Ratiometric fluorescent probe for sensing <i>Streptococcus mutans</i> glucosyltransferase, a key factor in the formation of dental caries

Feng, Lei; Yan, Qingsong; Zhang, Baojing; Tian, Xiangge; Wang, Chao; Yu, Zhenlong; Cui, Jingnan; Guo, Dean; Ma, Xiaochi; James, Tony D.

doi:10.1039/c9cc00440h

Cited by 28 publications

(16 citation statements)

References 26 publications

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“…showed that acarbose also inhibits GSs, [10] and its mode of action was confirmed by a cocrystal structure [11] . Compounds from plant sources such as polyphenols in green tea extracts, [12] theaflavins in black tea extracts, [13] curcumin [14] and oxyresveratrol [15] showed marked inhibitory effects on the biofilm of the cariogenic pathogen Streptococcus mutans , however, high concentrations and sufficient time were required. Their antibiofilm activities were mainly exerted through direct inhibition of the bacterial GTFs or down‐regulation of GTF expression [12–15] .…”

Section: Introductionmentioning

confidence: 87%

“…Compounds from plant sources such as polyphenols in green tea extracts, [12] theaflavins in black tea extracts, [13] curcumin [14] and oxyresveratrol [15] showed marked inhibitory effects on the biofilm of the cariogenic pathogen Streptococcus mutans , however, high concentrations and sufficient time were required. Their antibiofilm activities were mainly exerted through direct inhibition of the bacterial GTFs or down‐regulation of GTF expression [12–15] . On the other hand, small‐molecule GTF inhibitors can be categorized into just two groups, hydroxychalcones and compounds with a high number of heteroatoms, especially nitrogen [16] .…”

Section: Introductionmentioning

confidence: 99%

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Potential Dental Biofilm Inhibitors: Dynamic Combinatorial Chemistry Affords Sugar‐Based Molecules that Target Bacterial Glucosyltransferase

et al. 2020

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We applied dynamic combinatorial chemistry (DCC) to find novel ligands of the bacterial virulence factor glucosyltransferase (GTF) 180. GTFs are the major producers of extracellular polysaccharides, which are important factors in the initiation and development of cariogenic dental biofilms. Following a structure‐based strategy, we designed a series of 36 glucose‐ and maltose‐based acylhydrazones as substrate mimics. Synthesis of the required mono‐ and disaccharide‐based aldehydes set the stage for DCC experiments. Analysis of the dynamic combinatorial libraries (DCLs) by UPLC‐MS revealed major amplification of four compounds in the presence of GTF180. Moreover, we found that derivatives of the glucose‐acceptor maltose at the C1‐hydroxy group act as glucose‐donors and are cleaved by GTF180. The synthesized hits display medium to low binding affinity (KD values of 0.4–10.0 mm) according to surface plasmon resonance. In addition, they were investigated for inhibitory activity in GTF‐activity assays. The early‐stage DCC study reveals that careful design of DCLs opens up easy access to a broad class of novel compounds that can be developed further as potential inhibitors.

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Section: Introductionmentioning

confidence: 87%

Section: Introductionmentioning

confidence: 99%

Potential Dental Biofilm Inhibitors: Dynamic Combinatorial Chemistry Affords Sugar‐Based Molecules that Target Bacterial Glucosyltransferase

et al. 2020

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“…In the study of Feng et al [58], the most abundant polyphenols isolated from green tea were catechin and 1,4,6-tri-O-galloyl-βD-glucose. Catechin derivatives as gallocatechin gallate (0.32 mM) and epigallocatechin gallate (0.31 mM) were able to inhibit S. mutans glucosyltransferases.…”

Section: Antibacterial Activitymentioning

confidence: 99%

Polyphenols in Dental Applications

2020

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(1) Background: polyphenols are a broad class of molecules extracted from plants and have a large repertoire of biological activities. Biomimetic inspiration from the effects of tea or red wine on the surface of cups or glass lead to the emergence of versatile surface chemistry with polyphenols. Owing to their hydrogen bonding abilities, coordination chemistry with metallic cations and redox properties, polyphenols are able to interact, covalently or not, with a large repertoire of chemical moieties, and can hence be used to modify the surface chemistry of almost all classes of materials. (2) Methods: the use of polyphenols to modify the surface properties of dental materials, mostly enamel and dentin, to afford them with better adhesion to resins and improved biological properties, such as antimicrobial activity, started more than 20 years ago, but no general overview has been written to our knowledge. (3) Results: the present review is aimed to show that molecules from all the major classes of polyphenolics allow for low coast improvements of dental materials and engineering of dental tissues.

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“…[7][8][9] Newbrun et al showed that acarbose also inhibits GSs, [10] and its mode of action was confirmed by a cocrystal structure. [11] Compounds from plant sources such as polyphenols in green tea extracts, [12] theaflavins in black tea extracts, [13] curcumin [14] and oxyresveratrol [15] showed marked inhibitory effects on the biofilm of the cariogenic pathogen Streptococcus mutans, however, high concentrations and suffi-cient time were required. Their antibiofilm activities were mainly exerted through direct inhibition of the bacterial GTFs or down-regulation of GTF expression.…”

Section: Introductionmentioning

confidence: 99%

Cover Feature: Potential Dental Biofilm Inhibitors: Dynamic Combinatorial Chemistry Affords Sugar‐Based Molecules that Target Bacterial Glucosyltransferase (ChemMedChem 1/2021)

et al. 2020

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Ratiometric fluorescent probe for sensing Streptococcus mutans glucosyltransferase, a key factor in the formation of dental caries

Abstract: A naphthalimide-based ratiometric fluorescent probe was designed for sensing (and inhibitor screening) of pathogenic bacterial glucosyltransferases associated with the formation of dental caries.

Cited by 28 publications

References 26 publications

Potential Dental Biofilm Inhibitors: Dynamic Combinatorial Chemistry Affords Sugar‐Based Molecules that Target Bacterial Glucosyltransferase

Potential Dental Biofilm Inhibitors: Dynamic Combinatorial Chemistry Affords Sugar‐Based Molecules that Target Bacterial Glucosyltransferase

Polyphenols in Dental Applications

Cover Feature: Potential Dental Biofilm Inhibitors: Dynamic Combinatorial Chemistry Affords Sugar‐Based Molecules that Target Bacterial Glucosyltransferase (ChemMedChem 1/2021)

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