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Volumn 16, Issue 14, 2008, Pages 6764-6777

A re-examination of the difluoromethylenesulfonic acid group as a phosphotyrosine mimic for PTP1B inhibition

Author keywords

Non peptidyl inhibitors; Phosphotyrosine mimics; PTP1B

Indexed keywords

[2 BROMO 4 (4' BROMO 3' SULFAMOYLBIPHENYL 4 YLMETHYL SULFANYLMETHYL)PHENYL] METHANESULFONATE; [2 BROMO 4 (4' BROMO 3' SULFAMOYLBIPHENYL 4 YLMETHYL SULFANYLMETHYL)PHENYL]DIFLUOROMETHANESULFONATE; [2 BROMO 4 [4' BROMO 3' (DIFLUOROSULFAMOYLMETHYL)BIPHENYL 4 YLMETHYLSULFANYLMETHYL]PHENYL]DIFLUOROMETHANESULFONIC ACID; [[2 BROMO 4 (4' BROMO 3' SULFAMOYLBIPHENYL 4 YLMETHYL SULFANYLMETHYL) PHENYL]DIFLUOROMETHYL]PHOSPHONIC ACID; [[2 BROMO 4 [4' BROMO 3' DIFLUOROSULFAMOYLMETHYL)BIPHENYL 4 YLMETHYLSULFANYLMETHYL]PHENYL]DIFLUOROMETHYL]PHOSPHONIC ACID; DIFLUOROMETHYLENESULFONIC ACID; PHOSPHOTYROSINE; PROTEIN TYROSINE PHOSPHATASE 1B; PROTEIN TYROSINE PHOSPHATASE 1B INHIBITOR; UNCLASSIFIED DRUG;

EID: 47349122949     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.05.062     Document Type: Article
Times cited : (35)

References (43)
  • 16
    • 47349130121 scopus 로고    scopus 로고
    • Sing, L. C.; Lau, C. K.; Therien, M.; Gauthier, J.-Y.; Bayly, C.; Dufresne, C.; Fortin, R.; Leblanc, Y. International Application, Patent Cooperation Treaty Patent WO 2001/70753.
    • Sing, L. C.; Lau, C. K.; Therien, M.; Gauthier, J.-Y.; Bayly, C.; Dufresne, C.; Fortin, R.; Leblanc, Y. International Application, Patent Cooperation Treaty Patent WO 2001/70753.
  • 24
    • 0037132579 scopus 로고    scopus 로고
    • note
    • Benzyl bromide 21 has been prepared in 77% yield by refluxing a solution of 3-bromo-4-methylbenzoic acid methyl ester, N-bromosuccinimide, and cat. benzoyl peroxide in carbon tetrachloride for 10 h. See: Curran, D. P.; Yang, F.; Cheong, J.-h. J. Am. Chem. Soc. 2002, 124, 14993. We have found that compound 21 can be prepared in a 93% yield by subjecting a refluxing solution of 3-bromo-4-methylbenzoic acid methyl ester, N-bromosuccinimide, and cat. benzoyl peroxide in benzene to a 250 W lamp for 6 h.
  • 32
    • 47349110198 scopus 로고    scopus 로고
    • note
    • m of the substrate, DIFMUP, under our conditions was found to be the same (5 μM) as that determined by MerckFrosst in the absence of DMSO (see Ref. 20).
  • 33
    • 0027336612 scopus 로고
    • 3Na)OH and standard manual Fmoc solid-phase peptide synthesis techniques. See:
    • 3Na)OH and standard manual Fmoc solid-phase peptide synthesis techniques. See:. Miranda M.T.M., Liddle R.A., and Rivier J.E. J. Med. Chem. 36 (1993) 1681
    • (1993) J. Med. Chem. , vol.36 , pp. 1681
    • Miranda, M.T.M.1    Liddle, R.A.2    Rivier, J.E.3
  • 34
    • 47349115598 scopus 로고    scopus 로고
    • note
    • It is also possible that this large difference in potency between the DFMS and DFMP inhibitors is because the DFMP group is dianionic at pH 6.5 and PTP1B prefers to bind the dianionic DFMP-based inhibitors as opposed to the monoanionic DFMS-based inhibitors. However, as mentioned earlier, previous studies (see Refs. 5c and 10) suggest that PTP1B binds the monoanionic and dianionic forms of DFMP-bearing inhibitors equally well.
  • 40
    • 47349087654 scopus 로고    scopus 로고
    • Erlanson, D. A.; McDowell, R. S.; He, M. M.; Randal, M.; Simmons, R. L.; Kung, J.; Waight, A.; Hansen, S. K.
    • Erlanson, D. A.; McDowell, R. S.; He, M. M.; Randal, M.; Simmons, R. L.; Kung, J.; Waight, A.; Hansen, S. K.
  • 43
    • 0035854750 scopus 로고    scopus 로고
    • A pFLAG plasmid expressing the catalytic domain (residues 1-298) of human PTP1B was expressed in BL21 (DE3) cells and purified according to a two-step purification protocol (Cibracon blue affinity column and Sepharose Q anion exchange column) previously described by Asante-Appiah et al. See:
    • A pFLAG plasmid expressing the catalytic domain (residues 1-298) of human PTP1B was expressed in BL21 (DE3) cells and purified according to a two-step purification protocol (Cibracon blue affinity column and Sepharose Q anion exchange column) previously described by Asante-Appiah et al. See:. Asante-Appiah E., Ball K., Bateman K., Skorey K., Friesen R., Desponts C., Payette P., Bayly C., Zamboni R., Scapin G., Ramachandran C., Kennedy B.P. J. Biol. Chem. 276 (2001) 26036
    • (2001) J. Biol. Chem. , vol.276 , pp. 26036
    • Asante-Appiah, E.1    Ball, K.2    Bateman, K.3    Skorey, K.4    Friesen, R.5    Desponts, C.6    Payette, P.7    Bayly, C.8    Zamboni, R.9    Scapin, G.10    Ramachandran, C.11    Kennedy, B.P.12


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.