Comparing micellar, hemolytic, and antibacterial properties of di- and tricarboxyl dendritic amphiphiles

Maisuria, Bhadreshkumar B.; Actis, Marcelo L.; Hardrict, Shauntrece Nicole; Falkinham, Joseph O.; Cole, Michael F.; Cihlar, R. L.; Peters, Stephen M.; Macri, Richard V.; Sugandhi, Eko W.; Williams, André; Poppe, Michael; Esker, Alan R.; Gandour, Richard D.

doi:10.1016/j.bmc.2011.03.036

Cited by 27 publications

(26 citation statements)

References 27 publications

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“…MBC was measured by spreading 10 l of the content of the wells on M7H10 agar, and the MBC was defined as the lowest concentration resulting in 99.9% reduced CFU/ml compared to the inoculum density. Hemolysis measurements were performed as described by Maisuria et al (16). Cytotoxicity measurements of the transition metal-amino acid complexes were determined using Vero cells and the CellTiter 96 One Solution Cell Proliferation assay (Promega Corp., Madison, WI).…”

Section: Antimycobacterial Transition Metal Complexesmentioning

confidence: 99%

Transition Metal–α-Amino Acid Complexes with Antibiotic Activity against Mycobacterium spp

Karpin

Merola

Falkinham

2013

Antimicrob Agents Chemother

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Synthetic iridium-, rhodium-, and ruthenium-amino acid complexes with hydrophobic L-amino acids have antibiotic activity against Mycobacterium spp., including Mycobacterium bovis BCG and the rapidly growing species Mycobacterium abscessus and Mycobacterium chelonae. Concentrations of transition metal-amino acid complexes demonstrating hemolysis or cytotoxicity were 10-to 25-fold higher than were the MICs.

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Section: Antimycobacterial Transition Metal Complexesmentioning

confidence: 99%

Transition Metal–α-Amino Acid Complexes with Antibiotic Activity against Mycobacterium spp

Karpin

Merola

Falkinham

2013

Antimicrob Agents Chemother

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“…The ÀTDS agg term is positive for double tailed amphiphiles with tail lengths exceeding 12 carbons [4 (M-P,14,14), 5 (M-P,16,16), 9 (M-1, 14,14), and 10 (M-1, 16,16)]. This suggests that the entropy gained from the release of water from hydrophobic units is smaller than the decrease in entropy of amphiphiles due to the formation à Typically the 1st injection is ignored.…”

Section: Critical Aggregation Concentration and Heat Of Aggregate Formentioning

confidence: 99%

“…This reaction produces primarily 12, along with a highly insoluble biscationic byproduct (a result of two benzylic bromides being substituted with trimethylamine), which can be effectively removed by an extraction protocol as detailed in the Methods and materials section. Substitution of the two remaining benzylic bromides on 12 was accomplished using excess dimethylalkylamine (NMe 2 (CH 2 ) nÀ1 CH 3 , where n = 8, 10,12,14,16) in ethanol at reflux producing the M-1 series of amphiphilic products 6-10 (20-75% yield). Compounds are named as follows: M-X,n,n where M refers to the Mesitylene core, and X and n represent the attached groups: P indicates a pyridinium; a number indicates the number of carbon atoms in the alkyl group of a dimethylalkylammonium (e.g., 1 = trimethylammonium; 8 = octyldimethylammonium).…”

Section: Synthesismentioning

confidence: 99%

“…The MIC then increases for amphiphiles with tail lengths exceeding this optimal length. [14][15][16][17][18][19][20][21] Variations in spacing between head groups can also impact the MIC. For example, studies conducted by our labs show that amphiphiles with a 5-carbon spacer between two cationic head groups are the most biologically active.…”

Section: Introductionmentioning

confidence: 99%

“…13 A large variety of novel amphiphiles has been synthesized in an effort to increase effectiveness and specificity. [14][15][16][17][18][19][20][21][22][23][24] Amphiphile structure, including size and relative number of hydrophobic tails and hydrophilic head groups, governs colloidal characteristics including the critical aggregation concentration (CAC) and thermodynamic properties. 25 At concentrations below the CAC, amphiphiles tend to align at the air-water interface in equilibrium with dissolved monomers in solution.…”

Section: Introductionmentioning

confidence: 99%

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Colloidal and antibacterial properties of novel triple-headed, double-tailed amphiphiles: Exploring structure–activity relationships and synergistic mixtures

Marafino

Gallagher

Barragan

et al. 2015

Bioorganic & Medicinal Chemistry

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Two novel series of tris-cationic, tripled-headed, double-tailed amphiphiles were synthesized and the effects of tail length and head group composition on the critical aggregation concentration (CAC), thermodynamic parameters, and minimum inhibitory concentration (MIC) against six bacterial strains were investigated. Synergistic antibacterial combinations of these amphiphiles were also identified. Amphiphiles in this study are composed of a benzene core with three benzylic ammonium bromide groups, two of which have alkyl chains, each 8-16 carbons in length. The third head group is a trimethylammonium or pyridinium. Log of critical aggregation concentration (log[CAC]) and heat of aggregation (ΔHagg) were both inversely proportional to the length of the linear hydrocarbon chains. Antibacterial activity increases with tail length until an optimal tail length of 12 carbons per chain, above which, activity decreased. The derivatives with two 12 carbon chains had the best antibacterial activity, killing all tested strains at concentrations of 1-2μM for Gram-positive and 4-16μM for Gram-negative bacteria. The identity of the third head group (trimethylammonium or pyridinium) had minimal effect on colloidal and antibacterial activity. The antibacterial activity of several binary combinations of amphiphiles from this study was higher than activity of individual amphiphiles, indicating that these combinations are synergistic. These amphiphiles show promise as novel antibacterial agents that could be used in a variety of applications.

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Scaffold‐Hopping of Multicationic Amphiphiles Yields Three New Classes of Antimicrobials

et al. 2015

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Quaternary ammonium compounds (QACs) are a vital class of antiseptics. Recent investigations into their construction are uncovering novel and potent multicationic variants. Based on a trisQAC precedent, we have implemented a scaffold-hopping approach to develop alternative QAC architectures that display 1-3 long alkyl chains in specific projections from cyclic and branched core structures bearing 3-4 nitrogen atoms. The preparation of 30 QAC structures allowed for correlation of scaffold structure with antimicrobial activity. We identified QACs with limited conformational flexibility that have improved bioactivity against planktonic bacteria as compared to their linear counterparts. We also confirmed that resistance, as evidenced by an increased minimum inhibitory concentration (MIC) for methicillin-resistant Staphylococcus aureus (MRSA) compared to methicillin-susceptible Staphylococcus aureus (MSSA), can reduce efficacy up to 64-fold for monocationic QACs. Differentiation of antimicrobial and anti-biofilm activity, however, was not observed, suggesting that these compounds utilize a non-specific mode of eradication.

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Comparing micellar, hemolytic, and antibacterial properties of di- and tricarboxyl dendritic amphiphiles

Cited by 27 publications

References 27 publications

Transition Metal–α-Amino Acid Complexes with Antibiotic Activity against Mycobacterium spp

Transition Metal–α-Amino Acid Complexes with Antibiotic Activity against Mycobacterium spp

Colloidal and antibacterial properties of novel triple-headed, double-tailed amphiphiles: Exploring structure–activity relationships and synergistic mixtures

Scaffold‐Hopping of Multicationic Amphiphiles Yields Three New Classes of Antimicrobials

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