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Chemical Compound Review

Borane     borane

Synonyms: Borane(3), CHEBI:30149, AC1L1MAI, [BH3], BH3, ...
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Disease relevance of borane

  • Preferential accumulation of 10B in tumors was achieved by continuous infusion of the sulfhydryl borane dimer, Na4(10)B24H22S2, at a rate of 45-50 micrograms of 10B per g of body weight per day from day 11 to day 14 after tumor initiation (day 0) [1].
  • Axonal polyneuropathy after acute dimethylamine borane intoxication [2].
  • A CD 344 rat glioma model currently used to investigate boron neutron capture therapy (BNCT) was used to demonstrate an increased survival rate after thermal neutron irradiation enhanced by administration of 10B-enriched polyhedral borane, Na2B12H11SH [3].
  • The reduction of serum triglycerides correlated with ability of the borane compound to suppress liver fatty acid synthetase activity [4].
  • The development of tumor-localizing boron compounds was discussed, including the sulfhydryl-containing polyhedral borane, sodium borocaptate (Na2B12H11SH), and boronophenylalanine (BPA), both of which are currently being used clinically in Japan as capture agents for malignant brain tumors and melanomas, respectively [5].

Psychiatry related information on borane

  • Butirosin (Ia), 5''-amino-5''-deoxy-(Ic), 3',4'-dideoxy-(Ie), and 5''-amino-3',4',5''-trideoxy-butirosin A (If) were converted into the corresponding 1'''-deoxo derivatives, Ib, Id, Ig, and Ih by borane reduction [6].

High impact information on borane

  • An efficient asymmetric synthesis of an estrogen receptor modulator by sulfoxide-directed borane reduction [7].
  • Either TRPC internalization by CalyA or treatment with the inositol triphosphate receptor inhibitor 2-aminoethoxydiphenyl borane resulted in the loss of PMN SOCE [8].
  • However, it is likely that 2-aminoethoxydiphenyl borane does not inhibit through an action on the IP(3) receptor because the drug was equally effective in wild-type DT40 B-cells and in DT40 B-cells whose genes for all three IP(3) receptors had been disrupted [9].
  • The reaction of the [Li(THF)(4)](+) salt of dimesityl-1,8-naphthalenediylborate with [Me(2)NCH(2)]I affords a borane (1-(Mes(2)B)-8-(Me(2)NCH(2))-C(10)H(6)) which can be converted into a cationic borane [3](+) ([1-(Mes(2)B)-8-(Me(3)NCH(2))-C(10)H(6)](+)) by methylation with MeOTf [10].
  • Complex 17 further reacts with diboron to form Ir(H)(Beg)(4)(bpy) (E(a) = 8.0 kcal/mol), followed by the reductive elimination of borane H-Beg (E(a) = 2.6 kcal/mol) to regenerate Ir(Beg)(3)(bpy), when diboron exists in excess in the reaction solution [11].

Chemical compound and disease context of borane

  • Seven to 12 days later the boron-10-enriched polyhedral borane, Na2B12H11SH, was administered intravenously at a dose of 50 mg/kg body weight at varying time intervals ranging from 3 to 23.5 hours before neutron irradiation [12].
  • Three boron derivatives, i.e. trimethylamine-carbomethoxyborane, tetrakis-mu-(trimethylamine-boranecarboxylato)-bis(trimethylamine- carboxyborane)-dicopper(II), and N,N-dimethyl-n-octadecylamine borane were evaluated for acute toxicity in male mice, at 1, 2 or 5 x their therapeutic dose in rodents for pharmacological activity [13].

Biological context of borane

  • The in situ hydrolysis of a single bonded CF(3) group is found to be a simple, unprecedented route to a new borane carbonyl [14].
  • A series of polyhedral borane derivatives containing protein-binding functional groups has been synthesized [15].
  • The overall hydrolysis rates of borane complexes (BH(4)(-), H(3)N-BH(3)) in the acidity range of 0.2-10 M HCl were several orders of magnitude lower than those predicted by kinetics laws and obtained in the pH range of 3.8-14 [16].
  • Except when the POH function was blocked by phenyl groups the phosphorylation invariably resulted in a greatly enhanced uptake of the borane into tumors and improved the tumor/blood boron ratio [17].
  • In the intramolecular cyclization of enynes, the previously reported system (NaBH(4)-InCl(3)) has a problem of side reactions with the coexistent borane [18].

Anatomical context of borane


Associations of borane with other chemical compounds

  • Reaction of vanadocene [V(Cp)2] with "activated" nitrile R1CN.L (L: Lewis acid), obtained by the reaction of borane adducts (L = BR3; R = C6F5, 2,6-F2C6H3, 3,4,5-F3C6H2) with nitriles (CH3CN, F3CC6H4CN), yields the borane adduct of vanada(IV)azirine complexes [V(Cp)2(eta 2-R1C = N.L)] [21].
  • Squid (Todarodes pacificus) retinochrome was reduced to N-retinyl protein with borane dimethylamine and cleaved by CNBr [22].
  • The use of a borane-protected phosphane which is deprotected at the time of the ligation reaction led to the best results observed thus far in terms of stability toward oxidation and reactivity [23].
  • The putative Ins(1,4,5)P3 receptor antagonist 2-aminoethoxydiphenyl borane reduced the response to CXCR2 activation by interleukin-8, as did sustained inhibition of phosphatidylinositol 4-kinase with wortmannin, suggesting the involvement of phosphoinositides in the potentiation [24].
  • Success has been achieved suing a 4-methacryloyloxyethyltrimellitate anhydride/methyl methacrylate-tri-n-butyl borane system which allows the generation of a layer of hybridised dentin [25].

Gene context of borane

  • In the acid reduction, pyridine borane selectively reduced all six tryptophans in lysozyme to dihydrotryptophan while all other amino acids remained intact [26].
  • The second approach started from 3-p-methoxybenzyloxypropanal and a crotyl borane reagent derived from (-)-alpha-pinene to set both stereocenters in a single step and provided the dephenyl analogue, tert-butyl (5S,6R,2E)-5-[(tert-butyldimethylsilyl)oxy]-6-methyl-2, 7-octadienoate, in five steps [27].
  • The monomeric sulfhydryl borane (BSH) compound has been used clinically in Japan and preclinically in the U.S.A. Recently, new compounds have been developed: a dimeric sulfhydryl borane (BSSB), a boronophenylalanine (BPA), and two porphyrin complexes (BOPP and VCDP) [28].
  • RALBP was fairly stable even in the presence of hydroxylamine (100 mM), but was affected by sodium borohydride (30 mM) or borane dimethylamine (400 mM), with the retinal reduced to retinol [29].

Analytical, diagnostic and therapeutic context of borane

  • 7. The boron concentration obtained in the tumor corresponds to 22.2% injected dose (i.d.) per g of tissue, a value analogous to the most promising polyhedral borane anions investigated for liposomal delivery and subsequent application in boron neutron capture therapy [30].
  • The polyhedral borane ion [n-B20H18]2- reacts with liquid ammonia in the presence of a suitable base to produce an apical-equatorial (ae) isomer of the [B20H17NH3]3- ion, [1-(2'-B10H9)-2-NH3B10H8]3-. The structure of this product has been confirmed by 11B NMR spectroscopy and x-ray crystallography [31].
  • 1"-Oxobufuralol (3) was reduced with a complex of (2S)-(-)-2-amino-3-methyl-1,1-diphenylbutan-1-ol and borane, yielding 2, which had a 95:5 ratio of the possible 1"R and 1"S isomers as determined by HPLC [32].
  • Exploration of the electrophoretic behaviour of borane cluster anions and of the capability of capillary electrophoresis to separate them chirally [33].
  • Mild periodate oxidation of certain commercially available crosslinked agarose beads (Sepharose CL-4B and CL-6B) results in the generation of aldehydo groups which were useful for immobilization of amino compounds by reductive amination using pyridine borane [34].


  1. Boron neutron capture therapy of intracerebral rat gliosarcomas. Joel, D.D., Fairchild, R.G., Laissue, J.A., Saraf, S.K., Kalef-Ezra, J.A., Slatkin, D.N. Proc. Natl. Acad. Sci. U.S.A. (1990) [Pubmed]
  2. Axonal polyneuropathy after acute dimethylamine borane intoxication. Kuo, H.C., Huang, C.C., Chu, C.C., Chu, N.S. Arch. Neurol. (2006) [Pubmed]
  3. Ultrastructural microvascular response to boron neutron capture therapy in an experimental model. Goodman, J.H., McGregor, J.M., Clendenon, N.R., Gahbauer, R.A., Barth, R.F., Soloway, A.H., Fairchild, R.G. Neurosurgery (1989) [Pubmed]
  4. Antihyperlipidemic activity of amine cyanoboranes, amine carboxyboranes, and related compounds. Hall, I.H., Das, M.K., Harchelroad, F., Wisian-Neilson, P., McPhail, A.T., Spielvogel, B.F. Journal of pharmaceutical sciences. (1981) [Pubmed]
  5. Boron neutron capture therapy for cancer. Realities and prospects. Barth, R.F., Soloway, A.H., Fairchild, R.G., Brugger, R.M. Cancer (1992) [Pubmed]
  6. 1-N-Alkyl analogs of butirosin. Hayashi, T., Saeki, H., Takeda, N., Ohko, E. J. Antibiot. (1979) [Pubmed]
  7. An efficient asymmetric synthesis of an estrogen receptor modulator by sulfoxide-directed borane reduction. Song, Z.J., King, A.O., Waters, M.S., Lang, F., Zewge, D., Bio, M., Leazer, J.L., Javadi, G., Kassim, A., Tschaen, D.M., Reamer, R.A., Rosner, T., Chilenski, J.R., Mathre, D.J., Volante, R.P., Tillyer, R. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
  8. Cytoskeletal reorganization internalizes multiple transient receptor potential channels and blocks calcium entry into human neutrophils. Itagaki, K., Kannan, K.B., Singh, B.B., Hauser, C.J. J. Immunol. (2004) [Pubmed]
  9. Role of the phospholipase C-inositol 1,4,5-trisphosphate pathway in calcium release-activated calcium current and capacitative calcium entry. Broad, L.M., Braun, F.J., Lievremont, J.P., Bird, G.S., Kurosaki, T., Putney, J.W. J. Biol. Chem. (2001) [Pubmed]
  10. Fluoride ion capture from water with a cationic borane. Chiu, C.W., Gabba??, F.P. J. Am. Chem. Soc. (2006) [Pubmed]
  11. Iridium-catalyzed borylation of benzene with diboron. Theoretical elucidation of catalytic cycle including unusual iridium(v) intermediate. Tamura, H., Yamazaki, H., Sato, H., Sakaki, S. J. Am. Chem. Soc. (2003) [Pubmed]
  12. Boron neutron capture therapy of a rat glioma. Clendenon, N.R., Barth, R.F., Gordon, W.A., Goodman, J.H., Alam, F., Staubus, A.E., Boesel, C.P., Yates, A.J., Moeschberger, M.L., Fairchild, R.G. Neurosurgery (1990) [Pubmed]
  13. Acute toxicity of amine-boranes and related derivatives in mice. Hall, I.H., Reynolds, D.J., Chang, J., Spielvogel, B.F., Griffin, T.S., Docks, E.L. Arch. Pharm. (Weinheim) (1991) [Pubmed]
  14. Tris(trifluoromethyl)borane carbonyl, (CF3)3BCO-synthesis, physical, chemical and spectroscopic properties, gas phase, and solid state structure. Finze, M., Bernhardt, E., Terheiden, A., Berkei, M., Willner, H., Christen, D., Oberhammer, H., Aubke, F. J. Am. Chem. Soc. (2002) [Pubmed]
  15. Protein-binding polyhedral boranes. Sneath, R.L., Wright, J.E., Soloway, A.H., O'Keefe, S.M., Dey, A.S., Smolnycki, W.D. J. Med. Chem. (1976) [Pubmed]
  16. Role of hydroboron intermediates in the mechanism of chemical vapor generation in strongly acidic media. D'Ulivo, A., Onor, M., Pitzalis, E. Anal. Chem. (2004) [Pubmed]
  17. Synthesis and tumor-uptake study of phosphate esters of polyhedral hydroxyboranes. Bechtold, R.A., Kaczmarczyk, A. J. Med. Chem. (1975) [Pubmed]
  18. Triethylsilane-indium(III) chloride system as a radical reagent. Hayashi, N., Shibata, I., Baba, A. Org. Lett. (2004) [Pubmed]
  19. Effect of 2-(methacryloxy)ethyl phenyl hydrogen phosphate on adhesion to dentin. Wang, T., Nakabayashi, N. J. Dent. Res. (1991) [Pubmed]
  20. Effects of exposure to 4-META/MMA-TBB resin on pulp cell viability. Imaizumi, N., Kondo, H., Ohya, K., Kasugai, S., Araki, K., Kurosaki, N. J. Med. Dent. Sci. (2006) [Pubmed]
  21. Reactivity of vanadocene with a nitrile -C identical to N bond activated by a tris(fluorophenyl)borane as Lewis acid: formation of borane adducts of vanada(IV)azirine complexes--EPR evidence for an intramolecular C-F...V interaction. Choukroun, R., Lorber, C., Donnadieu, B. Chemistry (Weinheim an der Bergstrasse, Germany) (2002) [Pubmed]
  22. Amino acid sequence surrounding the retinal-binding site in retinochrome of the squid, Todarodes pacificus. Hara-Nishimura, I., Kondo, M., Nishimura, M., Hara, R., Hara, T. FEBS Lett. (1993) [Pubmed]
  23. On the preparation of carbohydrate-protein conjugates using the traceless Staudinger ligation. Grandjean, C., Boutonnier, A., Guerreiro, C., Fournier, J.M., Mulard, L.A. J. Org. Chem. (2005) [Pubmed]
  24. Cross talk between P2Y2 nucleotide receptors and CXC chemokine receptor 2 resulting in enhanced Ca2+ signaling involves enhancement of phospholipase C activity and is enabled by incremental Ca2+ release in human embryonic kidney cells. Werry, T.D., Wilkinson, G.F., Willars, G.B. J. Pharmacol. Exp. Ther. (2003) [Pubmed]
  25. Dental biomaterials and the healing of dental tissue. Nakabayashi, N. Biomaterials (2003) [Pubmed]
  26. Pyridine borane as a reducing agent for proteins. Wong, W.S., Osuga, D.T., Feeney, R.E. Anal. Biochem. (1984) [Pubmed]
  27. Total synthesis of cryptophycin-24 (Arenastatin A) amenable to structural modifications in the C16 side chain. Eggen, M., Mossman, C.J., Buck, S.B., Nair, S.K., Bhat, L., Ali, S.M., Reiff, E.A., Boge, T.C., Georg, G.I. J. Org. Chem. (2000) [Pubmed]
  28. Intracellular distribution of various boron compounds for use in boron neutron capture therapy. Nguyen, T., Brownell, G.L., Holden, S.A., Teicher, B.A. Biochem. Pharmacol. (1993) [Pubmed]
  29. Isolation and characterization of a retinal-binding protein from the squid retina. Ozaki, K., Terakita, A., Hara, R., Hara, T. Vision Res. (1987) [Pubmed]
  30. Synthesis and in vivo murine evaluation of Na4[1-(1'-B10H9)-6-SHB10H8] as a potential agent for boron neutron capture therapy. Feakes, D.A., Waller, R.C., Hathaway, D.K., Morton, V.S. Proc. Natl. Acad. Sci. U.S.A. (1999) [Pubmed]
  31. Na3[B20H17NH3]: synthesis and liposomal delivery to murine tumors. Feakes, D.A., Shelly, K., Knobler, C.B., Hawthorne, M.F. Proc. Natl. Acad. Sci. U.S.A. (1994) [Pubmed]
  32. Enantioselective and diastereoselective hydroxylation of bufuralol. Absolute configuration of the 7-(1-hydroxyethyl)-2-[1-hydroxy-2-(tert-butylamino)ethyl]benzofurans, the benzylic hydroxylation metabolites. Weerawarna, S.A., Geisshüsler, S.M., Murthy, S.S., Nelson, W.L. J. Med. Chem. (1991) [Pubmed]
  33. Exploration of the electrophoretic behaviour of borane cluster anions and of the capability of capillary electrophoresis to separate them chirally. Slavícek, V., Grüner, B., Vespalec, R. Journal of chromatography. A. (2003) [Pubmed]
  34. Immobilization of proteins on oxidized crosslinked Sepharose preparations by reductive amination. Stults, N.L., Asta, L.M., Lee, Y.C. Anal. Biochem. (1989) [Pubmed]
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