Boron’s journey: advances in the study and application of pharmacokinetics

References

• Scorei R. Is boron a prebiotic element? A mini-review of the essentiality of boron for the appearance of life on earth. Orig Life Evol Biosph. 2012;42:3–17.
   PubMed Web of Science ®Google Scholar
• Nielsen FH. Boron in human and animal nutrition. Plant Soil. 1997;193:199–208.
   Web of Science ®Google Scholar
• Soriano-Ursúa MA, Das BC, Trujillo-Ferrara JG. Boron containing compounds: chemico-biological properties and expanding medicinal potential in prevention, diagnosis and therapy. Expert Opin Ther Pat. 2014;24:485–500.
   PubMed Web of Science ®Google Scholar
• Nielsen FH. The emergence of boron as nutritionally important throughout the life cycle. Nutrition. 2016;16:512–514.
   Web of Science ®Google Scholar
• Hunt CD. Dietary boron: progress in establishing essential roles in human physiology. J Trace Elem Med Biol. 2012;26:157–160.
   PubMed Web of Science ®Google Scholar
• Chapin RE, Ku WW, Kenney MA, et al. The effects of dietary boron on bone strength in rats. Fundam Appl Toxicol. 1997;35:205–215.
   PubMedGoogle Scholar
• Devirian TA, Volpe SL. The physiological effects of dietary boron. Crit Rev Food Sci Nutr. 2003;43:219–231.
   PubMed Web of Science ®Google Scholar
• Baker SJ, Sanders V, Akama T, et al. Boron-containing small molecules as anti-inflammatory agents. US8501712. 2013.
   Google Scholar
• Akama T, Zhang YK, Ding CZet al. Boron-containing small molecules as anti-inflammatory agents. US8039450. 2011.
   Google Scholar
• Ban HS, Nakamura H. Boron-based drug design. Chem Rec. 2015;15:616–635.
   PubMed Web of Science ®Google Scholar
• Geninatti-Crich S, Deagostino A, Toppino A, et al. Boronated compounds for imaging guided BNCT applications. Anticancer Agents Med Chem. 2012;12:543–553.
   PubMed Web of Science ®Google Scholar
• Ciustea M, Ciustea G Combination therapy and methods for treatment and prevention of hyperproliferative diseases. US20150094277. 2015.
   Google Scholar
• Scorei RI, Popa R Jr. Boron-containing compounds as preventive and chemotherapeutic agents for cancer. Anticancer Agents Med Chem. 2010;10:346–351.
   PubMed Web of Science ®Google Scholar
• Li X, Hanagata N, Wang X, et al. Multimodal luminescent-magnetic boron nitride nanotubes@NaGdF₄: eustructures for cancer therapy. Chem Commun (Camb). 2014;50(33):4371–4374.
   PubMed Web of Science ®Google Scholar
• Srebnik M, Takrouri K, Shalom E Novel amine-borane compounds and uses thereof. US20100284914. 2010.
   Google Scholar
• Chang YT, Lee SC, Kang NY, et al. Bodipy structure fluorescence probes for diverse biological applications. WO2013095305A1. 2013.
   Google Scholar
• Kracke GR, Sevryugina Y, Hawthorne MF Cluster boron compounds and uses thereof. US9217002. 2015.
   Google Scholar
• Wheeler C, Todd D, Chen P, et al. Polymorphs of (S)-3-aminomethyl-7-(3-hydroxy-propoxy)-3H-benzo[C][1,2]oxaborol-1-OL. US8461364. 2013.
   Google Scholar
• Dunach I, Olivero S, Pintaric C Process for preparing boronic acids and esters in the presence of magnesium metal. US20110282090. 2011.
   Google Scholar
• Pietrzkowski Z Boron-containing compositions and methods therefor. From PCT Int. Appl. US20140274919. 2014.
   Google Scholar
• Coronado D, Merchant T Compounds and nail polish. WO2015171186. 2015.
   Google Scholar
• Markham A. Tavaborole: first global approval. Drugs.  2014;74:1555–1558.
   Google Scholar
• Murrell DF, Gebauer K, Spelman L, et al. Crisaborole topical oinment, 2% in adults with atopic dermatitis: a phase 2a, vehicle-controlled, proof-of-concept study. J Drugs In Dermatol. 2015;14:1108–1112.
   PubMed Web of Science ®Google Scholar
• Akama T, Balko TW, Defauw JM Boron-containing small molecules. US20160000813. 2016.
   Google Scholar
• Ito Y, Mizuno T, Yoshino K, et al. Biological evaluation of dopamine analogues containing phenylboronic acid group as new boron carriers. Appl Radiat Isot. 2011;69:1771–1773.
   PubMed Web of Science ®Google Scholar
• Reddy RK, Glinka T, Totrov M, et al. Boronic acid derivatives and therapeutic uses thereof. WO2016003929A1. 2016.
   Google Scholar
• Sikora A, Zielonka J, Adamus J, et al. Reaction between peroxynitrite and triphenylphosphonium-substituted arylboronic acid isomers: identification of diagnostic marker products and biological implications. Chem Res Toxicol. 2013;26:856–867.
   PubMed Web of Science ®Google Scholar
• Tanaka M, Fujiwara T. Physiological roles and transport mechanisms of boron: perspectives from plants. Pflugers Arch. 2008;456:671–677.
   PubMed Web of Science ®Google Scholar
• Nozawa A, Fujiwara T, Proteins imparting boron-tolerance and genes thereof. CN1930292B. 2014.
   Google Scholar
• Park M, Li Q, Shcheynikov N, et al. Borate transport and cell growth and proliferation. Not Only Plants. Cell Cycle. 2005;4:24–26.
   PubMed Web of Science ®Google Scholar
• Nielsen FH. Update on human health effects of boron. J Trace Elem Med Biol. 2014;28:383–387.
   PubMed Web of Science ®Google Scholar
• Wester RC, Hartway T, Maibach HI, et al. In vitro percutaneous absorption of boron as boric acid, borax, and disodium octaborate tetrahydrate in human skin. Biol Trace Elem Res. 2013;66:111–120.
   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.
   Web of Science ®Google Scholar
• Li X, Zhi C, Hanagata N, et al. Boron nitride nanotubes functionalized with mesoporous silica for intracellular delivery of chemotherapy drugs. Chem Commun (Camb). 2013;49(66):7337–7339.
   PubMed Web of Science ®Google Scholar
• Ciofani G. Potential applications of boron nitride nanotubes as drug delivery systems. Expert Opin Drug Deliv. 2010;7(8):889–893.
   PubMed Web of Science ®Google Scholar
• Liu B, Qi W, Tian L, et al. In vivo biodistribution and toxicity of highly soluble PEG-coated boron nitride in mice. Nanoscale Res Lett. 2015;10:478.
   PubMed Web of Science ®Google Scholar
• Xiong H, Zhou D, Qi Y, et al. Doxorubicin-loaded carborane-conjugated polymeric nanoparticles as delivery system for combination cancer therapy. Biomacromolecules. 2015;16:3980–3988.
   PubMed Web of Science ®Google Scholar
• Calabrese G, Nesnas JJ, Barbu E, et al. The formulation of polyhedral boranes for the boron neutron capture therapy of cancer. Drug Discov Today. 2012;17:153–159.
   PubMed Web of Science ®Google Scholar
• Genady AR. Promising carboranylquinazolines for boron neutron capture therapy: synthesis, characterization, and in vitro toxicity evaluation. Eur J Med Chem. 2009;44:409–416.
   PubMed Web of Science ®Google Scholar
• Ohta K, Ogawa T, Endo Y. Estrogenic activity of B-fluorinated o-carborane-1,2-bisphenol synthesized via S(N)Ar reaction. Bioorg Med Chem Lett. 2012;22:4728–4730.
   PubMed Web of Science ®Google Scholar
• Calvaresi M, Zerbetto FJ. In silico carborane docking to proteins and potential drug targets. Chem Inf Model. 2011;51:1882–1896.
   PubMed Web of Science ®Google Scholar
• Hawkins PM, Jelliss PA, Nonaka N, et al. Permeability of the blood-brain barrier to a rhenacarborane. J Pharmacol Exp Ther. 2009;329:608–614.
   PubMed Web of Science ®Google Scholar
• Marepally SR, Yao ML, Kabalka GW. Boronated carbohydrate derivatives as potential boron neutron capture therapy reagents.Future Med Chem. 2013;5:693–704.
   PubMed Web of Science ®Google Scholar
• Satapathy R, Dash BP, Bode BP, et al. New classes of carborane-appended 5-thio-D-glucopyranose derivatives. Dalton Trans. 2012;41:8982–8988.
   PubMed Web of Science ®Google Scholar
• Raissi H, Mollania F. Immunosuppressive agent leflunomide: a SWNTs-immobilized dihydroortate dehydrogenase inhibitory effect and computational study of its adsorption properties on zigzag single walled (6, 0) carbon and boron nitride nanotubes as controlled drug delivery devices. Eur J Pharm Sci. 2014;56:37–54.
   PubMed Web of Science ®Google Scholar
• Genchi GG, Ciofani G. Bioapplications of boron nitride nanotubes. Nanomedicine (Lond). 2015;10(22):3315–3319.
   PubMed Web of Science ®Google Scholar
• Ciofani G, Danti S, Genchi GG, et al. Pilot in vivo toxicological investigation of boron nitride nanotubes. Int J Nanomedicine. 2012;7:19–24.
   PubMed Web of Science ®Google Scholar
• Zhang N, Liu H, Kan H, et al. The influence of surface-active agent on the micro-morphology and crystallinity of spherical hexagonal boron nitride. J Nanosci Nanotechnol. 2015;15:6218–6224.
   PubMed Web of Science ®Google Scholar
• Brooks JA Anti-fungal powder having enhanced excipient properties. US2003/0224063. 2003.
   Google Scholar
• Del Rosso JQ, Plattner JJ. From the test tube to the treatment room: fundamentals of boron-containing compounds and their relevance to dermatology. J Clin Aesthet Dermatol. 2014;7:13–21.
   PubMedGoogle Scholar
• McClary CA, Taylor MS. Applications of organoboron compounds in carbohydrate chemistry and glycobiology: analysis, separation, protection, and activation. Carbohydr Res. 2013;381:112–122.
   PubMed Web of Science ®Google Scholar
• Touchet S, Carreaux F, Carboni B, et al. Aminoboronic acids and esters: from synthetic challenges to the discovery of unique classes of enzyme inhibitors. Chem Soc Rev. 2011;40:3895–3914.
   PubMed Web of Science ®Google Scholar
• Hunter P. Not boring at all. Boron is the new carbon in the quest for novel drug candidates. EMBO Rep. 2009;10:125–128.
   PubMed Web of Science ®Google Scholar
• Benkovic SJ, Baker SJ, Alley MR, et al. Identification of borinic esters as inhibitors of bacterial cell growth and bacterial methyltransferases, CcrM and MenH. J Med Chem. 2005;48:7468–7476.
   PubMed Web of Science ®Google Scholar
• Pappin B, Kiefel MJ, Houston TA. Boron-carbohydrate interactions. In: Chuan-Fa C, editor. Carbohydrates - comprehensive studies on glycobiology and glycotechnology. InTech; 2012. p. 37–54. doi:10.5772/50630
   Google Scholar
• Aziz-Ketuli K, Hadi AH. Boronate derivatives of functionally diverse catechols: stability studies. Molecules. 2010;15:2347–2356.
   PubMed Web of Science ®Google Scholar
• He L, Fullenkamp DE, Rivera JG, et al. pH responsive self-healing hydrogels formed by boronate–catecholcomplexation. Chem Commun. 2011;47:7497–7499.
   PubMed Web of Science ®Google Scholar
• Schmidt E, Dooley N, Ford SJ, et al. Physicochemical investigation of the influence of saccharide-based parenteral formulation excipients on l-p-boronphenylalanine solubilisation for boron neutron capture therapy. J Pharm Sci. 2012;101:223–232.
   PubMed Web of Science ®Google Scholar
• Burnham BS. Synthesis and pharmacological activities of amineboranes. Curr Med Chem. 2005;12:1995–2010.
   PubMed Web of Science ®Google Scholar
• Ni Y, Wu J. Far-red and near infrared BODIPY dyes: synthesis and applications for fluorescent pH probes and bio-imaging. Org Biomol Chem. 2014;12:3774–3791.
   PubMed Web of Science ®Google Scholar
• Dong H, Wang S, Galligan JJ, et al. Boron-doped diamond nano/microelectrodes for biosensing and in vitro measurements. Front Biosci (Schol Ed). 2011;3:518–540.
   PubMedGoogle Scholar
• Song MJ, Lee SK, Kim JH, et al. Dopamine sensor based on a boron-doped diamond electrode modified with a polyaniline/Au nanocomposites in the presence of ascorbic acid. Anal Sci. 2012;28:583–587.
   PubMed Web of Science ®Google Scholar
• Bernard CE, Harrass MC, Manning MJ. Boric acid and inorganic borate pesticides. Hayes’ handbook of pesticide toxicology. Amsterdam: Elsevier Inc; 2010. p. 2033–2053.
   Google Scholar
• Strong PL. Boric acid and inorganic borate pesticides. Handbook of pesticide toxicology. 2nd ed. San Diego: Academic Press; 2001. p. 1429–1437.
   Google Scholar
• Takano J, Miwa K, Fujiwara T. Boron transport mechanisms: collaboration of channels and transporters. Trends Plant Sci. 2008;13:451–457.
   PubMed Web of Science ®Google Scholar
• Chaumont F, Tyerman SD. Aquaporins: highly regulated channels controlling plant water relations. Plant Physiol. 2014;164:1600.
   PubMed Web of Science ®Google Scholar
• Liao SF, Monegue JS, Lindemann MD, et al. Dietary supplementation of boron differentially alters expression of borate transporter (NaBCl) mRNA by jejunum and kidney of growing pigs. Biol Trace Elem Res. 2010;143:901–912.
   PubMed Web of Science ®Google Scholar
• Scorei R, Ciubar R, Iancu C, et al. In vitro effects of calcium fructoborate on fMLP-stimulated human neutrophil granulocytes. Biol Trace Elem Res. 2007;118:27–37.
   PubMed Web of Science ®Google Scholar
• Furikado Y, Nagahata T, Okamoto T, et al. Universal reaction mechanism of boronic acids with diols in aqueous solution: kinetics and the basic concept of a conditional formation constant. Chemistry. 2014;20:13194–13202.
   PubMed Web of Science ®Google Scholar
• Kabu M, Akosman MS. Biological effects of boron. In: Reviews of environmental contamination and toxicology, vol. 225. New York: Springer-Verlag; 2013. p. 57–76. doi:10.1007/978-1-4614-6470-9_2
   PubMed Web of Science ®Google Scholar
• Hill AP, Young RJ. Getting physical in drug discovery: a contemporary perspective on solubility and hydrophobicity. Drug Discov Today. 2010;15:648–655.
   PubMed Web of Science ®Google Scholar
• Price CJ, Strong PL, Murray FJ, et al. Blood boron concentrations in pregnant rats fed boric acid throughout gestation. Reprod Toxicol. 1997;11:833–842.
   PubMed Web of Science ®Google Scholar
• Moseman RF. Chemical disposition of boron in animals and humans. Environ Health Perspect. 1994;102(S7):113–117.
   PubMed Web of Science ®Google Scholar
• Dinca L, Scorei R. Boron in human nutrition and its regulations use. J Nutr Ther. 2013;2:22–29.
   Google Scholar
• Ku WW, Chapin RE. Mechanism of the testicular toxicity of boric acid in rats: in vivo and in vitro studies. Environ Health Perspect. 1994;102:(S7):99-105.
   Web of Science ®Google Scholar
• Newnham RE. Agricultural practices affect arthritis. Nutr Health. 1991;7:89–100.
   PubMedGoogle Scholar
• Johnson EW Prevention and treatment of osteochondrosis in animals and humans. From PCT Int. Appl. US20120328715. 2012.
   Google Scholar
• Bauer WF, Johnson DA, Steele SM, et al. Gross boron determination in biological samples by inductively coupled plasma-atomic emission spectroscopy. Strahlenther Onkol. 1989;165:176–179.
   PubMed Web of Science ®Google Scholar
• McCoy H, Kenney MA, Montgomery C, et al. Relation of boron to the composition and mechanical properties of bone. Environ Health Perspect. 1994;102(S7):49–53.
   PubMed Web of Science ®Google Scholar
• De Simone U, Manzo L, Ferrari C, et al. Short and long-term exposure of CNS cell lines to BPA-f a radiosensitizer for boron neutron capture therapy: safety dose evaluation by a battery of cytotoxicity tests. Neurotoxicology. 2013;35:84–90.
   PubMed Web of Science ®Google Scholar
• European Food Safety Authority (EFSA). Scientific opinion on the re-evaluation of boric acid (E 284) and sodium tetraborate (borax) (E 285) as food additives. EFSA J. 2013;11:1–52.
   Google Scholar
• Meacham S, Karakas S. Boron in human health: evidence for dietary recommendations and public policies. Open Miner Process. 2010;3:36–53.
   Google Scholar
• Hosmane N. Boron science new technologies and applications. Boca Raton (FL): CRC Press; 2011.
   Google Scholar
• Gorustovich AA, Steimetz T, Nielsen FH, et al. Histomorphometric study of alveolar bone healing in rats fed a boron-deficient diet. Anat Rec (Hoboken). 2008;291:441–447.
   PubMedGoogle Scholar
• Tang J, Zheng XT, Xiao K, et al. Effect of boric acid supplementation on the expression of BDNF in African Ostrich chick brain. Biol Trace Elem Res. 2016;170:208–215.
   PubMed Web of Science ®Google Scholar
• Levêque D, Carvalho MCM, Maloisel F. Review Clinical pharmacokinetics of bortezomib. In Vivo. 2007;21:273–278.
   PubMed Web of Science ®Google Scholar
• Osawa T, Naito T, Kaneko T, et al. Blood distribution of bortezomib and its kinetics in multiple myeloma patients. Clin Biochem. 2014;47(15):54–59.
   PubMed Web of Science ®Google Scholar
• Portu A, Postuma I, Gadan MA, et al. Reprint of inter-comparison of boron concentration measurements at INFN-University of Pavia (Italy) and CNEA (Argentina). Appl Radiat Isot. 2015;106:171–175.
   PubMed Web of Science ®Google Scholar
• Barth RF, H Vicente M, Harling OK, et al. Current status of boron neutron capture therapy of high grade gliomas and recurrent head and neck cancer. Radiat Oncol. 2012;7:1–21.
   PubMed Web of Science ®Google Scholar
• Schwartz R, Davidson T. Pharmacology, pharmacokinetics, and practical applications of bortezomib. Oncology (Williston Park). 2004;18(14S11):14–21.
   PubMedGoogle Scholar
• Benderdour M, Bui-Van T, Dicko A, et al. In vivo and in vitro effects of boron and boronated compounds. J Trace Element Med Biol. 1998;12:2–7.
   PubMed Web of Science ®Google Scholar
• Soriano-Ursúa MA, Mancilla-Percino T, Querejeta E, et al. Give boron a chance: boron containing compounds reach ionotropic and metabotropic transmembrane receptors. Mini Rev Med Chem. 2011;11:1031–1038.
   PubMed Web of Science ®Google Scholar
• Das BC, Thapa P, Karki R, et al. Boron chemicals in diagnosis and therapeutics. Future Med Chem. 2013;5:653–676.
   PubMed Web of Science ®Google Scholar
• Li X, Cao JH, Li Y, et al. Activity-based probe for specific photoaffinity labeling gamma-aminobutyric acid B (GABAB) receptors on living cells: design, synthesis, and biological evaluation. J Med Chem. 2008;51:3057–3060.
   PubMed Web of Science ®Google Scholar
• White MA, Cerqueira AB, Whitman CA, et al. Determination of phase stability of elemental boron. Angew Chem Int Ed Engl. 2015;54:3626–3629.
   PubMed Web of Science ®Google Scholar
• Emsley J. The elements. Oxford, UK: Clarendon Press; 1989.
   Google Scholar
• Adachi S, Cognetta AB 3rd, Niphakis MJ, et al. Facile synthesis of borofragments and their evaluation in activity-based protein profiling. Chem Commun (Camb). 2015;51:3608–3611.
   PubMed Web of Science ®Google Scholar
• Jarnagin K, Chanda S, Coronado D, et al. Crisaborole topical ointment, 2%: a nonsteroidal, topical, anti-inflammatory phosphodsiesterase 4 inhibitor in clinical development for the treatment of atopic dermatitis. JDD. 2016 April;15(4):390.
   PubMed Web of Science ®Google Scholar
• Pekol T, Daniels JS, Labutti J, et al. Human metabolism of the proteasome inhibitor bortezomib: identification of circulating metabolites. Drug Metab Dispos. 2005;33:771–777.
   PubMed Web of Science ®Google Scholar
• Hall DG. Boronic acids - preparation, applications in organic synthesis and medicine.; chapter 13. In Applications of boronic acids in chemical biology and medicinal chemistry, 2nd. Weinheim: Wiley-VCH; 2005.
   Google Scholar
• Uttamsingh V, Lu C, Miwa G, et al. Relative contributions of the five major human cytochromes p450, 1a2, 2c9, 2c19, 2d6, and 3a4, to the hepatic metabolism of the proteasome inhibitor bortezomib. Drug Metab Dispos. 2005;33:1723–1728.
   PubMed Web of Science ®Google Scholar
• Nielsen FH. Biochemical and physiologic consequences of boron deprivation in humans. Environ Health Perspect. 1994;102(S7):59–63.
   PubMed Web of Science ®Google Scholar
• Ku WW, Chapin RE, Moseman RF, et al. Tissue disposition of boron in male Fischer rats. Toxicol Appl Pharmacol. 1991;111:145–151.
   PubMed Web of Science ®Google Scholar
• Murray FJ. A comparative review of the pharmacokinetics of boric acid in rodents and humans. Biol Trace Elem Res. 1998;66:331–341.
   Google Scholar
• Leal TB, Remick SC, Takimoto CH, et al. Dose-escalating and pharmacological study of bortezomib in adult cancer patients with impaired renal function: a national cancer institute organ dysfunction working group study. Cancer Chemother Pharmacol. 2011;68:1439–1447.
   PubMed Web of Science ®Google Scholar
• Boens N, Leen V, Dehaen W. Fluorescent indicators based on BODIPY. Chem Soc Rev. 2012;41:1130–1172.
   PubMed Web of Science ®Google Scholar
• Singh APs, Lee KM, Murale DP, et al. Novel sulphur-rich BODIPY systems that enable stepwise fluorescent O-atom turn-on and H2O2 neuronal system probing. Chem Commun (Camb). 2012;48:7298–7300.
   PubMed Web of Science ®Google Scholar
• Moreau P, Karamanesht II, Domnikova N, et al. Pharmacokinetic, pharmacodynamic and covariate analysis of subcutaneous versus intravenous administration of bortezomib in patients with relapsed multiple myeloma. Clin Pharmacokinet. 2012;51:823–829.
   PubMed Web of Science ®Google Scholar
• Soriano-Ursúa MA, Correa-Basurto J, Romero-Huerta J, et al. Pharmacokinetic parameters and a theoretical study about metabolism of BR-AEA (a salbutamol derivative) in rabbit. J Enzyme Inhib Med Chem. 2010;25:340–346.
   PubMed Web of Science ®Google Scholar
• Zhou HB, Nettles KW, Bruning JB, et al. Elemental isomerism: a boron-nitrogen surrogate for a carbon-carbon double bond increases the chemical diversity of estrogen receptor ligands. Chem Biol. 2007;14:659–669.
   PubMedGoogle 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.
   PubMed Web of Science ®Google Scholar
• Ohta K, Goto T, Fujii S, et al. Crystal structure, docking study and structure-activity relationship of carborane-containing androgen receptor antagonist 3-(12-hydroxymethyl-1,12-dicarba-closo-dodecaboran-1-yl)benzonitrile. Bioorg Med Chem. 2011;19:3540–3548.
   PubMed Web of Science ®Google Scholar
• Sene S, McLane J, Schaub N, et al. Formulation of benzoxaborole drugs in PLLA: from materials preparation to in vitro release kinetics and cellular assays. J Mater Chem B. 2016;4:257–272.
   Web of Science ®Google Scholar
• Viñas C. The uniqueness of boron as a novel challenging element for drugs in pharmacology, medicine and for smart biomaterials. Future Med Chem. 2013;5:617–619.
   PubMed Web of Science ®Google Scholar
• Groudine MT, Hawthorne MF Boron-containing hormone analogs and methods of their use in imaging or killing cells having hormone receptors. EP0729363B1. 2003.
   Google Scholar
• Fernández E, Whiting A. Synthesis and application of organoboron compounds. Vol. 49. Heidelberg: Springer; 2015.
   Google Scholar
• Zhou H, Ding D, Zhou Yet al. Boron-containing small molecules as antiprotozoal agents. US20110207701. 2011.
   Google Scholar
• Baker SJ, Hernandez VS, Sharma R, et al. Boron-containing small molecules. EP2164331A4. 2011.
   Google Scholar