Vesicle Formation from N-Alkylindoles: Implications for Tryptophan-Water Interactions

Abel, Ernesto; Fedders, Megan F.; Gokel, George W.

doi:10.1021/ja00109a010

Cited by 45 publications

(34 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Compounds 3b-e further show good solubility in MeCN, THF, DMSO, and DMF. The decyl chains give 3d a greasy texture, in line with the amphiphilic properties of 1-decylindole reported by Abel et al [15]. Variation of the N-substituent in this new [4Fe-4S] cluster family thus allows effective tuning of cluster lipophilicity.…”

Section: -Methylindole-3-thiol (2b)supporting

confidence: 81%

“…Unsubstituted indole-3-thiol 2a [7,9] and its methyl- [13] and benzyl-substituted [6] analogs 2b and 2e have been prepared previously by Harris's method, although synthetic details for 2b and 2e were not reported. Two alkyl-substituted indole-3-thiols with longer aliphatic substituents (2c = pentyl, 2d = decyl) were prepared analogously from the known compounds 1-pentylindole [14] and 1-decylindole [15]. The two-step yields of thiols 2b-e ranged from 40% to 63%.…”

Section: -Methylindole-3-thiol (2b)mentioning

confidence: 99%

See 1 more Smart Citation

N-Substituted indole-3-thiolate [4Fe–4S] clusters with a unique and tunable combination of spectral and redox properties

Geer

Koten

et al. 2008

Inorganica Chimica Acta

View full text Add to dashboard Cite

A series of N-substituted indole-3-thiols, synthesized by sequential alkylation, thiouronium salt formation, and hydrolysis, are used to generate a novel family of [4Fe-4S] clusters. The redox transitions of the clusters deviate from those of other [4Fe-4S] cluster families, with half-wave potentials lying in a range midway between those of [4Fe-4S] clusters bound by aliphatic thiolate ligands and those bound by thiophenolate-based ligands. In UV-vis spectroscopy, the new cluster family shows absorption maxima that are among the most redshifted reported thus far in [4Fe-4S] cluster chemistry. The indole-3-thiolate ligand thus leads to a highly specific and uncommon combination of [4Fe-4S] cluster properties, which can be fine-tuned by facile derivatization at the indole nitrogen atom.

show abstract

Section: -Methylindole-3-thiol (2b)supporting

confidence: 81%

Section: -Methylindole-3-thiol (2b)mentioning

confidence: 99%

N-Substituted indole-3-thiolate [4Fe–4S] clusters with a unique and tunable combination of spectral and redox properties

Geer

Koten

et al. 2008

Inorganica Chimica Acta

View full text Add to dashboard Cite

show abstract

“…An examination of the KcsA voltage gated potassium channel from Streptomyces lividans suggests that the indole residues of all the tryptophans in the structure occur at the insulator-midpolar boundary [45]. Tryptophan is the rarest of the 20 common amino acids and appears to play an important role as a stabilizing element [46][47][48] (Fig. 6).…”

Section: Design Criteria For Hydraphilesmentioning

confidence: 99%

Coordination and transport of alkali metal cations through phospholipid bilayer membranes by hydraphile channels

Gokel

Daschbach

2008

Coordination Chemistry Reviews

Self Cite

View full text Add to dashboard Cite

Hydraphiles are synthetic ionophores that were designed to mimic some properties of protein channels that conduct such cations as sodium. They use macrocyclic (crown) polyethers as amphiphilic headgroups and as entry and exit portals. Their overall length is controlled by covalent links between the two headgroups (distal macrocycles) and the "central relay" unit, typically also an azacrown. The hydraphiles insert in the bilayer membranes of synthetic phospholipid vesicles or vital cells and mediate the transport of cations. The hydraphiles were intended to be models but they are functional channels. Because they are symmetric, they are non-rectifying but they show open-close behavior characteristic of natural channels. Because they are non-rectifying, when they insert into a microbial membrane, they lead to a rapid change in osmotic balance that proves fatal to bacteria.

show abstract

“…21 We found that treatment with NaH in THF followed by reaction with an alkyl halide afforded the N-alkylated indoles in yields of about 60%. 22 The by-product was likely the 3-isomer, but this was not isolated. A similarly conducted reaction using LiH instead of NaH gave the corresponding 3-alkyl derivatives.…”

Section: Indole As An Amphiphilic Head Groupmentioning

confidence: 99%

Tryptophan in Membrane-Active Synthetic Antimicrobials

2017

JERP

View full text Add to dashboard Cite

Herein, we summarize the background data that has led to a new class of antimicrobial amphiphiles and present recent results showing reversal of resistance to antibiotics in an Escherichia coli strain incorporating a tetracycline-selective efflux pump. In addition, two types of amphiphiles that show antibiotic potency enhancement or resistance reversal are discussed, along with our knowledge on the evolution that led to the active structures. One family is based on macrocyclic crown polyethers, which are known to insert into both liposomal and bacterial bilayers; these compounds are termed as hydraphiles and consist of three diazacrown rings linked by alkyl spacers and terminated by benzyl groups. In contrast, the second type of amphiphiles use tryptophans as the terminal, membrane anchoring residues; in this group of amphiphiles, two tryptophans are connected by alkyl chains or aryl groups. In both cases, however, the antibacterial activity of certain members of each family was apparent. Further, the amphiphiles have been shown to act as adjuvants that increase the potency of such antimicrobials as tetracycline and even to have re-sensitized a tetracycline-resistant E. coli strain to the antibiotic.

show abstract

Vesicle Formation from N-Alkylindoles: Implications for Tryptophan-Water Interactions

Cited by 45 publications

References 0 publications

N-Substituted indole-3-thiolate [4Fe–4S] clusters with a unique and tunable combination of spectral and redox properties

N-Substituted indole-3-thiolate [4Fe–4S] clusters with a unique and tunable combination of spectral and redox properties

Coordination and transport of alkali metal cations through phospholipid bilayer membranes by hydraphile channels

Tryptophan in Membrane-Active Synthetic Antimicrobials

Contact Info

Product

Resources

About