메뉴 건너뛰기




Volumn 56, Issue 6, 2013, Pages 2415-2428

Discovery of allosteric modulators of factor XIa by targeting hydrophobic domains adjacent to its heparin-binding site

Author keywords

[No Author keywords available]

Indexed keywords

ANION; ANTITHROMBOCYTIC AGENT; BLOOD CLOTTING FACTOR 11A; BLOOD CLOTTING INHIBITOR; CATION; DERMATAN SULFATE HEXASACCHARIDE; HEPARIN; HEPARIN PENTASACCHARIDE; OCTASACCHARIDE; QUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 84875743348     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm301757v     Document Type: Article
Times cited : (41)

References (55)
  • 2
    • 79959866687 scopus 로고    scopus 로고
    • Functions of chondroitin sulfate and heparan sulfate in the developing brain
    • Maeda, N.; Ishii, M.; Nishimura, K.; Kamimura, K. Functions of chondroitin sulfate and heparan sulfate in the developing brain Neurochem. Res. 2011, 36, 1228-1240
    • (2011) Neurochem. Res. , vol.36 , pp. 1228-1240
    • Maeda, N.1    Ishii, M.2    Nishimura, K.3    Kamimura, K.4
  • 3
    • 78149358266 scopus 로고    scopus 로고
    • Molecular mechanisms of antithrombin-heparin regulation of blood clotting proteinases. A paradigm for understanding proteinase regulation by serpin family protein proteinase inhibitors
    • Olson, S. T.; Richard, B.; Izaguirre, G.; Schedin-Weiss, S.; Gettins, P. G. Molecular mechanisms of antithrombin-heparin regulation of blood clotting proteinases. A paradigm for understanding proteinase regulation by serpin family protein proteinase inhibitors Biochimie 2010, 92, 1587-1596
    • (2010) Biochimie , vol.92 , pp. 1587-1596
    • Olson, S.T.1    Richard, B.2    Izaguirre, G.3    Schedin-Weiss, S.4    Gettins, P.G.5
  • 4
    • 56649100319 scopus 로고    scopus 로고
    • The structure of glycosaminoglycans and their interactions with proteins
    • Gandhi, N. S.; Mancera, R. L. The structure of glycosaminoglycans and their interactions with proteins Chem. Biol. Drug Des. 2008, 72, 455-482
    • (2008) Chem. Biol. Drug Des. , vol.72 , pp. 455-482
    • Gandhi, N.S.1    Mancera, R.L.2
  • 5
    • 1242269948 scopus 로고    scopus 로고
    • New antithrombin-based anticoagulants
    • Desai, U. R. New antithrombin-based anticoagulants Med. Res. Rev. 2004, 24, 151-181
    • (2004) Med. Res. Rev. , vol.24 , pp. 151-181
    • Desai, U.R.1
  • 6
    • 33746614761 scopus 로고    scopus 로고
    • Interactions between heparan sulfate and proteins: The concept of specificity
    • Kreuger, J.; Spillmann, D.; Lindahl, U. Interactions between heparan sulfate and proteins: the concept of specificity J. Cell Biol. 2006, 174, 323-327
    • (2006) J. Cell Biol. , vol.174 , pp. 323-327
    • Kreuger, J.1    Spillmann, D.2    Lindahl, U.3
  • 7
    • 34447512941 scopus 로고    scopus 로고
    • Heparan sulfate-protein interactions - A concept for drug design
    • Lindahl, U. Heparan sulfate-protein interactions-A concept for drug design Thromb. Haemostasis 2007, 98, 109-115
    • (2007) Thromb. Haemostasis , vol.98 , pp. 109-115
    • Lindahl, U.1
  • 8
    • 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
  • 11
    • 27844483424 scopus 로고    scopus 로고
    • Heparan sulfate mimicry: A synthetic glycoconjugate that recognizes the heparin binding domain of interferon-gamma inhibits the cytokine activity
    • Sarrazin, S.; Bonnaffé, D.; Lubineau, A.; Lortat-Jacob, H. Heparan sulfate mimicry: A synthetic glycoconjugate that recognizes the heparin binding domain of interferon-gamma inhibits the cytokine activity J. Biol. Chem. 2005, 280, 37558-37564
    • (2005) J. Biol. Chem. , vol.280 , pp. 37558-37564
    • Sarrazin, S.1    Bonnaffé, D.2    Lubineau, A.3    Lortat-Jacob, H.4
  • 12
    • 4644266139 scopus 로고    scopus 로고
    • Synthesis of tailor-made glycoconjugate mimetics of heparan sulfate that bind IFN-γ in the nanomolar range
    • Lubineau, A.; Lortat-Jacob, H.; Gavard, O.; Sarrazin, S.; Bonnaffé, D. Synthesis of tailor-made glycoconjugate mimetics of heparan sulfate that bind IFN-γ in the nanomolar range Chem.-Eur. J. 2004, 10, 4265-4282
    • (2004) Chem. - Eur. J. , vol.10 , pp. 4265-4282
    • Lubineau, A.1    Lortat-Jacob, H.2    Gavard, O.3    Sarrazin, S.4    Bonnaffé, D.5
  • 15
    • 15744392518 scopus 로고    scopus 로고
    • Use of sulfated linked cyclitols as heparan sulfate mimetics to probe the heparin/heparan sulfate binding specificity of proteins
    • Freeman, C.; Liu, L.; Banwell, M. G.; Brown, K. J.; Bezos, A.; Ferro, V.; Parish, C. R. Use of sulfated linked cyclitols as heparan sulfate mimetics to probe the heparin/heparan sulfate binding specificity of proteins J. Biol. Chem. 2005, 280, 8842-8849
    • (2005) J. Biol. Chem. , vol.280 , pp. 8842-8849
    • Freeman, C.1    Liu, L.2    Banwell, M.G.3    Brown, K.J.4    Bezos, A.5    Ferro, V.6    Parish, C.R.7
  • 16
    • 0842306880 scopus 로고    scopus 로고
    • Dendritic polyglycerol sulfates as new heparin analogues and potent inhibitors of the complement system
    • Türk, H.; Haag, R.; Alban, S. Dendritic polyglycerol sulfates as new heparin analogues and potent inhibitors of the complement system Bioconjugate Chem. 2004, 15, 162-167
    • (2004) Bioconjugate Chem. , vol.15 , pp. 162-167
    • Türk, H.1    Haag, R.2    Alban, S.3
  • 17
    • 0037179617 scopus 로고    scopus 로고
    • Interaction of designed sulfated flavanoids with antithrombin: Lessons on the design of organic activators
    • Gunnarsson, G. T.; Desai, U. R. Interaction of designed 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
  • 18
    • 0037075832 scopus 로고    scopus 로고
    • Designing small, nonsugar activators of antithrombin using hydropathic interaction analyses
    • Gunnarsson, G. T.; Desai, U. R. Designing small, nonsugar activators of antithrombin using hydropathic interaction analyses J. Med. Chem. 2002, 45, 1233-1243
    • (2002) J. Med. Chem. , vol.45 , pp. 1233-1243
    • Gunnarsson, G.T.1    Desai, U.R.2
  • 21
    • 13444282264 scopus 로고    scopus 로고
    • Synthesis of per-sulfated flavonoids using 2,2,2-trichloro ethyl protecting group and their factor Xa inhibition potential
    • Gunnarsson, G. T.; Riaz, M.; Adams, J.; Desai, U. R. Synthesis of per-sulfated flavonoids using 2,2,2-trichloro ethyl protecting group and their factor Xa inhibition potential Bioorg. Med. Chem. 2005, 13, 1783-1789
    • (2005) Bioorg. Med. Chem. , vol.13 , pp. 1783-1789
    • Gunnarsson, G.T.1    Riaz, M.2    Adams, J.3    Desai, U.R.4
  • 23
    • 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
  • 25
    • 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
  • 26
    • 84864953109 scopus 로고    scopus 로고
    • Designing allosteric regulators of thrombin. Monosulfated benzofuran dimers selectively interact with arg173 of exosite II to induce inhibition
    • Abdel Aziz, M. H.; Sidhu, P. S.; Liang, A.; Kim, J. Y.; Mosier, P. D.; Zhou, Q.; Farrell, D. H.; Desai, U. R. Designing allosteric regulators of thrombin. Monosulfated benzofuran dimers selectively interact with arg173 of exosite II to induce inhibition J. Med. Chem. 2012, 55, 6888-6897
    • (2012) J. Med. Chem. , vol.55 , pp. 6888-6897
    • Abdel Aziz, M.H.1    Sidhu, P.S.2    Liang, A.3    Kim, J.Y.4    Mosier, P.D.5    Zhou, Q.6    Farrell, D.H.7    Desai, U.R.8
  • 27
    • 80053109628 scopus 로고    scopus 로고
    • Identification of the site of binding of sulfated, low molecular weight lignins on thrombin
    • Abdel Aziz, M. H.; Mosier, P. D.; Desai, U. R. Identification of the site of binding of sulfated, low molecular weight lignins on thrombin Biochem. Biophys. Res. Commun. 2011, 413, 348-352
    • (2011) Biochem. Biophys. Res. Commun. , vol.413 , pp. 348-352
    • Abdel Aziz, M.H.1    Mosier, P.D.2    Desai, U.R.3
  • 28
    • 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
  • 29
    • 34548040716 scopus 로고    scopus 로고
    • Rapid and efficient microwave-assisted synthesis of highly sulfated organic scaffolds
    • 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
    • (2007) Tetrahedron Lett. , vol.48 , pp. 6754-6758
    • Raghuraman, A.1    Riaz, M.2    Hindle, M.3    Desai, U.R.4
  • 30
    • 84855781095 scopus 로고    scopus 로고
    • Sulfated, low molecular weight lignins inhibit a select group of heparin-binding serine proteases
    • Henry, B. L.; Thakkar, J. N.; Liang, A.; Desai, U. R. Sulfated, low molecular weight lignins inhibit a select group of heparin-binding serine proteases Biochem. Biophys. Res. Commun. 2012, 417, 382-386
    • (2012) Biochem. Biophys. Res. Commun. , vol.417 , pp. 382-386
    • Henry, B.L.1    Thakkar, J.N.2    Liang, A.3    Desai, U.R.4
  • 31
    • 67949112120 scopus 로고    scopus 로고
    • Update on the physiology and pathology of factor IX activation by factor XIa
    • Smith, S. B.; Gailani, D. Update on the physiology and pathology of factor IX activation by factor XIa Expert Rev. Hematol. 2008, 1, 87-98
    • (2008) Expert Rev. Hematol. , vol.1 , pp. 87-98
    • Smith, S.B.1    Gailani, D.2
  • 32
    • 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
  • 34
    • 0037099395 scopus 로고    scopus 로고
    • A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes
    • Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes Angew. Chem., Int. Ed. 2002, 41, 2596-2599
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 2596-2599
    • Rostovtsev, V.V.1    Green, L.G.2    Fokin, V.V.3    Sharpless, K.B.4
  • 37
    • 0026639860 scopus 로고
    • The interaction of glycosaminoglycans with heparin cofactor II: Structure and activity of a high-affinity dermatan sulfate hexasaccharide
    • Tollefsen, D. M. The interaction of glycosaminoglycans with heparin cofactor II: Structure and activity of a high-affinity dermatan sulfate hexasaccharide Adv. Exp. Med. Biol. 1992, 313, 167-176
    • (1992) Adv. Exp. Med. Biol. , vol.313 , pp. 167-176
    • Tollefsen, D.M.1
  • 38
    • 77956521262 scopus 로고    scopus 로고
    • Understanding dermatan sulfate-heparin cofactor II interaction through virtual library screening
    • Raghuraman, A.; Mosier, P. D.; Desai, U. R. Understanding dermatan sulfate-heparin cofactor II interaction through virtual library screening ACS Med. Chem. Lett. 2010, 1, 281-285
    • (2010) ACS Med. Chem. Lett. , vol.1 , pp. 281-285
    • Raghuraman, A.1    Mosier, P.D.2    Desai, U.R.3
  • 39
    • 67649962435 scopus 로고    scopus 로고
    • First steps in the direction of synthetic, allosteric, direct inhibitors of thrombin and factor Xa
    • Verghese, J.; Liang, A.; Sidhu, P. S.; Hindle, M.; Zhou, Q.; Desai, U. R. First steps in the direction of synthetic, allosteric, direct inhibitors of thrombin and factor Xa Bioorg. Med. Chem. Lett. 2009, 19, 4126-4129
    • (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 4126-4129
    • Verghese, J.1    Liang, A.2    Sidhu, P.S.3    Hindle, M.4    Zhou, Q.5    Desai, U.R.6
  • 40
    • 84873898236 scopus 로고    scopus 로고
    • Sulfated pentagalloylglucoside 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 pentagalloylglucoside 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
  • 42
    • 0017188327 scopus 로고
    • Serum-protein binding as a determinant of warfarin body clearance and anticoagulant effect
    • Yacobi, A.; Udall, J. A.; Levy, G. Serum-protein binding as a determinant of warfarin body clearance and anticoagulant effect Clin. Pharmacol. Ther. 1976, 19, 552-558
    • (1976) Clin. Pharmacol. Ther. , vol.19 , pp. 552-558
    • Yacobi, A.1    Udall, J.A.2    Levy, G.3
  • 43
    • 0025378934 scopus 로고
    • Structure and ligand binding properties of human serum albumin
    • Kragh-Hansen, U. Structure and ligand binding properties of human serum albumin Dan. Med. Bull. 1990, 37, 57-84
    • (1990) Dan. Med. Bull. , vol.37 , pp. 57-84
    • Kragh-Hansen, U.1
  • 44
    • 36148962373 scopus 로고    scopus 로고
    • A novel allosteric pathway of thrombin inhibition. Exosite II mediated potent inhibition of thrombin by chemo-enzymatic, sulfated dehydropolymers of 4-hydroxycinnamic acids
    • Henry, B. L.; Monien, B. H.; Bock, P. E.; Desai, U. R. A novel allosteric pathway of thrombin inhibition. Exosite II mediated potent inhibition of thrombin by chemo-enzymatic, sulfated dehydropolymers of 4-hydroxycinnamic acids J. Biol. Chem. 2007, 282, 31891-31899
    • (2007) J. Biol. Chem. , vol.282 , pp. 31891-31899
    • Henry, B.L.1    Monien, B.H.2    Bock, P.E.3    Desai, U.R.4
  • 45
    • 0030069068 scopus 로고    scopus 로고
    • Influence of heparin, protamine and Polybrene on the time integral of thrombin generation (endogenous thrombin potential)
    • Rotteveel, R. C.; Roozendaal, K. J.; Weijers, R. N.; Eijsman, L. Influence of heparin, protamine and Polybrene on the time integral of thrombin generation (endogenous thrombin potential) Haemostasis 1996, 26, 1-10
    • (1996) Haemostasis , vol.26 , pp. 1-10
    • Rotteveel, R.C.1    Roozendaal, K.J.2    Weijers, R.N.3    Eijsman, L.4
  • 47
    • 33745253758 scopus 로고    scopus 로고
    • Factor XIa as a possible new target of antithrombotic therapy
    • Goto, S. Factor XIa as a possible new target of antithrombotic therapy J. Thromb. Haemostasis 2006, 4, 1494-1495
    • (2006) J. Thromb. Haemostasis , vol.4 , pp. 1494-1495
    • Goto, S.1
  • 49
    • 80052467986 scopus 로고    scopus 로고
    • A small-molecule factor XIa inhibitor produces antithrombotic efficacy with minimal bleeding time prolongation in rabbits
    • Wong, P. C.; Crain, E. J.; Watson, C. A.; Schumacher, W. A. A small-molecule factor XIa inhibitor produces antithrombotic efficacy with minimal bleeding time prolongation in rabbits J. Thromb. Thrombolysis 2011, 32, 129-137
    • (2011) J. Thromb. Thrombolysis , vol.32 , pp. 129-137
    • Wong, P.C.1    Crain, E.J.2    Watson, C.A.3    Schumacher, W.A.4
  • 55
    • 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


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.