Advertisement

Interaction of the anticancer gallium(III) complexes of 8-hydroxyquinoline and maltol with human serum proteins

  • Éva A. Enyedy
  • Orsolya Dömötör
  • Krisztina Bali
  • Anasztázia Hetényi
  • Tiziano Tuccinardi
  • Bernhard K. Keppler
Original Paper

Graphical abstract

Keywords

Solution equilibrium Albumin Transferrin Binding affinity Fluorescence 

Abbreviations

apoTf

Apotransferrin

GaM

Tris(3-hydroxy-2-methyl-4H-pyran-4-onato)gallium(III)

HEPES

4-(2-Hydroxyethyl)-1-piperazineethanesulfonic acid

HMM

High molecular mass

HSA

Human serum albumin

HQ

8-Hydroxyquinoline

KP46

Tris(8-quinolinolato)gallium(III)

LMM

Low molecular mass

PDB

Protein Data Bank

STD

Saturation transfer difference

Tf

Human serum transferrin

Notes

Acknowledgments

This work was supported by the Hungarian Research Foundation OTKA projects PD103905 and PD83600, and by the European Union and the State of Hungary, cofinanced by the European Social Fund in the framework of TÁMOP-4.2.4.A/2-11/1-2012-0001 “National Excellence Program”.

Supplementary material

775_2014_1211_MOESM1_ESM.pdf (915 kb)
Supplementary material 1 (PDF 914 kb)

References

  1. 1.
    Jung Y, Lippard SJ (2007) Chem Rev 107:1387–1407PubMedCrossRefGoogle Scholar
  2. 2.
    Jakupec MA, Keppler BK (2004) Curr Top Med Chem 4:1575–1583PubMedCrossRefGoogle Scholar
  3. 3.
    Bernstein LR, Tanner T, Godfrey C, Noll B (2000) Met Based Drugs 7:33–47PubMedCentralPubMedCrossRefGoogle Scholar
  4. 4.
    Collery P, Keppler BK, Madoulet C, Desoize B (2002) Crit Rev Oncol Hematol 42:283–296PubMedCrossRefGoogle Scholar
  5. 5.
    Jakupec MA, Galanski M, Arion VB, Hartinger CG, Keppler BK (2008) Dalton Trans 183–194Google Scholar
  6. 6.
    Hofheinz RD, Dittrich C, Jakupec MA, Drescher A, Jaehde U, Gneist M, Graf von Keyserlingk N, Keppler BK, Hochhaus A (2005) Int J Clin Pharmacol Ther 43:590–591PubMedCrossRefGoogle Scholar
  7. 7.
  8. 8.
    Bernstein LR, Hoeven JJM, Boer RO (2011) Anticancer Agents Med Chem 11:585–590PubMedCrossRefGoogle Scholar
  9. 9.
    Narasimhan J, Antholine WE, Chitambar CR (1992) Biochem Pharmacol 44:2403–2408PubMedCrossRefGoogle Scholar
  10. 10.
    Groessl M, Bytzek A, Hartinger CG (2009) Electrophoresis 30:2720–2727PubMedCrossRefGoogle Scholar
  11. 11.
    Bernstein LR (2005) In: Gielen M, Tiekink BRT (eds) Metallotherapeutic drugs and metal-based diagnostic agents: the use of metals in medicine. Wiley, London, pp 259 − 277Google Scholar
  12. 12.
    Bernstein LR (1998) Pharmacol Rev 50:665–682PubMedGoogle Scholar
  13. 13.
    Lessa JA, Parrilha GL, Beraldo H (2012) Inorg Chim Acta 393:53–63CrossRefGoogle Scholar
  14. 14.
    Enyedy ÉA, Dömötör O, Varga E, Kiss T, Trondl R, Hartinger CG, Keppler BK (2012) J Inorg Biochem 117:189–197PubMedCrossRefGoogle Scholar
  15. 15.
    Rudnev AV, Foteeva LS, Kowol C, Berger R, Jakupec MA, Arion VB, Timerbaev AR, Keppler BK (2006) J Inorg Biochem 100:1819–1826PubMedCrossRefGoogle Scholar
  16. 16.
    Hummer AA, Bartel C, Arion VB, Jakupec MA, Meyer-Klaucke W, Geraki T, Quinn PD, Mijovilovich A, Keppler BK, Rompel A (2012) J Med Chem 55:5601–5613PubMedCrossRefGoogle Scholar
  17. 17.
    Timerbaev AR (2009) Metallomics 1:193–198PubMedCrossRefGoogle Scholar
  18. 18.
    Fanali G, Masi A, Trezza V, Marino M, Fasano M, Ascenzi P (2012) Mol Aspects Med 33:209–290PubMedCrossRefGoogle Scholar
  19. 19.
    Kratz F (2008) J Control Release 132:171–183PubMedCrossRefGoogle Scholar
  20. 20.
    Harris WR (1992) Clin Chem 38:1809–1818PubMedGoogle Scholar
  21. 21.
    Bal W, Sokołowska M, Kurowska E, Faller P (2013) Biochim Biophys Acta 1830:5444–5455PubMedCrossRefGoogle Scholar
  22. 22.
    Sudlow G, Birkett DJ, Wade DN (1975) Mol Pharmacol 11:824–832PubMedGoogle Scholar
  23. 23.
    Sudlow G, Birkett DJ, Wade DN (1976) Mol Pharmacol 12:1052–1061PubMedGoogle Scholar
  24. 24.
    Carter DC, Ho JX (1994) Adv Protein Chem 45:153–204PubMedCrossRefGoogle Scholar
  25. 25.
    Peters T Jr (1985) Adv Protein Chem 37:161–245PubMedCrossRefGoogle Scholar
  26. 26.
    He XM, Carter DC (1992) Nature 358:209–215PubMedCrossRefGoogle Scholar
  27. 27.
    Zsila F (2013) Mol Pharm 10:1668–1682PubMedCrossRefGoogle Scholar
  28. 28.
    Enyedy ÉA, Horváth L, Hetényi A, Tuccinardi T, Hartinger CG, Keppler BK, Kiss T (2011) Bioorg Med Chem 19:4202–4210PubMedCrossRefGoogle Scholar
  29. 29.
    Mayer M, Meyer B (1999) Angew Chem Int Ed 38:1784–1788CrossRefGoogle Scholar
  30. 30.
    Morris GM, Huey R, Lindstrom W, Sanner MF, Belew RK, Goodsell DS, Olson AJ (2009) J Comput Chem 30:2785–2791PubMedCentralPubMedCrossRefGoogle Scholar
  31. 31.
    Vreven T, Morokuma K, Farkas O, Schlegel HB, Frisch MJ (2003) J Comput Chem 24:760–769PubMedCrossRefGoogle Scholar
  32. 32.
    Harris WR, Pecoraro VL (1983) Biochemistry 22:292–299PubMedCrossRefGoogle Scholar
  33. 33.
    James NG, Berger CL, Byrne SL, Smith VC, MacGillivray RT, Mason AB (2007) Biochemistry 46:10603–10611PubMedCrossRefGoogle Scholar
  34. 34.
    Sun H, Cox MC, Li H, Sadler PJ (1997) Struct Bond 88:71–102CrossRefGoogle Scholar
  35. 35.
    Harris WR, Messori L (2002) Coord Chem Rev 228:237–262CrossRefGoogle Scholar
  36. 36.
    Farkas E, Kozma E, Kiss T, Toth I, Kurzak B (1995) J Chem Soc Dalton Trans 447–481Google Scholar
  37. 37.
    Chasteen ND, Grady JK, Holloway CE (1986) Inorg Chem 25:2754–2760CrossRefGoogle Scholar
  38. 38.
    Lakowicz JR (2006) Principles of fluorescence spectroscopy, 3rd edn. Springer, New YorkCrossRefGoogle Scholar
  39. 39.
    Zékány L, Nagypál I (1985) In: Leggett DL (ed) Computational methods for the determination of stability constants. Plenum, New York, pp 291–353CrossRefGoogle Scholar
  40. 40.
    Allen FH (2002) Acta Crystallogr B 58:380–388PubMedCrossRefGoogle Scholar
  41. 41.
    Wang Y, Zhang WX, Li YQ, Ye L, Yang GD (1999) Chem Mater 11:530–532CrossRefGoogle Scholar
  42. 42.
    Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JAJ, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam NJ, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian 09, revision D.01. Gaussian, WallingfordGoogle Scholar
  43. 43.
    Becke AD (1988) Phys Rev A 38:3098–3100PubMedCrossRefGoogle Scholar
  44. 44.
    Miehlich B, Savin A, Stoll H, Preuss H (1989) Chem Phys Lett 157:200–206CrossRefGoogle Scholar
  45. 45.
    Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE (2000) Nucleic Acids Res 28:235–242Google Scholar
  46. 46.
    Ghuman J, Zunszain PA, Petitpas I, Bhattacharya AA, Otagiri M, Curry S (2005) J Mol Biol 353:38–52PubMedCrossRefGoogle Scholar
  47. 47.
    Wang ZM, Ho JX, Ruble JR, Rose J, Ruker F, Ellenburg M, Murphy R, Click J, Soistman E, Wilkerson L, Carter DC (2013) Biochim Biophys Acta 1830:5356–5374PubMedCrossRefGoogle Scholar
  48. 48.
    Pettersen EF, Goddard TD, Huang CC, Couch GS, Greenblatt DM, Meng EC, Ferrin TE (2004) J Comput Chem 25:1605–1612PubMedCrossRefGoogle Scholar

Copyright information

© SBIC 2014

Authors and Affiliations

  • Éva A. Enyedy
    • 1
  • Orsolya Dömötör
    • 1
    • 2
  • Krisztina Bali
    • 1
  • Anasztázia Hetényi
    • 3
  • Tiziano Tuccinardi
    • 4
  • Bernhard K. Keppler
    • 5
  1. 1.Department of Inorganic and Analytical ChemistryUniversity of SzegedSzegedHungary
  2. 2.MTA-SZTE Bioinorganic Chemistry Research GroupSzegedHungary
  3. 3.Department of Medical ChemistryUniversity of SzegedSzegedHungary
  4. 4.Department of PharmacyUniversity of PisaPisaItaly
  5. 5.Institute of Inorganic ChemistryUniversity of ViennaViennaAustria

Personalised recommendations