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<p>Mannose functionalized mesoporous silica nanoparticles (MSNs) offer a promising approach for developing more targeted, effective, and safer cancer therapies. For many of the applications, immobilization of carbohydrates like mannose onto MSNs is a crucial aspect, and in most cases, mannose moieties are connected through <i>O</i>-glycosidic linkages that are susceptible to acidic/enzymatic hydrolysis. To generate a stable mannose-functionalized MSN, we designed a novel <i>C</i>(14)-<i>α</i>-mannosylated tetradeca-1-yne. The key steps involved in the synthesis of <i>C</i>-mannosylated alkyne are C1-alkynylation of tri-<i>O</i>-acetyl-D-glucal with 1-trimethylsilyl-tetradec-1-yne, followed by stereoselective dihydroxylation and the isomerization of the internal triple bond to a terminal position. This mannose ligand was then immobilized onto azidopropyl-functionalized SBA-15 through the Cu(I)-catalyzed azide-alkyne click (CuAAC) reaction. Various physical techniques such as low-angle powder XRD, N<sub>2</sub> adsorption isotherms (BET), Fourier transform infrared (FTIR), high-resolution transmission electron microscopy (HRTEM), field emission scanning electron microscopy (FE-SEM), and thermogravimetric analysis (TGA) have been employed to characterize this <i>C</i>-mannosyl SBA-15 silica matrix. We evaluated the binding ability of <i>C</i>-mannosyl SBA-15 nanoparticles by using fluorescein-labelled Con-A as a target protein.</p> Graphical abstract <p>We document the synthesis of a novel novel <i>C</i>(14)-<i>α</i>-mannosylated tetradeca-1-yne from tri-<i>O</i>-acetyl-D-glucal its immobilization onto azidopropyl-functionalized SBA-15 through the Cu(I)-catalyzed azide-alkyne click (CuAAC) reaction. The successfully immobilization of mannosyl units on SBA-15 and retention of the pore structure of SBA-15 after the incorporation of the organic molecules has been established with the help of various physical techniques and the binding ability of <i>C</i>-mannosyl SBA-15 nanoparticles by using fluorescein-labeled Con-A as a target protein.</p> <p></p>

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Design and synthesis of C-α-D-mannopyranoside linked mesoporous silica nanoparticles

  • 期刊论文

  • 发表日期：

    2025年3月26日

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  • Hemanth K Nechooli,
  • Vilas Ramtenki,
  • Chepuri V Suneel Kumar,
  • B L V Prasad,
  • Chepuri V Ramana

摘要

Mannose functionalized mesoporous silica nanoparticles (MSNs) offer a promising approach for developing more targeted, effective, and safer cancer therapies. For many of the applications, immobilization of carbohydrates like mannose onto MSNs is a crucial aspect, and in most cases, mannose moieties are connected through O-glycosidic linkages that are susceptible to acidic/enzymatic hydrolysis. To generate a stable mannose-functionalized MSN, we designed a novel C(14)-α-mannosylated tetradeca-1-yne. The key steps involved in the synthesis of C-mannosylated alkyne are C1-alkynylation of tri-O-acetyl-D-glucal with 1-trimethylsilyl-tetradec-1-yne, followed by stereoselective dihydroxylation and the isomerization of the internal triple bond to a terminal position. This mannose ligand was then immobilized onto azidopropyl-functionalized SBA-15 through the Cu(I)-catalyzed azide-alkyne click (CuAAC) reaction. Various physical techniques such as low-angle powder XRD, N2 adsorption isotherms (BET), Fourier transform infrared (FTIR), high-resolution transmission electron microscopy (HRTEM), field emission scanning electron microscopy (FE-SEM), and thermogravimetric analysis (TGA) have been employed to characterize this C-mannosyl SBA-15 silica matrix. We evaluated the binding ability of C-mannosyl SBA-15 nanoparticles by using fluorescein-labelled Con-A as a target protein.

Graphical abstract

We document the synthesis of a novel novel C(14)-α-mannosylated tetradeca-1-yne from tri-O-acetyl-D-glucal its immobilization onto azidopropyl-functionalized SBA-15 through the Cu(I)-catalyzed azide-alkyne click (CuAAC) reaction. The successfully immobilization of mannosyl units on SBA-15 and retention of the pore structure of SBA-15 after the incorporation of the organic molecules has been established with the help of various physical techniques and the binding ability of C-mannosyl SBA-15 nanoparticles by using fluorescein-labeled Con-A as a target protein.