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  1. Article ; Online: Assessment of a host-guest interaction in a bilayer membrane model.

    Kumari, Harshita / Negin, Saeedeh / Eisenhart, Andrew / Patel, Mohit B / Beck, Thomas L / Heinrich, Frank / Spikes, Helena J / Gokel, George W

    RSC advances

    2022  Volume 12, Issue 49, Page(s) 32046–32055

    Abstract: Supramolecular interactions are well recognized and many of them have been extensively studied in chemistry. The formation of supramolecular complexes that rely on weak force interactions are less well studied in bilayer membranes. Herein, a supported ... ...

    Abstract Supramolecular interactions are well recognized and many of them have been extensively studied in chemistry. The formation of supramolecular complexes that rely on weak force interactions are less well studied in bilayer membranes. Herein, a supported bilayer membrane is used to probe the penetration of a complex between tetracycline and a macrocyclic polyether. In a number of bacterial systems, the presence of the macrocycle has been found to significantly enhance the potency of the antimicrobial
    Language English
    Publishing date 2022-11-10
    Publishing country England
    Document type Journal Article
    ISSN 2046-2069
    ISSN (online) 2046-2069
    DOI 10.1039/d2ra03851j
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article: Antimicrobial and Adjuvant Potencies of Di-

    Patel, Mohit B / Spikes, Helena / Bailey, Robert S / Connell, Thomas / Gill, Hannah / Gokel, Michael R / Harris, Rebecca / Meisel, Joseph W / Negin, Saeedeh / Yin, Shanheng Andrew / Gokel, George W

    Antibiotics (Basel, Switzerland)

    2023  Volume 12, Issue 10

    Abstract: Lariat ethers are macrocyclic polyethers-crown ethers-to which sidearms are appended. 4,13-Diaza-18-crown-6 having twin alkyl chains at the nitrogens show biological activity. They exhibit antibiotic activity, but when co-administered at with an FDA- ... ...

    Abstract Lariat ethers are macrocyclic polyethers-crown ethers-to which sidearms are appended. 4,13-Diaza-18-crown-6 having twin alkyl chains at the nitrogens show biological activity. They exhibit antibiotic activity, but when co-administered at with an FDA-approved antibiotic, the latter's potency is often strongly enhanced. Potency enhancements and resistance reversals have been documented in vitro for a range of Gram-negative and Gram-positive bacteria with a variety of antimicrobials. Strains of
    Language English
    Publishing date 2023-10-05
    Publishing country Switzerland
    Document type Journal Article
    ZDB-ID 2681345-2
    ISSN 2079-6382
    ISSN 2079-6382
    DOI 10.3390/antibiotics12101513
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  3. Article ; Online: Synthetic ionophores as non-resistant antibiotic adjuvants.

    Patel, Mohit B / Garrad, Evan / Meisel, Joseph W / Negin, Saeedeh / Gokel, Michael R / Gokel, George W

    RSC advances

    2019  Volume 9, Issue 4, Page(s) 2217–2230

    Abstract: Antimicrobial resistance is a world-wide health care crisis. New antimicrobials must both exhibit potency and thwart the ability of bacteria to develop resistance to them. We report the use of synthetic ionophores as a new approach to developing non- ... ...

    Abstract Antimicrobial resistance is a world-wide health care crisis. New antimicrobials must both exhibit potency and thwart the ability of bacteria to develop resistance to them. We report the use of synthetic ionophores as a new approach to developing non-resistant antimicrobials and adjuvants. Most studies involving amphiphilic antimicrobials have focused on either developing synthetic amphiphiles that show ion transport, or developing non-cytotoxic analogs of such peptidic amphiphiles as colistin. We have rationally designed, prepared, and evaluated crown ether-based synthetic ionophores ('hydraphiles') that show selective ion transport through bilayer membranes and are toxic to bacteria. We report here that hydraphiles exhibit a broad range of antimicrobial properties and that they function as adjuvants in concert with FDA-approved antibiotics against multi-drug resistant (MDR) bacteria. Studies described herein demonstrate that benzyl C
    Language English
    Publishing date 2019-01-17
    Publishing country England
    Document type Journal Article
    ISSN 2046-2069
    ISSN (online) 2046-2069
    DOI 10.1039/c8ra07641c
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  4. Article: Reversal of Tetracycline Resistance in Escherichia coli by Noncytotoxic bis(Tryptophan)s

    Meisel, Joseph W / Garrad Evan / Gokel George W / Patel Mohit B / Stanton Ryan A

    Journal of the American Chemical Society. 2016 Aug. 24, v. 138, no. 33

    2016  

    Abstract: Nine bis(tryptophan) derivatives (BTs) and two control compounds were synthesized and tested for antimicrobial activity against two Escherichia coli strains and a Staphylococcus aureus strain. The effects of linker type, shape, and conformational ... ...

    Abstract Nine bis(tryptophan) derivatives (BTs) and two control compounds were synthesized and tested for antimicrobial activity against two Escherichia coli strains and a Staphylococcus aureus strain. The effects of linker type, shape, and conformational rigidity were manifested in dramatic differences in altering tetracycline potency when coadministered with that antibiotic. A reversal of resistance was observed for an E. coli strain having a TetA efflux pump. Survival of mammalian cells was assayed with good result.
    Keywords antibacterial properties ; Escherichia coli ; mammals ; Staphylococcus aureus ; tetracycline ; transporters
    Language English
    Dates of publication 2016-0824
    Size p. 10571-10577.
    Publishing place American Chemical Society
    Document type Article
    ZDB-ID 3155-0
    ISSN 1520-5126 ; 0002-7863
    ISSN (online) 1520-5126
    ISSN 0002-7863
    DOI 10.1021%2Fjacs.6b05578
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    In stock of ZB MED Bonn / Germany

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  5. Article ; Online: Hydraphile synthetic ion channels alter root architecture in Arabidopsis thaliana.

    Patel, Mohit B / Stavri, Ariel / Curvey, Nichole S / Gokel, George W

    Chemical communications (Cambridge, England)

    2014  Volume 50, Issue 78, Page(s) 11562–11564

    Abstract: The presence of low concentrations of hydraphile synthetic amphiphiles have been found to dramatically alter the primary/lateral root architectural balance in the A. thaliana plant model system and a correlation to ion transport by the hydraphiles is ... ...

    Abstract The presence of low concentrations of hydraphile synthetic amphiphiles have been found to dramatically alter the primary/lateral root architectural balance in the A. thaliana plant model system and a correlation to ion transport by the hydraphiles is consistent with the effects.
    MeSH term(s) Arabidopsis/growth & development ; Crown Ethers/chemistry ; Crown Ethers/toxicity ; Ion Channels/chemistry ; Ion Channels/metabolism ; Ion Transport/drug effects ; Plant Roots/chemistry ; Plant Roots/drug effects ; Plant Roots/growth & development
    Chemical Substances Crown Ethers ; Ion Channels
    Language English
    Publishing date 2014-10-09
    Publishing country England
    Document type Journal Article ; Research Support, U.S. Gov't, Non-P.H.S.
    ZDB-ID 1472881-3
    ISSN 1364-548X ; 1359-7345 ; 0009-241X
    ISSN (online) 1364-548X
    ISSN 1359-7345 ; 0009-241X
    DOI 10.1039/c4cc04769a
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  6. Article ; Online: Reversal of Tetracycline Resistance in Escherichia coli by Noncytotoxic bis(Tryptophan)s.

    Meisel, Joseph W / Patel, Mohit B / Garrad, Evan / Stanton, Ryan A / Gokel, George W

    Journal of the American Chemical Society

    2016  Volume 138, Issue 33, Page(s) 10571–10577

    Abstract: Nine bis(tryptophan) derivatives (BTs) and two control compounds were synthesized and tested for antimicrobial activity against two Escherichia coli strains and a Staphylococcus aureus strain. The effects of linker type, shape, and conformational ... ...

    Abstract Nine bis(tryptophan) derivatives (BTs) and two control compounds were synthesized and tested for antimicrobial activity against two Escherichia coli strains and a Staphylococcus aureus strain. The effects of linker type, shape, and conformational rigidity were manifested in dramatic differences in altering tetracycline potency when coadministered with that antibiotic. A reversal of resistance was observed for an E. coli strain having a TetA efflux pump. Survival of mammalian cells was assayed with good result.
    Language English
    Publishing date 2016-08-24
    Publishing country United States
    Document type Journal Article
    ZDB-ID 3155-0
    ISSN 1520-5126 ; 0002-7863
    ISSN (online) 1520-5126
    ISSN 0002-7863
    DOI 10.1021/jacs.6b05578
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    In stock of ZB MED Bonn / Germany

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  7. Article ; Online: Antibiotic Potency against E. coli Is Enhanced by Channel-Forming Alkyl Lariat Ethers.

    Negin, Saeedeh / Patel, Mohit B / Gokel, Michael R / Meisel, Joseph W / Gokel, George W

    Chembiochem : a European journal of chemical biology

    2016  Volume 17, Issue 22, Page(s) 2153–2161

    Abstract: Several N,N'-bis(n-alkyl-4,13-diaza[18]crown-6) lariat ethers were found to significantly enhance the potency of rifampicin and tetracycline, but not erythromycin and kanamycin, against the non-pathogenic DH5α and K-12 strains of Escherichia coli when ... ...

    Abstract Several N,N'-bis(n-alkyl-4,13-diaza[18]crown-6) lariat ethers were found to significantly enhance the potency of rifampicin and tetracycline, but not erythromycin and kanamycin, against the non-pathogenic DH5α and K-12 strains of Escherichia coli when administered at levels below their minimum inhibitory concentrations (MICs). The enhancements in antibiotic potency observed for the lariat ethers ranged from three- to 20-fold, depending on the strain of E. coli, the antibiotic, and the lengths of the alkyl chains attached at the macroring nitrogen atoms. The dialkyl lariat ethers, previously thought to only be cation carriers, formed well-behaved, ion-conducting pores in soybean asolectin membranes, as judged by planar bilayer conductance measurements. The ability of lariat ethers to form stable pores, which appeared to be aggregated, depended in part on alkyl chain length and in part on the composition of the bilayer membrane in which they were studied.
    MeSH term(s) Anti-Bacterial Agents/chemistry ; Anti-Bacterial Agents/metabolism ; Anti-Bacterial Agents/pharmacology ; Crown Compounds/chemistry ; Escherichia coli/drug effects ; Escherichia coli/growth & development ; Ethers/chemistry ; Ethers/metabolism ; Ethers/pharmacology ; Lipid Bilayers/chemistry ; Lipid Bilayers/metabolism ; Microbial Sensitivity Tests ; Rifampin/chemistry ; Rifampin/pharmacology ; Tetracycline/chemistry ; Tetracycline/pharmacology
    Chemical Substances Anti-Bacterial Agents ; Crown Compounds ; Ethers ; Lipid Bilayers ; Tetracycline (F8VB5M810T) ; Rifampin (VJT6J7R4TR)
    Language English
    Publishing date 2016-11-17
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 2020469-3
    ISSN 1439-7633 ; 1439-4227
    ISSN (online) 1439-7633
    ISSN 1439-4227
    DOI 10.1002/cbic.201600428
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  8. Article: Hydraphile synthetic ion channels alter root architecture in Arabidopsis thaliana

    Patel, Mohit B / Stavri, Ariel / Curvey, Nichole S / Gokel, George W

    Chemical communications. 2014 Sept. 4, v. 50, no. 78

    2014  

    Abstract: The presence of low concentrations of hydraphile synthetic amphiphiles have been found to dramatically alter the primary/lateral root architectural balance in the A. thaliana plant model system and a correlation to ion transport by the hydraphiles is ... ...

    Abstract The presence of low concentrations of hydraphile synthetic amphiphiles have been found to dramatically alter the primary/lateral root architectural balance in the A. thaliana plant model system and a correlation to ion transport by the hydraphiles is consistent with the effects.
    Keywords Arabidopsis thaliana ; chemical compounds ; chemical reactions ; ion channels ; models ; root systems ; roots ; surfactants
    Language English
    Dates of publication 2014-0904
    Size p. 11562-11564.
    Publishing place The Royal Society of Chemistry
    Document type Article
    ZDB-ID 1472881-3
    ISSN 1364-548X ; 1359-7345 ; 0009-241X
    ISSN (online) 1364-548X
    ISSN 1359-7345 ; 0009-241X
    DOI 10.1039/c4cc04769a
    Database NAL-Catalogue (AGRICOLA)

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  9. Article: The aqueous medium-dimethylsulfoxide conundrum in biological studies

    Negin, Saeedeh / Gokel, George W / Gokel, Michael R / Osborn, David C / Patel, Mohit B / Sedinkin, Sergey L

    RSC advances. 2015 Jan. 06, v. 5, no. 11

    2015  

    Abstract: A series of straight and branched chain pyrogallol[4]arenes was studied and found to be essentially nontoxic to two strains of E. coli. An apparent enhancement of potency observed for kanamycin against E. coli was found to be due to the presence of DMSO ... ...

    Abstract A series of straight and branched chain pyrogallol[4]arenes was studied and found to be essentially nontoxic to two strains of E. coli. An apparent enhancement of potency observed for kanamycin against E. coli was found to be due to the presence of DMSO in the growth media. Quantitative studies are presented that assay the effect of DMSO concentration on the apparent potency of kanamycin against E. coli.
    Keywords aromatic hydrocarbons ; culture media ; dimethyl sulfoxide ; Escherichia coli ; kanamycin ; pyrogallol
    Language English
    Dates of publication 2015-0106
    Size p. 8088-8093.
    Publishing place The Royal Society of Chemistry
    Document type Article
    ISSN 2046-2069
    DOI 10.1039/c4ra15217d
    Database NAL-Catalogue (AGRICOLA)

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  10. Article ; Online: Hydraphiles enhance antimicrobial potency against Escherichia coli, Pseudomonas aeruginosa, and Bacillus subtilis.

    Patel, Mohit B / Garrad, Evan C / Stavri, Ariel / Gokel, Michael R / Negin, Saeedeh / Meisel, Joseph W / Cusumano, Zachary / Gokel, George W

    Bioorganic & medicinal chemistry

    2016  Volume 24, Issue 12, Page(s) 2864–2870

    Abstract: Hydraphiles are synthetic amphiphiles that form ion-conducting pores in liposomal membranes. These pores exhibit open-close behavior when studied by planar bilayer conductance techniques. In previous work, we showed that when co-administered with various ...

    Abstract Hydraphiles are synthetic amphiphiles that form ion-conducting pores in liposomal membranes. These pores exhibit open-close behavior when studied by planar bilayer conductance techniques. In previous work, we showed that when co-administered with various antibiotics to the DH5α strain of Escherichia coli, they enhanced the drug's potency. We report here potency enhancements at low concentrations of hydraphiles for the structurally and mechanistically unrelated antibiotics erythromycin, kanamycin, rifampicin, and tetracycline against Gram negative E. coli (DH5α and K-12) and Pseudomonas aeruginosa, as well as Gram positive Bacillus subtilis. Earlier work suggested that potency increases correlated to ion transport function. The data presented here comport with the function of hydraphiles to enhance membrane permeability in addition to, or instead of, their known function as ion conductors.
    MeSH term(s) Anti-Bacterial Agents/pharmacokinetics ; Anti-Bacterial Agents/pharmacology ; Bacillus subtilis/drug effects ; Bacillus subtilis/metabolism ; Erythromycin/pharmacokinetics ; Erythromycin/pharmacology ; Escherichia coli/drug effects ; Escherichia coli/metabolism ; Escherichia coli Infections/drug therapy ; Humans ; Kanamycin/pharmacokinetics ; Kanamycin/pharmacology ; Microbial Sensitivity Tests ; Permeability/drug effects ; Pseudomonas Infections/drug therapy ; Pseudomonas aeruginosa/drug effects ; Pseudomonas aeruginosa/metabolism ; Rifampin/pharmacokinetics ; Rifampin/pharmacology ; Surface-Active Agents/chemistry ; Surface-Active Agents/pharmacology ; Tetracycline/pharmacokinetics ; Tetracycline/pharmacology
    Chemical Substances Anti-Bacterial Agents ; Surface-Active Agents ; Kanamycin (59-01-8) ; Erythromycin (63937KV33D) ; Tetracycline (F8VB5M810T) ; Rifampin (VJT6J7R4TR)
    Language English
    Publishing date 2016-06-15
    Publishing country England
    Document type Journal Article
    ZDB-ID 1161284-8
    ISSN 1464-3391 ; 0968-0896
    ISSN (online) 1464-3391
    ISSN 0968-0896
    DOI 10.1016/j.bmc.2016.04.058
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    In stock of ZB MED Cologne/Königswinter

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