Recent developments with boron as a platform for novel drug design

References

• Chellanand P, Sadler PJ. The elements of life and medicines. Phil Trans R Soc A. 2015;373:1–56.
   Google Scholar
• Das BC, Thapa P, Karki R, et al. Boron chemicals in diagnosis and therapeutics. Future Med Chem. 2013;5:653–676. doi:10.4155/fmc.13.38.
   PubMed Web of Science ®Google Scholar
• Baker SJ, Ding CZ, Akama T, et al. Therapeutic potential of boron containing compounds. Future Med Chem. 2009;1:1275–1288. doi:10.4155/fmc.09.71.
   PubMed Web of Science ®Google Scholar
• Adams J, Behnke M, Chen SW, et al. Potent and selective inhibitors of the proteasome: dipeptidyl boronic acids. Bioorg Med Chem Lett. 1998;8:333–338. doi:10.1016/S0960-894X(98)00029-8.
   PubMed Web of Science ®Google Scholar
• Rock FL, Mao W, Yaremchuk A, et al. An antifungal agent inhibits an aminoacyl-tRNA synthetase by trapping tRNA in the editing site. Science. 2007;316:1759–1761. doi:10.1126/science.1142109.
   PubMed Web of Science ®Google Scholar
• Barth RF, Coderre JA, Vicente MGH, et al. Boron neutron capture therapy of cancer. Curr Status Future Prospects. 2005;11:3987–4002.
   Google Scholar
• Vitale AA, Hoffmann G, Pomilio AB. Boron containing bioactive molecules: an approach to boron neutron capture therapy. Mol Med Chem. 2005;8:1–49.
   Google Scholar
• Wang W, Gao X, Wang B. Boronic acid-based sensors. Current Org Chem. 2002;6:1285–1317. doi:10.2174/1385272023373446.
   Web of Science ®Google Scholar
• Brooks WLA, Sumerlin BS. Synthesis and applications of boronic acid-containing polymers: from materials to medicine. Chem Rev. 2015. doi:10.1021/acs.chemrev.5b00300.
   PubMed Web of Science ®Google Scholar
• Whyte GF, Vilar R, Woscholsk R. Molecular recognition with boronic acids – applications in chemical biology. J Chem Biol. 2013;6:161–174. doi:10.1007/s12154-013-0099-0.
   PubMedGoogle Scholar
• Hosmane NS, editor. Boron Science: new technologies and applications. Boca Raton (FL): CRC Press; 2011.
   Google Scholar
• Yang W, Gao X, Wang B. Boronic acid compounds as potential pharmaceutical agents. Med Res Rev. 2003;23:346–368. doi:10.1002/med.10043.
   PubMed Web of Science ®Google Scholar
• Ban HS, Nakamura H. Boron-based drug design. Chem Rec. 2015;15:616–635. doi:10.1002/tcr.201402100.
   PubMed Web of Science ®Google Scholar
• Dembitsky VM, Smoum R, Al-Quntar AA, et al. Natural occurrence of boron-containing compounds in plants, algae and microorganisms. Plant Science. 2002;163:931–942. doi:10.1016/S0168-9452(02)00174-7.
   Web of Science ®Google Scholar
• Lutz O, Humpfer E, Spraul M. Ascertainment of boric-acid esters in wine by 11B-NMR. Naturwissen. 1991;78:67–69. doi:10.1007/BF01206257.
   Web of Science ®Google Scholar
• Chen X, Schauder S, Potier N, et al. Structural identification of a bacterial quorum-sensing signal containing boron. Nature. 2002;415:545–549. doi:10.1038/415545a.
   PubMed Web of Science ®Google Scholar
• Hutter R, Keller-Schierlein W, Knusel F, et al. Stoffwechselprodukte von Microrganismen. Boromycin Helv Chim Acta. 1967;50:1533–1539. doi:10.1002/hlca.19670500612.
   PubMed Web of Science ®Google Scholar
• Crisaborole is a novel boron-containing small molecule that is being studied for its inhibition of PDE4 and reduction of the production of TNF-alpha. [cited 2016 Jan 6]. Available from: anacor Pharmaceutical company webside www.anacor.com
   Google Scholar
• Jacobs RT, Nare B, Wring SA, et al. SCYX-7158, an orally-active benzoxaborole for the treatment of stage 2 human African trypanosomiasis. PLoS Negl Trop Dis. 2011;5:e1151. doi:10.1371/journal.pntd.0001370.
   PubMed Web of Science ®Google Scholar
• Garcia-Soria G, Gonzalez-Galvez G, Argoud GM, et al. The dipeptidyl peptidase-4 inhibitor PHX1149 improves blood glucose control in patients with type 2 diabetes mellitus. Diabets Obes Metab. 2008;10:293–300. doi:10.1111/j.1463-1326.2008.00868.x.
   PubMed Web of Science ®Google Scholar
• Ban HS, Usui T, Nabeyama W, et al. Discovery of boron-conjugated 4-anilinoquinazoline as a prolonged inhibitor of EGFR tyrosine kinase. Org Biomol Chem. 2009;7:4415–4427. doi:10.1039/b816235b.
   PubMed Web of Science ®Google Scholar
• Mendes RE, Alley MR, Sader HS, et al. Potency and spectrum of activity of AN3365, a novel boron-containing protein synthesis inhibitor, tested against clinical isolates of enterobacteriaceae and nonfermentative gram-negative bacilli. Antimicrob Agents Chemother. 2013;57:2849–2857. doi:10.1128/AAC.00160-13.
   PubMed Web of Science ®Google Scholar
• Ramakumar K, Kv T, Gundla R, et al. Discovery of 3-acetyl-4-hydroxy-2-pyranone derivatives and their difluoridoborate complexes as anovel class of HIV-1 integrase inhibitors. Bioorg Med Chem. 2008;16:8988–8998. doi:10.1016/j.bmc.2008.08.067.
   PubMed Web of Science ®Google Scholar
• FiercePharma special reports, Velcade. [cited 2016 Jan 6]. Available from: http://www.fiercepharma.com/special-reports/velcade/top-20-orphan-drugs-2018
   Google Scholar
• Heying TL, Ager JW, Clark SL, et al. A new series of organoboranes. I. Carboranes from the reaction of decaborane with acetylenic compounds. Inorg Chem. 1963;2:1089–1092. doi:10.1021/ic50010a002.
   Web of Science ®Google Scholar
• Fein MM, Bobinski J, Mayes N, et al. Carboranes. I. The preparation and chemistry of 1-isopropenylcarborane and its derivatives (A new family of stable closoboranes). Inorg Chem. 1963;2:1111–1115. doi:10.1021/ic50010a007.
   Web of Science ®Google Scholar
• Grimes RN. Carboranes. 2nd ed. Amsterdam: Academic Press; 2011.
   Google Scholar
• Casanova J, editor. The borane, carborane, carbocation continuum. New York: John Wiley and Sons, Inc; 1998.
   Google Scholar
• Leśnikowski ZJ. Boron units as pharmacophors – new applications and opportunities of boron cluster chemistry. Coll Czech Chem Commun. 2007;72:1646–1658. doi:10.1135/cccc20071646.
   Google Scholar
• Hawthorne MF. Advances at the interface of polyhedral borane chemistry and medicine. Comment Inorg Chem. 2010;31:153–163. doi:10.1080/02603594.2010.520258.
   Web of Science ®Google Scholar
• Scholz M, Hey-Hawkins E. Carbaboranes as pharmacophores: properties, synthesis, and application strategies. Chem Rev. 2011;111:7035–7062. doi:10.1021/cr200038x.
   PubMed Web of Science ®Google Scholar
• Issa F, Kassiou M, Rendina LM. Boron in drug discovery: Carboranes as unique pharmacophores in biologically active compounds. Chem Rev. 2011;111:5701–5722. doi:10.1021/cr2000866.
   PubMed Web of Science ®Google Scholar
• Lesnikowski ZJ. New opportunities in boron chemistry for medical applications. In: Hosmane NS, editor. Boron sciences. New technologies and applications. Boca Raton, FL: CRC Press; 2011. p. 3–19.
   Google Scholar
• Yamamoto K, Endo Y. Utility of boron clusters for drug design. Hansch-Fujita hydrophobic parameters of dicarba-closo-dodecarboranyl groups. Bioorg Med Chem Lett. 2001;11:2389–2392. doi:10.1016/S0960-894X(01)00438-3.
   PubMed Web of Science ®Google Scholar
• Laubengayer AW, Rysz WR. The dipole moments of the isomers of dicarbadecaborane, B10H10C2H21. Inorg Chem. 1965;4:1513–1514. doi:10.1021/ic50032a043.
   Web of Science ®Google Scholar
• Fanfrlk J, Lepsik M, Horinek D, et al. Interaction of carboranes with biomolecules: formation of dihydrogen bonds. ChemPhysChem. 2006;7:1100–1105. doi:10.1002/cphc.200500648.
   PubMed Web of Science ®Google Scholar
• Dou J, Su F, Nie Y, et al. Self-assembled 2D supramolecular networks of copper(I) carborane complexes through C–H⋯H–B dihydrogen bonding interactions. Dalton Trans. 2008;4152–4156. doi:10.1039/b801339j.
   PubMed Web of Science ®Google Scholar
• Planas JG, Viñas C, Teixidor F, et al. Self-assembly of mercaptane-metallacarborane complexes by an unconventional cooperative effect: a C-H … S-H … H-B hydrogen/dihydrogen bond interaction. J Am Chem Soc. 2005;16:15976–15982. doi:10.1021/ja055210w.
   Web of Science ®Google Scholar
• Mader P, Pecina A, Cigler P, et al. Carborane-based carbonic anhydrase inhibitors: Insight into CAII/CAIX specificity from a high-resolution crystal structure, modeling, and quantum chemical calculations. BioMed Res Int. 2014;2014:389869.
   Google Scholar
• Pecina A, Lepsík M, Rezac J, et al. QM/MM Calculations reveal the different nature of the interaction of two carborane-based sulfamide inhibitors of human carbonic anhydrase II. J Phys Chem B. 2013;117:16096–16104. doi:10.1021/jp410216m.
   PubMed Web of Science ®Google Scholar
• Fujii S, Masuno H, Taoda Y, et al. Boron cluster-based development of potent nonsecosteroidal vitamin D receptor ligands: direct observation of hydrophobic interaction between protein surface and carborane. J Am Chem Soc. 2011;133:20933–20941. doi:10.1021/ja208797n.
   PubMed Web of Science ®Google Scholar
• Otero R, Seoane S, Sigueiro R, et al. Carborane-based design of a potent vitamin D receptor agonist. Chem Sci. 2016;7:1033–1037. doi:10.1039/C5SC03084F.
   Web of Science ®Google Scholar
• Fischli W, Leukart O, Schwyzer R. Hormone-receptor interactions. Carboranylalanine (Car) as a phenylalanine analogue: reactions with chymotrypsin. Helv Chim Acta. 1977;60:959–963. doi:10.1002/hlca.19770600326.
   PubMed Web of Science ®Google Scholar
• Hawthorne MF, Maderna A. Applications of radiolabeled boron clusters to the diagnosis and treatment of cancer. Chem Rev. 1999;99:3421–3434.
   PubMed Web of Science ®Google Scholar
• Valliant JF, Guenther KJ, King AS, et al. The medicinal chemistry of carboranes. Coord Chem Rev. 2002;232:173–230. doi:10.1016/S0010-8545(02)00087-5.
   Web of Science ®Google Scholar
• Lesnikowski ZJ, Olejniczak AB, Schinazi RF. At the crossroads of biological and inorganic chemistry - oligonucleotides and oligophosphates containing boron clusters. In: Schinazi RF, Liotta DC, editors. Frontiers in nucleic acids. Tucker, GA: IHL Press, Informed Horizons, LLC; 2004. p. 577–592.
   Google Scholar
• Endo Y, Yamamoto K, Kagechika H, Utility of boron clusters for drug design. Relation between estrogen receptor binding affinity and hydrophobicity of phenols bearing various types of carboranyl groups. Bioorg Med Chem Lett. 2003;13:4089–4092. and references cited therein.
   PubMed Web of Science ®Google Scholar
• Endo Y, Iijima T, Yamakoshi Y, et al. Potent estrogen agonists based on carborane as a hydrophobic skeletal structure. A new medicinal application of boron clusters. Chem Biol. 2001;8:341–355. doi:10.1016/S1074-5521(01)00016-3.
   PubMed Web of Science ®Google Scholar
• Fujii S, Ohta K, Tokuhito GT, et al. Acidic heterocycles as novel hydrophilic pharmacophore of androgen receptor ligands with a carborane core structure. Bioorg Med Chem. 2009;17:344–350. doi:10.1016/j.bmc.2008.10.060.
   PubMed Web of Science ®Google Scholar
• Wilkinson SM, Gunosewoyo H, Barron ML, et al. The first CNS-active carborane: A novel P2X7 receptor antagonist with antidepressant activity. ACS Chem Neurosci. 2014;5:335−9. doi:10.1021/cn500054n.
   PubMed Web of Science ®Google Scholar
• Cígler P, Kozísek M, Rezácová P, et al. From nonpeptide toward noncarbon protease inhibitors: metallacarboranes as specific and potent inhibitors of HIV protease. Proc Natl Acad Sci USA. 2005;102:15394–15399. doi:10.1073/pnas.0507577102.
   PubMed Web of Science ®Google Scholar
• Scholz M, Bensdorf K, Gust R, et al. Asborin: The carbaborane analogue of aspirin. ChemMedChem. 2009;4:746–748. doi:10.1002/cmdc.200900072.
   PubMed Web of Science ®Google Scholar
• Neumann W, Xu S, Sarosi MB, et al. nido-Dicarbaborate induces potent and selective inhibition of cyclooxygenase-2. ChemMedChem. 2015. doi:10.1002/cmdc.201500199.
   Web of Science ®Google Scholar
• Brynda J, Mader P, Sicha V, et al. Carborane-based carbonic anhydrase inhibitors. Angew Chem Int Ed. 2013;52:13760–13763. doi:10.1002/anie.201307583.
   PubMed Web of Science ®Google Scholar
• Kracke GR, VanGordon MR, Sevryugina YV, et al. Carborane-derived local anesthetics are isomer dependent. ChemMedChem. 2015;10:62–67. doi:10.1002/cmdc.201402369.
   PubMed Web of Science ®Google Scholar
• Bednarska K, Olejniczak AB, Wojtczak BA, et al. Adenosine and 2ʹ-deoxyadenosine modified with boron cluster pharmacophores as new classes of human blood platelet function modulators. ChemMedChem. 2010;5:749–756. doi:10.1002/cmdc.201000075.
   PubMed Web of Science ®Google Scholar
• Bednarska K, Olejniczak AB, Piskała A, et al. Effect of adenosine modified with a boron cluster pharmacophore on reactive oxygen species production by human neutrophils. Bioorg Med Chem. 2012;20:6621–6629. doi:10.1016/j.bmc.2012.09.039.
   PubMed Web of Science ®Google Scholar
• Scholz M, Kaluderovic GN, Kommera H, et al. Carbaboranes as pharmacophores: similarities and differences between aspirin and asborin. Eur J Med Chem. 2011;46:1131–1139. doi:10.1016/j.ejmech.2011.01.030.
   PubMed Web of Science ®Google Scholar
• Scholz M, Steinhagen M, Heiker JT, et al. Asborin inhibits aldo/keto reductase 1A1. ChemMedChem. 2011;6:89–93. doi:10.1002/cmdc.201000368.
   PubMed Web of Science ®Google Scholar
• Scholz M, Blobaum AL, Marnett LJ, et al. Synthesis and evaluation of carbaborane derivatives of indomethacin as cyclooxygenase inhibitors. Bioorg Med Chem. 2011;19:3242–3248. doi:10.1016/j.bmc.2011.03.054.
   PubMed Web of Science ®Google Scholar
• Scholz M, Blobaum AL, Marnett LJ, et al. ortho-Carbaborane derivatives of indomethacin as cyclooxygenase (COX)-2 selective inhibitors. Bioorg Med Chem. 2012;20:4830–4837. doi:10.1016/j.bmc.2012.05.063.
   PubMed Web of Science ®Google Scholar
• Laube M, Neumann W, Scholz M, et al. 2-carbaborane-3-phenyl-1H-indoles—synthesis via McMurry reaction and cyclooxygenase (COX) inhibition activity. ChemMedChem. 2013;8:329–335. doi:10.1002/cmdc.201200455.
   PubMed Web of Science ®Google Scholar
• Olejniczak AB, Adamska AM, Paradowska E, et al. Modification of selected anti-HCMV drugs with lipophilic boron cluster modulator. Acta Pol Pharm Drug Res. 2013;70:489–504.
   PubMed Web of Science ®Google Scholar
• Białek-Pietras M, Olejniczak AB, Paradowska E, et al. Synthesis and in vitro antiviral activity of lipophilic pyrimidine nucleoside/carborane conjugates. J Organomet Chem. 2015;798:99–105. doi:10.1016/j.jorganchem.2015.07.002.
   Web of Science ®Google Scholar
• Gabel D. Boron clusters in medicinal chemistry: perspectives and problems. Pure Appl Chem. 2015;87:173–179. doi:10.1515/pac-2014-1007.
   Web of Science ®Google Scholar