메뉴 건너뛰기




Volumn 8, Issue 1, 2017, Pages

Multicomponent mapping of boron chemotypes furnishes selective enzyme inhibitors

Author keywords

[No Author keywords available]

Indexed keywords

BETA AMINOBORONIC ACID; BORONIC ACID DERIVATIVE; CARBONYL DERIVATIVE; ENZYME INHIBITOR; HYDROLASE; ORGANOBORON DERIVATIVE; UNCLASSIFIED DRUG; BORON; BORON DERIVATIVE;

EID: 85034947197     PISSN: None     EISSN: 20411723     Source Type: Journal    
DOI: 10.1038/s41467-017-01319-4     Document Type: Article
Times cited : (29)

References (45)
  • 1
    • 84935859794 scopus 로고    scopus 로고
    • Recent developments in the chemistry and biological applications of benzoxaboroles
    • Adamczyk-Woźniak, A., Borys, K. M. & Sporzyński, A. Recent developments in the chemistry and biological applications of benzoxaboroles. Chem. Rev. 115, 5224-5247 (2015).
    • (2015) Chem. Rev. , vol.115 , pp. 5224-5247
    • Adamczyk-Woźniak, A.1    Borys, K.M.2    Sporzyński, A.3
  • 2
    • 77951815067 scopus 로고    scopus 로고
    • Therapeutic potential of boron-containing compounds
    • Baker, S. J. et al. Therapeutic potential of boron-containing compounds. Future Med. Chem. 1, 1275-1288 (2009).
    • (2009) Future Med. Chem. , vol.1 , pp. 1275-1288
    • Baker, S.J.1
  • 3
    • 79958711382 scopus 로고    scopus 로고
    • Boron-containing inhibitors of synthetases
    • Baker, S. J., Tomsho, J. W. & Benkovic, S. J. Boron-containing inhibitors of synthetases. Chem. Soc. Rev. 40, 4279-4285 (2011).
    • (2011) Chem. Soc. Rev. , vol.40 , pp. 4279-4285
    • Baker, S.J.1    Tomsho, J.W.2    Benkovic, S.J.3
  • 4
    • 84876850505 scopus 로고    scopus 로고
    • Boron chemicals in diagnosis and therapeutics
    • Das, B. C. et al. Boron chemicals in diagnosis and therapeutics. Future Med. Chem. 5, 653-676 (2013).
    • (2013) Future Med. Chem. , vol.5 , pp. 653-676
    • Das, B.C.1
  • 5
    • 84865088209 scopus 로고    scopus 로고
    • Boron containing compounds as protease inhibitors
    • Smoum, R., Rubinstein, A., Dembitsky, V. M. & Srebnik, M. Boron containing compounds as protease inhibitors. Chem. Rev. 112, 4156-4220 (2012).
    • (2012) Chem. Rev. , vol.112 , pp. 4156-4220
    • Smoum, R.1    Rubinstein, A.2    Dembitsky, V.M.3    Srebnik, M.4
  • 6
    • 79959410937 scopus 로고    scopus 로고
    • Aminoboronic acids and esters: From synthetic challenges to the discovery of unique classes of enzyme inhibitors
    • Touchet, S., Carreaux, F., Carboni, B., Bouillon, A. & Boucher, J.-L. Aminoboronic acids and esters: From synthetic challenges to the discovery of unique classes of enzyme inhibitors. Chem. Soc. Rev. 40, 3895-3914 (2011).
    • (2011) Chem. Soc. Rev. , vol.40 , pp. 3895-3914
    • Touchet, S.1    Carreaux, F.2    Carboni, B.3    Bouillon, A.4    Boucher, J.-L.5
  • 7
    • 3042577683 scopus 로고    scopus 로고
    • Approval summary for bortezomib for injection in the treatment of multiple myeloma
    • Bross, P. F. et al. Approval summary for bortezomib for injection in the treatment of multiple myeloma. Clin. Cancer. Res. 10, 3954-3964 (2004).
    • (2004) Clin. Cancer. Res. , vol.10 , pp. 3954-3964
    • Bross, P.F.1
  • 8
    • 77950238258 scopus 로고    scopus 로고
    • Evaluation of the proteasome inhibitor MLN9708 in preclinical models of human cancer
    • Kupperman, E. et al. Evaluation of the proteasome inhibitor MLN9708 in preclinical models of human cancer. Cancer Res. 70, 1970-1980 (2010).
    • (2010) Cancer Res. , vol.70 , pp. 1970-1980
    • Kupperman, E.1
  • 9
    • 84872109533 scopus 로고    scopus 로고
    • A first in human phase I study of the proteasome inhibitor CEP-18770 in patients with advanced solid tumours and multiple myeloma
    • Gallerani, E. et al. A first in human phase I study of the proteasome inhibitor CEP-18770 in patients with advanced solid tumours and multiple myeloma. Eur. J. Cancer 49, 290-296 (2013).
    • (2013) Eur. J. Cancer , vol.49 , pp. 290-296
    • Gallerani, E.1
  • 10
    • 0037405256 scopus 로고    scopus 로고
    • Boronic acid compounds as potential pharmaceutical agents
    • Yang, W., Gao, X. & Wang, B. Boronic acid compounds as potential pharmaceutical agents. Med. Res. Rev. 23, 346-368 (2003).
    • (2003) Med. Res. Rev. , vol.23 , pp. 346-368
    • Yang, W.1    Gao, X.2    Wang, B.3
  • 11
    • 85026356593 scopus 로고    scopus 로고
    • The versatility of boron in biological target engagement
    • Diaz, D. B. & Yudin, A. K. The versatility of boron in biological target engagement. Nat. Chem. 9, 731-742 (2017).
    • (2017) Nat. Chem. , vol.9 , pp. 731-742
    • Diaz, D.B.1    Yudin, A.K.2
  • 12
    • 33947659939 scopus 로고    scopus 로고
    • 20S protasome and its inhibitors: Crystallographic knowledge for drug development
    • Borissenko, L. & Groll, M. 20S protasome and its inhibitors: Crystallographic knowledge for drug development. Chem. Rev. 107, 687-717 (2007).
    • (2007) Chem. Rev. , vol.107 , pp. 687-717
    • Borissenko, L.1    Groll, M.2
  • 13
    • 61449206184 scopus 로고    scopus 로고
    • The persisting challenge of selective and specific proteasome inhibition
    • Groll, M., Huber, R. & Moroder, L. The persisting challenge of selective and specific proteasome inhibition. J. Pept. Sci. 15, 58-66 (2009).
    • (2009) J. Pept. Sci. , vol.15 , pp. 58-66
    • Groll, M.1    Huber, R.2    Moroder, L.3
  • 14
    • 0036882396 scopus 로고    scopus 로고
    • Irreversible inhibitors of serine, cysteine, and threonine proteases
    • Powers, J. C., Asgian, J. L., Ekici, Ö. D. & James, K. E. Irreversible inhibitors of serine, cysteine, and threonine proteases. Chem. Rev. 102, 4639-4750 (2002).
    • (2002) Chem. Rev. , vol.102 , pp. 4639-4750
    • Powers, J.C.1    Asgian, J.L.2    Ekici, Ö.3    James, K.E.4
  • 15
    • 0035902222 scopus 로고    scopus 로고
    • Direct mono-N-methylation of solid-supported amino acids: A useful application of the Matteson rearrangement of α-aminoalkylboronic esters
    • Laplante, C. & Hall, D. G. Direct mono-N-methylation of solid-supported amino acids: A useful application of the Matteson rearrangement of α-aminoalkylboronic esters. Org. Lett. 3, 1487-1490 (2001).
    • (2001) Org. Lett. , vol.3 , pp. 1487-1490
    • Laplante, C.1    Hall, D.G.2
  • 16
    • 0000322228 scopus 로고
    • Synthesis of 1-amino-2-phenylethane-1-boronic acid derivatives
    • Matteson, D. S. & Sadhu, K. M. Synthesis of 1-amino-2-phenylethane-1-boronic acid derivatives. Organometallics. 3, 614-618 (1984).
    • (1984) Organometallics. , vol.3 , pp. 614-618
    • Matteson, D.S.1    Sadhu, K.M.2
  • 17
    • 9444226868 scopus 로고    scopus 로고
    • The world of β-and γ-peptides comprised of homologated proteinogenic amino acids and other components
    • Seebach, D., Beck, A. K. & Bierbaum, D. J. The world of β-and γ-peptides comprised of homologated proteinogenic amino acids and other components. Chem. Biodivers. 1, 1111-1239 (2004).
    • (2004) Chem. Biodivers. , vol.1 , pp. 1111-1239
    • Seebach, D.1    Beck, A.K.2    Bierbaum, D.J.3
  • 18
    • 0032835609 scopus 로고    scopus 로고
    • Structure-activity relationship of HIV-1 protease inhibitors containing α-hydroxy-β-amino acids. Detailed study of P1 site
    • Takashiro, E. et al. Structure-activity relationship of HIV-1 protease inhibitors containing α-hydroxy-β-amino acids. Detailed study of P1 site. Bioorganic Med. Chem. 7, 2063-2072 (1999).
    • (1999) Bioorganic Med. Chem. , vol.7 , pp. 2063-2072
    • Takashiro, E.1
  • 19
    • 84882246299 scopus 로고    scopus 로고
    • α-Boryl isocyanides enable facile preparation of bioactive boropeptides
    • Zajdlik, A. et al. α-Boryl isocyanides enable facile preparation of bioactive boropeptides. Angew. Chem. Int. Ed. 52, 8411-8415 (2013).
    • (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 8411-8415
    • Zajdlik, A.1
  • 20
    • 84923165733 scopus 로고    scopus 로고
    • Facile synthesis of borofragments and their evaluation in activity-based protein profiling
    • Adachi, S. et al. Facile synthesis of borofragments and their evaluation in activity-based protein profiling. Chem. Commun. 51, 3608-3611 (2015).
    • (2015) Chem. Commun. , vol.51 , pp. 3608-3611
    • Adachi, S.1
  • 21
    • 84992179827 scopus 로고    scopus 로고
    • Synthesis of aminoboronic acid derivatives from amines and amphoteric boryl carbonyl compounds
    • Diaz, D. B. et al. Synthesis of aminoboronic acid derivatives from amines and amphoteric boryl carbonyl compounds. Angew. Chemie Int. Ed. 55, 12659-12663 (2016).
    • (2016) Angew. Chemie Int. Ed. , vol.55 , pp. 12659-12663
    • Diaz, D.B.1
  • 22
    • 78649496901 scopus 로고    scopus 로고
    • Nitrile-containing pharmaceuticals: Efficacious roles of the nitrile pharmacophore
    • Fleming, F. F., Yao, L., Ravikumar, P. C., Funk, L. & Shook, B. C. Nitrile-containing pharmaceuticals: Efficacious roles of the nitrile pharmacophore. J. Med. Chem. 53, 7902-7917 (2010).
    • (2010) J. Med. Chem. , vol.53 , pp. 7902-7917
    • Fleming, F.F.1    Yao, L.2    Ravikumar, P.C.3    Funk, L.4    Shook, B.C.5
  • 23
    • 0027222710 scopus 로고
    • Urinary metabolites of pinacidil: I. Isolation and identification of the metabolites in rat urine
    • Sakamoto, K. & Nakamura, Y. Urinary metabolites of pinacidil: I. Isolation and identification of the metabolites in rat urine. Xenobiotica. 23, 391-400 (1993).
    • (1993) Xenobiotica. , vol.23 , pp. 391-400
    • Sakamoto, K.1    Nakamura, Y.2
  • 24
    • 0027313663 scopus 로고
    • Urinary metabolites of pinacidil. II. Species difference in the metabolism of pinacidil
    • Sakamoto, K. & Nakamura, Y. Urinary metabolites of pinacidil. II. Species difference in the metabolism of pinacidil. Xenobiotica 23, 649-656 (1993).
    • (1993) Xenobiotica , vol.23 , pp. 649-656
    • Sakamoto, K.1    Nakamura, Y.2
  • 25
    • 0023522371 scopus 로고
    • Metabolism of nilvadipine, a new dihydropyridine calcium antagonist, in rats and dogs
    • Terashita, S. et al. Metabolism of nilvadipine, a new dihydropyridine calcium antagonist, in rats and dogs. Xenobiotica. 17, 1415-1425 (1987).
    • (1987) Xenobiotica. , vol.17 , pp. 1415-1425
    • Terashita, S.1
  • 26
    • 77950920638 scopus 로고    scopus 로고
    • 14C]lersivirine to healthy volunteers
    • 14C]lersivirine to healthy volunteers. Drug Metab. Dispos. 38, 789-800 (2010).
    • (2010) Drug Metab. Dispos. , vol.38 , pp. 789-800
    • Vourvahis, M.1
  • 28
    • 35148828100 scopus 로고    scopus 로고
    • Novel scaffold for cathepsin K inhibitors
    • Teno, N. et al. Novel scaffold for cathepsin K inhibitors. Bioorganic Med. Chem. Lett. 17, 6096-6100 (2007).
    • (2007) Bioorganic Med. Chem. Lett. , vol.17 , pp. 6096-6100
    • Teno, N.1
  • 29
    • 80052332176 scopus 로고    scopus 로고
    • Amphoteric α-boryl aldehydes
    • He, Z. & Yudin, A. K. Amphoteric α-boryl aldehydes. J. Am. Chem. Soc. 133, 13770-13773 (2011).
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 13770-13773
    • He, Z.1    Yudin, A.K.2
  • 30
    • 80052305738 scopus 로고    scopus 로고
    • p3) boronate building blocks
    • 3) boronate building blocks. J. Am. Chem. Soc. 133, 13774-13777 (2011).
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 13774-13777
    • Li, J.1    Burke, M.D.2
  • 31
    • 84919363201 scopus 로고    scopus 로고
    • Boron-containing enamine and enamide linchpins in the synthesis of nitrogen heterocycles
    • St. Denis, J. D. et al. Boron-containing enamine and enamide linchpins in the synthesis of nitrogen heterocycles. J. Am. Chem. Soc. 136, 17669-17673 (2014).
    • (2014) J. Am. Chem. Soc. , vol.136 , pp. 17669-17673
    • St Denis, J.D.1
  • 32
    • 84867774444 scopus 로고    scopus 로고
    • Oxidative geminal functionalization of organoboron compounds
    • He, Z. et al. Oxidative geminal functionalization of organoboron compounds. Angew. Chem. Int. Ed. 51, 11092-11096 (2012).
    • (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 11092-11096
    • He, Z.1
  • 33
    • 85011422702 scopus 로고    scopus 로고
    • β-aminoboronic acids with carbohydrate derivatives
    • Garrett, G. E., Diaz, D. B., Yudin, A. K. & Taylor, M. S. β-aminoboronic acids with carbohydrate derivatives. Chem. Commun. 53, 1809-1812 (2017).
    • (2017) Chem. Commun. , vol.53 , pp. 1809-1812
    • Garrett, G.E.1    Diaz, D.B.2    Yudin, A.K.3    Taylor, M.S.4
  • 34
    • 33847020445 scopus 로고    scopus 로고
    • Catalytic one-pot, three-component acyl-strecker reaction
    • Pan, S. & List, B. Catalytic one-pot, three-component acyl-strecker reaction. Synlett. 2, 318-320 (2007).
    • (2007) Synlett. , vol.2 , pp. 318-320
    • Pan, S.1    List, B.2
  • 35
    • 33745590830 scopus 로고    scopus 로고
    • 3N-catalyzed three-component condensation of aldehydes, amines and cyanides: A high yielding synthesis of α-aminonitriles
    • 3N-catalyzed three-component condensation of aldehydes, amines and cyanides: a high yielding synthesis of α-aminonitriles. Tetrahedron Lett. 47, 5759-5762 (2006).
    • (2006) Tetrahedron Lett. , vol.47 , pp. 5759-5762
    • Paraskar, A.S.1    Sudalai, A.2
  • 36
    • 80054054097 scopus 로고    scopus 로고
    • The metabolic serine hydrolases and their functions in mammalian physiology and disease
    • Long, J. Z. & Cravatt, B. F. The metabolic serine hydrolases and their functions in mammalian physiology and disease. Chem. Rev. 111, 6022-6063 (2011).
    • (2011) Chem. Rev. , vol.111 , pp. 6022-6063
    • Long, J.Z.1    Cravatt, B.F.2
  • 37
    • 84902142324 scopus 로고    scopus 로고
    • Enzyme inhibitor discovery by activity-based protein profiling
    • Niphakis, M. J. & Cravatt, B. F. Enzyme inhibitor discovery by activity-based protein profiling. Annu. Rev. Biochem. 83, 341-377 (2014).
    • (2014) Annu. Rev. Biochem. , vol.83 , pp. 341-377
    • Niphakis, M.J.1    Cravatt, B.F.2
  • 38
    • 84937784363 scopus 로고    scopus 로고
    • Selective N-hydroxyhydantoin carbamate inhibitors of mammalian serine hydrolases
    • Cognetta, A. B. III et al. Selective N-hydroxyhydantoin carbamate inhibitors of mammalian serine hydrolases. Chem. Biol. 22, 928-937 (2015).
    • (2015) Chem. Biol. , vol.22 , pp. 928-937
    • Cognetta, I.I.I.A.B.1
  • 39
    • 35348938545 scopus 로고    scopus 로고
    • The role of fluorine in medicinal chemistry
    • Shah, P. & Westwell, A. D. The role of fluorine in medicinal chemistry. J. Enzyme Inhib. Med. Chem. 22, 527-540 (2007).
    • (2007) J. Enzyme Inhib. Med. Chem. , vol.22 , pp. 527-540
    • Shah, P.1    Westwell, A.D.2
  • 40
    • 80054856731 scopus 로고    scopus 로고
    • Metabolomics annotates ABHD3 as a physiologic regulator of medium-chain phospholipids
    • Long, J. Z. et al. Metabolomics annotates ABHD3 as a physiologic regulator of medium-chain phospholipids. Nat. Chem. Biol. 7, 763-765 (2011).
    • (2011) Nat. Chem. Biol. , vol.7 , pp. 763-765
    • Long, J.Z.1
  • 41
    • 79959376326 scopus 로고    scopus 로고
    • Click-generated triazole ureas as ultrapotent in vivo-active serine hydrolase inhibitors
    • Adibekian, A. et al. Click-generated triazole ureas as ultrapotent in vivo-active serine hydrolase inhibitors. Nat. Chem. Biol. 7, 469-478 (2011).
    • (2011) Nat. Chem. Biol. , vol.7 , pp. 469-478
    • Adibekian, A.1
  • 42
    • 34247396011 scopus 로고    scopus 로고
    • A practical recipe for stable isotope labeling by amino acids in cell culture (SILAC)
    • Ong, S. & Mann, M. A practical recipe for stable isotope labeling by amino acids in cell culture (SILAC). Nat. Protoc. 1, 2650-2660 (2007).
    • (2007) Nat. Protoc. , vol.1 , pp. 2650-2660
    • Ong, S.1    Mann, M.2
  • 43
    • 67650506936 scopus 로고    scopus 로고
    • Open access chemical and clinical probes to support drug discovery
    • Edwards, A. M., Bountra, C., Kerr, D. J. & Willson, T. M. Open access chemical and clinical probes to support drug discovery. Nat. Chem. Biol. 5, 436-440 (2009).
    • (2009) Nat. Chem. Biol. , vol.5 , pp. 436-440
    • Edwards, A.M.1    Bountra, C.2    Kerr, D.J.3    Willson, T.M.4
  • 44
    • 8544253237 scopus 로고    scopus 로고
    • Assignment of endogenous substrates to enzymes by global metabolite profiling
    • Saghatelian, A. et al. Assignment of endogenous substrates to enzymes by global metabolite profiling. Biochemistry 43, 14332-14339 (2004).
    • (2004) Biochemistry , vol.43 , pp. 14332-14339
    • Saghatelian, A.1
  • 45
    • 84928574539 scopus 로고    scopus 로고
    • ABHD4 regulates multiple classes of N-acyl phospholipids in the mammalian central nervous system
    • Lee, H., Simon, G. M. & Cravatt, B. F. ABHD4 regulates multiple classes of N-acyl phospholipids in the mammalian central nervous system. Biochemistry 54, 2539-2549 (2015).
    • (2015) Biochemistry , vol.54 , pp. 2539-2549
    • Lee, H.1    Simon, G.M.2    Cravatt, B.F.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.