메뉴 건너뛰기




Volumn 57, Issue 11, 2014, Pages 4805-4818

Designing allosteric inhibitors of factor XIa. Lessons from the interactions of sulfated pentagalloylglucopyranosides

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLAMIDE; BLOOD CLOTTING FACTOR 11; BLOOD CLOTTING FACTOR 11A; BLOOD CLOTTING FACTOR 11A INHIBITOR; BLOOD CLOTTING INHIBITOR; ENZYME PRECURSOR; HEPARIN; PENTAGALLOYLGLUCOPYRANOSIDE DERIVATIVE; SULFATE; THROMBIN; UNCLASSIFIED DRUG;

EID: 84902438454     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm500311e     Document Type: Article
Times cited : (50)

References (57)
  • 1
    • 84873898236 scopus 로고    scopus 로고
    • J. Med Chem. 2013, 56, 867-878
    • (2013) J. Med Chem. , vol.56 , pp. 867-878
  • 2
    • 77956752875 scopus 로고    scopus 로고
    • Clinical burden of venous thromboembolism
    • Ruppert, A.; Lees, M.; Steinle, T. Clinical burden of venous thromboembolism Curr. Med. Res. Opin. 2010, 26, 2465-2473
    • (2010) Curr. Med. Res. Opin. , vol.26 , pp. 2465-2473
    • Ruppert, A.1    Lees, M.2    Steinle, T.3
  • 3
    • 84901730044 scopus 로고    scopus 로고
    • Management of bleeding and reversal strategies for oral anticoagulants: Clinical practice considerations
    • Nutescu, E. A.; Dager, W. E.; Kalus, J. S.; Lewin, J. J., III; Cipolle, M. D. Management of bleeding and reversal strategies for oral anticoagulants: clinical practice considerations Am. J. Health Syst. Pharm. 2013, 70, 1914-1929
    • (2013) Am. J. Health Syst. Pharm. , vol.70 , pp. 1914-1929
    • Nutescu, E.A.1    Dager, W.E.2    Kalus, J.S.3    Lewin III, J.J.4    Cipolle, M.D.5
  • 4
    • 84891667212 scopus 로고    scopus 로고
    • An updated review of target-specific oral anticoagulants used in stroke prevention in atrial fibrillation, venous thromboembolic disease, and acute coronary syndromes
    • Cove, C. L.; Hylek, E. M. An updated review of target-specific oral anticoagulants used in stroke prevention in atrial fibrillation, venous thromboembolic disease, and acute coronary syndromes J. Am. Heart Assoc. 2013, 2, e000136
    • (2013) J. Am. Heart Assoc. , vol.2 , pp. 000136
    • Cove, C.L.1    Hylek, E.M.2
  • 5
    • 84885403809 scopus 로고    scopus 로고
    • Novel thrombin and factor Xa inhibitors: Challenges to reversal of their anticoagulation effects
    • Yates, S.; Sarode, R. Novel thrombin and factor Xa inhibitors: challenges to reversal of their anticoagulation effects Curr. Opin. Hematol. 2013, 20, 552-557
    • (2013) Curr. Opin. Hematol. , vol.20 , pp. 552-557
    • Yates, S.1    Sarode, R.2
  • 6
    • 84880829151 scopus 로고    scopus 로고
    • Anticoagulation beyond direct thrombin and factor Xa inhibitors: Indications for targeting the intrinsic pathway?
    • van Montfoort, M. L.; Meijers, J. C. M. Anticoagulation beyond direct thrombin and factor Xa inhibitors: indications for targeting the intrinsic pathway? Thromb. Haemost. 2013, 110, 223-232
    • (2013) Thromb. Haemost. , vol.110 , pp. 223-232
    • Van Montfoort, M.L.1    Meijers, J.C.M.2
  • 7
    • 34248387034 scopus 로고    scopus 로고
    • Arterial and venous thrombosis in rare congenital bleeding disorders: A critical review
    • Girolami, A.; Ruzzon, E.; Tezza, F.; Scandellari, R.; Vettore, S.; Girolami, B. Arterial and venous thrombosis in rare congenital bleeding disorders: a critical review Haemophilia 2006, 12, 345-351
    • (2006) Haemophilia , vol.12 , pp. 345-351
    • Girolami, A.1    Ruzzon, E.2    Tezza, F.3    Scandellari, R.4    Vettore, S.5    Girolami, B.6
  • 8
    • 43249088304 scopus 로고    scopus 로고
    • Reduced incidence of ischemic stroke in patients with severe factor XI deficiency
    • Salomon, O.; Steinberg, D. M.; Koren-Morag, N.; Tanne, D.; Seligsohn, U. Reduced incidence of ischemic stroke in patients with severe factor XI deficiency Blood 2008, 111, 4113-4117
    • (2008) Blood , vol.111 , pp. 4113-4117
    • Salomon, O.1    Steinberg, D.M.2    Koren-Morag, N.3    Tanne, D.4    Seligsohn, U.5
  • 9
    • 78149254900 scopus 로고    scopus 로고
    • Coagulation factor XI as a novel target for antithrombotic treatment
    • Löwenberg, E. C.; Meijers, J. C. M.; Monia, B. P.; Levi, M. Coagulation factor XI as a novel target for antithrombotic treatment J. Thromb. Haemost. 2010, 8, 2349-2357
    • (2010) J. Thromb. Haemost. , vol.8 , pp. 2349-2357
    • Löwenberg, E.C.1    Meijers, J.C.M.2    Monia, B.P.3    Levi, M.4
  • 10
    • 67849097372 scopus 로고    scopus 로고
    • FXI deficiency in humans
    • Seligsohn, U. FXI deficiency in humans J. Thromb. Haemost. 2009, 7, 84-87
    • (2009) J. Thromb. Haemost. , vol.7 , pp. 84-87
    • Seligsohn, U.1
  • 12
  • 16
    • 0042243616 scopus 로고    scopus 로고
    • Factor XI-dependence of surface- and tissue factor-initiated thrombus propagation in primates
    • DOI 10.1182/blood-2003-01-0324
    • Gruber, A.; Hanson, S. R. Factor XI-dependence of surface- and tissue factor-initiated thrombus propagation in primates Blood 2003, 102, 953-955 (Pubitemid 36917789)
    • (2003) Blood , vol.102 , Issue.3 , pp. 953-955
    • Gruber, A.1    Hanson, S.R.2
  • 17
  • 20
    • 67949118828 scopus 로고    scopus 로고
    • Structural and functional features of factor XI
    • Gailani, D.; Smith, S. B. Structural and functional features of factor XI J. Thromb. Haemost. 2009, 7, 75-78
    • (2009) J. Thromb. Haemost. , vol.7 , pp. 75-78
    • Gailani, D.1    Smith, S.B.2
  • 21
    • 77950978248 scopus 로고    scopus 로고
    • Structure and function of factor XI
    • Emsley, J.; McEwan, P. A.; Gailani, D. Structure and function of factor XI Blood 2010, 115, 2569-2577
    • (2010) Blood , vol.115 , pp. 2569-2577
    • Emsley, J.1    McEwan, P.A.2    Gailani, D.3
  • 22
    • 0032568840 scopus 로고    scopus 로고
    • A binding site for heparin in the apple 3 domain of factor XI
    • DOI 10.1074/jbc.273.26.16382
    • Ho, D. H.; Badellino, K.; Baglia, F. A.; Walsh, P. N. A binding site for heparin in the apple 3 domain of factor XI J. Biol. Chem. 1998, 273, 16382-16390 (Pubitemid 28311418)
    • (1998) Journal of Biological Chemistry , vol.273 , Issue.26 , pp. 16382-16390
    • Ho, D.H.1    Badelllino, K.2    Baglia, F.A.3    Walsh, P.N.4
  • 23
    • 0032553436 scopus 로고    scopus 로고
    • Characterization of a heparin binding site on the heavy chain of factor XI
    • DOI 10.1074/jbc.273.47.31153
    • Zhao, M.; Abdel-Razek, T.; Sun, M. F.; Gailani, D. Characterization of a heparin-binding site on the heavy chain of factor XI J. Biol. Chem. 1998, 273, 31153-31159 (Pubitemid 28533127)
    • (1998) Journal of Biological Chemistry , vol.273 , Issue.47 , pp. 31153-31159
    • Zhao, M.1    Abdel-Razek, T.2    Sun, M.-F.3    Gailani, D.4
  • 24
    • 0035954370 scopus 로고    scopus 로고
    • Localization of a heparin binding site in the catalytic domain of factor XIa
    • Badellino, K. O.; Walsh, P. N. Localization of a heparin binding site in the catalytic domain of FXIa Biochemistry 2001, 40, 7569-7580 (Pubitemid 32578022)
    • (2001) Biochemistry , vol.40 , Issue.25 , pp. 7569-7580
    • Badellino, K.O.1    Walsh, P.N.2
  • 25
    • 61749093027 scopus 로고    scopus 로고
    • Characterization of a heparin-binding site on the catalytic domain of factor XIa: Mechanism of heparin acceleration of factor XIa inhibition by the serpins antithrombin and C1-inhibitor
    • Yang, L.; Sun, M. F.; Gailani, D.; Rezaie, A. R. Characterization of a heparin-binding site on the catalytic domain of factor XIa: mechanism of heparin acceleration of factor XIa inhibition by the serpins antithrombin and C1-inhibitor Biochemistry 2009, 48, 1517-1524
    • (2009) Biochemistry , vol.48 , pp. 1517-1524
    • Yang, L.1    Sun, M.F.2    Gailani, D.3    Rezaie, A.R.4
  • 26
    • 84255201932 scopus 로고    scopus 로고
    • Polyphosphate is a cofactor for the activation of factor XI by thrombin
    • Choi, S. H.; Smith, S. A.; Morrissey, J. H. Polyphosphate is a cofactor for the activation of factor XI by thrombin Blood 2011, 118, 6963-6970
    • (2011) Blood , vol.118 , pp. 6963-6970
    • Choi, S.H.1    Smith, S.A.2    Morrissey, J.H.3
  • 27
    • 2942562194 scopus 로고    scopus 로고
    • Allosteric modification of factor XIa functional activity upon binding to polyanions
    • DOI 10.1021/bi049808c
    • Sinha, D.; Badellino, K. O.; Marcinkiewicz, M.; Walsh, P. N. Allosteric modification of factor XIa functional activity upon binding to polyanions Biochemistry 2004, 43, 7593-7600 (Pubitemid 38745775)
    • (2004) Biochemistry , vol.43 , Issue.23 , pp. 7593-7600
    • Sinha, D.1    Badellino, K.O.2    Marcinkiewicz, M.3    Walsh, P.N.4
  • 28
    • 84881538094 scopus 로고    scopus 로고
    • The promise of sulfated synthetic small molecules as modulators of glycosaminoglycan function
    • Desai, U. R. The promise of sulfated synthetic small molecules as modulators of glycosaminoglycan function Future Med. Chem. 2013, 5, 1363-1366
    • (2013) Future Med. Chem. , vol.5 , pp. 1363-1366
    • Desai, U.R.1
  • 29
    • 84879593914 scopus 로고    scopus 로고
    • Designing allosteric regulators of thrombin. Exosite 2 features multiple subsites that can be targeted by sulfated small molecules for inducing inhibition
    • Sidhu, P. S.; Abdel Aziz, M. H.; Sarkar, A.; Mehta, A. Y.; Zhou, Q.; Desai, U. R. Designing allosteric regulators of thrombin. Exosite 2 features multiple subsites that can be targeted by sulfated small molecules for inducing inhibition J. Med. Chem. 2013, 56, 5059-5070
    • (2013) J. Med. Chem. , vol.56 , pp. 5059-5070
    • Sidhu, P.S.1    Abdel Aziz, M.H.2    Sarkar, A.3    Mehta, A.Y.4    Zhou, Q.5    Desai, U.R.6
  • 30
    • 79961220817 scopus 로고    scopus 로고
    • Rational design of potent, small, synthetic allosteric inhibitors of thrombin
    • Sidhu, P. S.; Liang, A.; Mehta, A. Y.; Abdel Aziz, M. H.; Zhou, Q.; Desai, U. R. Rational design of potent, small, synthetic allosteric inhibitors of thrombin J. Med. Chem. 2011, 54, 5522-5531
    • (2011) J. Med. Chem. , vol.54 , pp. 5522-5531
    • Sidhu, P.S.1    Liang, A.2    Mehta, A.Y.3    Abdel Aziz, M.H.4    Zhou, Q.5    Desai, U.R.6
  • 31
    • 78149280530 scopus 로고    scopus 로고
    • Design and synthesis of macrocyclic indoles targeting blood coagulation cascade Factor XIa
    • Hanessian, S.; Larsson, A.; Fex, T.; Knecht, W.; Blomberg, N. Design and synthesis of macrocyclic indoles targeting blood coagulation cascade Factor XIa Bioorg. Med. Chem. Lett. 2010, 20, 6925-6928
    • (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 6925-6928
    • Hanessian, S.1    Larsson, A.2    Fex, T.3    Knecht, W.4    Blomberg, N.5
  • 38
    • 84873898236 scopus 로고    scopus 로고
    • Sulfated pentagalloyl-glucoside is a potent, allosteric, and selective inhibitor of factor XIa
    • Al-Horani, R. A.; Ponnusamy, P.; Mehta, A. Y.; Gailani, D.; Desai, U. R. Sulfated pentagalloyl-glucoside is a potent, allosteric, and selective inhibitor of factor XIa J. Med. Chem. 2013, 56, 867-878
    • (2013) J. Med. Chem. , vol.56 , pp. 867-878
    • Al-Horani, R.A.1    Ponnusamy, P.2    Mehta, A.Y.3    Gailani, D.4    Desai, U.R.5
  • 39
    • 84875743348 scopus 로고    scopus 로고
    • Discovery of allosteric modulators of factor XIa by targeting hydrophobic domains adjacent to its heparin-binding site
    • Karuturi, R.; Al-Horani, R. A.; Mehta, S. C.; Gailani, D.; Desai, U. R. Discovery of allosteric modulators of factor XIa by targeting hydrophobic domains adjacent to its heparin-binding site J. Med. Chem. 2013, 56, 2415-2428
    • (2013) J. Med. Chem. , vol.56 , pp. 2415-2428
    • Karuturi, R.1    Al-Horani, R.A.2    Mehta, S.C.3    Gailani, D.4    Desai, U.R.5
  • 40
    • 84899534776 scopus 로고    scopus 로고
    • Allosteric inhibition of human factor XIa: Discovery of monosulfated benzofurans as a class of promising inhibitors
    • Argade, M. D.; Mehta, A. Y.; Sarkar, A.; Desai, U. R. Allosteric inhibition of human factor XIa: Discovery of monosulfated benzofurans as a class of promising inhibitors J. Med. Chem. 2014, 57, 3559-3569
    • (2014) J. Med. Chem. , vol.57 , pp. 3559-3569
    • Argade, M.D.1    Mehta, A.Y.2    Sarkar, A.3    Desai, U.R.4
  • 41
    • 17444437348 scopus 로고    scopus 로고
    • Efficient total synthesis of the natural products 2,3,4,6-tetra-O- galloyl-D-glucopyranose, 1,2,3,4,6-penta-O-galloyl-D-glucopyranose and the unnatural 1,2,3,4,6-penta-O-galloyl-D-glucopyranose
    • DOI 10.1016/S0040-4020(97)00702-3, PII S0040402097007023
    • Khanbabaee, K.; Lötzerich, K. Efficient total synthesis of the natural products 2,3,4,6-tetra- O -galloyl- d -glucopyranose, 1,2,3,4,6-Penta- O -galloyl-β- d -glucopyranose and the unnatural 1,2,3,4,6-penta- O -galloyl-α- d -glucopyranose Tetrahedron 1997, 53, 10725-10732 (Pubitemid 27308549)
    • (1997) Tetrahedron , vol.53 , Issue.31 , pp. 10725-10732
    • Khanbabaee, K.1    Lotzerich, K.2
  • 43
    • 0032571333 scopus 로고    scopus 로고
    • Mechanism of heparin activation of antithrombin. Role of individual residues of the pentasaccharide activating sequence in the recognition of native and activated states of antithrombin
    • DOI 10.1074/jbc.273.13.7478
    • Desai, U. R.; Petitou, M.; Björk, I.; Olson, S. T. Mechanism of heparin activation of antithrombin. Role of individual residues of the pentasaccharide activating sequence in the recognition of native and activated states of antithrombin J. Biol. Chem. 1998, 273, 7478-7487 (Pubitemid 28152771)
    • (1998) Journal of Biological Chemistry , vol.273 , Issue.13 , pp. 7478-7487
    • Desai, U.R.1    Petitou, M.2    Bjork, I.3    Olson, S.T.4
  • 44
    • 77749246417 scopus 로고    scopus 로고
    • Sulfated, low-molecular-weight lignins are potent inhibitors of plasmin, in addition to thrombin and factor Xa: Novel opportunity for controlling complex pathologies
    • Henry, B. L.; Abdel Aziz, M.; Zhou, Q.; Desai, U. R. Sulfated, low-molecular-weight lignins are potent inhibitors of plasmin, in addition to thrombin and factor Xa: novel opportunity for controlling complex pathologies Thromb. Haemost. 2010, 103, 507-515
    • (2010) Thromb. Haemost. , vol.103 , pp. 507-515
    • Henry, B.L.1    Abdel Aziz, M.2    Zhou, Q.3    Desai, U.R.4
  • 46
    • 80052343772 scopus 로고    scopus 로고
    • Designing nonsaccharide allosteric activators of antithrombin for accelerated inhibition of factor Xa
    • Al-Horani, R. A.; Liang, A.; Desai, U. R. Designing nonsaccharide allosteric activators of antithrombin for accelerated inhibition of factor Xa J. Med. Chem. 2011, 54, 6125-6138
    • (2011) J. Med. Chem. , vol.54 , pp. 6125-6138
    • Al-Horani, R.A.1    Liang, A.2    Desai, U.R.3
  • 48
    • 84869073602 scopus 로고    scopus 로고
    • On the specificity of heparin/heparan sulfate binding to proteins. Anion-binding sites on antithrombin and thrombin are fundamentally different
    • Mosier, P. D.; Krishnasamy, C.; Kellogg, G. E.; Desai, U. R. On the specificity of heparin/heparan sulfate binding to proteins. Anion-binding sites on antithrombin and thrombin are fundamentally different PLoS One 2012, 7, e48632
    • (2012) PLoS One , vol.7 , pp. 48632
    • Mosier, P.D.1    Krishnasamy, C.2    Kellogg, G.E.3    Desai, U.R.4
  • 49
    • 0028923498 scopus 로고
    • Thermodynamics of charged oligopeptide-heparin interactions
    • Mascotti, D. P.; Lohman, T. M. Thermodynamics of charged oligopeptide-heparin interactions Biochemistry 1995, 34, 2908-2915
    • (1995) Biochemistry , vol.34 , pp. 2908-2915
    • Mascotti, D.P.1    Lohman, T.M.2
  • 52
    • 0025730441 scopus 로고
    • Quantitative characterization of the thrombin-heparin interaction: Discrimination between specific and nonspecific binding models
    • Olson, S. T.; Halvorson, H. R.; Björk, I. Quantitative characterization of the thrombin-heparin interaction. Discrimination between specific and nonspecific binding models J. Biol. Chem. 1991, 266, 6342-6352 (Pubitemid 21906224)
    • (1991) Journal of Biological Chemistry , vol.266 , Issue.10 , pp. 6342-6352
    • Olson, S.T.1    Halvorson, H.R.2    Bjork, I.3
  • 53
    • 0037179617 scopus 로고    scopus 로고
    • Interaction of sulfated flavanoids with antithrombin: Lessons on the design of organic activators
    • Gunnarsson, G. T.; Desai, U. R. Interaction of sulfated flavanoids with antithrombin: lessons on the design of organic activators J. Med. Chem. 2002, 45, 4460-4470
    • (2002) J. Med. Chem. , vol.45 , pp. 4460-4470
    • Gunnarsson, G.T.1    Desai, U.R.2
  • 54
    • 68949090333 scopus 로고    scopus 로고
    • Interaction of antithrombin with sulfated, low molecular weight lignins. Opportunities for potent, selective modulation of antithrombin function
    • Henry, B. L.; Connell, J.; Liang, A.; Krishnasamy, C.; Desai, U. R. Interaction of antithrombin with sulfated, low molecular weight lignins. Opportunities for potent, selective modulation of antithrombin function J. Biol. Chem. 2009, 284, 20897-20908
    • (2009) J. Biol. Chem. , vol.284 , pp. 20897-20908
    • Henry, B.L.1    Connell, J.2    Liang, A.3    Krishnasamy, C.4    Desai, U.R.5
  • 55
    • 34548040716 scopus 로고    scopus 로고
    • Rapid and efficient microwave-assisted synthesis of highly sulfated organic scaffolds
    • DOI 10.1016/j.tetlet.2007.07.100, PII S0040403907014232
    • Raghuraman, A.; Riaz, M.; Hindle, M.; Desai, U. R. Rapid and efficient microwave-assisted synthesis of highly sulfated organic scaffolds Tetrahedron Lett. 2007, 48, 6754-6758 (Pubitemid 47284242)
    • (2007) Tetrahedron Letters , vol.48 , Issue.38 , pp. 6754-6758
    • Raghuraman, A.1    Riaz, M.2    Hindle, M.3    Desai, U.R.4
  • 56
    • 77949655328 scopus 로고    scopus 로고
    • Chemical sulfation of small molecules-advances and challenges
    • Al-Horani, R. A.; Desai, U. R. Chemical sulfation of small molecules-advances and challenges Tetrahedron 2010, 66, 2907-2918
    • (2010) Tetrahedron , vol.66 , pp. 2907-2918
    • Al-Horani, R.A.1    Desai, U.R.2
  • 57
    • 0000008523 scopus 로고    scopus 로고
    • Quenching of Fluorescence
    • in, 2nd ed. Kluwe Academic/Plenum: New York
    • Lakowicz, J. R. Quenching of Fluorescence, in Principles of Fluorescence Spectroscopy, 2nd ed.; Kluwe Academic/Plenum: New York, 1999; pp 237-265.
    • (1999) Principles of Fluorescence Spectroscopy , pp. 237-265
    • Lakowicz, J.R.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.