Antimicrobial Conjugated Oligoelectrolytes Containing Triphenylphosphonium Solubilizing Groups

Conjugated oligoelectrolytes (COEs) are an emerging class of amphiphilic antimicrobial compounds with a modular molecular framework suitable for simple chemical derivatization. Here, a series of COE derivatives with a stilbene‐conjugated segment and triphenylphosphonium (TPP) pendant groups was desi...

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Published inChemistry : a European journal Vol. 29; no. 26; pp. e202203803 - n/a
Main Authors Chan, Samuel J. W., Zhang, Kaixi, Zhu, Ji‐Yu, Bazan, Guillermo C.
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 08.05.2023
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Abstract Conjugated oligoelectrolytes (COEs) are an emerging class of amphiphilic antimicrobial compounds with a modular molecular framework suitable for simple chemical derivatization. Here, a series of COE derivatives with a stilbene‐conjugated segment and triphenylphosphonium (TPP) pendant groups was designed and synthesized to understand how lipophilic cationic groups impact antimicrobial activity. In vitro evaluations against ESKAPE pathogens showed broad‐spectrum activity towards multi‐drug resistant (MDR) bacteria and mycobacteria, with TPP groups enhancing antimicrobial activity towards clinically relevant Gram‐negative strains compared to their ammonium analogues. We studied the interactions of DM6P, the most active TPP‐COE compound, with various membrane assays. Treatment of bacterial cells with DM6P showed enhanced permeability of cell membranes without inducing the development of significant bacterial resistance. Moreover, DM6P eliminated 99.99 % of methicillin‐resistant Staphyloccocus aureus (MRSA) in an in vivo wound model. These results represent a promising chemical strategy for increasing the activity spectrum of membrane‐active COE antibiotics to tackle challenging drug‐resistant targets. PPh3 helps protect against pathogens: Conjugated oligoelectrolytes are a modular molecular platform for the design of novel antimicrobial agents. Substituting terminal alkylammonium cationic groups with more lipophilic triphenylphosphonium counterparts enabled bactericidal activity towards ESKAPE pathogens and clinically relevant mycobacteria. In vivo efficacy was verified in a murine wound model, at clinically relevant dosages.
AbstractList Conjugated oligoelectrolytes (COEs) are an emerging class of amphiphilic antimicrobial compounds with a modular molecular framework suitable for simple chemical derivatization. Here, a series of COE derivatives with a stilbene‐conjugated segment and triphenylphosphonium (TPP) pendant groups was designed and synthesized to understand how lipophilic cationic groups impact antimicrobial activity. In vitro evaluations against ESKAPE pathogens showed broad‐spectrum activity towards multi‐drug resistant (MDR) bacteria and mycobacteria, with TPP groups enhancing antimicrobial activity towards clinically relevant Gram‐negative strains compared to their ammonium analogues. We studied the interactions of DM6P , the most active TPP‐COE compound, with various membrane assays. Treatment of bacterial cells with DM6P showed enhanced permeability of cell membranes without inducing the development of significant bacterial resistance. Moreover, DM6P eliminated 99.99 % of methicillin‐resistant Staphyloccocus aureus (MRSA) in an in vivo wound model. These results represent a promising chemical strategy for increasing the activity spectrum of membrane‐active COE antibiotics to tackle challenging drug‐resistant targets.
Conjugated oligoelectrolytes (COEs) are an emerging class of amphiphilic antimicrobial compounds with a modular molecular framework suitable for simple chemical derivatization. Here, a series of COE derivatives with a stilbene‐conjugated segment and triphenylphosphonium (TPP) pendant groups was designed and synthesized to understand how lipophilic cationic groups impact antimicrobial activity. In vitro evaluations against ESKAPE pathogens showed broad‐spectrum activity towards multi‐drug resistant (MDR) bacteria and mycobacteria, with TPP groups enhancing antimicrobial activity towards clinically relevant Gram‐negative strains compared to their ammonium analogues. We studied the interactions of DM6P, the most active TPP‐COE compound, with various membrane assays. Treatment of bacterial cells with DM6P showed enhanced permeability of cell membranes without inducing the development of significant bacterial resistance. Moreover, DM6P eliminated 99.99 % of methicillin‐resistant Staphyloccocus aureus (MRSA) in an in vivo wound model. These results represent a promising chemical strategy for increasing the activity spectrum of membrane‐active COE antibiotics to tackle challenging drug‐resistant targets. PPh3 helps protect against pathogens: Conjugated oligoelectrolytes are a modular molecular platform for the design of novel antimicrobial agents. Substituting terminal alkylammonium cationic groups with more lipophilic triphenylphosphonium counterparts enabled bactericidal activity towards ESKAPE pathogens and clinically relevant mycobacteria. In vivo efficacy was verified in a murine wound model, at clinically relevant dosages.
Conjugated oligoelectrolytes (COEs) are an emerging class of amphiphilic antimicrobial compounds with a modular molecular framework suitable for simple chemical derivatization. Here, a series of COE derivatives with a stilbene-conjugated segment and triphenylphosphonium (TPP) pendant groups was designed and synthesized to understand how lipophilic cationic groups impact antimicrobial activity. In vitro evaluations against ESKAPE pathogens showed broad-spectrum activity towards multi-drug resistant (MDR) bacteria and mycobacteria, with TPP groups enhancing antimicrobial activity towards clinically relevant Gram-negative strains compared to their ammonium analogues. We studied the interactions of DM6P, the most active TPP-COE compound, with various membrane assays. Treatment of bacterial cells with DM6P showed enhanced permeability of cell membranes without inducing the development of significant bacterial resistance. Moreover, DM6P eliminated 99.99 % of methicillin-resistant Staphyloccocus aureus (MRSA) in an in vivo wound model. These results represent a promising chemical strategy for increasing the activity spectrum of membrane-active COE antibiotics to tackle challenging drug-resistant targets.
Author Bazan, Guillermo C.
Zhang, Kaixi
Zhu, Ji‐Yu
Chan, Samuel J. W.
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Issue 26
Keywords conjugated oligoelectrolytes
MEMBRANE PERTURBATION
DRUG DISCOVERY
MITOCHONDRIA
MECHANISMS
BACTERIAL
RESISTANT STAPHYLOCOCCUS-AUREUS
mycobacteria
MOLECULAR DESIGN
PEPTIDES
INHIBITION
antimicrobial agents
structure-activity relationships
CELL-ENVELOPE
phosphonium
structure−activity relationships
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  contributor:
    fullname: Ventola C. L.
– ident: e_1_2_8_70_1
  doi: 10.3389/fmicb.2018.01627
– ident: e_1_2_8_28_2
  doi: 10.1021/jm00265a023
– ident: e_1_2_8_49_1
– ident: e_1_2_8_13_2
  doi: 10.1128/AAC.00477-08
– ident: e_1_2_8_31_2
  doi: 10.1111/j.1476-5381.1979.tb13690.x
– ident: e_1_2_8_56_1
  doi: 10.1021/jm101356p
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Snippet Conjugated oligoelectrolytes (COEs) are an emerging class of amphiphilic antimicrobial compounds with a modular molecular framework suitable for simple...
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StartPage e202203803
SubjectTerms Ammonium
Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - pharmacology
Anti-Infective Agents
Antibiotics
Antiinfectives and antibacterials
Antimicrobial activity
Antimicrobial agents
Bacteria
Cell Membrane
Cell membranes
Chemistry
Chemistry, Multidisciplinary
conjugated oligoelectrolytes
Drug resistance
Lipophilic
Membrane permeability
Methicillin
Methicillin-Resistant Staphylococcus aureus
Microbial Sensitivity Tests
mycobacteria
phosphonium
Physical Sciences
Science & Technology
Stilbene
structure−activity relationships
Title Antimicrobial Conjugated Oligoelectrolytes Containing Triphenylphosphonium Solubilizing Groups
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fchem.202203803
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000943422300001
https://www.ncbi.nlm.nih.gov/pubmed/36738304
https://www.proquest.com/docview/2811051321
https://search.proquest.com/docview/2773125232
Volume 29
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