Skip to main content
SpringerLink
Log in

Non-coordination planer cis-and trans-configuration of cis-[Pt(II)(mixed-NH3/RNH2)(3-OH-cyclobutane-1,1-dicarboxylate)]: separation, characterization, and anticancer activity

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

Two isomers of cis-[Pt(II)(mixed-NH3/RNH2)(3-OH-cyclobutane-1,1-dicarboxylate)] (R = cycopentyl, cyclohexyl) were separated, structurally characterized and tested for their anticancer activity. X-ray structural analysis revealed that this isomerism originates from two opposite spatial orientations of the hydroxyl group on the cyclobutane ring in relation to the coordinated NH3, resulting in cis- and trans-configurations. The two isomers have approximately equal anticancer activity, probably due to a relatively long distance between the hydroxyl group and the Pt(II) coordination plane. Therefore, the separation of such isomers is not recommended during drug development.

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
Fig. 6

Similar content being viewed by others

References

  1. X. Han, J. Sun, Y. Wang, Z. He, Med. Res. Rev. 35, 1268 (2015)

    Article  CAS  Google Scholar 

  2. X. Chen, Y. Wu, H. Dong, C.Y. Zhang, Y. Zhang, Curr. Mol. Med. 13, 1603 (2013)

    Article  CAS  Google Scholar 

  3. J.W. Nial, W. Shonag, E.C. Gemma, O. Rabbab, Dalton Trans. 39, 8113 (2010)

    Article  Google Scholar 

  4. T.C. Johnstone, K. Suntharalingam, S.J. Lippard, Chem. Rev. 116, 3436 (2016)

    Article  CAS  Google Scholar 

  5. C. Barnard, Johns. Matthey Technol. Rev. 61, 52 (2017)

    Article  Google Scholar 

  6. M. Drees, W.M. Dengler, H.R. Hendriks, L.R. Kelland, H.H. Fiebig, Eur. J. Cancer 31, 356 (1995)

    Article  Google Scholar 

  7. M.A. Jakupec, M. Galanski, B.K. Keppler, Biochem. Pharmacol. 146, 1 (2003)

    CAS  Google Scholar 

  8. W. Liu, J. Su, J. Jiang, X. Li, Q. Ye, H. Zhou, J. Chen, Y. Li, Nat. Sci. Rep. 3, 2464 (2013)

    Article  Google Scholar 

  9. S.A. Sadeek, W.H. El-Shwiniy, J. Iran. Chem. Soc. 14, 1711 (2017)

    Article  CAS  Google Scholar 

  10. S.A. Sadeek, M. Sherif, A.E. El-Hamid, W.H. El-Shwiniy, Res. Chem. Intermed. 42, 3183 (2016)

    Article  CAS  Google Scholar 

  11. H.W. El-Shwiniy, A.Z. Wael, Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 199, 290 (2018)

    Article  CAS  Google Scholar 

  12. G.M. Sheldrick, Acta Crystallogr. A 64, 112 (2008)

    Article  CAS  Google Scholar 

  13. W. Liu, Q. Ye, J. Jiang, L. Lou, Y. Xu, C. Xie, M. Xie, ChemMedChem 8, 1465 (2013)

    Article  CAS  Google Scholar 

  14. W. Liu, X. Chen, Q. Ye, S. Hou, L. Lou, C. XiSe, Platin. Met. Rev. 56, 248 (2012)

    Article  CAS  Google Scholar 

  15. W. Liu, X. Chen, Q. Ye, Y. Xu, C. Xie, L. Lou, Inorg. Chem. 50, 5324 (2011)

    Article  CAS  Google Scholar 

  16. J. Zhao, S. Gou, Y. Sun, R. Yin, Z. Wang, Chem. Eur. J. 18, 14276 (2012)

    Article  CAS  Google Scholar 

  17. J. Zhao, S. Gou, Y. Sun, L. Fang, Z. Wang, Inorg. Chem. 51, 10317 (2012)

    Article  CAS  Google Scholar 

  18. L. Kelland, Nat. Rev. Cancer 7, 573 (2007)

    Article  CAS  Google Scholar 

  19. S. Dilruba, G.V. Kalayda, Cancer Chemother. Pharmacol. 77, 1103 (2016)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was supported by the Natural Science Foundation of China (Grant Number 21661018); Yunnan Provincial R&D Project of China (Grant Numbers 2014BC010 and 2017ZF010).

Author information

Authors and Affiliations

  1. State Key Laboratory for Platinum Group Metals, Kunming Institute of Precious Metals, Kunming, Yunnan, People’s Republic of China

    Jing Jiang, Anli Gao, Shuqian Hou & Weiping Liu

  2. Lincan Maternal and Child Health Care Hospital, Kaiyuan, Yunnan, People’s Republic of China

    Jie Qiu

  3. Shanghai Institute of Materia Medica, Chinese Academy of Science, Shanghai, People’s Republic of China

    Liguang Lou

Authors
  1. Jing Jiang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jie Qiu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Liguang Lou
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Anli Gao
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Shuqian Hou
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Weiping Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Weiping Liu.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 487 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Jiang, J., Qiu, J., Lou, L. et al. Non-coordination planer cis-and trans-configuration of cis-[Pt(II)(mixed-NH3/RNH2)(3-OH-cyclobutane-1,1-dicarboxylate)]: separation, characterization, and anticancer activity. Res Chem Intermed 44, 6479–6487 (2018). https://doi.org/10.1007/s11164-018-3503-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-018-3503-0

Keywords

Search

Navigation