메뉴 건너뛰기




Volumn 59, Issue 13, 2016, Pages 6370-6386

Optimization of Cyclic Plasmin Inhibitors: From Benzamidines to Benzylamines

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; ANTIFIBRINOLYTIC AGENT; APROTININ; BENZAMIDINE DERIVATIVE; BENZYLAMINE DERIVATIVE; DIAMINE DERIVATIVE; N (4 CARBAMIMIDOYLBENZYL) 14 [(N CYCLOHEXYLSULFAMOYL)AMINO] 3,7,13 TRIOXO 2,8,12 TRIAZA 5(1,4) PIPERAZINA 1,9(1,4) DIBENZENACYCLOPENTADECAPHANE 11 CARBOXAMIDE; N (4 CARBAMIMIDOYLBENZYL) 16 [(N CYCLOHEXYLSULFAMOYL)AMINO] 3,9,15 TRIOXO 2,10,14 TRIAZA 6(1,4) PIPERAZINA 1,11(1,4) DIBENZENACYCLOHEPTADECAPHANE 13 CARBOXAMIDE; N (4 CARBAMIMIDOYLBENZYL) 3,7,13 TRIOXO 14 (3 PHENYLPROPANAMIDO) 2,8,12 TRIAZA 5(1,4) PIPERAZINA 1,9(1,4) DIBENZENACYCLOPENTADECAPHANE 11 CARBOXAMIDE; N (4 CARBAMIMIDOYLBENZYL) 3,9,15 TRIOXO 16 (3 PHENYLPROPANAMIDO) 2,10,14 TRIAZA 6(1,4) PIPERAZINA 1,11(1,4) DIBENZENACYCLOHEPTADECAPHANE 13 CARBOXAMIDE; N [4 (AMINOMETHYL)BENZYL] 16 [(N CYCLOHEXYLSULFAMOYL)AMINO] 3,9,15 TRIOXO 2,10,14 TRIAZA 6(1,4) PIPERAZINA 1,11(1,4) DIBENZENACYCLOHEPTADECAPHANE 13 CARBOXAMIDE; N [4 (AMINOMETHYL)BENZYL] 3,9,15 TRIOXO (16 PHENYL SULFONAMIDO) 2,10,14 TRIAZA 6(1,4) PIPERAZINA 1,11(1,4) DIBENZENACYCLOHEPTADECAPHANE 13 CARBOXAMIDE; PLASMIN; PLASMIN INHIBITOR; TRYPSIN; UNCLASSIFIED DRUG;

EID: 84978765403     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/acs.jmedchem.6b00606     Document Type: Article
Times cited : (17)

References (50)
  • 1
    • 84927019728 scopus 로고    scopus 로고
    • The fibrinolytic system-more than fibrinolysis?
    • Draxler, D. F.; Medcalf, R. L. The fibrinolytic system-more than fibrinolysis? Transfus. Med. Rev. 2015, 29, 102-109 10.1016/j.tmrv.2014.09.006
    • (2015) Transfus. Med. Rev. , vol.29 , pp. 102-109
    • Draxler, D.F.1    Medcalf, R.L.2
  • 2
    • 16844384895 scopus 로고    scopus 로고
    • Structure and function of the plasminogen/plasmin system
    • Castellino, F. J.; Ploplis, V. A. Structure and function of the plasminogen/plasmin system Thromb. Haemostasis 2005, 93, 647-654 10.1160/TH04-12-0842
    • (2005) Thromb. Haemostasis , vol.93 , pp. 647-654
    • Castellino, F.J.1    Ploplis, V.A.2
  • 3
    • 84869069142 scopus 로고    scopus 로고
    • Cell surface remodeling by plasmin: A new function for an old enzyme
    • Deryugina, E. I.; Quigley, J. P. Cell surface remodeling by plasmin: a new function for an old enzyme J. Biomed. Biotechnol. 2012, 2012, 564259 10.1155/2012/564259
    • (2012) J. Biomed. Biotechnol. , vol.2012 , pp. 564259
    • Deryugina, E.I.1    Quigley, J.P.2
  • 4
    • 84856579667 scopus 로고    scopus 로고
    • Natural and engineered plasmin inhibitors: Applications and design strategies
    • Swedberg, J. E.; Harris, J. M. Natural and engineered plasmin inhibitors: applications and design strategies ChemBioChem 2012, 13, 336-348 10.1002/cbic.201100673
    • (2012) ChemBioChem , vol.13 , pp. 336-348
    • Swedberg, J.E.1    Harris, J.M.2
  • 7
    • 80155192757 scopus 로고    scopus 로고
    • Plasminogen receptor S100A10 is essential for the migration of tumor-promoting macrophages into tumor sites
    • Phipps, K. D.; Surette, A. P.; O'Connell, P. A.; Waisman, D. M. Plasminogen receptor S100A10 is essential for the migration of tumor-promoting macrophages into tumor sites Cancer Res. 2011, 71, 6676-6683 10.1158/0008-5472.CAN-11-1748
    • (2011) Cancer Res. , vol.71 , pp. 6676-6683
    • Phipps, K.D.1    Surette, A.P.2    O'Connell, P.A.3    Waisman, D.M.4
  • 9
    • 67649970765 scopus 로고    scopus 로고
    • Increased stratum corneum serine protease activity in acute eczematous atopic skin
    • Voegeli, R.; Rawlings, A. V.; Breternitz, M.; Doppler, S.; Schreier, T.; Fluhr, J. W. Increased stratum corneum serine protease activity in acute eczematous atopic skin Br. J. Dermatol. 2009, 161, 70-77 10.1111/j.1365-2133.2009.09142.x
    • (2009) Br. J. Dermatol. , vol.161 , pp. 70-77
    • Voegeli, R.1    Rawlings, A.V.2    Breternitz, M.3    Doppler, S.4    Schreier, T.5    Fluhr, J.W.6
  • 10
    • 84891402880 scopus 로고    scopus 로고
    • Stratum corneum proteases and dry skin conditions
    • Rawlings, A. V.; Voegeli, R. Stratum corneum proteases and dry skin conditions Cell Tissue Res. 2013, 351, 217-235 10.1007/s00441-012-1501-x
    • (2013) Cell Tissue Res. , vol.351 , pp. 217-235
    • Rawlings, A.V.1    Voegeli, R.2
  • 11
    • 43149119483 scopus 로고    scopus 로고
    • Pharmacologic methods to reduce perioperative bleeding
    • Levy, J. H. Pharmacologic methods to reduce perioperative bleeding Transfusion 2008, 48, 31s-38s 10.1111/j.1537-2995.2007.01574.x
    • (2008) Transfusion , vol.48 , pp. 31s-38s
    • Levy, J.H.1
  • 13
    • 34249821653 scopus 로고    scopus 로고
    • Prevention and treatment of major blood loss
    • Mannucci, P. M.; Levi, M. Prevention and treatment of major blood loss N. Engl. J. Med. 2007, 356, 2301-2311 10.1056/NEJMra067742
    • (2007) N. Engl. J. Med. , vol.356 , pp. 2301-2311
    • Mannucci, P.M.1    Levi, M.2
  • 14
    • 39549100109 scopus 로고    scopus 로고
    • Aprotinin during coronary-artery bypass grafting and risk of death
    • Schneeweiss, S.; Seeger, J. D.; Landon, J.; Walker, A. M. Aprotinin during coronary-artery bypass grafting and risk of death N. Engl. J. Med. 2008, 358, 771-783 10.1056/NEJMoa0707571
    • (2008) N. Engl. J. Med. , vol.358 , pp. 771-783
    • Schneeweiss, S.1    Seeger, J.D.2    Landon, J.3    Walker, A.M.4
  • 15
    • 76249100902 scopus 로고    scopus 로고
    • High-dose tranexamic Acid is associated with nonischemic clinical seizures in cardiac surgical patients
    • Murkin, J. M.; Falter, F.; Granton, J.; Young, B.; Burt, C.; Chu, M. High-dose tranexamic Acid is associated with nonischemic clinical seizures in cardiac surgical patients Anesth. Analg. 2010, 110, 350-353 10.1213/ANE.0b013e3181c92b23
    • (2010) Anesth. Analg. , vol.110 , pp. 350-353
    • Murkin, J.M.1    Falter, F.2    Granton, J.3    Young, B.4    Burt, C.5    Chu, M.6
  • 16
    • 77955117750 scopus 로고    scopus 로고
    • Mortality associated with administration of high-dose tranexamic acid and aprotinin in primary open-heart procedures: A retrospective analysis
    • Sander, M.; Spies, C. D.; Martiny, V.; Rosenthal, C.; Wernecke, K. D.; von Heymann, C. Mortality associated with administration of high-dose tranexamic acid and aprotinin in primary open-heart procedures: a retrospective analysis Crit. Care 2010, 14, R148 10.1186/cc9216
    • (2010) Crit. Care , vol.14 , pp. R148
    • Sander, M.1    Spies, C.D.2    Martiny, V.3    Rosenthal, C.4    Wernecke, K.D.5    Von Heymann, C.6
  • 18
    • 84907972088 scopus 로고    scopus 로고
    • Recent advances on plasmin inhibitors for the treatment of fibrinolysis-related disorders
    • Al-Horani, R. A.; Desai, U. R. Recent advances on plasmin inhibitors for the treatment of fibrinolysis-related disorders Med. Res. Rev. 2014, 34, 1168-1216 10.1002/med.21315
    • (2014) Med. Res. Rev. , vol.34 , pp. 1168-1216
    • Al-Horani, R.A.1    Desai, U.R.2
  • 19
    • 80053401993 scopus 로고    scopus 로고
    • Plasmin substrate binding site cooperativity guides the design of potent peptide aldehyde inhibitors
    • Swedberg, J. E.; Harris, J. M. Plasmin substrate binding site cooperativity guides the design of potent peptide aldehyde inhibitors Biochemistry 2011, 50, 8454-8462 10.1021/bi201203y
    • (2011) Biochemistry , vol.50 , pp. 8454-8462
    • Swedberg, J.E.1    Harris, J.M.2
  • 20
    • 0034531728 scopus 로고    scopus 로고
    • Development of potent and selective plasmin and plasma kallikrein inhibitors and studies on the structure-activity relationship
    • Okada, Y.; Tsuda, Y.; Tada, M.; Wanaka, K.; Okamoto, U.; Hijikata-Okunomiya, A.; Okamoto, S. Development of potent and selective plasmin and plasma kallikrein inhibitors and studies on the structure-activity relationship Chem. Pharm. Bull. 2000, 48, 1964-1972 10.1248/cpb.48.1964
    • (2000) Chem. Pharm. Bull. , vol.48 , pp. 1964-1972
    • Okada, Y.1    Tsuda, Y.2    Tada, M.3    Wanaka, K.4    Okamoto, U.5    Hijikata-Okunomiya, A.6    Okamoto, S.7
  • 22
    • 84956738192 scopus 로고    scopus 로고
    • Active site-directed plasmin inhibitors: Extension on the P2 residue
    • Hidaka, K.; Gohda, K.; Teno, N.; Wanaka, K.; Tsuda, Y. Active site-directed plasmin inhibitors: Extension on the P2 residue Bioorg. Med. Chem. 2016, 24, 545-553 10.1016/j.bmc.2015.12.009
    • (2016) Bioorg. Med. Chem. , vol.24 , pp. 545-553
    • Hidaka, K.1    Gohda, K.2    Teno, N.3    Wanaka, K.4    Tsuda, Y.5
  • 23
    • 0014404233 scopus 로고
    • Comparative studies on the inhibition of trypsin, plasmin, and thrombin by derivatives of benzylamine and benzamidine
    • Markwardt, F.; Landmann, H.; Walsmann, P. Comparative studies on the inhibition of trypsin, plasmin, and thrombin by derivatives of benzylamine and benzamidine Eur. J. Biochem. 1968, 6, 502-506 10.1111/j.1432-1033.1968.tb00473.x
    • (1968) Eur. J. Biochem. , vol.6 , pp. 502-506
    • Markwardt, F.1    Landmann, H.2    Walsmann, P.3
  • 24
    • 84922742841 scopus 로고    scopus 로고
    • Comparative study on the inhibition of plasmin and delta-plasmin via benzamidine derivatives
    • Alves, N. J.; Kline, J. A. Comparative study on the inhibition of plasmin and delta-plasmin via benzamidine derivatives Biochem. Biophys. Res. Commun. 2015, 457, 358-362 10.1016/j.bbrc.2014.12.117
    • (2015) Biochem. Biophys. Res. Commun. , vol.457 , pp. 358-362
    • Alves, N.J.1    Kline, J.A.2
  • 25
    • 58749083266 scopus 로고    scopus 로고
    • CU-2010 - A novel small molecule protease inhibitor with antifibrinolytic and anticoagulant properties
    • Dietrich, W.; Nicklisch, S.; Koster, A.; Spannagl, M.; Giersiefen, H.; van de Locht, A. CU-2010-a novel small molecule protease inhibitor with antifibrinolytic and anticoagulant properties Anesthesiology 2009, 110, 123-130 10.1097/ALN.0b013e318191408c
    • (2009) Anesthesiology , vol.110 , pp. 123-130
    • Dietrich, W.1    Nicklisch, S.2    Koster, A.3    Spannagl, M.4    Giersiefen, H.5    Van De Locht, A.6
  • 26
    • 84856829711 scopus 로고    scopus 로고
    • A new strategy for the development of highly potent and selective plasmin inhibitors
    • Saupe, S. M.; Steinmetzer, T. A new strategy for the development of highly potent and selective plasmin inhibitors J. Med. Chem. 2012, 55, 1171-1180 10.1021/jm2011996
    • (2012) J. Med. Chem. , vol.55 , pp. 1171-1180
    • Saupe, S.M.1    Steinmetzer, T.2
  • 27
    • 84873887907 scopus 로고    scopus 로고
    • Development of new cyclic plasmin inhibitors with excellent potency and selectivity
    • Saupe, S. M.; Leubner, S.; Betz, M.; Klebe, G.; Steinmetzer, T. Development of new cyclic plasmin inhibitors with excellent potency and selectivity J. Med. Chem. 2013, 56, 820-831 10.1021/jm3012917
    • (2013) J. Med. Chem. , vol.56 , pp. 820-831
    • Saupe, S.M.1    Leubner, S.2    Betz, M.3    Klebe, G.4    Steinmetzer, T.5
  • 28
    • 0001396685 scopus 로고
    • The slow-binding and slow, tight-binding inhibition of enzyme-catalysed reactions
    • Morrison, J. The slow-binding and slow, tight-binding inhibition of enzyme-catalysed reactions Trends Biochem. Sci. 1982, 7, 102-105 10.1016/0968-0004(82)90157-8
    • (1982) Trends Biochem. Sci. , vol.7 , pp. 102-105
    • Morrison, J.1
  • 29
    • 0030895222 scopus 로고    scopus 로고
    • Design of highly potent noncovalent thrombin inhibitors that utilize a novel lipophilic binding pocket in the thrombin active site
    • Tucker, T. J.; Lumma, W. C.; Mulichak, A. M.; Chen, Z.; Naylor-Olsen, A. M.; Lewis, S. D.; Lucas, R.; Freidinger, R. M.; Kuo, L. C. Design of highly potent noncovalent thrombin inhibitors that utilize a novel lipophilic binding pocket in the thrombin active site J. Med. Chem. 1997, 40, 830-832 10.1021/jm960762y
    • (1997) J. Med. Chem. , vol.40 , pp. 830-832
    • Tucker, T.J.1    Lumma, W.C.2    Mulichak, A.M.3    Chen, Z.4    Naylor-Olsen, A.M.5    Lewis, S.D.6    Lucas, R.7    Freidinger, R.M.8    Kuo, L.C.9
  • 30
  • 37
    • 34548827704 scopus 로고    scopus 로고
    • Evaluation of aprotinin and tranexamic acid in different in vitro and in vivo models of fibrinolysis, coagulation and thrombus formation
    • Sperzel, M.; Huetter, J. Evaluation of aprotinin and tranexamic acid in different in vitro and in vivo models of fibrinolysis, coagulation and thrombus formation J. Thromb. Haemostasis 2007, 5, 2113-2118 10.1111/j.1538-7836.2007.02717.x
    • (2007) J. Thromb. Haemostasis , vol.5 , pp. 2113-2118
    • Sperzel, M.1    Huetter, J.2
  • 38
    • 84857380650 scopus 로고    scopus 로고
    • Rational approaches to improving selectivity in drug design
    • Huggins, D. J.; Sherman, W.; Tidor, B. Rational approaches to improving selectivity in drug design J. Med. Chem. 2012, 55, 1424-1444 10.1021/jm2010332
    • (2012) J. Med. Chem. , vol.55 , pp. 1424-1444
    • Huggins, D.J.1    Sherman, W.2    Tidor, B.3
  • 40
    • 0019490781 scopus 로고
    • Concentration of plasminogen and antiplasmin in plasma and serum
    • Cederholm-Williams, S. A. Concentration of plasminogen and antiplasmin in plasma and serum J. Clin. Pathol. 1981, 34, 979-981 10.1136/jcp.34.9.979
    • (1981) J. Clin. Pathol. , vol.34 , pp. 979-981
    • Cederholm-Williams, S.A.1
  • 41
    • 0026510317 scopus 로고
    • High-dose aprotinin therapy: A review of the first five years' experience
    • Royston, D. High-dose aprotinin therapy: a review of the first five years' experience J. Cardiothorac. Vasc. Anesth. 1992, 6, 76-100 10.1016/1053-0770(91)90052-U
    • (1992) J. Cardiothorac. Vasc. Anesth. , vol.6 , pp. 76-100
    • Royston, D.1
  • 43
    • 0023158165 scopus 로고
    • The pharmacodynamics of synthetic thrombin inhibitors of the basic type substituted n-alpha arylsulfonylated phenylalanine amide
    • Kaiser, B.; Hauptmann, J.; Markwardt, F. The pharmacodynamics of synthetic thrombin inhibitors of the basic type substituted n-alpha arylsulfonylated phenylalanine amide Pharmazie 1987, 42, 119-121
    • (1987) Pharmazie , vol.42 , pp. 119-121
    • Kaiser, B.1    Hauptmann, J.2    Markwardt, F.3
  • 45
    • 33847797810 scopus 로고
    • An improved synthesis of sulfamoyl chlorides
    • Kloek, J. A.; Leschinsky, K. L. An improved synthesis of sulfamoyl chlorides J. Org. Chem. 1976, 41, 4028-4029 10.1021/jo00887a022
    • (1976) J. Org. Chem. , vol.41 , pp. 4028-4029
    • Kloek, J.A.1    Leschinsky, K.L.2
  • 46
    • 29744462377 scopus 로고    scopus 로고
    • Synthesis and in vitro enzyme hydrolysis of trioxadiaza- and tetraoxadiaza-crown ether-based complexing agents with disposable ester pendant arms
    • Iványi, T.; Lázár, I. Synthesis and in vitro enzyme hydrolysis of trioxadiaza- and tetraoxadiaza-crown ether-based complexing agents with disposable ester pendant arms Synthesis 2005, 2005, 3555-3564 10.1055/s-2005-918442
    • (2005) Synthesis , vol.2005 , pp. 3555-3564
    • Iványi, T.1    Lázár, I.2
  • 47
    • 84877763765 scopus 로고    scopus 로고
    • Identification of the first synthetic inhibitors of the type II transmembrane serine protease TMPRSS2 suitable for inhibition of influenza virus activation
    • Meyer, D.; Sielaff, F.; Hammami, M.; Böttcher-Friebertshäuser, E.; Garten, W.; Steinmetzer, T. Identification of the first synthetic inhibitors of the type II transmembrane serine protease TMPRSS2 suitable for inhibition of influenza virus activation Biochem. J. 2013, 452, 331-343 10.1042/BJ20130101
    • (2013) Biochem. J. , vol.452 , pp. 331-343
    • Meyer, D.1    Sielaff, F.2    Hammami, M.3    Böttcher-Friebertshäuser, E.4    Garten, W.5    Steinmetzer, T.6
  • 48
    • 0014308079 scopus 로고
    • On the purification of thrombin preparations
    • Walsmann, P. On the purification of thrombin preparations Pharmazie 1968, 23, 401-402
    • (1968) Pharmazie , vol.23 , pp. 401-402
    • Walsmann, P.1
  • 50
    • 84966707964 scopus 로고    scopus 로고
    • Changing the selectivity profile - From substrate analog inhibitors of thrombin and factor Xa to potent matriptase inhibitors
    • DOI
    • Maiwald, A.; Hammami, M.; Wagner, S.; Heine, A.; Klebe, G.; Steinmetzer, T. Changing the selectivity profile-from substrate analog inhibitors of thrombin and factor Xa to potent matriptase inhibitors. J. Enzyme Inhib. Med. Chem. 2016, DOI: 10.3109/14756366.2016.1172574.
    • (2016) J. Enzyme Inhib. Med. Chem.
    • Maiwald, A.1    Hammami, M.2    Wagner, S.3    Heine, A.4    Klebe, G.5    Steinmetzer, T.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.