg Med Chem Lett 19:180
Hall BG, Barlow M (2005) J Antimicrob Chemother 55:1050
Livermore DM (1998) J Antimicrob Chemother 41:25
Hartman BJ, Tomasz A (1984) J Bacteriol 158:513
Zervosen A, Sauvage E, Frère J-M, Charlier P, Luxen A (2012) Molecules 17:12478
Bush K, Jacoby GA, Medeiros AA (1995) Antimicrob Agents Chemother 39:1211
Beesley T, Gascoyne N, Knott-Hunziker V, Petursson S, Waley S, Jaurin B, Grundstrom T (1983) Biochem J 209:229
Knott-Hunziker V, Petursson S, Waley SG, Jaurin B, Grundstrom T (1982) Biochem J 207:315
Coudron PE (2005) J Clin Microbiol 43:4163
Weston GS, Blazquez J, Baquero F, Shoichet BK (1998) J Med Chem 41:4577
Pechenov A, Stefanova ME, Nicholas RA, Peddi S, Gutheil WG (2003) Biochemistry 42:579
Nicola G, Peddi S, Stefanova M, Nicholas RA, Gutheil WG, Davies C (2005) Biochemistry 44:8207
Ness S, Martin R, Kindler AM, Paetzel M, Gold M, Jensen SE, Jones JB, Strynadka NC (2000) J Biochem 39:5312
Morandi F, Caselli E, Morandi S, Focia PJ, Blazquez J, Shoichet BK, Prati F (2003) J Am Chem Soc 125:685
Chen Y, Shoichet B, Bonnet R (2005) J Am Chem Soc 127:5423
Bailey PJ, Cousins G, Snow GA, White A (1980) J Antimicrob Agents Chemother 17:549
Dewar M (1964) Progress in boron chemistry, vol 1. Macmillan, New York
Gronowitz S, Dahlgren T, Namtvedt J, Roos C, Rosen G, Sjoberg B, Forsgren U (1971) Acta Pharm Suec 8:623
Ni N, Choudhary G, Peng H, Li M, Chou H-T, Lu C-D, Gilbert ES, Wang B (2009) Chem Biol Drug Des 74:51
Ni N, Choudhary G, Li M, Wang B (2009) Biochem Biophys Res Commun 382:153
Ni N, Li M, Wang J, Wang B (2009) Med Res Rev 29:65
Peng H, Cheng Y, Ni N, Li M, Choudhary G, Chou H, Lu C-D, Tai PC, Wang B (2009) Abstracts of Papers of the American Chemical Society, p 238
Baker SJ, Zhang YK, Akama T, Lau A, Zhou H, Hernandez V, Mao WM, Alley MRK, Sanders V, Plattner JJ (2006) J Med Chem 49:4447
Seiradake E, Mao W, Hernandez V, Baker SJ, Plattner JJ, Alley MRK, Cusack S (2009) J Mol Biol 390:196
Rock FL, Mao WM, Yaremchuk A, Tukalo M, Crepin T, Zhou HC, Zhang YK, Hernandez V, Akama T, Baker SJ, Plattner JJ, Shapiro L, Martinis SA, Benkovic SJ, Cusack S, Alley MRK (2007) Science 316:1759
Melnikova I (2009) Nat Rev Drug Discov 8:353
Quan ML, Pruitt JR, Ellis CD, Liauw AY, Galemmo RA, Stouten PFW, Wityak J, Knabb RM, Thoolen MJ, Wong PC, Wexler RR (1997) Bioorg Med Chem Lett 7:2813
Quan ML, Wityak J, Dominguez C, Duncia JV, Kettner CA, Ellis CD, Liauw AY, Park JM, Santella JB, Knabb RM, Thoolen MJ, Weber PC, Wexler RR (1997) Bioorg Med Chem Lett 7:1595
Fevig JM, Cacciola J, Alexander RS, Knabb RM, Lam GN, Wong PC, Wexler RR (1998) Bioorg Med Chem Lett 8:3143
Fevig JM, Buriak J, Cacciola J, Alexander RS, Kettner CA, Knabb RM, Pruitt JR, Weber PC, Wexler RR (1998) Bioorg Med Chem Lett 8:301
Leiting B, Pryor KD, Wu JK, Marsilio F, Patel RA, Craik CS, Ellman JA, Cummings RT, Thornberry NA (2003) Biochem J 371:525
von GTW, Trevillyan JM (2006) Drug Dev Res 67:627
Coutts SJ, Kelly TA, Snow RJ, Kennedy CA, Barton RW, Adams J, Krolikowski DA, Freeman DM, Campbell SJ et al. (1996) J Med Chem 39:2087
Hu Y, Ma L, Wu M, Wong MS, Li B, Corral S, Yu Z, Nomanbhoy T, Alemayehu S, Fuller SR, Rosenblum JS, Rozenkrants N, Minimo LC, Ripka WC, Szardenings AK, Kozarich JW, Shreder KR (2005) Bioorg Med Chem Lett 15:4239
Tran T, Quan C, Edosada CY, Mayeda M, Wiesmann C, Sutherlin D, Wolf BB (2007) Bioorg Med Chem Lett 17:1438
Lai JH, Wu W, Zhou Y, Maw HH, Liu Y, Milo LJ Jr, Poplawski SE, Henry GD, Sudmeier JL, Sanford DG, Bachovchin WW (2007) J Med Chem 50:2391
Garcia-Soria G, Gonzalez-Galvez G, Argoud GM, Gerstman M, Littlejohn TW III, Schwartz SL, O'Farrell AM, Li X, Cherrington JM, Bennett C, Guler HP (2008) Diabetes Obes Metab 10:293
Gupta R, Walunj SS, Tokala RK, Parsa KVL, Singh SK, Pal M (2009) Curr Drug Targets 10:71
Marepally SR, Yao M-L, Kabalka GW (2013) Future Med Chem 5:693
Krzeslak A, Pomorski L, Gaj Z, Lipinska A (2003) Cancer Lett 196:101
Srinivas U, Pahlsson P, Lundblad A (1996) Scand J Immunol 44:197
Mannori G, Crottet P, Cecconi O, Hanasaki K, Aruffo A, Nelson RM, Varki A, Bevilacqua MP (1995) Cancer Res 55:4425
Goodman JL, Nelson CM, Klein MB, Hayes SF, Weston BW (1999) J Clin Invest 103:407
Grundner C, Pancera M, Kang JM, Koch M, Sodroski J, Wyatt R (2004) Virology 330:233
Azevedo-Pereira JM, Santos-Costa Q, Mansinho K, Moniz-Pereira J (2003) Virology 313:136
Clark GF, Oehninger S, Patankar MS, Koistinen R, Dell A, Morris HR, Koistinen H, Seppala M (1996) Hum Reprod 11:467
Fukumori T, Takenaka Y, Yoshii T, Kim HRC, Hogan V, Inohara H, Kagawa S, Raz A (2003) Cancer Res 63:8302
Grassadonia A, Tinari N, Iurisci I, Piccolo E, Cumashi A, Innominato P, D'Egidio M, Natoli C, Piantelli M, Iacobelli S (2002) Glycoconj J 19:551
Gifford R (2013) ChemPhysChem 14:2032
Hatano K, Matsuoka K, Terunuma D (2013) Chem Soc Rev 42:4574
Becker B, Cooper MA (2011) J Mol Recognit 24:754
Gabius HJ, Andre S, Jimenez-Barbero J, Romero A, Solis D (2011) Trends Biochem Sci 36:298
Lei JP, Ju HX (2012) Chem Soc Rev 41:2122
Zeng XQ, Andrade CAS, Oliveira MDL, Sun XL (2012) Anal Bioanal Chem 402:3161
Ye C, Kiriyama K, Mistuoka C, Kannagi R, Ito K, Watanabe T, Kondo K, Akiyama S, Takagi H (1995) Int J Cancer 61:455
Karnati VV, Gao XM, Gao SH, Yang WQ, Ni WJ, Sankar S, Wang BH (2002) Bioorg Med Chem Lett 12:3373
Dai C, Cazares LH, Wang L, Chu Y, Wang SL, Troyer DA, Semmes OJ, Drake RR, Wang B (2011) Chem Commun 47:10338
Thiery G, Anselmi E, Audebourg A, Darii E, Abarbri M, Terris B, Tabet J-C, Gut IG (2008) Proteomics 8:3725
Rauser S, Marquardt C, Balluff B, Deininger SR-O, Albers C, Belau E, Hartmer R, Suckau D, Specht K, Ebert MP, Schmitt M, Aubele M, Höfler H, Walch A (2010) J. Proteome Res 9:1854
Schwamborn K, Caprioli RM (2010) Nat Rev Cancer 10:639
Chaurand PSM, Caprioli RM (1999) Anal Chem 71:5263
Shchepinov M, Korshun V (2003) Chem Soc Rev 32:170
Zhang K, Baeckstrom D, Brevinge H, Hansson GC (1996) J Cell Biochem 60:538
Yamada N, Chung YS, Maeda K, Sawada T, Ikehara T, Nishino H, Okuno M, Sowa M (1995) Invasion Metastasis 15:95
Nakamori S, Kameyama M, Imaoka S, Furukawa H, Ishikawa O, Sasaki Y, Izumi Y, Irimura T (1997) Dis Colon Rectum 40:420
Tanaka K, Togo S, Nanko M, Ishikawa T, Ichikawa Y, Yamaoka H, Shimada H (1999) Hepatogastroenterol 46:875
Zhang J, Nakayama J, Ohyama C, Suzuki M, Suzuki A, Fukuda M, Fukuda MN (2002) Cancer Res 62:4194
Chu Y, Wang D, Wang K, Liu ZL, Weston B, Wang B (2013) Bioorg Med Chem Lett 23:6307
Liu S, Wollenberger U, Halámek J, Leupold E, Stöcklein W, Warsinke A, Scheller FW (2005) Chem Eur J 11:4239
Song W, Jeong SH, Kim JS, Kim HS, Shin DH, Roh KH, Lee KM (2007) Diagn Microbiol Infect Dis 57:315
Wannapob R, Kanatharana P, Limbut W, Numnuam A, Asawatreratanakul P, Thammakhet C, Thavarungkul P (2010) Biosens Bioelectron 26:357
Saito S, Massie TL, Maeda T, Nakazumi H, Colyer CL (2012) Anal Chem 84:2452
Saito S, Maeda T, Nakazumi H, Colyer CL (2012) Anal Sci 29:157
Upadhyay S, Sen MR, Bhattacharjee A (2011) J Med Microbiol 60:691
Rosi NL, Mirkin CA (2005) Chem Rev 105:1547
Iqbal SS, Mayo MW, Bruno JG, Bronk BV, Batt CA, Chambers JP (2000) Biosens Bioelectron 15:549
Diltemiz SE, Ersöz A, Hür D, Keçili R, Say R (2013) Mater Sci Eng C Mater Biol Appl 33(2):824–830
Amano Y, Cheng Q (2005) Anal Bioanal Chem 381:156
Schofield D, Dimmock N (1996) J Virol Methods 62:33
Sato T, Ishii M, Ohtake F, Nagata K, Terabayashi T, Kawanishi Y, Okahata Y (1999) Glycoconj J 16:223
Takeuchi M, Yamamoto M, Shinkai S (1997) Chem Commun 1997:1731
Suenaga H, Mikami M, Sandanayake KRAS, Shinkai S (1995) Tetrahedron Lett 36:4825
Takeuchi M, Mizuno T, Shinmori H, Nakashima M, Shinkai S (1996) Tetrahedron 52:1195
Kijima H, Takeuchi M, Shinkai S (1998) Chem Lett 1998:781
Imada T, Kijima H, Takeuchi M, Shinkai S (1996) Tetrahedron 52:2817
Adhikiri DP, Heagy MD (1999) Tetrahedron Lett 40:7893
Cao H, Diaz DI, DiCesare N, Lakowicz JR, Heagy MD (2002) Org Lett 4:1503
Cao H, McGill T, Heagy MD (2004) J Org Chem 69:2959
Cao Z, Nandhikonda P, Heagy MD (2009) J Org Chem 74:3544
Davis CJ, Lewis PT, McCarroll ME, Read MW, Cueto R, Strongin RM (1999) Org Lett 1:331
Lewis PT, Davis CJ, Cabell LA, He M, Read MW, McCarroll ME, Strongin RM (2000) Org Lett 2:589
He M, Johnson RJ, Escobedo JO, Beck PA, Kim KK, St Luce NN, Davis CJ, Lewis PT, Fronczek FR, Melancon BJ, Mrse AA, Treleaven WD, Strongin RM (2002) J Am Chem Soc 124:5000
Kim KK, Escobedo JO, St Luce NN, Rusin O, Wong D, Strongin RM (2003) Org Lett 5:5007
Lim S, Escobedo JO, Lowry M, Strongin RM (2011) Chem Commun 47:8295
Badugu R, Lakowicz JR, Geddes CD (2005) Talanta 66:569
DiCesare N, Lakowicz JR (2001) Chem Commun 2001:2022
DiCesare N, Lakowicz JR (2001) J Phys Chem A 105:6834
Di Cesare N, Lakowicz JR (2001) J Photoch Photobio A 143:39
James TD, Shinmori H, Shinkai S (1997) Chem Commun 1997:71
Cooper CR, James TD (1998) Chem Lett 27:883
Arimori S, Bosch LI, Ward CJ, James TD (2001) Tetrahedron Lett 42:4553
Arimori S, Bosch LI, Ward CJ, James TD (2002) Tetrahedron Lett 43:911
Scrafton DK, Taylor JE, Mahon MF, Fossey JS, James TD (2008) J Org Chem 73:2871
Zhao J, Davidson MG, Mahon MF, Kociok-Köhn G, James TD (2004) J Am Chem Soc 126:16179
Bosch LI, Mahon MF, James TD (2004) Tetrahedron Lett 45:2859
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Draganov, A., Wang, D., Wang, B. (2014). The Future of Boron in Medicinal Chemistry: Therapeutic and Diagnostic Applications. In: Schwarz, J. (eds) Atypical Elements in Drug Design. EGC 2015. Topics in Medicinal Chemistry, vol 17. Springer, Cham. https://doi.org/10.1007/7355_2014_65
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