Skip to main content
SpringerLink
Log in

Synthesis, Crystal Structure, Interaction with BSA and Antibacterial Activity of La(III) and Sm(III) Complexes with Enrofloxacin

  • Original Paper
  • Published:
Journal of Fluorescence Aims and scope Submit manuscript

Abstract

Two new La(III) and Sm(III) complexes with enrofloxacin (HER, 1-cyclopropyl-7-(4-ethyl-1-piperazinyl)-6-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid, C19H21FN3O3), [La2(ER)6(H2O)2]·14H2O(1) and [Sm2(ER)6(H2O)2]·14H2O(2) have been synthesized and characterized by elemental analysis, FT-IR, TG-DTG and X-ray single crystal diffraction. Both of the complexes are triclinic system with space group Pī. The structure of the complexes show that each rare earth atom in both complexes was nine-coordinated. Two of the enrofloxacin ions acted as tridentate chelate and bridging ligands, while the others as bidentate chelate ligands. The binding reaction between the complexes and bovine serum albumin (BSA) was studied by UV-vis absorption spectra and fluorescence spectroscopy. The results indicated that the two complexes had a quite strong ability to quench the fluorescence from BSA and the binding reaction was mainly a static quenching process. The binding constants K A /(L·mol−1) were 1.46 × 105(1) and 8.59 × 106(2) and one binding site was formed. The synchronous spectroscopy suggested that tryptophan residues were placed in BSA. It was also found that the two complexes exhibited greater antimicrobial activity than enrofloxacin at given concentrations.

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
Fig. 9
Fig. 10

Similar content being viewed by others

References

  1. Guo M, Zou JW, Yi PG, Shang ZC, Hu GX, Yu QS (2004) Binding Interaction of Gatifloxacin with Bovine Serum Albumin. Anal Sci 20:465–470

    Article  PubMed  CAS  Google Scholar 

  2. Wang YP, Wei YL, Dong C (2006) Study on the interaction of 3, 3-bis(4-hydroxy-1-naphthyl)-phthalide with bovine serum albumin by fluorescence spectroscopy. J Photochem Photobiol A 177:6–11

    Article  CAS  Google Scholar 

  3. Flarakos J, Morand KL, Vouros P (2005) High-Throughput Solution-Based Medicinal Library Screening against Human Serum Albumin. Anal Chem 77:1345–1353

    Article  PubMed  CAS  Google Scholar 

  4. Pasquali F, Manfreda G (2007) Mutant prevention concentration of ciprofloxacin and enrofloxacin against Escherichia coli, Salmonella Typhimurium and Pseudomonas aeruginosa. Vet Microbiol 119:304–310

    Article  PubMed  CAS  Google Scholar 

  5. e Souza MJ, Bittencourt CF, Morsch LM (2002) LC determination of enrofloxacin. J Pharm Biomed Anal 28:1197–1199

    Article  Google Scholar 

  6. Boothe DM (1994) Enrofloxacin revisited. Vet Med 89:744–753

    Google Scholar 

  7. e Souza MJ, Bittencourt CF, e Souza Fillho PS (2004) Microbiological assay for enrofloxacin injection. Int J Pharm 271:287–291

    Article  PubMed  CAS  Google Scholar 

  8. Tarushi A, Psomas G, Raptopoulou CP, Psycharis V, Kessissoglou DP (2009) Structure and DNA-binding properties of bis(quinolonato)bis(pyridine)zinc(II) complexes. Polyhedron 28:3272–3278

    Article  CAS  Google Scholar 

  9. Efthimiadou EK, Katsaros N, Karaliota A, Psomas G (2007) Synthesis, characterization, antibacterial activity, and interaction with DNA of the vanadyl-enrofloxacin complex. Bioorg Med Chem Lett 17:1238–1242

    Article  PubMed  CAS  Google Scholar 

  10. Zhu WZ, Lin QY, Lu M, Hu RD, Zheng XL, Cheng JP, Wang YY (2009) Synthesis, Characterization, DNA-Binding and Antiproliferative Activity of Nd(III) Complexes With N-(Nitrogen Heterocyclic) Norcantharidin Acylamide Acid. J Fluoresc 19:857–866

    Article  PubMed  CAS  Google Scholar 

  11. Komiyama M, Takeda N, Shigekawa H (1999) Hydrolysis of DNA and RNA by lanthanide ions: mechanistic studies leading to new applications. Chem Comm 16:1443–1451

    Article  Google Scholar 

  12. Zhang XJ, Xing YH, Han J, Zeng XQ, Ge MF, Niu SY (2008) A Series of Novel Ln-Succinate-Oxalate Coordination Polymers: Synthesis, Structure, Thermal Stability, and Fluorescent Properties. Cryst Growth Des 8:3680–3688

    Article  CAS  Google Scholar 

  13. Sheldrick GM (1997) SHELXS 97. Program for the Solution of Crystal Structures. University of Gottingen, Germany

    Google Scholar 

  14. Sheldrick GM (1997) SHELXL 97. Program for the Refinement of Crystal Structures. University of Gottingen, Germany

    Google Scholar 

  15. Deacon GB, Phillips RJ (1980) Relationships between the carbon-oxygen stretching frequencies of carboxylato complexes and the type of carboxylate coordination. Coord Chem Rev 33:227–250

    Article  CAS  Google Scholar 

  16. Zhang F, Zhang QQ, Wang WG, Wang XL (2006) Synthesis and DNA binding studies by spectroscopic and PARAFAC methods of a ternary copper(II) complex. J Photochem Photobiol A 184:241–249

    Article  CAS  Google Scholar 

  17. Neogi S, Bharadwaj PK (2006) Metal-organic frameworks of lanthanide (III) ions with a podand bearing terminal carboxylates: Identification of water clusters of different nuclearity. Polyhedron 25:1491–1497

    Article  CAS  Google Scholar 

  18. Thirumurugan A, Natarajan S (2005) Hydrothermal synthesis, structure and luminescent properties of one-dimensional lanthanide benzenedicarboxylates, [M(NO3)M2(C12H8N2)2][(C8H4O4)4]·H2O, (M = La, Pr), possessing infinite M–O–M linkages. J Mater Chem 15:4588–4594

    Article  CAS  Google Scholar 

  19. Hu DX, Luo F, Che YX, Zheng JM (2007) Construction of Lanthanide Metal—Organic Frameworks by Flexible Aliphatic Dicarboxylate Ligands Plus a Rigid m-Phthalic Acid Ligand. Cryst Growth Des 7:1733–1737

    Article  CAS  Google Scholar 

  20. Zhang GQ, Yang GQ, Ma JS (2006) Hydrothermal Syntheses and Characterization of Novel 3D Open-Framework and 2D Grid Lanthanide Fumarates: Ln2(fum)3(H2fum)(H2O)2 (Ln = Ce or Nd), [Sm2(fum)3(H2O)4](H2O)3, and [Yb2(fum)3(H2O)4](H2O)2. Cryst Growth Des 6:933–939

    Article  CAS  Google Scholar 

  21. Song YS, Yan B, Weng LH (2007) Four distinctive 1-D lanthanide carboxylate coordination polymers: Synthesis, crystal structures and spectral properties. Polyhedron 26:4591–4601

    Article  CAS  Google Scholar 

  22. Shen XC, Yuan Q, Liang H, Yan HG, He XW (2003) Hysteresis effects of the interaction between serum albumins and silver nanoparticles. Sci China B 46:387–398

    Article  CAS  Google Scholar 

  23. Hu YJ, Liu Y, Pi ZB, Qu SS (2005) Interaction of cromolyn sodium with human serum albumin: A fluorescence quenching study. Bioorg Med Chem 13:6609–6614

    Article  PubMed  CAS  Google Scholar 

  24. Ashoka S, Seetharamappa J, Kandagal PB, Shaikh SMT (2006) Investigation of the interaction between trazodone hydrochloride and bovine serum albumin. J Lumin 121:179–186

    Article  CAS  Google Scholar 

  25. Xiao JB, Wei XL, Wang YF, Liu CX (2009) Fluorescence resonance energy-transfer affects the determination of the affinity between ligand and proteins obtained by fluorescence quenching method. Spectrochim Acta A 74:977–982

    Article  Google Scholar 

  26. Lakow JR, Weber G (1973) Quenching of Fluorescence by Oxygen. A Probe for Structural Fluctuations in Macromolecules. Biochem 12:4161–4170

    Article  Google Scholar 

  27. Jiang CQ, Gao MX, He JX (2002) Study of the interaction between terazosin and serum albumin Synchronous fluorescence determination of terazosin. Anal Chim Acta 452:185–189

    Article  CAS  Google Scholar 

  28. Li GZ, Liu YM, Guo XY, Wang JJ (2006) Study on the Interaction between Bovine Serum Albumins and Topotecan Hydrochloride or I rinotecan Hydrochloride. Acta Chim Sinica 64:679–685

    CAS  Google Scholar 

  29. Kragh-Hansen U (1981) Molecular Aspects of Ligand Binding to Serum Albumin. Pharmacol Rev 33:17–53

    PubMed  CAS  Google Scholar 

  30. Xie MX, Xu XY, Wang YD, Liu Y (2005) Spectroscopic Investigation of the Interaction between 2, 3-Dihydro-4’, 5, 7-trihydroxyflavone and Human Serum Albumin. Acta Chim Sinica 63:2055–2062

    CAS  Google Scholar 

  31. Kang YZ, Shen HB, Luo YQ, Yang HF, Shao L (2002) Spectral Study on the Interaction of Rare Earth Ions with BSA. Chin Rare Earths chinese 23:22–25

    Google Scholar 

  32. Wang CX, Yan FF, Zhang YX, Ye L (2007) Spectroscopic investigation of the interaction between rifabutin and bovine serum albumin. J Photochem Photobiol A 192:23–28

    Article  CAS  Google Scholar 

  33. Förster T, Sinanoglu O (1996) Modern quantum chemistry, vol 3. Academic, New York

    Google Scholar 

  34. Yang J, Jing ZH, Jie JJ, Guo P (2009) Fluorescence spectroscopy study on the interaction between Gossypol and bovine serum albumin. J Mol Struct 920:227–230

    Article  CAS  Google Scholar 

  35. Liu JQ, Tian JN, Zhang JY, Hu ZD, Chen XG (2003) Interaction of magnolol with bovine serum albumin: a fluorescence-quenching study. Anal Bioanal Chem 376:864–867

    Article  PubMed  CAS  Google Scholar 

  36. Zhang ZQ, Liang GX (2005) Flow injection on-line oxidizing fluorometry coupled to dialysis sampling for the study of carbamazepine–protein binding. Anal Chim Acta 536:145–151

    Article  CAS  Google Scholar 

  37. Peters T (1985) Serum albumin. Adv Protein Chem 37:161–245

    Article  PubMed  CAS  Google Scholar 

  38. Zhang GW, Wang AP, Jiang T, Guo JB (2008) Interaction of the irisflorentin with bovine serum albumin: A fluorescence quenching study. J Mol Struct 891:93–97

    Article  CAS  Google Scholar 

  39. He W, Li Y, Xue C, Hu Z, Chen XG, Sheng FL (2005) Effect of Chinese medicine alpinetin on the structure of human serum albumin. Bioorg Med Chem 13:1837–1845

    Article  PubMed  CAS  Google Scholar 

  40. Wang YQ, Zhang HM, Zhang GC, Zhou QH, Fei ZH, Liu ZT, Li ZX (2008) Fluorescence spectroscopic investigation of the interaction between benzidine and bovine hemoglobin. J Mol Struct 886:77–84

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work received financial support from the Natural Science Foundation of Zhejiang Province, China (Grant No. Y407301).

Author information

Authors and Affiliations

  1. Zhejiang Key Laboratory for Reaction Chemistry on Solid Surfaces, Jinhua, 321004, China

    Yan-Jun Wang, Rui-Ding Hu & Qiu-Yue Lin

  2. College of Chemical and Life Science, Zhejiang Normal University, Jinhua, 321004, China

    Yan-Jun Wang, Dong-Hua Jiang, Ping-Hua Zhang, Qiu-Yue Lin & Yun-Yun Wang

Authors
  1. Yan-Jun Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Rui-Ding Hu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Dong-Hua Jiang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Ping-Hua Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Qiu-Yue Lin
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Yun-Yun Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Qiu-Yue Lin.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Wang, YJ., Hu, RD., Jiang, DH. et al. Synthesis, Crystal Structure, Interaction with BSA and Antibacterial Activity of La(III) and Sm(III) Complexes with Enrofloxacin. J Fluoresc 21, 813–823 (2011). https://doi.org/10.1007/s10895-010-0775-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10895-010-0775-1

Keywords

Search

Navigation