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Chemical Compound Review

CHEBI:38267     boronic acid

Synonyms: BH(OH)2, AC1L1VP1, hydridodihydroxidoboron
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Disease relevance of boronic acid


High impact information on boronic acid

  • Given their affinity and specificity for arginase, boronic acid inhibitors are especially useful for probing the role of arginase in living systems [6].
  • The structure of the plasmid-mediated beta-lactamase TEM-1 has been solved in complex with a designed boronic acid inhibitor (1R)-1-acetamido-2-(3-carboxyphenyl)ethane boronic acid at 1.7 A resolution [7].
  • Lastly, we synthesized two boronic acid transition state analogs that mimic cephalothin and found substitutions at Arg-244 markedly affect both the affinity and kinetics of binding to the chiral, deacylation transition state inhibitor [8].
  • The nonenzymatic glycation of glomerular basement membranes (GBMs) from 14 diabetic and 19 nondiabetic human subjects was determined after boronic acid affinity and high-performance cation-exchange chromatography of their NaB[3H]4-reduced ketoamine adducts [9].
  • The amount of nonenzymatic glycosylation present in normal and diabetic rat peripheral nerve myelin, whole brain, brain myelin, and individual myelin protein components was determined using NaB3H4 reduction followed by either boronic acid affinity chromatography or SDS-polyacrylamide gel electrophoresis (SDS-PAGE) [10].

Chemical compound and disease context of boronic acid

  • The structure of the complex formed between alpha-lytic protease, a serine protease secreted by Lysobacter enzymogenes, and N-tert-butyloxycarbonylalanylprolylvaline boronic acid (Ki = 0.35 nM) has been studied by X-ray crystallography to a resolution of 2.0 A [11].

Biological context of boronic acid


Anatomical context of boronic acid

  • We demonstrate that the cis-6 boronic acid bioisostere of CA-4: (1) inhibits tubulin assembly, (2) competitively displaces colchicine, and (3) is a low-nanomolar inhibitor of human cancer cell lines [17].
  • Here we show that three high-affinity inhibitors of furin efficiently blocked killing of murine J774A.1 macrophages by recombinant protective antigen plus lethal factor: RRD-eglin and RRDG-eglin, developed by engineering the protein protease inhibitor eglin c, and the peptide boronic acid inhibitor acetyl-Arg-Glu-Lys-boroArg pinanediol [18].
  • Characterization of peptidyl boronic acid inhibitors of mammalian 20 S and 26 S proteasomes and their inhibition of proteasomes in cultured cells [19].
  • We have designed and synthesized a highly lipophilic boronic acid (11) with a molecular shape that makes it much more effective at carrying sugars through organic membranes than a previously used steroidal boronic acid [20].
  • Boronic acid was introduced in the polymer as recognition site of sugar residues existing on the plasma membrane surface of lymphocyte, since it makes a covalent bonding with polyol compounds including sugars [21].

Associations of boronic acid with other chemical compounds


Gene context of boronic acid

  • Transition state analogue boronic acid inhibitors mimicking the structures and interactions of good penicillin substrates for the TEM-1 beta-lactamase of Escherchia coli were designed using graphic analyses based on the enzyme's 1.7 A crystallographic structure [27].
  • To our knowledge, this is the first report on P450-mediated drug-drug interaction potential of proteasome inhibitors or boronic acid containing therapeutics [28].
  • The X-ray crystal structure of a fully active, truncated form of human arginase II complexed with a boronic acid transition state analogue inhibitor has been determined at 2.7 A resolution [29].
  • Inhibition of dipeptidyl peptidase IV (CD26) by peptide boronic acid dipeptides [30].
  • 2.4 A resolution crystal structure of the prototypical hormone-processing protease Kex2 in complex with an Ala-Lys-Arg boronic acid inhibitor [31].

Analytical, diagnostic and therapeutic context of boronic acid


  1. Mitochondrial-mediated disregulation of Ca2+ is a critical determinant of Velcade (PS-341/bortezomib) cytotoxicity in myeloma cell lines. Landowski, T.H., Megli, C.J., Nullmeyer, K.D., Lynch, R.M., Dorr, R.T. Cancer Res. (2005) [Pubmed]
  2. Mechanism of HIV-1 Tat induced inhibition of antigen-specific T cell responsiveness. Subramanyam, M., Gutheil, W.G., Bachovchin, W.W., Huber, B.T. J. Immunol. (1993) [Pubmed]
  3. Hepatitis C virus NS3 protease requires its NS4A cofactor peptide for optimal binding of a boronic acid inhibitor as shown by NMR. Archer, S.J., Camac, D.M., Wu, Z.J., Farrow, N.A., Domaille, P.J., Wasserman, Z.R., Bukhtiyarova, M., Rizzo, C., Jagannathan, S., Mersinger, L.J., Kettner, C.A. Chem. Biol. (2002) [Pubmed]
  4. Crystal structure of Escherichia coli penicillin-binding protein 5 bound to a tripeptide boronic acid inhibitor: a role for Ser-110 in deacylation. Nicola, G., Peddi, S., Stefanova, M., Nicholas, R.A., Gutheil, W.G., Davies, C. Biochemistry (2005) [Pubmed]
  5. Crystal structure of Enterobacter cloacae 908R class C beta-lactamase bound to iodo-acetamido-phenyl boronic acid, a transition-state analogue. Wouters, J., Fonzé, E., Vermeire, M., Frère, J.M., Charlier, P. Cell. Mol. Life Sci. (2003) [Pubmed]
  6. Arginase: structure, mechanism, and physiological role in male and female sexual arousal. Christianson, D.W. Acc. Chem. Res. (2005) [Pubmed]
  7. Structure-based design of a potent transition state analogue for TEM-1 beta-lactamase. Strynadka, N.C., Martin, R., Jensen, S.E., Gold, M., Jones, J.B. Nat. Struct. Biol. (1996) [Pubmed]
  8. Probing active site chemistry in SHV beta-lactamase variants at Ambler position 244. Understanding unique properties of inhibitor resistance. Thomson, J.M., Distler, A.M., Prati, F., Bonomo, R.A. J. Biol. Chem. (2006) [Pubmed]
  9. Nonenzymatic glycation of basement membranes from human glomeruli and bovine sources. Effect of diabetes and age. Garlick, R.L., Bunn, H.F., Spiro, R.G. Diabetes (1988) [Pubmed]
  10. Excessive nonenzymatic glycosylation of peripheral and central nervous system myelin components in diabetic rats. Vlassara, H., Brownlee, M., Cerami, A. Diabetes (1983) [Pubmed]
  11. Serine protease mechanism: structure of an inhibitory complex of alpha-lytic protease and a tightly bound peptide boronic acid. Bone, R., Shenvi, A.B., Kettner, C.A., Agard, D.A. Biochemistry (1987) [Pubmed]
  12. Boronic acid inhibitors of porcine pancreatic lipase. Garner, C.W. J. Biol. Chem. (1980) [Pubmed]
  13. X-ray crystallographic study of boronic acid adducts with subtilisin BPN' (Novo). A model for the catalytic transition state. Matthews, D.A., Alden, R.A., Birktoft, J.J., Freer, S.T., Kraut, J. J. Biol. Chem. (1975) [Pubmed]
  14. Stereochemical and regiochemical trends in the selective detection of saccharides. Jiang, S., Escobedo, J.O., Kim, K.K., Alptürk, O., Samoei, G.K., Fakayode, S.O., Warner, I.M., Rusin, O., Strongin, R.M. J. Am. Chem. Soc. (2006) [Pubmed]
  15. Affinity electrophoresis for monitoring terminal phosphorylation and the presence of queuosine in RNA. Application of polyacrylamide containing a covalently bound boronic acid. Igloi, G.L., Kössel, H. Nucleic Acids Res. (1985) [Pubmed]
  16. Structure-activity relationships of boronic acid inhibitors of dipeptidyl peptidase IV. 1. Variation of the P2 position of Xaa-boroPro dipeptides. Coutts, S.J., Kelly, T.A., Snow, R.J., Kennedy, C.A., Barton, R.W., Adams, J., Krolikowski, D.A., Freeman, D.M., Campbell, S.J., Ksiazek, J.F., Bachovchin, W.W. J. Med. Chem. (1996) [Pubmed]
  17. Structure-based discovery of a boronic acid bioisostere of combretastatin A-4. Kong, Y., Grembecka, J., Edler, M.C., Hamel, E., Mooberry, S.L., Sabat, M., Rieger, J., Brown, M.L. Chem. Biol. (2005) [Pubmed]
  18. Protection from anthrax toxin-mediated killing of macrophages by the combined effects of furin inhibitors and chloroquine. Komiyama, T., Swanson, J.A., Fuller, R.S. Antimicrob. Agents Chemother. (2005) [Pubmed]
  19. Characterization of peptidyl boronic acid inhibitors of mammalian 20 S and 26 S proteasomes and their inhibition of proteasomes in cultured cells. Gardner, R.C., Assinder, S.J., Christie, G., Mason, G.G., Markwell, R., Wadsworth, H., McLaughlin, M., King, R., Chabot-Fletcher, M.C., Breton, J.J., Allsop, D., Rivett, A.J. Biochem. J. (2000) [Pubmed]
  20. Highly fructose selective transport promoted by boronic acids based on a pentaerythritol core. Draffin, S.P., Duggan, P.J., Duggan, S.A. Org. Lett. (2001) [Pubmed]
  21. Boronate-containing polymer as novel mitogen for lymphocytes. Miyazaki, H., Kikuchi, A., Koyama, Y., Okano, T., Sakurai, Y., Kataoka, K. Biochem. Biophys. Res. Commun. (1993) [Pubmed]
  22. Arginase-boronic acid complex highlights a physiological role in erectile function. Cox, J.D., Kim, N.N., Traish, A.M., Christianson, D.W. Nat. Struct. Biol. (1999) [Pubmed]
  23. Quantitative isolation of oligo- and polyadenosine-diphosphoribosylated proteins by affinity chromatography from livers of normal and dimethylnitrosamine-treated Syrian hamsters. In vivo and in vitro metabolism of the homopolymer. Romaschin, A.D., Kirsten, E., Jackowski, G., Kun, E. J. Biol. Chem. (1981) [Pubmed]
  24. Isolation of Escherichia coli precursor tRNAs containing modified nucleoside Q. Vögeli, G., Stewart, T.S., McCutchan, T., Söll, D. J. Biol. Chem. (1977) [Pubmed]
  25. Proteasome inhibitor PS-341 causes cell growth arrest and apoptosis in human glioblastoma multiforme (GBM). Yin, D., Zhou, H., Kumagai, T., Liu, G., Ong, J.M., Black, K.L., Koeffler, H.P. Oncogene (2005) [Pubmed]
  26. Subangstrom crystallography reveals that short ionic hydrogen bonds, and not a His-Asp low-barrier hydrogen bond, stabilize the transition state in serine protease catalysis. Fuhrmann, C.N., Daugherty, M.D., Agard, D.A. J. Am. Chem. Soc. (2006) [Pubmed]
  27. Structure-based design guides the improved efficacy of deacylation transition state analogue inhibitors of TEM-1 beta-Lactamase(,). Ness, S., Martin, R., Kindler, A.M., Paetzel, M., Gold, M., Jensen, S.E., Jones, J.B., Strynadka, N.C. Biochemistry (2000) [Pubmed]
  28. Investigation of drug-drug interaction potential of bortezomib in vivo in female Sprague-Dawley rats and in vitro in human liver microsomes. Lu, C., Gallegos, R., Li, P., Xia, C.Q., Pusalkar, S., Uttamsingh, V., Nix, D., Miwa, G.T., Gan, L.S. Drug Metab. Dispos. (2006) [Pubmed]
  29. Human arginase II: crystal structure and physiological role in male and female sexual arousal. Cama, E., Colleluori, D.M., Emig, F.A., Shin, H., Kim, S.W., Kim, N.N., Traish, A.M., Ash, D.E., Christianson, D.W. Biochemistry (2003) [Pubmed]
  30. Inhibition of dipeptidyl peptidase IV (CD26) by peptide boronic acid dipeptides. Pargellis, C.A., Campbell, S.J., Pav, S., Graham, E.T., Pitner, T.P. J. Enzym. Inhib. (1997) [Pubmed]
  31. 2.4 A resolution crystal structure of the prototypical hormone-processing protease Kex2 in complex with an Ala-Lys-Arg boronic acid inhibitor. Holyoak, T., Wilson, M.A., Fenn, T.D., Kettner, C.A., Petsko, G.A., Fuller, R.S., Ringe, D. Biochemistry (2003) [Pubmed]
  32. The principal site of nonenzymatic glycosylation of human serum albumin in vivo. Garlick, R.L., Mazer, J.S. J. Biol. Chem. (1983) [Pubmed]
  33. Increased glycated Cu,Zn-superoxide dismutase levels in erythrocytes of patients with insulin-dependent diabetis mellitus. Kawamura, N., Ookawara, T., Suzuki, K., Konishi, K., Mino, M., Taniguchi, N. J. Clin. Endocrinol. Metab. (1992) [Pubmed]
  34. Noninvasive continuous monitoring of physiological glucose using a monosaccharide-sensing contact lens. Badugu, R., Lakowicz, J.R., Geddes, C.D. Anal. Chem. (2004) [Pubmed]
  35. Liquid chromatography assay for routine monitoring of cellular ribavirin levels in blood. Inoue, Y., Homma, M., Matsuzaki, Y., Shibata, M., Matsumura, T., Ito, T., Mitamura, K., Tanaka, N., Kohda, Y. Antimicrob. Agents Chemother. (2004) [Pubmed]
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