Skip to main content
SpringerLink
Log in

Complexation of 1,3-Diamino-2-hydroxypropane-N,N,N',N'-tetraacetic Acid (DHPTA) with Heavy Lanthanides (Tb3+, Ho3+, Lu3+) in Aqueous Solution

  • Published:
Journal of Solution Chemistry Aims and scope Submit manuscript

Abstract

Thermodynamic equilibria of complexes of 1,3-diamino-2-hydroxypropane-N,N,N',N'-tetraacetic acid (DHPTA) with heavy lanthanides (Tb3+, Ho3+ and Lu3+) in aqueous solution have been investigated with potentiometry, spectrophotometry, luminescence spectroscopy and nuclear magnetic resonance spectroscopy (NMR). The results identified three 1:1 Ln/DHPTA (Ln: Tb3+, Ho3+ and Lu3+) complexes with different degrees of deprotonation, LnL−, Ln(H−1L)2−, and Ln(OH)(H−1L)3−, where H−1 represents the deprotonation of the hydroxyl group between two methyliminodiacetate groups in the DHPTA structure. The alkoxide form of the DHPTA hydroxyl group directly binds to the lanthanide atom, forming highly strong chelation. The complex of Ln(H−1L)2− could be present as a dimeric or polymeric complex in solution.

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
Fig. 7
Fig. 8

Similar content being viewed by others

References

  1. Boros, E., Holland, J.P.: Chemical aspects of metal ion chelation in the synthesis and application antibody-based radiotracers. J. Label. Compd. Radiopharm. 61(9), 652–671 (2018)

    Article  CAS  Google Scholar 

  2. Kostelnik, T.I., Orvig, C.: Radioactive main group and rare earth metals for imaging and therapy. Chem. Rev. 119(2), 902–956 (2019)

    Article  CAS  Google Scholar 

  3. Banerjee, S., Pillai, M.R.A., Knapp, F.F.: Lutetium-177 therapeutic radiopharmaceuticals: linking chemistry, radiochemistry, and practical applications. Chem. Rev. 115(8), 2934–2974 (2015)

    Article  CAS  Google Scholar 

  4. Cutler, C.S., Hennkens, H.M., Sisay, N., Huclier-Markai, S., Jurisson, S.S.: Radiometals for combined imaging and therapy. Chem. Rev. 113(2), 858–883 (2013)

    Article  CAS  Google Scholar 

  5. Amoroso, A.J., Fallis, I.A., Pope, S.J.A.: Chelating agents for radiolanthanides: applications to imaging and therapy. Coord. Chem. Rev. 340, 198–219 (2017)

    Article  CAS  Google Scholar 

  6. Boros, E., Packard, A.B.: Radioactive transition metals for imaging and therapy. Chem. Rev 119(2), 870–901 (2019)

    Article  CAS  Google Scholar 

  7. Dale, A.V., Pandya, D.N., Kim, J.Y., Lee, H., Ha, Y.S., Bhatt, N., Kim, J., Seo, J.J., Lee, W., Kim, S.H., Yoon, Y.-R., An, G.I., Yoo, J.: Non-cross-bridged tetraazamacrocyclic chelator for stable 64Cu-based radiopharmaceuticals. ACS Med. Chem. Lett. 4(10), 927–931 (2013)

    Article  CAS  Google Scholar 

  8. Price, E.W., Orvig, C.: Matching chelators to radiometals for radiopharmaceuticals. Chem. Soc. Rev. 43(1), 260–290 (2014)

    Article  CAS  Google Scholar 

  9. Polyakova, I.N., Sergienko, V.S., Martsinko, E.E., Seifullina, I.I., Chebanenko, E.A.: 1,3-Diamino-2-hydroxypropane-N, N, N′, N-tetraacetic acid: crystal and molecular structures. Russ. J. Coord. Chem. 44(2), 155–161 (2018)

    Article  CAS  Google Scholar 

  10. Zhong, W., Parkinson, J.A., Parsons, S., Oswald, I.D.H., Coxall, R.A., Sadler, P.J.: Structure and dynamics of dinuclear zirconium(IV) complexes. Inorg. Chem. 43(12), 3561–3572 (2004)

    Article  CAS  Google Scholar 

  11. Nakai, M., Funabiki, T., Ohtsuki, C., Harada, M., Ichimura, A., Tanaka, R., Kinoshita, I., Mikuriya, M., Benten, H., Ohkita, H., Ito, S., Obata, M., Yano, S.: Structure and photochemical properties of (μ–alkoxo)bis(μ–carboxylato)diruthenium complexes with naphthylacetate ligands. Inorg. Chem. 45(7), 3048–3056 (2006)

    Article  CAS  Google Scholar 

  12. Kanamori, K., Nishida, K., Miyata, N., Shimoyama, T., Hata, K., Mihara, C., Okamoto, K.-I., Abe, Y., Hayakawa, S., Matsugo, S.: Mononuclear and dinuclear monoperoxovanadium(V) complexes with a hetero ligand. 1.1 self-decomposition reaction, detection of reactive oxygen species, and oxidizing ability. Inorg. Chem. 43(22), 7127–7140 (2004)

    Article  CAS  Google Scholar 

  13. Jameson, D.L., Xie, C.L., Hendrickson, D.N., Potenza, J.A., Schugar, H.J.: molecular structure and magnetic properties of a novel Fe(III) tetranuclear complex containing oxo, alkoxo, and carbonato bridges. J. Am. Chem. Soc. 109(3), 740–746 (1987)

    Article  CAS  Google Scholar 

  14. Powell, J.E., Ling, D.R., Tse, P.K.: Complexes of rare-earth elements with 1,3-diamino-2-hydroxypropane-N,N,N',N'-tetraacetic acid. Inorg. Chem. 25(4), 585–586 (1986)

    Article  CAS  Google Scholar 

  15. Choi, K.Y., Kim, K.S., Hong, C.P.: Dissociation kinetics of linear polyaminopolycarboxylate complexes of lanthanides(III). Bull. Korean Chem. Soc. 15(9), 782–785 (1994)

    CAS  Google Scholar 

  16. Tircsó, G., Bényei, A., Brücher, E., Kis, A., Király, R.: Equilibria and structure of the lanthanide(III)-2-hydroxy-1,3-diaminopropane-N, N, N’, N’-tetraacetate complexes: formation of alkoxo–bridged dimers in solid state and solution. Inorg. Chem. 45(13), 4951–4962 (2006)

    Article  Google Scholar 

  17. Miyashita, Y., Sanada, M., Yamada, Y., Fujisawa, K., Okamoto, K.-I.: Novel alkoxo–bridged lanthanide(III) dinuclear complexes: crystal structure of Na4[Yb2(μ–DPTA–O)2] (H4DPTA–OH = 1,3-diamino-2-hydroxypropane-N, N, N', N'-tetraacetic acid). Chem. Lett. 31(8), 840–841 (2002)

    Article  Google Scholar 

  18. Miyashita, Y., Sanada, M., Islam, M.M., Amir, N., Koyano, T., Ikeda, H., Fujisawa, K., Okamoto, K.-I.: Selective formation of lanthanide(III) complexes with polyaminopolycarboxylate: unprecedented tetranuclear neodymium(III) complex containing alkoxo and carboxylato bridges. Inorg. Chem. Commun. 8, 785–788 (2005)

    Article  CAS  Google Scholar 

  19. Gran, G.: Determination of the equivalence point in potentiometric titrations. Part II. Analyst 77(920), 661–671 (1952)

    Article  CAS  Google Scholar 

  20. Liu, B., Dong, L., Yu, Q., Li, X., Wu, F., Tan, Z., Luo, S.: Thermodynamic study on the protonation reactions of glyphosate in aqueous solution: potentiometry, calorimetry and NMR spectroscopy. J. Phys. Chem. B 120(9), 2132–2137 (2016)

    Article  CAS  Google Scholar 

  21. Li, Q., Liu, B., Mu, W., Yu, Q., Tian, Y., Liu, G., Yang, Y., Li, X., Luo, S.: Protonation states of glufosinate in aqueous solution. J. Solution Chem. 47(4), 705–714 (2018)

    Article  CAS  Google Scholar 

  22. Gans, P., Sabatini, A., Vacca, A.: investigation of equilibria in solution determination of equilibrium constants with the HYPERQUAD suite of programs. Talanta 43(10), 1739–1753 (1996)

    Article  CAS  Google Scholar 

  23. Alderighi, L., Gans, P., Ienco, A., Peters, D., Sabatini, A., Vacca, A.: Hyperquad simulation and speciation (HYSS): a utility program for the investigation of equilibria involving soluble and partially soluble species. Coord. Chem. Rev. 184(1), 311–318 (1999)

    Article  CAS  Google Scholar 

  24. Kumar, K., Jin, T., Wang, X., Desreux, J.F., Tweedle, M.F.: Effect of ligand basicity on the formation and dissociation equilibria and kinetics of Gd3+ complexes of macrocyclic polyamino carboxylates. Inorg. Chem. 33(17), 3823–3829 (1994)

    Article  CAS  Google Scholar 

  25. Kou, F., Yang, S., Zhang, L., Teat, S.J., Tian, G.: Complexation of Ho(III) with tetraalkyl–diglycolamide in aqueous solutions and a solid state compared in organic solutions of solvent extraction. Inorg. Chem. Commun. 71, 41–44 (2016)

    Article  CAS  Google Scholar 

  26. Horrocks, W.D., Schmidt, G.F., Sudnick, D.R., Kittrell, C., Bernheim, R.A.: Laser-induced lanthanide ion luminescence lifetime measurements by direct excitation of metal ion levels A new class of structural probe for calcium-binding proteins and nucleic acids. J. Am. Chem. Soc. 99(7), 2378–2380 (1977)

    Article  CAS  Google Scholar 

  27. Horrocks, W.D., Sudnick, D.R.: Lanthanide ion probes of structure in biology Laser-induced luminescence decay constants provide a direct measure of the number of metal-coordinated water molecules. J. Am. Chem. Soc. 101(2), 334–340 (1979)

    Article  CAS  Google Scholar 

  28. Li, X., Zhang, Z., Martin, L.R., Luo, S., Rao, L.: Complexation of uranium(VI) with N-(2-hydroxyethyl)ethylenediamine-N, N’,N’-triacetic acid in aqueous solution: thermodynamic studies and coordination analyses. Inorg. Chem. 57(13), 7684–7693 (2018)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors thank the National Natural Science Foundation of China (Grant Nos. 41573122 and 21976165).

Author information

Authors and Affiliations

  1. The Affiliated Hospital of Southwest Medical University, Southwest Medical University, Luzhou, 646000, Sichuan, China

    Liqing Zhu & Yue Chen

  2. Institute of Nuclear Physics and Chemistry, China Academy of Engineering Physics, Mianyang, 621999, Sichuan, China

    Bijun Liu, Xia Yang, Liangang Zhuo, Wanjun Mu, Yuchuan Yang, Hongyuan Wei & Xingliang Li

  3. Key Laboratory of Nuclear Medicine and Molecular Imaging of Sichuan Province, Mianyang, 621999, China

    Yue Chen & Hongyuan Wei

Authors
  1. Liqing Zhu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Bijun Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Xia Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Liangang Zhuo
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Wanjun Mu
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Yue Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Yuchuan Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Hongyuan Wei
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Xingliang Li
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Xingliang Li.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 17 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zhu, L., Liu, B., Yang, X. et al. Complexation of 1,3-Diamino-2-hydroxypropane-N,N,N',N'-tetraacetic Acid (DHPTA) with Heavy Lanthanides (Tb3+, Ho3+, Lu3+) in Aqueous Solution. J Solution Chem 49, 166–178 (2020). https://doi.org/10.1007/s10953-020-00950-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10953-020-00950-y

Keywords

Search

Navigation