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Phosphinic Peptides as Potent Inhibitors of Zinc-Metalloproteases

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Phosphorus Chemistry I

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 360))

Abstract

The development of transition-state analogs is a major objective in enzymology, not only for developing potent inhibitors of enzymes but also for dissecting enzyme catalytic mechanisms. Phosphinic peptides, which share closed structural similarities with the transition-state of peptide substrate upon hydrolysis, have thus been considered for identifying potent inhibitors of proteases. Focusing on the zinc-proteases family, this review presents the most important synthetic efforts performed to obtain the desired compounds. Crystal structures of the phosphinic peptides in interaction with their zinc-protease targets are reported to illustrate the structural features which may explain the potency of these compounds and how they contribute to uncover key enzyme catalytic residues. Based on a remarkable metabolic stability, phosphinic peptides can be used to probe the in vivo function of zinc-proteases. Progress on chemistry and better understanding on the functional roles of zinc-proteases should allow transferring these compounds from shelf to clinic.

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References

  1. Turk B (2006) Nat Rev Drug Discov 5:785–799

    CAS  Google Scholar 

  2. Puente XS, Sanchez LM, Overall CM, Lopez-Otin C (2003) Nat Rev Genet 4:544–558

    CAS  Google Scholar 

  3. Lopez-Otin C, Matrisian LM (2007) Nat Rev Cancer 7:800–808

    CAS  Google Scholar 

  4. Zaman MA, Oparil S, Calhoun DA (2002) Nat Rev Drug Discov 1:621–636

    CAS  Google Scholar 

  5. Peyman A, Budt KH, Spanig J, Ruppert D (1993) Angew Chem Int Ed Engl 32:1720–1722

    Google Scholar 

  6. Sheng XC, Casarez A, Cai R, Clarke MO, Chen X, Cho A, Delaney Iv WE, Doerffler E, Ji M, Mertzman M, Pakdaman R, Pyun HJ, Rowe T, Wu Q, Xu J, Kim CU (2012) Bioorg Med Chem Lett 22:1394–1396

    CAS  Google Scholar 

  7. Ondetti MA, Condon ME, Reid J, Sabo EF, Cheung HS, Cushman DW (1979) Biochemistry 18:1427–1430

    CAS  Google Scholar 

  8. Holmes MA, Matthews BW (1981) Biochemistry 20:6912–6920

    CAS  Google Scholar 

  9. Petrillo EW Jr, Ondetti MA (1982) Med Res Rev 2:1–41

    CAS  Google Scholar 

  10. Devel L, Czarny B, Beau F, Georgiadis D, Stura E, Dive Vincent V (2010) Biochimie 92:1501–1508

    CAS  Google Scholar 

  11. Christianson DW, Lipscomb WN (1988) J Am Chem Soc 110:5560–5565

    CAS  Google Scholar 

  12. Holden HM, Tronrud DE, Monzingo AF, Weaver LH, Matthews BW (1987) Biochemistry 26:8542–8553

    CAS  Google Scholar 

  13. Hanson JE, Kaplan AP, Bartlett PA (1989) Biochemistry 28:6294–6305

    CAS  Google Scholar 

  14. Mookhtiar KA, Marlowe CK, Bartlett PA, Van Wart HE (1987) Biochemistry 26:1962–1965

    CAS  Google Scholar 

  15. Dive V, Yiotakis A, Nicolaou A, Toma F (1990) Eur J Biochem 191:685–693

    CAS  Google Scholar 

  16. Yiotakis A, Lecoq A, Nicolaou A, Labadie J, Dive V (1994) Biochem J 303:323–327

    CAS  Google Scholar 

  17. Merz KM Jr, Kollman PA (1989) J Am Chem Soc 111:5649–5658

    CAS  Google Scholar 

  18. Morgan BP, Scholtz JM, Ballinger MD, Zipkin ID, Bartlett PA (1991) J Am Chem Soc 113:297–307

    CAS  Google Scholar 

  19. Yiotakis A, Georgiadis D, Matziari M, Makaritis A, Dive V (2004) Curr Org Chem 8:1135–1158

    CAS  Google Scholar 

  20. Mucha A (2012) Molecules 17:13530–13568

    CAS  Google Scholar 

  21. Thottathil JK, Ryono DE, Przybyla CA, Moniot JL, Neubeck R (1984) Tetrahedron Lett 25:4741–4744

    CAS  Google Scholar 

  22. McKittrick BA, Stamford AW, Weng X, Ma K, Chackalamannil S, Czarniecki M, Cleven RM, Fawzi AB (1996) Bioorg Med Chem Lett 6:1629–1634

    Google Scholar 

  23. Miller DJ, Hammond SM, Anderluzzi D, Bugg TDH (1998) J Chem Soc. Perkin Trans 1:131–142

    Google Scholar 

  24. Baylis EK, Campbell CD, Dingwall JG (1984) J Chem Soc. Perkin Trans 1:2845–2853

    Google Scholar 

  25. Cowart M, Kowaluk EA, Kohlhaas KL, Alexander KM, Kerwin JF Jr (1996) Bioorg Med Chem Lett 6:999–1002

    CAS  Google Scholar 

  26. Lecoq A, Yiotakis A, Dive V (1994) Synth Commun 24:2877–2882

    CAS  Google Scholar 

  27. Khomutov AR, Osipova TI, Khurs EN, Alferov KV, Khomutov RM (1996) Russ Chem Bull 45:1961–1964

    Google Scholar 

  28. Belyankin AV, Khomutov AR, Zhukov YN, Kartasheva ON, Khomutov RM (1997) Russ Chem Bull 46:133–136

    CAS  Google Scholar 

  29. Zhukov YN, Khomutov AR, Osipova TI, Khomutov RM (1999) Russ Chem Bull 48:1348–1351

    CAS  Google Scholar 

  30. Alferov KV, Zhukov YN, Khurs EN, Osipova TI, Khomutov RM (2001) Russ Chem Bull 50:316–318

    CAS  Google Scholar 

  31. Liboska R, Pícha J, Hančlová I, Buděšínský M, Šanda M, Jiráček J (2008) Tetrahedron Lett 49:5629–5631

    CAS  Google Scholar 

  32. Jiao XJ, Verbruggen C, Borloo M, Bollaert W, De Groot A, Dommisse R, Haemers A (1994) Synthesis 23–24

    Google Scholar 

  33. Li S, Whitehead JK, Hammer RP (2007) J Org Chem 72:3116–3118

    CAS  Google Scholar 

  34. Olszewski TK, Boduszek B (2011) Synthesis 437–442

    Google Scholar 

  35. Borloo M, Jiao XY, Wojtowicz H, Rajan P, Verbruggen C, Augustyns K, Haemers A (1995) Synthesis 1074–1076

    Google Scholar 

  36. Boyd EA, Chan WC, Loh VM Jr (1996) Tetrahedron Lett 37:1647–1650

    CAS  Google Scholar 

  37. Hatam M, Martens J (1995) Synth Commun 25:2553–2559

    CAS  Google Scholar 

  38. Mores A, Matziari M, Beau F, Cuniasse P, Yiotakis A, Dive V (2008) J Med Chem 51:2216–2226

    CAS  Google Scholar 

  39. Yamagishi T, Mori JI, Haruki T, Yokomatsu T (2011) Tetrahedron: Asymmetry 22:1358–1363

    CAS  Google Scholar 

  40. Haruki T, Yamagishi T, Yokomatsu T (2007) Tetrahedron: Asymmetry 18:2886–2893

    CAS  Google Scholar 

  41. McCleery PP, Tuck B (1989) J Chem Soc. Perkin Trans 1:1319–1329

    Google Scholar 

  42. Yao Q, Yuan C (2013) J Org Chem 78:6962–6974

    CAS  Google Scholar 

  43. Cristau HJ, Coulombeau A, Genevois-Borella A, Pirat JL (2001) Tetrahedron Lett 42:4491–4494

    CAS  Google Scholar 

  44. Cristau HJ, Coulombeau A, Genevois-Borella A, Sanchez F, Pirat JL (2002) J Organomet Chem 643–644:381–391

    Google Scholar 

  45. Buchardt J, Meldal M (2000) J Chem Soc Perkin Trans 1:3306–3310

    Google Scholar 

  46. Dorff PH, Chiu G, Goldstein SW, Morgan BP (1998) Tetrahedron Lett 39:3375–3378

    CAS  Google Scholar 

  47. Manzenrieder F, Kessler H (2009) Adv Exp Med Biol 611:11–12

    CAS  Google Scholar 

  48. Vassiliou S, Tzouma E (2013) J Org Chem 78:10069–10076

    CAS  Google Scholar 

  49. Schoen WR, Parsons WH (1988) Tetrahedron Lett 29:5201–5204

    CAS  Google Scholar 

  50. Gurulingappa H, Buckhaults P, Kumar SK, Kinzler KW, Vogelstein B, Khan SR (2003) Tetrahedron Lett 44:1871–1873

    CAS  Google Scholar 

  51. Gurulingappa H, Buckhalts P, Kinzler KW, Vogelstein B, Khan SR (2004) Bioorg Med Chem Lett 14:3531–3533

    CAS  Google Scholar 

  52. Matziari M, Nasopoulou M, Yiotakis A (2006) Org Lett 8:2317–2319

    CAS  Google Scholar 

  53. Chen S, Coward JK (1996) Tetrahedron Lett 37:4335–4338

    CAS  Google Scholar 

  54. Matziari M, Yiotakis A (2005) Org Lett 7:4049–4052

    CAS  Google Scholar 

  55. Rozhko LF, Ragulin VV (2005) Amino Acids 29:139–143

    CAS  Google Scholar 

  56. Dmitriev ME, Ragulin VV (2010) Tetrahedron Lett 51:2613–2616

    CAS  Google Scholar 

  57. Dmitriev ME, Ragulin VV (2012) Tetrahedron Lett 53:1634–1636

    CAS  Google Scholar 

  58. Ross FC, Botting NP, Leeson PD (1996) Bioorg Med Chem Lett 6:2643–2646

    CAS  Google Scholar 

  59. Bertenshaw SR, Rogers RS, Stern MK, Norman BH, Moore WM, Jerome GM, Branson LM, McDonald JF, McMahon EG, Palomo MA (1993) J Med Chem 36:173–176

    CAS  Google Scholar 

  60. Štrancar K, Boniface A, Blanot D, Gobec S (2007) Arch Pharm (Weinheim) 340:127–134

    Google Scholar 

  61. Chackalamannil S, Chung S, Stamford AW, McKittrick BA, Wang Y, Tsai H, Cleven R, Fawzi A, Czarniecki M (1996) Bioorg Med Chem Lett 6:1257–1260

    CAS  Google Scholar 

  62. Reiter LA, Rizzi JP, Pandit J, Lasut MJ, McGahee SM, Parikh VD, Blake JF, Danley DE, Laird ER, Lopez-Anaya A, Lopresti-Morrow LL, Mansour MN, Martinelli GJ, Mitchell PG, Owens BS, Pauly TA, Reeves LM, Schulte GK, Yocum SA (1999) Bioorg Med Chem Lett 9:127–132

    CAS  Google Scholar 

  63. Goulet JL, Kinneary JF, Durette PL, Stein RL, Harrison RK, Izquierdo-Martin M, Kuo DW, Lin TY, Hagmann WK (1994) Bioorg Med Chem Lett 4:1221–1224

    CAS  Google Scholar 

  64. Georgiadis D, Dive V, Yiotakis A (2001) J Org Chem 66:6604–6610

    CAS  Google Scholar 

  65. Reiter LA, Jones BP (1997) J Org Chem 62:2808–2812

    CAS  Google Scholar 

  66. Krapcho J, Turk C, Cushman DW, Powell JR, DeForrest JM, Spitzmiller ER, Karanewsky DS, Duggan M, Rovnyak G, Schwartz J, Natarajan S, Godfrey JD, Ryono DE, Neubeck R, Atwal KS, Petrillo EW Jr (1988) J Med Chem 31:1148–1160

    CAS  Google Scholar 

  67. Yiotakis A, Lecoq A, Vassiliou S, Raynal I, Cuniasse P, Dive V (1994) J Med Chem 37:2713–2720

    CAS  Google Scholar 

  68. Kende AS, Dong HQ, Liu X, Ebetino FH (2002) Tetrahedron Lett 43:4973–4976

    CAS  Google Scholar 

  69. Campagne JM, Coste J, Guillou L, Heitz A, Jouin P (1993) Tetrahedron Lett 34:4181–4184

    CAS  Google Scholar 

  70. Chen H, Noble F, Coric P, Fournie-Zaluski MC, Roques BP (1998) Proc Natl Acad Sci U S A 95:12028–12033

    CAS  Google Scholar 

  71. Reiter LA, Mitchell PG, Martinelli GJ, Lopresti-Morrow LL, Yocum SA, Eskra JD (2003) Bioorg Med Chem Lett 13:2331–2336

    CAS  Google Scholar 

  72. Manzenrieder F, Frank AO, Huber T, Dorner-Ciossek C, Kessler H (2007) Bioorg Med Chem 15:4136–4143

    CAS  Google Scholar 

  73. Chen H, Noble F, Mothé A, Meudal H, Coric P, Danascimento S, Roques BP, George P, Fournié-Zaluski MC (2000) J Med Chem 43:1398–1408

    CAS  Google Scholar 

  74. Makaritis A, Georgiadis D, Dive V, Yiotakis A (2003) Chem Eur J 9:2079–2094

    CAS  Google Scholar 

  75. Matziari M, Bauer K, Dive V, Yiotakis A (2008) J Org Chem 73:8591–8593

    CAS  Google Scholar 

  76. Lloyd J, Schmidt JB, Hunt JT, Barrish JC, Little DK, Tymiak AA (1996) Bioorg Med Chem Lett 6:1323–1326

    CAS  Google Scholar 

  77. Yiotakis A, Vassiliou S, Jiráček J, Dive V (1996) J Org Chem 61:6601–6605

    CAS  Google Scholar 

  78. Jiracek J, Yiotakis A, Vincent B, Lecoq A, Nicolaou A, Checler F, Dive V (1995) J Biol Chem 270:21701–21706

    CAS  Google Scholar 

  79. Jirácek J, Yiotakis A, Vincent B, Checler F, Dive V (1996) J Biol Chem 271:19606–19611

    Google Scholar 

  80. Dive V, Cotton J, Yiotakis A, Michaud A, Vassiliou S, Jiracek J, Vazeux G, Chauvet MT, Cuniasse P, Corvol P (1999) Proc Natl Acad Sci U S A 96:4330–4335

    CAS  Google Scholar 

  81. Buchardt J, Ferreras M, Krog-Jensen C, Delaissé JM, Foged NT, Meldal M (1999) Chem Eur J 5:2877–2884

    CAS  Google Scholar 

  82. Buchardt J, Schiødt CB, Krog-Jensen C, Delaissé JM, Foged NT, Meldal M (2000) J Comb Chem 2:624–638

    CAS  Google Scholar 

  83. Christensen C, Groth T, Schiødt CB, Foged NT, Meldal M (2003) QSAR Comb Sci 22:737–744

    CAS  Google Scholar 

  84. Devel L, Rogakos V, David A, Makaritis A, Beau F, Cuniasse P, Yiotakis A, Dive V (2006) J Biol Chem 281:11152–11160

    CAS  Google Scholar 

  85. Fields GB, Lauer-Fields J, Brew K, Lauer-Fields J, Hammer RP, Li S, Whitehead JK (2007) J Am Chem Soc 129:10408–10417

    Google Scholar 

  86. Bhowmick M, Sappidi RR, Fields GB, Lepore SD (2011) Biopolymers 96:1–3

    CAS  Google Scholar 

  87. Bhowmick M, Fields GB (2012) Int J Pept Res Ther 18:335–339

    CAS  Google Scholar 

  88. Georgiadis D, Matziari M, Yiotakis A (2001) Tetrahedron 57:3471–3478

    CAS  Google Scholar 

  89. Nasopoulou M, Matziari M, Dive V, Yiotakis A (2006) J Org Chem 71:9525–9527

    CAS  Google Scholar 

  90. Vitharana D, France JE, Scarpetti D, Bonneville GW, Majer P, Tsukamoto T (2002) Tetrahedron: Asymmetry 13:1609–1614

    CAS  Google Scholar 

  91. Chen H, Noble F, Roques BP, Fournié-Zaluski MC (2001) J Med Chem 44:3523–3530

    CAS  Google Scholar 

  92. Jullien N, Makritis A, Georgiadis D, Beau F, Yiotakis A, Dive V (2010) J Med Chem 53:208–220

    CAS  Google Scholar 

  93. Matziari M, Dellis D, Dive V, Yiotakis A, Samios J (2010) J Phys Chem B 114:421–428

    CAS  Google Scholar 

  94. Yiotakis A, Makaritis A, Georgiadis D, Matziari M, Dive V (2002) Peptides 2002:330–331

    Google Scholar 

  95. Parsons WH, Patchett AA, Bull HG, Schoen WR, Taub D, Davidson J, Combs PL, Springer JP, Gadebusch H, Weissberger B, Valiant ME, Mellin TN, Busch RD (1988) J Med Chem 31:1772–1778

    CAS  Google Scholar 

  96. Liu X, Hu XE, Tian X, Mazur A, Ebetino FH (2002) J Organomet Chem 646:212–222

    CAS  Google Scholar 

  97. Cristau HJ, Pirat JL, Virieux D, Monbrun J, Ciptadi C, Bekro YA (2005) J Organomet Chem 690:2472–2481

    CAS  Google Scholar 

  98. Monbrun J, Dayde B, Cristau HJ, Volle JN, Virieux D, Pirat JL (2011) Tetrahedron 67:540–545

    CAS  Google Scholar 

  99. Yamagishi T, Ichikawa H, Haruki T, Yokomatsu T (2008) Org Lett 10:4347–4350

    CAS  Google Scholar 

  100. Georgiadis D, Matziari M, Vassiliou S, Dive V, Yiotakis A (1999) Tetrahedron 55:14635–14648

    CAS  Google Scholar 

  101. Matziari M, Georgiadis D, Dive V, Yiotakis A (2001) Org Lett 3:659–660

    CAS  Google Scholar 

  102. Matziari M, Beau F, Cuniasse P, Dive V, Yiotakis A (2004) J Med Chem 47:325–336

    CAS  Google Scholar 

  103. David A, Steer D, Bregant S, Devel L, Makaritis A, Beau F, Yiotakis A, Dive V (2007) Angew Chem Int Ed Engl 46:3275–3277

    CAS  Google Scholar 

  104. Bregant S, Huillet C, Devel L, Dabert-Gay AS, Beau F, Thai R, Czarny B, Yiotakis A, Dive V (2009) J Proteome Res 8:2484–2494

    CAS  Google Scholar 

  105. Aminoethylphosphinic acid derivatives (1988) EP282219,

    Google Scholar 

  106. Vassiliou S, Xeilari M, Yiotakis A, Grembecka J, Pawełczak M, Kafarski P, Mucha A (2007) Bioorg Med Chem 15:3187–3200

    CAS  Google Scholar 

  107. Rogakos V, Georgiadis D, Dive V, Yiotakis A (2009) Org Lett 11:4696–4699

    CAS  Google Scholar 

  108. Nasopoulou M, Georgiadis D, Matziari M, Dive V, Yiotakis A (2007) J Org Chem 72:7222–7228

    CAS  Google Scholar 

  109. Yamagishi T, Kinbara A, Okubo N, Sato S, Fukaya H (2012) Tetrahedron: Asymmetry 23:1633–1639

    CAS  Google Scholar 

  110. Georgiadis D, Beau F, Czarny B, Cotton J, Yiotakis A, Dive V (2003) Circ Res 93:148–154

    CAS  Google Scholar 

  111. Georgiadis D, Cuniasse P, Cotton J, Yiotakis A, Dive V (2004) Biochemistry 43:8048–8054

    CAS  Google Scholar 

  112. Demange L, Dugave C (2001) Tetrahedron Lett 42:6295–6297

    CAS  Google Scholar 

  113. Yamagishi T, Tashiro N, Yokomatsu T (2011) J Org Chem 76:5472–5476

    CAS  Google Scholar 

  114. Anthony CS, Masuyer G, Sturrock ED, Acharya KR (2012) Curr Med Chem 19:845–855

    CAS  Google Scholar 

  115. Dive V, Chang CF, Yiotakis A, Sturrock ED (2009) Curr Pharm Des 15:3606–3621

    CAS  Google Scholar 

  116. Redelinghuys P, Nchinda AT, Sturrock ED (2005) Ann N Y Acad Sci 1056:160–175

    CAS  Google Scholar 

  117. Anthony CS, Corradi HR, Schwager SLU, Redelinghuys P, Georgiadis D, Dive V, Acharya KR, Sturrock ED (2010) J Biol Chem 285:35685–35693

    CAS  Google Scholar 

  118. Corradi HR, Chitapi I, Sewell BT, Georgiadis D, Dive V, Sturrock ED, Acharya KR (2007) Biochemistry 46:5473–5478

    CAS  Google Scholar 

  119. Roques BP, Noble F, Dauge V, Fournie-Zaluski MC, Beaumont A (1993) Pharmacol Rev 45:87–146

    CAS  Google Scholar 

  120. Patey G, De La Baume S, Schwartz JC, Gros C, Roques B, Fournie-Zaluski MC, Soroca-Lucas E (1981) Science 212:1153–1155

    CAS  Google Scholar 

  121. Roques BP, Lucas-Soroca E, Chaillet P, Costentin J, Fournie-Zaluski MC (1983) Proc Natl Acad Sci U S A 80:3178–3182

    CAS  Google Scholar 

  122. Matthews BW (1988) Acc Chem Res 21:341–347

    Google Scholar 

  123. Tiraboschi G, Jullian N, Thery V, Antonczak S, Fournie-Zaluski MC, Roques BP (1999) Protein Eng 12:141–149

    CAS  Google Scholar 

  124. Selkti M, Tomas A, Gaucher JF, Prange T, Fournie-Zaluski MC, Chen H, Roques BP (2003) Acta Crystallogr D Biol Crystallogr 59:1200–1205

    Google Scholar 

  125. Samuelsson B, Dahlen SE, Lindgren JA, Rouzer CA, Serhan CN (1987) Science 237:1171–1176

    CAS  Google Scholar 

  126. Thunnissen MM, Nordlund P, Haeggstrom JZ (2001) Nat Struct Biol 8:131–135

    CAS  Google Scholar 

  127. Tholander F, Muroya A, Roques BP, Fournie-Zaluski MC, Thunnissen MM, Haeggstrom JZ (2008) Chem Biol 15:920–929

    CAS  Google Scholar 

  128. Tanioka T, Hattori A, Masuda S, Nomura Y, Nakayama H, Mizutani S, Tsujimoto M (2003) J Biol Chem 278:32275–32283

    CAS  Google Scholar 

  129. Zervoudi E, Saridakis E, Birtley JR, Seregin SS, Reeves E, Kokkala P, Aldhamen YA, Amalfitano A, Mavridis IM, James E, Georgiadis D, Stratikos E (2013) Proc Natl Acad Sci U S A 110:19890–19895

    CAS  Google Scholar 

  130. McGowan S, Oellig CA, Birru WA, Caradoc-Davies TT, Stack CM, Lowther J, Skinner-Adams T, Mucha A, Kafarski P, Grembecka J, Trenholme KR, Buckle AM, Gardiner DL, Dalton JP, Whisstock JC (2010) Proc Natl Acad Sci U S A 107:2449–2454

    CAS  Google Scholar 

  131. Wang YX, Zhao L, Nagashima M, Vincelette J, Sukovich D, Li W, Subramanyam B, Yuan S, Emayan K, Islam I, Hrvatin P, Bryant J, Light DR, Vergona R, Morser J, Buckman BO (2007) Thromb Haemost 97:45–53

    CAS  Google Scholar 

  132. Adler M, Bryant J, Buckman B, Islam I, Larsen B, Finster S, Kent L, May K, Mohan R, Yuan S, Whitlow M (2005) Biochemistry 44:9339–9347

    CAS  Google Scholar 

  133. Adler M, Buckman B, Bryant J, Chang Z, Chu K, Emayan K, Hrvatin P, Islam I, Morser J, Sukovich D, West C, Yuan S, Whitlow M (2008) Acta Crystallogr Sect D Biol Crystallogr 64:149–157

    CAS  Google Scholar 

  134. Zhou J, Neale JH, Pomper MG, Kozikowski AP (2005) Nat Rev Drug Discov 4:1015–1026

    CAS  Google Scholar 

  135. Bostwick DG, Pacelli A, Blute M, Roche P, Murphy GP (1998) Cancer 82:2256–2261

    CAS  Google Scholar 

  136. Barinka C, Hlouchova K, Rovenska M, Majer P, Dauter M, Hin N, Ko YS, Tsukamoto T, Slusher BS, Konvalinka J, Lubkowski J (2008) J Mol Biol 376:1438–1450

    CAS  Google Scholar 

  137. Gomis-Ruth FX, Trillo-Muyo S, Stocker W (2012) Biol Chem 393:1027–1041

    CAS  Google Scholar 

  138. Grams F, Dive V, Yiotakis A, Yiallouros I, Vassiliou S, Zwilling R, Bode W, Stocker W (1996) Nat Struct Biol 3:671–675

    CAS  Google Scholar 

  139. Yiallouros I, Vassiliou S, Yiotakis A, Zwilling R, Stocker W, Dive V (1998) Biochem J 331:375–379

    CAS  Google Scholar 

  140. Yiallouros I, Grosse Berkhoff E, Stocker W (2000) FEBS Lett 484:224–228

    CAS  Google Scholar 

  141. Kawasaki A, Nakano H, Hosokawa A, Nakatsu T, Kato H, Watanabe K (2010) J Biol Chem 285:34972–34980

    CAS  Google Scholar 

  142. McGowan S, Porter CJ, Lowther J, Stack CM, Golding SJ, Skinner-Adams TS, Trenholme KR, Teuscher F, Donnelly SM, Grembecka J, Mucha A, Kafarski P, Degori R, Buckle AM, Gardiner DL, Whisstock JC, Dalton JP (2009) Proc Natl Acad Sci U S A 106:2537–2542

    CAS  Google Scholar 

  143. Fournie-Zaluski MC, Poras H, Roques BP, Nakajima Y, Ito K, Yoshimoto T (2009) Acta Crystallogr D Biol Crystallogr 65:814–822

    CAS  Google Scholar 

  144. Jozic D, Bourenkow G, Bartunik H, Scholze H, Dive V, Henrich B, Huber R, Bode W, Maskos K (2002) Structure 10:1097–1106

    CAS  Google Scholar 

  145. Czarny B, Stura EA, Devel L, Vera L, Cassar-Lajeunesse E, Beau F, Calderone V, Fragai M, Luchinat C, Dive V (2013) J Med Chem 56:1149–1159

    CAS  Google Scholar 

  146. Morrison RA, Singhvi SM, Peterson AE, Pocetti DA, Migdalof BH (1990) Drug Metab Dispos 18:253–257

    CAS  Google Scholar 

  147. Junot C, Gonzales MF, Ezan E, Cotton J, Vazeux G, Michaud A, Azizi M, Vassiliou S, Yiotakis A, Corvol P, Dive V (2001) J Pharmacol Exp Ther 297:606–611

    CAS  Google Scholar 

  148. Dive V, Andarawewa KL, Boulay A, Matziari M, Beau F, Guerin E, Rousseau B, Yiotakis A, Rio MC (2005) Int J Cancer 113:775–781

    CAS  Google Scholar 

  149. Defamie V, Laurens M, Patrono D, Devel L, Brault A, Saint-Paul MC, Yiotakis A, Barbry P, Gugenheim J, Crenesse D, Dive V, Huet PM, Mari B (2008) Hepatology 47:177–185

    CAS  Google Scholar 

  150. Johnson JL, Devel L, Czarny B, George SJ, Jackson CL, Rogakos V, Beau F, Yiotakis A, Newby AC, Dive V (2011) Arterioscler Thromb Vasc Biol 31:528–535

    CAS  Google Scholar 

  151. Marchant DJ, Bellac CL, Moraes TJ, Wadsworth SJ, Dufour A, Butler GS, Bilawchuk LM, Hendry RG, Robertson AG, Cheung CT, Ng J, Ang L, Luo Z, Heilbron K, Norris MJ, Duan W, Bucyk T, Karpov A, Devel L, Georgiadis D, Hegele RG, Luo H, Granville DJ, Dive V, McManus BM, Overall CM (2014) Nat Med 20:493–502

    CAS  Google Scholar 

  152. Cursio R, Mari B, Louis K, Rostagno P, Saint-Paul MC, Giudicelli J, Bottero V, Anglard P, Yiotakis A, Dive V, Gugenheim J, Auberger P (2002) FASEB J 16:93–95

    CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Laboratory of Organic Chemistry, University of Athens, Panepistimiopolis Zografou, 15771, Athens, Greece

    Dimitris Georgiadis

  2. CEA-Saclay, Service d’Ingénierie Moléculaire des Protéines Labex LERMIT, CEA-DSV-iBiTecS, 91191, Gif/Yvette, France

    Vincent Dive

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  1. Dimitris Georgiadis
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  2. Vincent Dive
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Correspondence to Dimitris Georgiadis .

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  1. Department of Chemistry, Texas Christian University, Fort Worth, Texas, USA

    Jean-Luc Montchamp

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Georgiadis, D., Dive, V. (2014). Phosphinic Peptides as Potent Inhibitors of Zinc-Metalloproteases. In: Montchamp, JL. (eds) Phosphorus Chemistry I. Topics in Current Chemistry, vol 360. Springer, Cham. https://doi.org/10.1007/128_2014_571

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