Phototransformation of amlodipine: degradation kinetics and identification of its photoproducts

PLoS One. 2014 Oct 3;9(10):e109206. doi: 10.1371/journal.pone.0109206. eCollection 2014.

Abstract

Nowadays, monitoring focuses on the primary compounds and does not include degradation products formed during various biological and chemical processes. Transformation products may have the same effects to human health and the environment or sometimes they can be more toxic than the parent compound. Unfortunately, knowledge about the formation of degradation products is still limited, however, can be very important for the environmental risk assessment. Firstly, the photodegradation kinetic of amlodipine was investigated in two experimental conditions: during the exposure to solar radiation and during the exposure to the light emitted by the xenon lamp. In all cases degradation of amlodipine followed a pseudo-first-order kinetics. In the next step, identification of transformation products of amlodipine formed during the exposure to xenon lamp irradiation was performed using ultra high performance liquid chromatography quadrupole time-of-flight mass spectrometry (UHPLC-QTOF-MS). As a result sixteen photoproducts were identified, their structures were elucidated and ultimately the transformation pathway was proposed. Fifteen compounds (out of 16 photoproducts) were newly identified and reported here for the first time; some of those compounds were formed from the first photoproduct, amlodipine pyridine derivative. Several analytes were formed only in acidic or basic conditions. Furthermore, the occurrence of amlodipine and its identified degradation products was investigated in environmental waters. Only one out of 16 compounds was found in wastewater effluent. The possibility of the sorption of examined analytes to sewage sludge particles was discussed based on QSAR.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amlodipine / chemistry*
  • Chromatography, High Pressure Liquid
  • Kinetics
  • Photolysis*
  • Quantitative Structure-Activity Relationship
  • Risk Assessment
  • Rivers / chemistry*
  • Wastewater / chemistry*
  • Water Pollutants, Chemical / analysis
  • Water Pollutants, Chemical / chemistry*

Substances

  • Waste Water
  • Water Pollutants, Chemical
  • Amlodipine

Grants and funding

This scientific work (as research project no. 2012/05/N/ST4/01991) has been financially supported within the framework of a grant awarded by the Polish National Science Centre (in the years 2013–2014). AJ has been financially supported for the preparation of a doctoral dissertation (that includes the research presented in the manuscript) within the funding of a doctoral scholarship awarded by the Polish National Science Centre on the basis of the decision number 2013/08/T/ST4/00637. The authors also acknowledge Professor Adriana Zaleska for providing access to xenon lamp used during the experiments. The funders had no role in study design, data collection and analysis, decision to publish, or preparation of the manuscript.