Comparing anti-HIV, antibacterial, antifungal, micellar, and cytotoxic properties of tricarboxylato dendritic amphiphiles

Macri, Richard V.; Karlovská, Janka; Doncel, Gustavo F.; Maisuria, Bhadreshkumar B.; Williams, André; Sugandhi, Eko W.; Falkinham, Joseph O.; Esker, Alan R.; Gandour, Richard D.

doi:10.1016/j.bmc.2009.02.055

Cited by 21 publications

(10 citation statements)

References 55 publications

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“…4 Gemini (dimeric) cationic amphiphiles in particular have received significant attention, 5 and the interesting physical properties 6 and antimicrobial activities 7 of these bis-cations have been described. Interesting developments have been made in the investigation of polyanionic structures by the groups of Falkinham and Gandour, [8][9][10][11][12] which have led to a series of dendritic amphiphiles, bearing three carboxylate groups that allow for attachment to surfaces (Fig. 1, left).…”

mentioning

confidence: 99%

The antimicrobial activity of mono-, bis-, tris-, and tetracationic amphiphiles derived from simple polyamine platforms

Paniak

Jennings

Shanahan

et al. 2014

Bioorganic & Medicinal Chemistry Letters

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mentioning

confidence: 99%

The antimicrobial activity of mono-, bis-, tris-, and tetracationic amphiphiles derived from simple polyamine platforms

Paniak

Jennings

Shanahan

et al. 2014

Bioorganic & Medicinal Chemistry Letters

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“…19 At concentrations near or above the CAC the amphiphile may act as a detergent, solubilizing the cell membrane-a mechanism of action that could be detrimental to prokaryotic cells. 17,19 Amphiphiles at sub-CAC levels are potent antibacterials at concentrations where detergent effects are not observed. It is recognized CAC values reported here (measured in G + = Gram-positive, G À = Gram-negative.…”

Section: Minimum Inhibitory Concentrationmentioning

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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“…The phisicochemical properties of dendrimers can be controlled during synthesis by selecting the core groups, the extent of branching, and the nature and/or number of functional groups on the surface. Dendrimers have been used as carriers of antiretroviral peptides and genes for HIV inhibition and more surprisingly, many recent studies showed that they themselves can be used as antiretroviral agents [83,85,86]. Dutta and coworkers loaded lamivudine into mannose-capped poly (propyleneimine) dendrimers [87].…”

Section: Dendrimersmentioning

confidence: 99%

Nanotechnology Approaches for Antiretroviral Drugs Delivery

Iannazzo¹,

Pistone²,

Romeo³

et al. 2015

Journal of AIDS and HIV infections

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The development of effective drug delivery approaches for the treatment of AIDS and HIV infection is a global challenge. The advent of multidrug, highly active antiretroviral therapy (HAART), have increased the life span of HIV-infected patients. However, it has not eradicated HIV infections, particularly in anatomically privileged sites, such as the brain, testes, gut, liver, kidney, and secondary lymphoid tissue. Several nanocarriers have been investigated in order to enhance the effective delivery of antiretroviral drugs for HIV prevention and therapy. This review focuses on the most recent and significant examples of nanotechnology-based approaches for the delivery of antiretroviral agents belonging to the classes of nucleoside-analog reverse transcriptase inhibitors (NRTIs) and nonnucleoside reverse transcriptase inhibitors (NNRTIs). Nanocarriers such as natural and synthetic polymeric nanoparticles, dendrimers, liposomes, and various drug conjugates have been discussed. These nanotechnology carriers are able to deliver the antiretroviral agents in a controlled and/or targeted manner thereby increasing the drug bioavailability and residence time at target sites with a considerable improvement in quality of HIV patients.

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Comparing anti-HIV, antibacterial, antifungal, micellar, and cytotoxic properties of tricarboxylato dendritic amphiphiles

Cited by 21 publications

References 55 publications

The antimicrobial activity of mono-, bis-, tris-, and tetracationic amphiphiles derived from simple polyamine platforms

The antimicrobial activity of mono-, bis-, tris-, and tetracationic amphiphiles derived from simple polyamine platforms

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

Nanotechnology Approaches for Antiretroviral Drugs Delivery

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