Skip to main content
Log in

Synthesis, spectroscopic analysis and structure deduction of gold(III), palladium(II) and platinum(II) complexes with the tripeptide glycyl-l-phenylalanyl-glycine

  • Published:
Transition Metal Chemistry Aims and scope Submit manuscript

Abstract

The coordination behaviour of the tripeptide glycyl-l-phenylalanyl-glycine (H-Gly-Phe-Gly-OH) with Au(III), Pd(II), and Pt(II) in both solution and in the solid state has been investigated experimentally. In addition, quantum chemical calculations have been carried out with a view to obtain the structures and spectroscopic properties of the ligand and its complexes. Both in solution and in the solid state the tripeptide interacts in a tetradentate manner with the Au(III) and Pd(II) ions through the NH2, two deprotonated amide N atoms and the COOgroup, forming [Au(H-Gly-Phe-Gly-OH)H−2)] × H2O and [Pd(H-Gly-l-Phe-Gly-OH)H−2)]Na × H2O complexes. The MN3O chromophores are calculated to be near planar. Interaction with cisplatin leads to the formation of a mononuclear complex with tridentate coordination of the ligand by NH2 and two N- atoms from the deprotonated amide groups ([Pt(H-Gly-l-Phe-Gly-OH)H−2)NH3] × 2H2O). The fourth coordination position of the Pt(II) is occupied by an NH3 ligand. The PtN4 chromophore is flat with a deviation from planarity of 0.3°.

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

Access this article

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

Instant access to the full article PDF.

Scheme 1
Scheme 2
Scheme 3
Scheme 4
Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Komeda S, Lutz M, Spek A, Chikuma M, Reedijk J (2000) Inorg Chem 39:4230. doi:10.1021/ic000273v

    Article  CAS  Google Scholar 

  2. Reedijk J (1996) Chem Commun 801 doi: 10.1039/cc9960000801

  3. Reedijk J (1999) Chem Rev 99:2499. doi:10.1021/cr980422f

    Article  CAS  Google Scholar 

  4. Van Zutphen S, Reedijk J (2005) Coord Chem Rev 249:2845. doi:10.1016/j.ccr.2005.03.005

    Article  Google Scholar 

  5. Van der Veer J, Van der Marel G, Van den Elst H, Reedijk J (1987) Inorg Chem 26:2212

    Google Scholar 

  6. Van Boom S, Chen B, Teuben J, Reedijk J (1999) Inorg Chem 38:1450. doi:10.1021/ic981086o

    Article  Google Scholar 

  7. Komeda S, Lutz M, Spek A, Yamanaka Y, Sato T, Chikuma M, Reedijk J (2002) J Am Chem Soc 124:4738. doi:10.1021/ja0168559

    Article  CAS  Google Scholar 

  8. Lippert B (ed) (1999) Cisplatin: Chemistry and Biochemistry of a leading anticancer drug. Wiley-VCH, Weinheim

    Google Scholar 

  9. Yang T, Tu C, Zhang J, Lin L, Zhang X, Qin L, Ding J, Xu Q, Guo Z (2003) Dalton Trans 3419. doi:10.1039/b305109a

  10. Pantoja E, Gallipoli A, Van Zutphen S, Komeda S, Reddy R, Jaganyi D, Lutz M, Tooke D, Spek A, Navarro-Ranninger C, Reedijk J (2006) J Inorg Biochem 100:1955. doi:10.1016/j.jinorgbio.2006.09.015

    Article  CAS  Google Scholar 

  11. Van Rijt S, Van Zutphen S, Den Dulk H, Brouwer J, Reedijk J (2006) Inorg Chim Acta 359:359

    Google Scholar 

  12. Teletchea S, Komeda S, Teuben J, Elizondo-Riojas M, Reedijk J, Kozelka J (2006) Chem-A Europ J 12:3741. doi:10.1002/chem.200500923

    Article  CAS  Google Scholar 

  13. Magistrato A, Ruggerone P, Spiegel K, Carloni P, Reedijk J (2006) J Phys Chem 110B:3604. doi:10.1021/jp054828p

    Google Scholar 

  14. Casini A, Mastrobuoni G, Temperini C, Gabbiani Ch, Francese S, Moneti G, Supuran G, Claudiu T, Scozzafava A, Messori L (2007) Chem Commun 156

  15. Gabbiani Ch, Casini A, Messori L (2007) Gold Bulletin 40:73

    CAS  Google Scholar 

  16. Messori L, Gabbiani C (2005) Metal Comp Cancer Chemother 355

  17. Messori L, Marcon G, Cinellu M, Agostina M, Coronnello M, Mini E, Gabbiani C, Chiara Q, Orioli P, Pierluigi P (2004) Bioorg Med Chem 12:6039. doi:10.1016/j.bmc.2004.09.014

    Article  CAS  Google Scholar 

  18. Messori L, Marcon G (2004) Metal Ions Biolog Syst 42:385

    Google Scholar 

  19. Messori L, Marcon G, Orioli P (2003) Bioinorg Chem Appl 1:177. doi:10.1155/S1565363303000141

    Article  CAS  Google Scholar 

  20. Marcon G, Messori L, Orioli P (2002) Exp Rev Antican Ther 2:337. doi:10.1586/14737140.2.3.337

    Article  CAS  Google Scholar 

  21. Yang T, Tu C, Zhang J, Lin L, Zhang X, Liu Q, Ding J, Xu Q, Guo Y (2003) Dalton Trans 3419. doi:10.1039/b305109a

  22. Best SL, Chattopadhyay T, Djuran M, Palmer P, Sadler P, Sovago I, Varnagy K (1997) Dalton Trans 2587

  23. Wienken M, Lippert B, Zangrando E, Randaccio L (1997) Inorg Chem 31:1983. doi:10.1021/ic00037a002

    Article  Google Scholar 

  24. Ivanova BB (2005) J Coord Chem 58:587. doi:10.1080/00958970500039033

    Article  CAS  Google Scholar 

  25. Koleva BB, Kolev T, Zareva S, Spiteller M (2007) J Mol Struct 831:165. doi:10.1016/j.molstruc.2006.07.036

    Article  CAS  Google Scholar 

  26. Kolev T, Ivanova B, Zareva S (2007) J Coord Chem 60:109. doi:10.1080/00958970600731620

    Article  CAS  Google Scholar 

  27. Kolev T, Zareva S, Koleva B, Spiteller M (2006) Inorg Chim Acta 359:4367. doi:10.1016/j.ica.2006.05.034

    Article  CAS  Google Scholar 

  28. Koleva B, Kolev T, Spiteller M (2006) Inorg Chim Acta http://dx.doi.org/10.1016/j.ica.2006.11.002

  29. Carotti S, Marcon G, Marussich M, Mazzei T, Messori L, Mini E, Orioli P (2000) Chem-Biolog Interac 125:29

    Article  CAS  Google Scholar 

  30. Oyama T, Kawamura M, Abiko T, Izumi Y, Watanabe M, Kumazawa E, Kuga H, Shiose Y, Kobayashi K (2007) Oncol Rep 17:653

    CAS  Google Scholar 

  31. Zhou Y, Tai G, Zhao Z, Liu Y, Bi H (2007) Fam Zhu Shen Gong Shuom CNXXEV CN 1973902 A 20070606

  32. Susaki H, Inoue K, Kuga H (1999) PCT Int Appl PIXXD2 WO 9961061 A1 19991202

  33. Ivanova BB, Arnaudov MG, Bontchev PR (2004) Spectrochim Acta 60A:855. doi:10.1016/S1386-1425(03)00310-X

    CAS  Google Scholar 

  34. Ivanova BB, Tsalev DL, Arnaudov MG (2006) Talanta 69:822. doi:10.1016/j.talanta.2005.11.026

    Article  CAS  Google Scholar 

  35. Ivanova BB, Simeonov V, Arnaudov MG, Tsalev DL (2007) Spectrochim Acta 67A:66. doi:10.1016/j.saa.2006.06.025

    CAS  Google Scholar 

  36. Koleva BB, Kolev T, Spassov T, Spiteller M (2008) J Incl Phenomen (in press)

  37. Ivanova BB (2005) Spectrochim Acta 62A:5

    Google Scholar 

  38. Ivanova BB, Mayer-Figge H (2005) J Coord Chem 58:653. doi:10.1080/00958970412331336295

    Article  CAS  Google Scholar 

  39. Ivanova BB (2005) J Mol Struct 738:233. doi:10.1016/j.molstruc.2004.12.036

    Article  CAS  Google Scholar 

  40. Bakalska R, Ivanova BB, Kolev T (2006) Centrl Europ J Chem 4:533. doi:10.2478/s11532-006-0018-0

    Article  CAS  Google Scholar 

  41. Ivanova BB (2006) J Mol Struct 782:122. doi:10.1016/j.molstruc.2005.08.004

    Article  CAS  Google Scholar 

  42. Ivanova BB, Kolev T, Zareva S (2006) Biopolymers 82:587. doi:10.1002/bip.20512

    Article  CAS  Google Scholar 

  43. Kolev T (2006) Biopolymers 83:39. doi:10.1002/bip.20525

    Article  CAS  Google Scholar 

  44. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA Jr, Stratmann RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas Ö, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Salvador P, Dannenberg JJ, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Baboul AG, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komáromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Andres JL, Gonzalez C, Head-Gordon M, Replogle ES, Pople JA (1998) Gaussian 98. Gaussian, Inc, Pittsburgh, PA

    Google Scholar 

  45. DALTON, a molecular electronic structure program, Release 2.0 (2005) http://www.kjemi.uio.no/software/dalton/dalton.html

  46. Zhurko GA, Zhurko DA (2005) DA ChemCraft: Tool for treatment of chemical data, Lite version build 08

  47. Toroz D, Van Mourik T (2007) Molec Phys 105:209. doi:10.1080/00268970601138762

    Article  CAS  Google Scholar 

  48. Toroz D, Van Mourik T (2006) Molec Phys 104:559. doi:10.1080/00268970500465274

    Article  CAS  Google Scholar 

  49. Birkedal H, Schwarzenbach D, Pattison P (2002) Chem Commun 2812

  50. Marsh RE, Glusker G (1996) Acta Crystallogr 14:1110. doi:10.1107/S0365110X61003296

    Article  Google Scholar 

  51. Yang T, Tu C, Zhang J, Lin L, Zhang H, Liu Q, Ding Q, Xu Z, Guo Z (2003) Dalton Trans 3419. doi: 10.1039/b305109a

  52. Milinkovic S, Parac T, Djuran M, Kostic N (1997) Dalton Trans 2771

  53. Shi D, Hambley T, Freeman H (1999) J Inorg Biochem 73:173. doi:10.1016/S0162-0134(99)00015-X

    Article  CAS  Google Scholar 

  54. Kozlowski H, Kozlowska G, Trebiatowska O (1977) J Org Magn Res 10:146

    Article  CAS  Google Scholar 

  55. Siebert A, Sheldrick WS (1997) Dalton Trans 385

  56. Frohling CD, Sheldrick WS (1997) Dalton Trans 4411

  57. Wolters D, Sheldrick WS (1999) Dalton Trans 1121

  58. Manka S, Becker F, Hohage O, Sheldrick WS (2004) J Inorg Biochem 98:1947. doi:10.1016/j.jinorgbio.2004.08.016

    Article  CAS  Google Scholar 

  59. Morgan DG, Bursey MM (1995) J Mass Spectrom 30:473. doi:10.1002/jms.1190300312

    Article  CAS  Google Scholar 

  60. Wang Y, Ke F, Siu K, Guevremont R (1996) J Mass Spectrom 31:34

    Google Scholar 

  61. Morgan D, Bursey M (1997) J Mass Spectrom 30:290. doi:10.1002/jms.1190300210

    Article  Google Scholar 

  62. Carr SR, Cassady C (1997) J Mass Spectrom 32:959. doi :10.1002/(SICI)1096-9888(199709)32:9<959::AID-JMS552>3.0.CO;2-5

    Article  CAS  Google Scholar 

Download references

Acknowledgments

B.K. wishes to thank the Alexander von Humboldt Foundation for the Fellowship and the Prof. W.S. Sheldrick for the useful and creative discussion. T.K. and M.S. wish to thank the DAAD for a grant within the priority program “Stability Pact South-Eastern Europe” and the Alexander von Humboldt Foundation.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Bojidarka B. Koleva.

Electronic supplementary material

Rights and permissions

Reprints and permissions

About this article

Cite this article

Koleva, B.B., Kolev, T., Lamshöft, M. et al. Synthesis, spectroscopic analysis and structure deduction of gold(III), palladium(II) and platinum(II) complexes with the tripeptide glycyl-l-phenylalanyl-glycine. Transition Met Chem 33, 911–919 (2008). https://doi.org/10.1007/s11243-008-9132-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11243-008-9132-5

Keywords

Navigation