Synthesis of Side Chain Derived Quaternary Ammonium N-Chloramines for Antibacterial Applications

doi:10.19894/j.issn.1000-0518.230394

Chinese Journal of Applied Chemistry ›› 2024, Vol. 41 ›› Issue (7): 966-975.DOI: 10.19894/j.issn.1000-0518.230394

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Synthesis of Side Chain Derived Quaternary Ammonium N-Chloramines for Antibacterial Applications

Ling-Dong LI¹^,²(), Song-Wei ZHANG², Wei-Lun ZHANG², Peng-Fei LIU², Jiang-Jiming YU², Hao ZHOU²

^1.State Key Laboratory of Fine Chemicals，Dalian University of Technology，Panjin 124221，China
^2.School of Chemical Engineering，Life and Ocean Science，Dalian University of Technology，Panjin 124221，China

Received:2023-12-19 Accepted:2024-05-15 Published:2024-07-01 Online:2024-08-03
Contact: Ling-Dong LI
About author:lild@dlut.edu.cn
Supported by:
the National Natural Science Foundation of China(41977197)

1. .pdf(1623KB)

Abstract

Abstract:

A series of side-chain derived quaternary ammonium （QA） N-chloramines （10-14） were designed and synthesized using commercial 5，5-dimethylhydantoin （DMH） as raw matesial， and the structures of precursors and corresponding N-chloramines were characterized. The antibacterial activity of chloramines 10-14 was preliminarily tested using Escherichia coli （E.coli） and Staphylococcus aureus （S.aureus） as model strains， and N-chloramine 1 as control. The results showed that antibacterial ability of 10-13 increased and then declined with the length of side chain increased. Namely， tributyl QA N-chloramine 12 with KL of 1.07±0.09 and 6.49 against S.aureus and E.coli， exhibited relatively higher antibacterial efficacy， possibly due to the preferable hydrophilic-lipophilic characteristic required for efficient contact killing. Furthermore， hydroxyethyl counterpart 14 achieved total killing of S.aureus and E.coli， demonstrating the towering antibacterial capability among N-chloramines 10-14， which may be attributed to its facile transportation across bacterial cell membrane. The series of efficacious N-chloramine disinfectants prepared in this work provide reference for the development of more efficient ionic N-chloramine antibacterial agents.

Key words: Quaternary ammonium N-chloramine, Multi-step chemical synthesis, Antibacterial ability, Hydrophilic-lipophilic balance, Side chain derivative

CLC Number:

O626.2

Ling-Dong LI, Song-Wei ZHANG, Wei-Lun ZHANG, Peng-Fei LIU, Jiang-Jiming YU, Hao ZHOU. Synthesis of Side Chain Derived Quaternary Ammonium N-Chloramines for Antibacterial Applications[J]. Chinese Journal of Applied Chemistry, 2024, 41(7): 966-975.

Figures/Tables 6

References 36

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Bacteria	Compound	c（active chloramine）/ （ mmol·L^－1）	5 min contact time		10 min contact time
Bacteria	Compound	c（active chloramine）/ （ mmol·L^－1）	KR/%	KL	KR/%	KL
S.aureus	1^a	0.56	22.61±2.22	0.11±0.01	62.33±3.32	0.42±0.04
	10a ^a	0	0	0	0	0
	10^a	0.56	25.21±1.39	0.13±0.01	63.71±1.39	0.44±0.02
	11a ^a	0	0	0	0	0
	11^a	0.56	30.47±2.77	0.16±0.01	77.29±4.99	0.64±0.10
	12a ^a	0	0	0	0	0
	12^a	0.56	36.56±4.99	0.20±0.06	91.41±1.94	1.07±0.09
	13a ^a	0	0	0	0	0
	13^a	0.56	36.33±1.11	0.19±0.01	69.53±2.49	0.52±0.03
	11a ^b	0	0	0	0	0
	11^b	0.56	20.5±0.07	0.10±0.01	70.86±1.20	0.54±0.02
	14a ^b	0	0	0	0	0
	14^b	0.56	100	6.92	100	6.92
E.coli	1^a	0.56	48.37±1.96	0.29±0.02	84.97±3.27	0.82±0.09
	10a ^a	0	0	0	0	0
	10^a	0.56	60.13±5.23	0.40±0.04	96.73±0.65	1.49±0.08
	11a ^a	0	0	0	0	0
	11^a	0.56	62.09±2.61	0.42±0.03	99.35±0.65	2.18±0.00
	12a ^a	0	0	0	0	0
	12^a	0.56	66.67±3.27	0.48±0.04	100±0.00	6.49
	13a ^a	0	0	0	0	0
	13^a	0.56	57.52±3.92	0.37±0.04	94.12±1.31	1.23±0.09
	11a ^b	0	0	0	0	0
	11^b	0.56	54.1±2.04	0.34±0.02	99.49±0.51	2.29±0.00
	14a ^b	0	0	0	0	0
	14^b	0.56	100	6.59	100	6.59

Bacteria	Compound	c（active chloramine）/ （ mmol·L^－1）	5 min contact time		10 min contact time
Bacteria	Compound	c（active chloramine）/ （ mmol·L^－1）	KR/%	KL	KR/%	KL
S.aureus	1^a	0.56	22.61±2.22	0.11±0.01	62.33±3.32	0.42±0.04
	10a ^a	0	0	0	0	0
	10^a	0.56	25.21±1.39	0.13±0.01	63.71±1.39	0.44±0.02
	11a ^a	0	0	0	0	0
	11^a	0.56	30.47±2.77	0.16±0.01	77.29±4.99	0.64±0.10
	12a ^a	0	0	0	0	0
	12^a	0.56	36.56±4.99	0.20±0.06	91.41±1.94	1.07±0.09
	13a ^a	0	0	0	0	0
	13^a	0.56	36.33±1.11	0.19±0.01	69.53±2.49	0.52±0.03
	11a ^b	0	0	0	0	0
	11^b	0.56	20.5±0.07	0.10±0.01	70.86±1.20	0.54±0.02
	14a ^b	0	0	0	0	0
	14^b	0.56	100	6.92	100	6.92
E.coli	1^a	0.56	48.37±1.96	0.29±0.02	84.97±3.27	0.82±0.09
	10a ^a	0	0	0	0	0
	10^a	0.56	60.13±5.23	0.40±0.04	96.73±0.65	1.49±0.08
	11a ^a	0	0	0	0	0
	11^a	0.56	62.09±2.61	0.42±0.03	99.35±0.65	2.18±0.00
	12a ^a	0	0	0	0	0
	12^a	0.56	66.67±3.27	0.48±0.04	100±0.00	6.49
	13a ^a	0	0	0	0	0
	13^a	0.56	57.52±3.92	0.37±0.04	94.12±1.31	1.23±0.09
	11a ^b	0	0	0	0	0
	11^b	0.56	54.1±2.04	0.34±0.02	99.49±0.51	2.29±0.00
	14a ^b	0	0	0	0	0
	14^b	0.56	100	6.59	100	6.59

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Synthesis of Side Chain Derived Quaternary Ammonium N-Chloramines for Antibacterial Applications

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