메뉴 건너뛰기




Volumn 290, Issue 27, 2015, Pages 16861-16872

Structure guided chemical modifications of propylthiouracil reveal novel small molecule inhibitors of cytochrome b5 reductase 3 that increase nitric oxide bioavailability

Author keywords

[No Author keywords available]

Indexed keywords

BIOCHEMISTRY; MOLECULES; NITRIC OXIDE;

EID: 84936816931     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.M114.629964     Document Type: Article
Times cited : (26)

References (36)
  • 1
    • 0014980147 scopus 로고
    • Structure guided chemical modifications of propylthiouracil reveal novel small molecule inhibitors of cytochrome b5 reductase 3 that increase nitric oxide bioavailability
    • Oshino, N., Imai, Y., and Sato, R. (1971) Structure Guided Chemical Modifications of Propylthiouracil Reveal Novel Small Molecule Inhibitors of Cytochrome b5 Reductase 3 That Increase Nitric Oxide Bioavailability. J. Biochem. 69, 155-167.
    • (1971) J. Biochem , vol.69 , pp. 155-167
    • Oshino, N.1    Imai, Y.2    Sato, R.3
  • 2
    • 0017391211 scopus 로고
    • Mechanism of C-5 double bond introduction in the biosynthesis of cholesterol by rat liver microsomes
    • Reddy, V. V., Kupfer, D., and Caspi, E. (1977) Mechanism of C-5 double bond introduction in the biosynthesis of cholesterol by rat liver microsomes. J. Biol. Chem. 252, 2797-2801.
    • (1977) J. Biol. Chem , vol.252 , pp. 2797-2801
    • Reddy, V.V.1    Kupfer, D.2    Caspi, E.3
  • 3
    • 0015032258 scopus 로고
    • Evidence for the participation of cytochrome b 5 in hepatic microsomal mixed-function oxidation reactions
    • Hildebrandt, A., and Estabrook, R. W. (1971) Evidence for the participation of cytochrome b 5 in hepatic microsomal mixed-function oxidation reactions. Arch. Biochem. Biophys. 143, 66-79.
    • (1971) Arch. Biochem. Biophys , vol.143 , pp. 66-79
    • Hildebrandt, A.1    Estabrook, R.W.2
  • 4
    • 73949092712 scopus 로고    scopus 로고
    • Cytochrome b5 and NADH cytochrome b5 reductase: Genotype-phenotype correlations for hydroxylamine reduction. Pharmacogenet
    • Sacco, J. C., and Trepanier, L. A. (2010) Cytochrome b5 and NADH cytochrome b5 reductase: genotype-phenotype correlations for hydroxylamine reduction. Pharmacogenet. Genomics 20, 26-37.
    • (2010) Genomics , vol.20 , pp. 26-37
    • Sacco, J.C.1    Trepanier, L.A.2
  • 5
    • 0015504064 scopus 로고
    • Soluble cytochrome b5 reductase from human erythrocytes
    • Passon, P. G., and Hultquist, D. E. (1972) Soluble cytochrome b5 reductase from human erythrocytes. Biochim. Biophys. Acta 275, 62-73.
    • (1972) Biochim. Biophys. Acta , vol.275 , pp. 62-73
    • Passon, P.G.1    Hultquist, D.E.2
  • 6
    • 0015237988 scopus 로고
    • Catalysis of methaemoglobin reduction by erythrocyte cytochrome b5 and cytochrome b5 reductase
    • Hultquist, D. E., and Passon, P. G. (1971) Catalysis of methaemoglobin reduction by erythrocyte cytochrome b5 and cytochrome b5 reductase. Nat. New Biol. 229, 252-254.
    • (1971) Nat. New Biol , vol.229 , pp. 252-254
    • Hultquist, D.E.1    Passon, P.G.2
  • 7
    • 42049097088 scopus 로고    scopus 로고
    • Recessive congenital methaemoglobinaemia: Cytochrome b5 reductase deficiency
    • Percy, M. J., and Lappin, T. R. (2008) Recessive congenital methaemoglobinaemia: cytochrome b5 reductase deficiency. Br. J. Haematol. 141, 298-308.
    • (2008) Br. J. Haematol , vol.141 , pp. 298-308
    • Percy, M.J.1    Lappin, T.R.2
  • 11
    • 84859487532 scopus 로고    scopus 로고
    • Nitric oxide synthases: Regulation and function
    • Förstermann, U., and Sessa, W. C. (2012) Nitric oxide synthases: Regulation and function. Eur. Heart J. 33, 829-837.
    • (2012) Eur. Heart J. , vol.33 , pp. 829-837
    • Förstermann, U.1    Sessa, W.C.2
  • 12
    • 0023198721 scopus 로고
    • Nitric oxide release accounts for the biological activity of endothelium-derived relaxing factor
    • Palmer, R. M., Ferrige, A. G., and Moncada, S. (1987) Nitric oxide release accounts for the biological activity of endothelium-derived relaxing factor. Nature 327, 524-526.
    • (1987) Nature , vol.327 , pp. 524-526
    • Palmer, R.M.1    Ferrige, A.G.2    Moncada, S.3
  • 13
    • 0023505509 scopus 로고
    • Endothelium-derived relaxing factor produced and released from artery and vein is nitric oxide
    • Ignarro, L. J., Buga, G. M., Wood, K. S., Byrns, R. E., and Chaudhuri, G. (1987) Endothelium-derived relaxing factor produced and released from artery and vein is nitric oxide. Proc. Natl. Acad. Sci. U.S.A. 84, 9265-9269.
    • (1987) Proc. Natl. Acad. Sci, U.S.A , vol.84 , pp. 9265-9269
    • Ignarro, L.J.1    Buga, G.M.2    Wood, K.S.3    Byrns, R.E.4    Chaudhuri, G.5
  • 14
    • 0019195506 scopus 로고
    • The obligatory role of endothelial cells in the relaxation of arterial smooth muscle by acetylcholine
    • Furchgott, R. F., and Zawadzki, J. V. (1980) The obligatory role of endothelial cells in the relaxation of arterial smooth muscle by acetylcholine. Nature 288, 373-376.
    • (1980) Nature , vol.288 , pp. 373-376
    • Furchgott, R.F.1    Zawadzki, J.V.2
  • 15
    • 0022860827 scopus 로고
    • Propylthiouracil, a selective inhibitor of NADH-cytochrome b5 reductase
    • Lee, E., and Kariya, K. (1986) Propylthiouracil, a selective inhibitor of NADH-cytochrome b5 reductase. FEBS Lett. 209, 49-51.
    • (1986) FEBS Lett , vol.209 , pp. 49-51
    • Lee, E.1    Kariya, K.2
  • 17
    • 84883247468 scopus 로고    scopus 로고
    • Lessons learned in empirical scoring with smina from the CSAR 2011 benchmarking exercise
    • Koes, D. R., Baumgartner, M. P., and Camacho, C. J. (2013) Lessons learned in empirical scoring with smina from the CSAR 2011 benchmarking exercise. J. Chem. Inf. Model. 53, 1893-1904.
    • (2013) J. Chem. Inf. Model , vol.53 , pp. 1893-1904
    • Koes, D.R.1    Baumgartner, M.P.2    Camacho, C.J.3
  • 18
    • 76149120388 scopus 로고    scopus 로고
    • AutoDock Vina: Improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading
    • Trott, O., and Olson, A. J. (2010) AutoDock Vina: Improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. J. Comput. Chem. 31, 455-461.
    • (2010) J. Comput. Chem , vol.31 , pp. 455-461
    • Trott, O.1    Olson, A.J.2
  • 19
    • 84864447594 scopus 로고    scopus 로고
    • ZINCPharmer: Pharmacophore search of the ZINC database
    • Koes, D. R., and Camacho, C. J. (2012) ZINCPharmer: pharmacophore search of the ZINC database. Nucleic Acids Res. 40, W409-W414.
    • (2012) Nucleic Acids Res , vol.40 , pp. 409-414
    • Koes, D.R.1    Camacho, C.J.2
  • 21
    • 0024353360 scopus 로고
    • Expression of human erythrocyte NADH-cytochrome b5 reductase as an -thrombin-cleavable fused protein in Escherichia coli
    • Shirabe, K., Yubisui, T., and Takeshita, M. (1989) Expression of human erythrocyte NADH-cytochrome b5 reductase as an -thrombin-cleavable fused protein in Escherichia coli. Biochim. Biophys. Acta 1008, 189-192.
    • (1989) Biochim. Biophys. Acta , vol.1008 , pp. 189-192
    • Shirabe, K.1    Yubisui, T.2    Takeshita, M.3
  • 22
    • 0346374717 scopus 로고    scopus 로고
    • Mammalian mitochondrial and microsomal cytochromes b5 exhibit divergent structural and biophysical characteristics
    • Altuve, A., Wang, L., Benson, D. R., and Rivera, M. (2004) Mammalian mitochondrial and microsomal cytochromes b5 exhibit divergent structural and biophysical characteristics. Biochem. Biophys. Res. Commun. 314, 602-609.
    • (2004) Biochem, Biophys. Res. Commun , vol.314 , pp. 602-609
    • Altuve, A.1    Wang, L.2    Benson, D.R.3    Rivera, M.4
  • 23
    • 0012614437 scopus 로고
    • The purification and properties of microsomal cytochrome reductase
    • Strittmatter, P., and Velick, S. F. (1957) The purification and properties of microsomal cytochrome reductase. J. Biol. Chem. 228, 785-799.
    • (1957) J. Biol. Chem , vol.228 , pp. 785-799
    • Strittmatter, P.1    Velick, S.F.2
  • 24
    • 0036545625 scopus 로고    scopus 로고
    • Isolation and culture of rat microvascular endothelial cells
    • Frye, C. A., and Patrick, C. W. Jr. (2002) Isolation and culture of rat microvascular endothelial cells. In Vitro Cell. Dev. Biol. Anim. 38, 208-212.
    • (2002) Vitro Cell., Dev. Biol. Anim , vol.38 , pp. 208-212
    • Frye, C.A.1    Patrick, C.W.2
  • 26
    • 22144479749 scopus 로고    scopus 로고
    • Heterocellular contact at the myoendothelial junction influences gap junction organization
    • Isakson, B. E., and Duling, B. R. (2005) Heterocellular contact at the myoendothelial junction influences gap junction organization. Circ. Res. 97, 44-51.
    • (2005) Circ. Res , vol.97 , pp. 44-51
    • Isakson, B.E.1    Duling, B.R.2
  • 27
    • 0026686480 scopus 로고
    • Culture of renal arteriolar smooth muscle cells: Mitogenic responses to angiotensin II
    • Dubey, R. K., Roy, A., and Overbeck, H. W. (1992) Culture of renal arteriolar smooth muscle cells: Mitogenic responses to angiotensin II. Circ. Res. 71, 1143-1152.
    • (1992) Circ. Res , vol.71 , pp. 1143-1152
    • Dubey, R.K.1    Roy, A.2    Overbeck, H.W.3
  • 28
    • 0032462878 scopus 로고    scopus 로고
    • Modulation by angiotensin II of isoproterenol-induced camp production in preglomerular microvascular smooth muscle cells from normotensive and genetically hypertensive rats
    • Mokkapatti, R., Vyas, S. J., Romero, G. G., Mi, Z., Inoue, T., Dubey, R. K., Gillespie, D. G., Stout, A. K., and Jackson, E. K. (1998) Modulation by angiotensin II of isoproterenol-induced cAMP production in preglomerular microvascular smooth muscle cells from normotensive and genetically hypertensive rats. J. Pharmacol. Exp. Ther. 287, 223-231.
    • (1998) J. Pharmacol. Exp. Ther , vol.287 , pp. 223-231
    • Mokkapatti, R.1    Vyas, S.J.2    Romero, G.G.3    Mi, Z.4    Inoue, T.5    Dubey, R.K.6    Gillespie, D.G.7    Stout, A.K.8    Jackson, E.K.9
  • 32
    • 0016351617 scopus 로고
    • Methemoglobin reductase (cytochrome b5 reductase) deficiency in congenital methemoglobinemia
    • Kitao, T., Sugita, Y., Yoneyama, Y., and Hattori, K. (1974) Methemoglobin reductase (cytochrome b5 reductase) deficiency in congenital methemoglobinemia. Blood 44, 879-884.
    • (1974) Blood , vol.44 , pp. 879-884
    • Kitao, T.1    Sugita, Y.2    Yoneyama, Y.3    Hattori, K.4
  • 33
    • 0029967559 scopus 로고    scopus 로고
    • Nitric oxide modulates angiotensin II- And norepinephrine-dependent vasoconstriction in rat kidney
    • Parekh, N., Dobrowolski, L., Zou, A. P., and Steinhausen, M. (1996) Nitric oxide modulates angiotensin II- And norepinephrine-dependent vasoconstriction in rat kidney. Am. J. Physiol. 270, R630-R635.
    • (1996) Am. J. Physiol , vol.270 , pp. 630-635
    • Parekh, N.1    Dobrowolski, L.2    Zou, A.P.3    Steinhausen, M.4
  • 34
    • 0028243794 scopus 로고
    • Influence of inhibition of endothelium-derived nitric oxide formation to effects of vasoconstrictor agents neuropeptide Y, clonidine, and ergonovine on coronary vascular resistance
    • Tsunoda, R., Okumura, K., Ishizaka, H., Matsunaga, T., and Yasue, H. (1994) Influence of inhibition of endothelium-derived nitric oxide formation to effects of vasoconstrictor agents neuropeptide Y, clonidine, and ergonovine on coronary vascular resistance. J. Cardiovasc. Pharmacol. 24, 87-94.
    • (1994) J. Cardiovasc. Pharmacol , vol.24 , pp. 87-94
    • Tsunoda, R.1    Okumura, K.2    Ishizaka, H.3    Matsunaga, T.4    Yasue, H.5
  • 35
    • 67649763457 scopus 로고    scopus 로고
    • Cytoglobin is expressed in the vasculature and regulates cell respiration and proliferation via nitric oxide dioxygenation
    • Halligan, K. E., Jourd'heuil, F. L., and Jourd'heuil, D. (2009) Cytoglobin is expressed in the vasculature and regulates cell respiration and proliferation via nitric oxide dioxygenation. J. Biol. Chem. 284, 8539-8547.
    • (2009) J. Biol. Chem , vol.284 , pp. 8539-8547
    • Halligan, K.E.1    Jourd'heuil, F.L.2    Jourd'heuil, D.3
  • 36
    • 0025098567 scopus 로고
    • Sodium nitroprusside alters ca2- flux components and ca2-dependent fluxes of k- And cl- in rat aorta
    • Magliola, L., and Jones, A. W. (1990) Sodium nitroprusside alters Ca2- flux components and Ca2-dependent fluxes of K- And Cl- in rat aorta. J. Physiol. 421, 411-424.
    • (1990) J. Physiol , vol.421 , pp. 411-424
    • Magliola, L.1    Jones, A.W.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.