PMID- 34288499 OWN - NLM STAT- MEDLINE DCOM- 20220223 LR - 20231108 IS - 1860-7187 (Electronic) IS - 1860-7179 (Print) IS - 1860-7179 (Linking) VI - 16 IP - 20 DP - 2021 Oct 15 TI - Synthesis and Antimicrobial Evaluation of Bis-morpholine Triazine Quaternary Ammonium Salts. PG - 3172-3176 LID - 10.1002/cmdc.202100409 [doi] AB - Efficient, environmentally and economically sustainable, and nontoxic antibacterial products are of global relevance in the fight against microorganism contamination. In this work, an easy and straightforward method for the synthesis of bis-morpholino triazine quaternary ammonium salts (bis-mTQAS) is reported, starting from 2,4,6-trichloro-1,3,5-triazine or 2,4-dichloro-6-methoxy-1,3,5-triazine and various N-alkylmorpholines. Bis-mTQAS were tested as antimicrobials against Gram-negative and Gram-positive bacterial strains. The best-performing bis-mTQAS were found to achieve total disinfection against Staphylococcus aureus ATCC 25923 and Escherichia coli ATCC 25922 at 50 and 400 mug/mL, respectively. Distinctively, bis-mTQAS with the highest antimicrobial efficiency had lowest cytotoxicity. CI - (c) 2021 The Authors. ChemMedChem published by Wiley-VCH GmbH. FAU - Morandini, Andrea AU - Morandini A AD - Dipartimento di Scienze Molecolari e Nanosistemi, Universita Ca' Foscari di Venezia, Via Torino 155, 30172, Venezia Mestre, Italy. FAU - Leonetti, Benedetta AU - Leonetti B AD - Brenta S.r.l. - Nine trees group, Viale Milano 26, 36075, Montecchio Maggiore, Vicenza, Italy. FAU - Riello, Pietro AU - Riello P AD - Dipartimento di Scienze Molecolari e Nanosistemi, Universita Ca' Foscari di Venezia, Via Torino 155, 30172, Venezia Mestre, Italy. AD - European Centre for Living Technology (ECLT) Ca' Bottacin, Dorsoduro 3911, 30123, Venice, Italy. FAU - Sole, Roberto AU - Sole R AD - Dipartimento di Scienze Molecolari e Nanosistemi, Universita Ca' Foscari di Venezia, Via Torino 155, 30172, Venezia Mestre, Italy. AD - CIRCC, Via C. Ulpiani 27, 70126, Bari, Italy. FAU - Gatto, Vanessa AU - Gatto V AD - Dipartimento di Scienze Molecolari e Nanosistemi, Universita Ca' Foscari di Venezia, Via Torino 155, 30172, Venezia Mestre, Italy. AD - Crossing S.r.l., Viale della Repubblica 193/b, 31100, Treviso, Italy. FAU - Caligiuri, Isabella AU - Caligiuri I AD - Pathology Unit, Centro di Riferimento Oncologico (CRO) IRCCS, Via F. Gallini 2, 33081, Aviano, Italy. FAU - Rizzolio, Flavio AU - Rizzolio F AD - Dipartimento di Scienze Molecolari e Nanosistemi, Universita Ca' Foscari di Venezia, Via Torino 155, 30172, Venezia Mestre, Italy. AD - Pathology Unit, Centro di Riferimento Oncologico (CRO) IRCCS, Via F. Gallini 2, 33081, Aviano, Italy. FAU - Beghetto, Valentina AU - Beghetto V AUID- ORCID: 0000-0001-8799-210X AD - Dipartimento di Scienze Molecolari e Nanosistemi, Universita Ca' Foscari di Venezia, Via Torino 155, 30172, Venezia Mestre, Italy. AD - Crossing S.r.l., Viale della Repubblica 193/b, 31100, Treviso, Italy. LA - eng PT - Journal Article DEP - 20210729 PL - Germany TA - ChemMedChem JT - ChemMedChem JID - 101259013 RN - 0 (Anti-Bacterial Agents) RN - 0 (Morpholines) RN - 0 (Quaternary Ammonium Compounds) RN - 0 (Salts) RN - 0 (Triazines) SB - IM MH - Anti-Bacterial Agents/chemical synthesis/chemistry/*pharmacology MH - Dose-Response Relationship, Drug MH - Escherichia coli/*drug effects MH - Microbial Sensitivity Tests MH - Molecular Structure MH - Morpholines/chemistry/*pharmacology MH - Quaternary Ammonium Compounds/chemistry/*pharmacology MH - Salts/chemistry/pharmacology MH - Staphylococcus aureus/*drug effects MH - Structure-Activity Relationship MH - Triazines/chemistry/*pharmacology PMC - PMC8596621 OTO - NOTNLM OT - QAS OT - antimicrobial agents OT - low toxicity antimicrobials OT - triazine quaternary ammonium salts COIS- The authors declare no conflict of interest. EDAT- 2021/07/22 06:00 MHDA- 2022/02/24 06:00 PMCR- 2021/11/17 CRDT- 2021/07/21 13:49 PHST- 2021/07/18 00:00 [revised] PHST- 2021/06/07 00:00 [received] PHST- 2021/07/22 06:00 [pubmed] PHST- 2022/02/24 06:00 [medline] PHST- 2021/07/21 13:49 [entrez] PHST- 2021/11/17 00:00 [pmc-release] AID - CMDC202100409 [pii] AID - 10.1002/cmdc.202100409 [doi] PST - ppublish SO - ChemMedChem. 2021 Oct 15;16(20):3172-3176. doi: 10.1002/cmdc.202100409. Epub 2021 Jul 29.