Dataset Information

Synthesis, Characterization, and Antimicrobial Evaluation of Random Poly(ester-Carbonate)s Bearing Pendant Primary Amine in the Main Chain.

ABSTRACT: Starting from primary amine bearing cyclic carbonate tert-butyl-(2-oxo-1,3-dioxan-5-yl) carbamate (TBODC) and caprolactone (CL), amphiphilic poly(caprolactone-ran-amino trimethyl carbonate)s (P(CL-ran-ATC)s) random copolymers with controlled molecular weight and composition were synthesized via ring opening polymerization (ROP) and deprotection, using stannous octoate (Sn(Oct)₂) as catalyst and benzyl alcohol (BnOH) as initiator. Therefore, hydrophilic/lipophilic ratio (HLR) of the P(CL-ran-ATC)s copolymers can be finely adjusted by the feed ratio of TBODC and CL. The antimicrobial activity against Staphylococcus aureus (S. aureus) and Escherichia coli (E. coli) of P(CL-ran-ATC)s were proportional to HLR, and P(CL-ran-ATC)s presented more vigorous bactericidal activity towards S. aureus. The minimum inhibitory concentration (MIC) values of P(CL-ran-ATC 50.9%) are 2000 ?g mL^-1 and 3000 ?g mL^-1 for S. aureus and E. coli. While P(CL-ran-ATC 50.9%) exhibited deficient hemolytic activity as 1.41%. In addition, the P(CL-ran-ATC)s showed extremely low cytotoxicity towards fibroblast L929 cells.

SUBMITTER: Dong P

PROVIDER: S-EPMC7696737 | biostudies-literature | 2020 Nov

REPOSITORIES: biostudies-literature

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Synthesis, Characterization, and Antimicrobial Evaluation of Random Poly(ester-Carbonate)s Bearing Pendant Primary Amine in the Main Chain.

Dong Peng P Feng Jing J Li Sujuan S Sun Tingli T Shi Qingshan Q Xie Xiaobao X

Polymers 20201110 11

Starting from primary amine bearing cyclic carbonate tert-butyl-(2-oxo-1,3-dioxan-5-yl) carbamate (TBODC) and caprolactone (CL), amphiphilic poly(caprolactone-ran-amino trimethyl carbonate)s (P(CL-ran-ATC)s) random copolymers with controlled molecular weight and composition were synthesized via ring opening polymerization (ROP) and deprotection, using stannous octoate (Sn(Oct)2) as catalyst and benzyl alcohol (BnOH) as initiator. Therefore, hydrophilic/lipophilic ...[more]

PMID: 33182730

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Project description:Glucoside detergents are successfully used for membrane protein crystallization mainly because of their ability to form small protein-detergent complexes. In a previous study, we introduced glucose neopentyl glycol (GNG) amphiphiles with a branched diglucoside structure that has facilitated high resolution crystallographic structure determination of several membrane proteins. Like other glucoside detergents, however, these GNGs were less successful than DDM in stabilizing membrane proteins, limiting their wide use in protein structural study. As a strategy to improve GNG efficacy for protein stabilization, we introduced two different alkyl chains (i.e., main and pendant chains) into the GNG scaffold while maintaining the branched diglucoside head group. Of these pendant-bearing GNGs (P-GNGs), three detergents (GNG-2,14, GNG-3,13 and GNG-3,14) were not only notably better than both DDM (a gold standard detergent) and the previously described GNGs at stabilizing all six membrane proteins tested here, but were also as efficient as DDM at membrane protein extraction. The results suggest that the C14 main chain of the P-GNGs is highly compatible with the hydrophobic widths of membrane proteins, while the C2/C3 pendant chain is effective at strengthening detergent hydrophobic interactions. Based on the marked effect on protein stability and solubility, these glucoside detergents hold significant potential for membrane protein structural study. Furthermore, the independent roles of the detergent two alkyl chains first introduced in this study have shed light on new amphiphile design for membrane protein study. STATEMENT OF SIGNIFICANCE: Detergent efficacy for protein stabilization tends to be protein-specific, thus it is challenging to find a detergent that is effective at stabilizing multiple membrane proteins. By incorporating a pendant chain into our previous GNG scaffold, we prepared pendant chain-bearing GNGs (P-GNGs) and identified three P-GNGs that were highly effective at stabilizing all membrane proteins tested here including two GPCRs. In addition, the new detergents were as efficient as DDM at extracting membrane proteins, enabling use of these detergents over the multiple steps of protein isolation. The key difference between the P-GNGs and other glucoside detergents, the presence of a pendant chain, is likely to be responsible for their markedly enhanced protein stabilization behavior.

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Dataset Information

Synthesis, Characterization, and Antimicrobial Evaluation of Random Poly(ester-Carbonate)s Bearing Pendant Primary Amine in the Main Chain.

Publications

Synthesis, Characterization, and Antimicrobial Evaluation of Random Poly(ester-Carbonate)s Bearing Pendant Primary Amine in the Main Chain.

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