Synthesis of 12-<i>O</i>-Mono- and Diglycosyl-oxystearates, a New Class of Agonists for the C-type Lectin Receptor Mincle

Huy, Le Van; Tanaka, Chiaki; Imai, Takashi; Yamasaki, Satoshi; Miyamoto, Tomofumi

doi:10.1021/acsmedchemlett.8b00413

Cited by 10 publications

(7 citation statements)

References 33 publications

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“…Nanomaterials usually refer to materials with one dimension or more within the range of 0.1-100 nm in the three-dimensional scale of tiny particles [7,8]. Fluorescent nanomaterials include organic fluorescent dyes [9], fluorescent proteins [10], QDs, MNCs, CDs, etc. Organic fluorescent dyes are the most common nano fluorescent probe materials.…”

Section: Introductionmentioning

confidence: 99%

Biological nanoscale fluorescent probes: From structure and performance to bioimaging

Wan

Zhang

et al. 2020

Reviews in Analytical Chemistry

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In recent years, nanomaterials have attracted lots of attention from researchers due to their unique properties. Nanometer fluorescent materials, such as organic dyes, semiconductor quantum dots (QDs), metal nano-clusters (MNCs), carbon dots (CDs), etc., are widely used in biological imaging due to their high sensitivity, short response time, and excellent accuracy. Nanometer fluorescent probes can not only perform in vitro imaging of organisms but also achieve in vivo imaging. This provides medical staff with great convenience in cancer treatment. Combined with contemporary medical methods, faster and more effective treatment of cancer is achievable. This article explains the response mechanism of three-nanometer fluorescent probes: the principle of induced electron transfer (PET), the principle of fluorescence resonance energy transfer (FRET), and the principle of intramolecular charge transfer (ICT), showing the semiconductor QDs, precious MNCs, and CDs. The excellent performance of the three kinds of nano fluorescent materials in biological imaging is highlighted, and the application of these three kinds of nano fluorescent probes in targeted biological imaging is also introduced. Nanometer fluorescent materials will show their significance in the field of biomedicine.

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Section: Introductionmentioning

confidence: 99%

Biological nanoscale fluorescent probes: From structure and performance to bioimaging

Wan

Zhang

et al. 2020

Reviews in Analytical Chemistry

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“…Only weak activity was detected for the methyl esters of the fatty acids derived from cleavage from the l -mannitol core, showing that the intact structure is required for full activity. A recent study reported Mincle signaling agonists developed from the side chains of 44-2 , but linked to 12-hydroxystearic acid …”

Section: Introductionmentioning

confidence: 99%

Synthetic β-1,2-Mannosyloxymannitol Glycolipid from the Fungus Malassezia pachydermatis Signals through Human Mincle

et al. 2019

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Mincle is a C-type lectin receptor of the innate immune system with the ability to sense pathogens and commensals through lipidic metabolites. While a growing number of bacterial glycolipids have been discovered that can signal through human Mincle, no fungal metabolites are known that can signal through the human form of this receptor. We report the total synthesis of a complex β-1,2-mannosyloxymannitol glycolipid from Malassezia pachydermatis 44-2, which was reported to signal through the murine Mincle receptor. Assembly of 44-2 was achieved through a highly convergent route that exploits symmetry elements inherent within this molecule and delineation of conditions that maintain the delicate L-mannitol triestertriol array. We show that 44-2 is a potent agonist of human Mincle signaling and constitutes the first fungal metabolite identified that can signal through the human Mincle receptor, providing new insights into antifungal immunity.

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“…C 8 GlcC 8 This work builds on related efforts exploring structure activity relationships of acyl-hexoses (as analogues of glucose monomycolate), 15,16 glycosyloxy-stearates (as analogues of the mannosyloxymannitol glycolipid from Malassezia pachydermatis), 28 glycerolipids (as analogues of glycerol monomycolate), 27,29 mono- 13 and diacyl trehaloses, 12,30 and lipidated diaroyltrehaloses (as analogues of brartemicin). 14,31 The present work is notable for the simplicity of the resulting agonists and the fact that unlike acyl-hexoses they exist as single stereoisomers.…”

Section: Nfat-gfp (%)mentioning

confidence: 99%

Design of Potent Mincle Signalling Agonists Based on an Alkyl b- Glucoside Template

SMITH¹,

Hosono²,

Nagata³

et al. 2020

Preprint

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Synthesis of 12-O-Mono- and Diglycosyl-oxystearates, a New Class of Agonists for the C-type Lectin Receptor Mincle

Cited by 10 publications

References 33 publications

Biological nanoscale fluorescent probes: From structure and performance to bioimaging

Biological nanoscale fluorescent probes: From structure and performance to bioimaging

Synthetic β-1,2-Mannosyloxymannitol Glycolipid from the Fungus Malassezia pachydermatis Signals through Human Mincle

Design of Potent Mincle Signalling Agonists Based on an Alkyl b- Glucoside Template

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