Skip to main content

Advertisement

SpringerLink
Log in

Mimic catechins to develop selective MMP-2 inhibitors

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

Matrix metalloproteinase 2 (MMP-2) is a well-known anticancer target belonging to the MMP family. Because of the bilateral role of MMPs in cancer, developing highly selective MMP-2 inhibitors is a current challenge. In this paper, we investigated the binding modes of green tea polyphenols epigallocatechin gallate and epicatechin into the active site of the MMP-2 enzyme. The structure-based analysis allowed the optimization of these hits and hence led to a better lead candidate. Moreover, using a pharmacophore model, we screened FooDB compounds and selected food components as potential MMP-2 inhibitors. The search for food-derived compounds that target this enzyme may represent a strategy to identify new lead molecules with improved safety profiles and provide indications about possible functional foods.

Graphical abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  1. Ohigashi H, Murakami A (2004) BioFactors 22:49

    Article  CAS  PubMed  Google Scholar 

  2. Mayne ST, Playdon MC, Rock CL (2016) Nat Rev Clin Oncol 13:504

    Article  PubMed  Google Scholar 

  3. Ravindran J, Prasad S, Aggarwal BB (2009) AAPS J 11:495

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  4. Gupta SC, Kismali G, Aggarwal BB (2013) BioFactors 39:2

    Article  CAS  PubMed  Google Scholar 

  5. Nasri H, Baradaran A, Shirzad H, Rafieian-Kopaei M (2014) Int J Prev Med 5:1487

    PubMed  PubMed Central  Google Scholar 

  6. Dai SX, Li WX, Han FF, Guo YC, Zheng JJ, Liu JQ, Wang Q, Gao YD, Li GH, Huang JF (2016) Sci Rep 6:25462

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. Solomonov I, Zehorai E, Talmi-Frank D, Wolf SG, Shainskaya A, Zhuravlev A, Kartvelishvily E, Visse R, Levin Y, Kampf N, Jaitin DA, David E, Amit I, Nagase H, Sagi I (2016) Proc Natl Acad Sci USA 113:10884

    Article  CAS  PubMed  Google Scholar 

  8. Liotta LA, Tryggvason K, Garbisa S, Hart I, Foltz CM, Shafie S (1980) Nature 284:67

    Article  CAS  PubMed  Google Scholar 

  9. Martin MD, Matrisian LM (2007) Cancer Metastasis Rev 26:717

    Article  CAS  PubMed  Google Scholar 

  10. Balbin M, Fueyo A, Tester AM, Pendas AM, Pitiot AS, Astudillo A, Overall CM, Shapiro SD, Lopez-Otin C (2003) Nat Genet 35:252

    Article  CAS  PubMed  Google Scholar 

  11. Dufour A, Overall CM (2013) Trends Pharmacol Sci 34:233

    Article  CAS  PubMed  Google Scholar 

  12. Levy DE, Lapierre F, Liang W, Ye W, Lange CW, Li X, Grobelny D, Casabonne M, Tyrrell D, Holme K, Nadzan A, Galardy RE (1998) J Med Chem 41:199

    Article  CAS  PubMed  Google Scholar 

  13. Drummond AH, Beckett P, Brown PD, Bone EA, Davidson AH, Galloway WA, Gearing AJ, Huxley P, Laber D, McCourt M, Whittaker M, Wood LM, Wright A (1999) Ann N Y Acad Sci 878:228

    Article  CAS  PubMed  Google Scholar 

  14. Agrawal A, Romero-Perez D, Jacobsen JA, Villarreal FJ, Cohen SM (2008) ChemMedChem 3:812

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  15. Rubino MT, Maggi D, Laghezza A, Loiodice F, Tortorella P (2011) Arch Pharm (Weinheim, Ger) 344:557

    Article  CAS  Google Scholar 

  16. Giustiniano M, Tortorella P, Agamennone M, Di Pizio A, Rossello A, Nuti E, Gomez-Monterrey I, Novellino E, Campiglia P, Vernieri E, Sala M, Bertamino A, Carotenuto A (2013) J Amino Acids 2013:178381

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  17. Di Pizio A, Agamennone M, Aschi M (2012) PLoS ONE 7:e47774

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  18. Di Pizio A, Agamennone M, Tortorella P (2016) Curr Top Med Chem 16:449

    Article  CAS  PubMed  Google Scholar 

  19. Di Pizio A, Laghezza A, Tortorella P, Agamennone M (2013) ChemMedChem 8:1475

    Article  CAS  PubMed  Google Scholar 

  20. Thomas NV, Kim SK (2010) Biochem Res Int 2010:845975

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  21. Smolarz HD, Załuski D (2009) Annales UMCS. Pharmacia 22:89

    Google Scholar 

  22. Mahmood T, Akhtar N (2013) Rejuvenation Res 16:91

    Article  PubMed  Google Scholar 

  23. Jha S, Kanaujia SP, Limaye AM (2016) Gene 593:126

    Article  CAS  PubMed  Google Scholar 

  24. Fassina G, Vene R, Morini M, Minghelli S, Benelli R, Noonan DM, Albini A (2004) Clin Cancer Res 10:4865

    Article  CAS  PubMed  Google Scholar 

  25. Chowdhury A, Nandy SK, Sarkar J, Chakraborti T, Chakraborti S (2017) Mol Cell Biochem 427:111

    Article  CAS  PubMed  Google Scholar 

  26. Dell’Agli M, Bellosta S, Rizzi L, Galli G, Canavesi M, Rota F, Parente R, Bosisio E, Romeo S (2005) Cell Mol Life Sci 62:2896

    Article  CAS  PubMed  Google Scholar 

  27. Tauro M, Laghezza A, Loiodice F, Piemontese L, Caradonna A, Capelli D, Montanari R, Pochetti G, Di Pizio A, Agamennone M, Campestre C, Tortorella P (2016) J Enzyme Inhib Med Chem 31(sup 4):25

    Article  CAS  PubMed  Google Scholar 

  28. Johnson AR, Pavlovsky AG, Ortwine DF, Prior F, Man CF, Bornemeier DA, Banotai CA, Mueller WT, McConnell P, Yan C, Baragi V, Lesch C, Roark WH, Wilson M, Datta K, Guzman R, Han HK, Dyer RD (2007) J Biol Chem 282:27781

    Article  CAS  PubMed  Google Scholar 

  29. Ball P (2008) Chem Rev 108:74

    Article  CAS  PubMed  Google Scholar 

  30. Ball P (2017) Proc Natl Acad Sci USA 114:13327

    Article  CAS  PubMed  Google Scholar 

  31. Southall NT, Dill KA, Haymet ADJ (2002) J Phys Chem B 106:521

    Article  CAS  Google Scholar 

  32. Michel J, Tirado-Rives J, Jorgensen WL (2009) J Am Chem Soc 131:15403

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  33. Krimmer SG, Cramer J, Betz M, Fridh V, Karlsson R, Heine A, Klebe G (2016) J Med Chem 59:10530

    Article  CAS  PubMed  Google Scholar 

  34. Lin EJ, Zhang X, Wang DY, Hong SZ, Li LY (2014) Bangl J Pharmacol 9:419

    Google Scholar 

  35. Ma CY, Ji WT, Chueh FS, Yang JS, Chen PY, Yu CC, Chung JG (2011) J Agr Food Chem 59:9032

    Article  CAS  Google Scholar 

  36. Decaneto E, Vasilevskaya T, Kutin Y, Ogata H, Grossman M, Sagi I, Havenith M, Lubitz W, Thiel W, Cox N (2017) Phys Chem Chem Phys 19:30316

    Article  CAS  PubMed  Google Scholar 

  37. Bertini I, Calderone V, Fragai M, Luchinat C, Maletta M, Yeo KJ (2006) Angew Chem Int Edit 45:7952

    Article  CAS  Google Scholar 

  38. Grossman M, Born B, Heyden M, Tworowski D, Fields GB, Sagi I, Havenith M (2011) Nat Struct Mol Biol 18:1102

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  39. Bucher D, Stouten P, Triballeau N (2018) J Chem Inf Model 58:692

    Article  CAS  PubMed  Google Scholar 

  40. Dhanaraj V, Williams MG, Ye QZ, Molina F, Johnson LL, Ortwine DF, Pavlovsky A, Rubin JR, Skeean RW, White AD, Humblet C, Hupe DJ, Blundell TL (1999) Croat Chem Acta 72:575

    CAS  Google Scholar 

  41. Rowsell S, Hawtin P, Minshull CA, Jepson H, Brockbank SM, Barratt DG, Slater AM, McPheat WL, Waterson D, Henney AM, Pauptit RA (2002) J Mol Biol 319:173

    Article  CAS  PubMed  Google Scholar 

  42. Nale SD, Jadhav VH (2016) Tetrahedron Lett 57:2652

    Article  CAS  Google Scholar 

  43. Puig T, Turrado C, Benhamu B, Aguilar H, Relat J, Ortega-Gutierrez S, Casals G, Marrero PF, Urruticoechea A, Haro D, Lopez-Rodriguez ML, Colomer R (2009) Clin Cancer Res 15:7608

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgements

The authors thank Ava Yuan Xue for the critical reading of the manuscript.

Author information

Authors and Affiliations

  1. Institute of Biochemistry, Food Science and Nutrition, The Robert H. Smith Faculty of Agriculture, Food and Environment, The Hebrew University, Rehovot, Israel

    Antonella Di Pizio

  2. Dipartimento di Farmacia, Università “G. d’Annunzio”, Chieti-Pescara, Chieti, Italy

    Mariangela Agamennone

  3. Dipartimento di Farmacia-Scienze del Farmaco, Università degli Studi “A. Moro” di Bari, Bari, Italy

    Antonio Laghezza, Fulvio Loiodice & Paolo Tortorella

Authors
  1. Antonella Di Pizio
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mariangela Agamennone
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Antonio Laghezza
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Fulvio Loiodice
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Paolo Tortorella
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Antonella Di Pizio.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Di Pizio, A., Agamennone, M., Laghezza, A. et al. Mimic catechins to develop selective MMP-2 inhibitors. Monatsh Chem 149, 1293–1300 (2018). https://doi.org/10.1007/s00706-018-2237-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-018-2237-4

Keywords

Search

Navigation