Biotic transformation products of sulfonamides in environmental water samples: High-resolution mass spectrometry-based tentative identification by a suspect screening approach

Carmela Maria Montone; Benedetta Giannelli Moneta; Sara Elsa Aita; Anna Laura Capriotti; Andrea Cerrato; Aldo Laganà; Angela Marchetti; Susy Piovesana; Marianna Villano; Chiara Cavaliere

doi:10.1016/j.jpba.2023.115292

Biotic transformation products of sulfonamides in environmental water samples: High-resolution mass spectrometry-based tentative identification by a suspect screening approach

J Pharm Biomed Anal. 2023 Apr 1:227:115292. doi: 10.1016/j.jpba.2023.115292. Epub 2023 Feb 13.

Authors

Affiliations

¹ Department of Chemistry, Sapienza University of Rome, p.le Aldo Moro 5, 00185 Rome, Italy. Electronic address: carmelamaria.montone@uniroma1.it.
² Department of Chemistry, Sapienza University of Rome, p.le Aldo Moro 5, 00185 Rome, Italy. Electronic address: benedetta.giannellimoneta@uniroma1.it.
³ Department of Chemistry, Sapienza University of Rome, p.le Aldo Moro 5, 00185 Rome, Italy. Electronic address: saraelsa.aita@uniroma1.it.
⁴ Department of Chemistry, Sapienza University of Rome, p.le Aldo Moro 5, 00185 Rome, Italy. Electronic address: annalaura.capriotti@uniroma1.it.
⁵ Department of Chemistry, Sapienza University of Rome, p.le Aldo Moro 5, 00185 Rome, Italy. Electronic address: andrea.cerrato@uniroma1.it.
⁶ Department of Chemistry, Sapienza University of Rome, p.le Aldo Moro 5, 00185 Rome, Italy. Electronic address: aldo.lagana@uniroma1.it.
⁷ Department of Chemistry, Sapienza University of Rome, p.le Aldo Moro 5, 00185 Rome, Italy. Electronic address: angela.marchetti@uniroma1.it.
⁸ Department of Chemistry, Sapienza University of Rome, p.le Aldo Moro 5, 00185 Rome, Italy. Electronic address: susy.piovesana@uniroma1.it.
⁹ Department of Chemistry, Sapienza University of Rome, p.le Aldo Moro 5, 00185 Rome, Italy. Electronic address: marianna.villano@uniroma1.it.
¹⁰ Department of Chemistry, Sapienza University of Rome, p.le Aldo Moro 5, 00185 Rome, Italy. Electronic address: chiara.cavaliere@uniroma1.it.

PMID: 36804291
DOI: 10.1016/j.jpba.2023.115292

Abstract

The presence of pharmaceuticals in the aquatic environment is mainly due to their release from the effluents of the wastewater treatment plants (WWTPs), which are unable to completely remove them and their transformation products (TPs). Sulfonamides (SAs) are a synthetic antibacterial class used for the treatment of both human and animal infections; they have often been reported in surface water, thus contributing to the antibiotic resistance emergency. Monitoring SA TPs should be important as well because they could still exert some pharmaceutical activity; however, many TPs are still unknown since several transformation processes are possible (e. g. human and animal metabolism, WWTP activities, environmental factors etc.). In this work, three of the most used SAs, i.e., sulfamethoxazole (SMX), sulfapyridine (SPY), and sulfadiazine (SDZ), were incubated for 20 days in a batch reactor with activated sludge under controlled conditions. Then, the water sample was extracted and analyzed by ultra-high performance liquid chromatography-high resolution mass spectrometry in the data dependent acquisition (DDA) mode. Starting from the literature data, the possible transformation pathways were studied, and for each SA, a list of TPs was hypothesized and used for the identification. The raw data files were processed with Compound Discoverer, and 44 TPs (18, 13, and 13 TPs for SMX, SPY, and SDZ, respectively), including multiple TPs, were manually validated. To overcome the limitation of the DDA, the identified TPs were used in an inclusion list to analyze WWTP samples by a suspect screening approach. In this way, 4 SMX TPs and 5 SPY TPs were tentatively identified together with their parent compounds. Among these TPs, 5 of 9 were acetylated forms, in agreement with previous literature reporting that acetylation is the predominant SA transformation.

Keywords: Activated sludge; Antibiotics; Compound discoverer; Emerging contaminants; Pharmaceutical metabolites; Wastewater treatment plants.

MeSH terms

Anti-Bacterial Agents / analysis
Humans
Mass Spectrometry
Sulfadiazine
Sulfamethoxazole
Sulfanilamide
Sulfapyridine
Sulfonamides* / chemistry
Water
Water Pollutants, Chemical* / analysis

Substances

Sulfonamides
Water
Water Pollutants, Chemical
Anti-Bacterial Agents
Sulfanilamide
Sulfamethoxazole
Sulfapyridine
Sulfadiazine