Design, synthesis, and evaluation of efflux substrate–metal chelator conjugates as potential antimicrobial agents

Zhang, Yanling; Ballard, C. Eric; Zheng, Shilong; Gao, Xingming; Ko, Ko-Chun; Yang, Hanfang; Brandt, Gary E. L.; Lou, Xinhui; Tai, Phang C.; Lu, Chung‐Dar; Wang, Binghe

doi:10.1016/j.bmcl.2006.10.094

Cited by 23 publications

(16 citation statements)

References 37 publications

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“…Selected 10-carbamoylalkylphenothiazines 5, possessing metal chelating groups (tertiary amines or aza-4-crown-14), showed significant activities against Gram-positive Bacillus subtilis with MIC's in the range of 7.8e30 mg/ml, higher than for the parent phenothiazine 1 or ampicillin. The authors suggested that the chelator-based agents were responsible for disruption of the metalion homeostasis in bacteria which can lead to cell stress or death [15]. Substituted 1,2,4-triazolylmethyl derivatives of phenothiazines 6 exhibited antibacterial activity against B. subtilis, Escherichia coli, Kliebsiella pneumonia and Salmonella typhimurium, some of them (when Z ¼ 2-, 4-Cl, 3-, 4-NO 2 , 3-, 4-Br) comparable with a reference drug streptomycin at 50 and 100 ppm concentrations.…”

Section: Antibacterial and Antifungal Activitiesmentioning

confidence: 99%

Recent progress in biological activities of synthesized phenothiazines

Pluta¹,

Morak‐Młodawska²,

Jeleń³

2011

European Journal of Medicinal Chemistry

264

122

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Section: Antibacterial and Antifungal Activitiesmentioning

confidence: 99%

Recent progress in biological activities of synthesized phenothiazines

Pluta¹,

Morak‐Młodawska²,

Jeleń³

2011

European Journal of Medicinal Chemistry

264

122

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“…Metal chelators can be used to that effect as their biostatic activity upon microorganisms has long been known. Their mode of action is thought to be the imposition of metal starvation on the microorganisms [8][9][10].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel Iron(III) chelators based on triaza macrocycle backbone and 1-hydroxy-2(H)-pyridin-2-one coordinating groups and their evaluation as antimicrobial agents

Workman

Hunter

Dover

et al. 2016

Journal of Inorganic Biochemistry

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Several novel chelators based on 1-hydroxy-2(1H)-pyridinone coordinating groups decorating a triaza macrocyclic backbone scaffold were synthesised as potential powerful Fe(3+) chelators capable of competing with bacterial siderophores. In particular, a novel chloromethyl derivative of 1-hydroxy-2(1H)-pyridinone exploiting a novel protective group for this family of coordinating groups was developed. These are the first examples of hexadentate chelators based on 1-hydroxy-2(1H)-pyridinone to be shown to have a biostatic activity against a range of pathogenic bacteria. Their efficacy as biostatic agents was assessed revealing that minor variations in the structure of the chelator can affect efficacy profoundly. The minimal inhibitory concentrations of our best tested novel chelators approach or are comparable to those for 1,4,7-tris(3-hydroxy-6-methyl-2-pyridylmethyl)-1,4,7-triazacyclononane, the best Fe(3+) chelator known to date. The retarding effect these chelators have on microbial growth suggests that they could have a potential application as a co-active alongside antibiotics in the fight against infections.

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“…These cyclophanes were obtained in poor yields (3-5 %) by a Suzuki-Miyaura cross coupling reaction Various other macrocycles with phenothiazine rings in the pendant arms, which revealed remarkable antibacterial activity, were also reported [34,58].…”

Section: Macrocycles With Phenothiazine Unitsmentioning

confidence: 95%

Macrocycles embedding phenothiazine or similar nitrogen and/or sulphur containing heterocycles

Rednic

Hădade

Bogdan

et al. 2014

J Incl Phenom Macrocycl Chem

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Macrocycles emerged as an important class of useful compounds with multiple applications ranging from selective complexation of different anions, cations or neutral molecules to the development of new sensors, materials with improved properties and biologically active compounds. In this review we focus our discussion on the synthesis and structural analysis of macrocycles containing dibenzoheterocycles with sulphur and/or nitrogen atoms in the central six-membered ring (i.e. 10H-phenothiazine, 9,10-dihydroacridine or acridane, acridone, thianthrene, phenoxathiine, acridine, phenazine). We further highlight selected application of these compounds as host molecules, DNA intercalating agents or enzyme inhibitors.

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Design, synthesis, and evaluation of efflux substrate–metal chelator conjugates as potential antimicrobial agents

Cited by 23 publications

References 37 publications

Recent progress in biological activities of synthesized phenothiazines

Recent progress in biological activities of synthesized phenothiazines

Synthesis of novel Iron(III) chelators based on triaza macrocycle backbone and 1-hydroxy-2(H)-pyridin-2-one coordinating groups and their evaluation as antimicrobial agents

Macrocycles embedding phenothiazine or similar nitrogen and/or sulphur containing heterocycles

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