Skip to main content

Advertisement

SpringerLink
Log in

Fate of antibacterial spiramycin in river waters

  • Original Paper
  • Published:
Analytical and Bioanalytical Chemistry Aims and scope Submit manuscript

Abstract

Spiramycin, a widely used veterinary macrolide antibiotic, was found at traceable levels (nanograms per litre range) in Po River water (N-Italy). The aqueous environmental fate of this antibiotic compound was studied through drug decomposition, the identification of the main and secondary transformation products (TPs), assessment of mineralisation and the investigation of drug TPs toxicity. Initially, laboratory experiments were performed, with the aim of stimulating the antibacterial transformation processes followed in aquatic systems. The TPs were identified through the employment of the liquid chromatography (LC)-mass spectrometry technique. Under illumination, spiramycin degraded rapidly and transformed into numerous organic (intermediate) compounds, of which 11 could be identified, formed through five initial transformation routes. These laboratory simulation experiments were verified in situ to check the mechanism previously supposed. Po River water was sampled and analysed (by LC-high-resolution mass spectrometry) at eight sampling points. Among the previously identified TPs, five of them were also found in the river water. Three of them seem to be formed through a direct photolysis process, while the other two are formed through indirect photolysis processes mediated by natural photo sensitisers. The transformation occurring in the aquatic system involved hydroxylation, demethylation and the detachment of forosamine or mycarose sugars. Toxicity assays using Vibrio fischeri proved that even if spiramycin did not exhibit toxicity, its transformation proceeded through the formation of toxic products.

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
Scheme 1
Fig. 2
Fig. 3
Scheme 2
Fig. 4
Fig. 5
Fig. 6
Fig. 7

Similar content being viewed by others

References

  1. Zwiener C (2007) Occurrence and analysis of pharmaceuticals and their transformation products in drinking water treatment. Anal Bioanal Chem 387:1159–1162

    Article  CAS  Google Scholar 

  2. Khetan SK, Collins TJ (2007) Human pharmaceuticals in the aquatic environment: a challenge to green chemistry. Chem Rev 107:2319–2364

    Article  CAS  Google Scholar 

  3. Barceló D, Petrovic M (2007) Pharmaceuticals and personal care products (PPCPs) in the environment Anal. Bioanal Chem 387:1141–1142

    Article  Google Scholar 

  4. Ellis JB (2006) Pharmaceutical and personal care products (PPCPs) in urban receiving waters. Environ Pollution 144(1):184–189

    Article  CAS  Google Scholar 

  5. Heberer T (2002) Occurrence, fate, and removal of pharmaceutical residues in the aquatic environment: a review of recent research data. Toxicol Lett 131:5–17

    Article  CAS  Google Scholar 

  6. Costanzo SD, Murby J, Bates J (2005) Ecosystem response to antibiotics entering the aquatic environment. Mar Pollut Bull 51(1–4):218–223

    Article  CAS  Google Scholar 

  7. Hao C, Zhao X, Yang P (2007) GC-MS and HPLC-MS analysis of bioactive pharmaceuticals and personal-care products in environmental matrices TrAC. Trends Anal Chem 26(6):569–580

    Article  CAS  Google Scholar 

  8. Rang HP, Dale MM, Ritter JM (2003) Pharmacology, 4th edn. Churchill Livingstone, Edinburgh

    Google Scholar 

  9. Abu-Gharbieh E, Vasina V, Poluzzi E, De Ponti F (2004) Antibacterial macrolides: a drug class with a complex pharmacological profile. Pharm Res 50(3):211–222

    Article  CAS  Google Scholar 

  10. Collignon P (1999) Vancomycin-resistant enterococci and use of avoparcin in animal feed: is there a link? Med J Australia 171:144–146

    CAS  Google Scholar 

  11. González de la Huebra MJ, Vincent U, Bordin G, Rodrıguez AR (2004) Characterisation of dirithromycin and spiramycin using high performance liquid chromatography and direct infusion mass spectrometry. Anal Chim Acta 503(2):247–256

    Article  Google Scholar 

  12. Sagan C, Salvador A, Dubreuil D, Poulet PP, Duffault D, Brumpt I (2005) Simultaneous determination of metronidazole and spiramycin I in human plasma, saliva and gingival crevicular fluid by LC-MS/MS. J Pharmac Biomed Anal 38:298–306

    Article  CAS  Google Scholar 

  13. Dubois M, Fluchard D, Sior E, Delahaut P (2001) Identification and quantification of five macrolide antibiotics in several tissues, eggs and milk by liquid chromatography-electrospray tandem mass spectrometry. J Chromat B 753:189–202

    Article  CAS  Google Scholar 

  14. Zhengqi Y, Weinberg HS (2007) Trace analysis of trimethoprim and sulfonamide, macrolide, quinolone, and tetracycline antibiotics in chlorinated drinking water using liquid chromatography electrospray tandem mass spectrometry. Anal Chem 79(3):1135–1144

    Article  Google Scholar 

  15. Kees F, Spangler S, Wellenhofer M (1998) Determination of macrolides in biological matrices by high-performance liquid chromatography with electrochemical detection. J Chromatogr A 812(1–2):287–293

    Article  CAS  Google Scholar 

  16. Castiglioni S, Fanelli R, Calamari D, Bagnati R, Zuccato E (2004) Methodological approaches for studying pharmaceuticals in the environment by comparing predicted and measured concentrations in River Po. Italy Regul Toxicol Pharmacol 39(1):25–32

    Article  CAS  Google Scholar 

  17. Zuccato E, Castiglioni S, Fanelli R, Reitano G, Bagnati R, Chiabrando C, Pomati F, Rossetti C, Calamari D (2006) Pharmaceutical in the environment in Italy: causes, occurrence, effects and control. Environ Sci Pollut Res 13(1):15–21

    Article  CAS  Google Scholar 

  18. Zuccato E, Calamari D, Natangelo M, Fanelli R (2000) Presence of therapeutic drugs in the environment. Lancet 355(9217):1789–1790

    Article  CAS  Google Scholar 

  19. Richardson MA, Kuhstoss S, Huber MLB, Ford L, Godfrey O, Turner JR, Nagaraja Rao R (1990) Cloning of spiramycin biosynthetic genes and their use in constructing streptomyces ambofaciens mutants defective in spiramycin biosynthesis. J Bacteriol 172(7):3790–3798

    CAS  Google Scholar 

  20. Ikeda OS, Kitao H (1979) Isolation and properties of spiramycin I 3-hydroxil acylase from streptomyces ambofaciens. J Biochem 86:1753–1758

    Google Scholar 

  21. Cherlet M, De Baere S, Croubels S, De Backer P (2002) Quantitation of tylosin in swine tissues by liquid chromatography combined with electrospray ionization mass spectrometry. Anal Chim Acta 473(1–2):167–175

    Article  CAS  Google Scholar 

  22. Mourier P, Brun A (1997) Study of the metabolism of spiramycin in pig liver. J Chromatography B 704:197–205

    Article  CAS  Google Scholar 

  23. Sakkas VA, Calza P, Medana C, Villioti AE, Baiocchi C, Pelizzetti E, Albanis T (2007) Heterogeneous photocatalytic degradation of the pharmaceutical agent salbutamol in aqueous titanium dioxide suspensions. Appl Catal B: Environ 77:135–144

    Article  CAS  Google Scholar 

  24. Molinari R, Pirillo F, Loddo V, Palmisano L (2006) Heterogeneous photocatalytic degradation of pharmaceuticals in water by using polycrystalline TiO2 and a nanofiltration membrane reactor. Catal Today 118:205–213

    Article  CAS  Google Scholar 

  25. Doll TE, Frimmel FH (2005) Removal of selected persistent organic pollutants by heterogeneous photocatalysis in water. Catal Today 101:195–202

    Article  CAS  Google Scholar 

  26. Calza P, Sakkas VA, Medana C, Baiocchi C, Dimou A, Pelizzetti E, Albanis T (2006) Photocatalytic degradation study of diclofenac over aqueous TiO2 suspensions. Appl Catal B: Environ 67:197

    Article  CAS  Google Scholar 

  27. Zwiener C, Frimmel FH (2000) Oxidative treatment of pharmaceuticals in water. Water Res 34:1881–1885

    Article  CAS  Google Scholar 

  28. Calza P, Medana C, Pazzi M, Baiocchi C, Pelizzetti E (2004) The photocatalytic process as a tool to identify metabolitic products formed from dopant substances: the case of buspirone. J Pharm Biomed Anal 35:9–19

    Article  CAS  Google Scholar 

  29. Marsh JR, Weiss PJ (1967) Solubility of antibiotics in twenty-six solvents. III. J. A.O.A.C 50:457–462

    CAS  Google Scholar 

  30. Nohara K, Hidaka H, Pelizzetti E, Serpone N (1997) Processes of formation of NH +4 and NO −3 ions during the photocatalyzed oxidation of N-containing compounds at the titania/water interface. J Photochem Photobiol A Chem 102(2–3):265–272

    Article  CAS  Google Scholar 

  31. Ramu K, Shringarpure S, Williamson JS (1995) A solution conformation analysis of forocidins-I and isoforocidins-I using NMR and molecular modeling. Pharm Res 12:621–629

    Article  CAS  Google Scholar 

  32. Boule P, Bahenmann DW, Robertson DW, Robertson PKJ (2005) The handbook of environmental chemistry. Springer, Berlin

    Google Scholar 

  33. Parvez S, Venkataraman C, Mukherji S (2006) A review on advantages of implementing luminescence inhibition test (Vibrio fischeri) for acute toxicity prediction of chemicals. Environ Int 32:265–268

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Analytical Chemistry and NIS Centre of Excellence, University of Turin, via P. Giuria 5, 10125, Turin, Italy

    P. Calza, S. Marchisio, C. Medana & C. Baiocchi

Authors
  1. P. Calza
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. Marchisio
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. C. Medana
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. C. Baiocchi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to P. Calza.

Electronic supplementary materials

Below is the link to the electronic supplementary material.

ESM 1

(PDF 525 kb)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Calza, P., Marchisio, S., Medana, C. et al. Fate of antibacterial spiramycin in river waters. Anal Bioanal Chem 396, 1539–1550 (2010). https://doi.org/10.1007/s00216-009-3318-3

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00216-009-3318-3

Keywords

Search

Navigation