Preparation of HA Hydrogel by Click Chemistry

2015 ◽  
Vol 1088 ◽  
pp. 286-289
Author(s):  
Yuan Cui ◽  
Jing Peng Zhang ◽  
Wei Zhang ◽  
Qian Duan
Keyword(s):  
Hyaluronic Acid ◽  
Click Chemistry ◽  
Molecular Design ◽  
Click Reaction ◽  
Side Chains ◽  
H Nmr ◽  
Hydrogel Formation

"Click chemistry" was used in this paper to get a novel hyaluronic acid (HA) hydrogel by modified HA molecules' side chains with azide and alkynyl groups to perform "Click" reaction. The HA hydrogel can be achieved "in situ" injection gel. The properties of the HA hydrogel can be controlled by controlling the amount of alkynyl and azide groups on side chains to achieve controllable HA hydrogel by HA molecular design. The reactant, product and hydrogel were characterized by 1H NMR, FTIR and morphology observation to determine the processes of reaction and can hydrogel formation.

In situ cross-linkable hyaluronic acid hydrogels using copper free click chemistry for cartilage tissue engineering

2018 ◽  
Vol 9 (1) ◽  
pp. 20-27 ◽  
Author(s):  
Sang-Soo Han ◽  
Hong Yeol Yoon ◽  
Ji Young Yhee ◽  
Myeong Ok Cho ◽  
Hye-Eun Shim ◽  
...  
Keyword(s):  
Tissue Engineering ◽  
Hyaluronic Acid ◽  
Click Chemistry ◽  
Click Reaction ◽  
Cartilage Tissue Engineering ◽  
Cartilage Tissue

We develop a biocompatible and in situ HA hydrogel via a bioorthogonal click reaction for cartilage tissue engineering.

scholarly journals Microfluidic Fabrication of Click Chemistry-Mediated Hyaluronic Acid Microgels: A Bottom-Up Material Guide to Tailor a Microgel’s Physicochemical and Mechanical Properties

Polymers ◽  
2020 ◽  
Vol 12 (8) ◽  
pp. 1760
Author(s):  
Thomas Heida ◽  
Oliver Otto ◽  
Doreen Biedenweg ◽  
Nicolas Hauck ◽  
Julian Thiele
Keyword(s):  
Mechanical Properties ◽  
Hyaluronic Acid ◽  
Click Chemistry ◽  
Cell Biology ◽  
Click Reaction ◽  
Droplet Microfluidics ◽  
Natural Polymers ◽  
Bottom Up ◽  
Multiple Binding Sites ◽  
Thermo Stability

The demand for tailored, micrometer-scaled biomaterials in cell biology and (cell-free) biotechnology has led to the development of tunable microgel systems based on natural polymers, such as hyaluronic acid (HA). To precisely tailor their physicochemical and mechanical properties and thus to address the need for well-defined microgel systems, in this study, a bottom-up material guide is presented that highlights the synergy between highly selective bio-orthogonal click chemistry strategies and the versatility of a droplet microfluidics (MF)-assisted microgel design. By employing MF, microgels based on modified HA-derivates and homobifunctional poly(ethylene glycol) (PEG)-crosslinkers are prepared via three different types of click reaction: Diels–Alder [4 + 2] cycloaddition, strain-promoted azide-alkyne cycloaddition (SPAAC), and UV-initiated thiol–ene reaction. First, chemical modification strategies of HA are screened in-depth. Beyond the microfluidic processing of HA-derivates yielding monodisperse microgels, in an analytical study, we show that their physicochemical and mechanical properties—e.g., permeability, (thermo)stability, and elasticity—can be systematically adapted with respect to the type of click reaction and PEG-crosslinker concentration. In addition, we highlight the versatility of our HA-microgel design by preparing non-spherical microgels and introduce, for the first time, a selective, hetero-trifunctional HA-based microgel system with multiple binding sites. As a result, a holistic material guide is provided to tailor fundamental properties of HA-microgels for their potential application in cell biology and (cell-free) biotechnology.

scholarly journals Improved method for synthesis of cysteine modified hyaluronic acid for in situ hydrogel formation

2015 ◽  
Vol 51 (47) ◽  
pp. 9662-9665 ◽  
Author(s):  
Xin Zhang ◽  
Pengcheng Sun ◽  
Lingzi Huangshan ◽  
Bi-Huang Hu ◽  
Phillip B. Messersmith
Keyword(s):  
Hyaluronic Acid ◽  
Chemical Modification ◽  
Hydroxyl Groups ◽  
Improved Method ◽  
Ether Bond ◽  
Hydrogel Formation ◽  
New Strategy ◽  
In Situ Hydrogel ◽  
Acid Conjugate

We developed a new strategy for the functionalization of hyaluronic acid by chemical modification of its C-6 hydroxyl groups through an ether bond to obtain a cysteine–hyaluronic acid conjugate.

Fast-forming BMSC-encapsulating hydrogels through bioorthogonal reaction for osteogenic differentiation

2018 ◽  
Vol 6 (10) ◽  
pp. 2578-2581 ◽  
Author(s):  
Yajie Zhang ◽  
Hong Chen ◽  
Tingting Zhang ◽  
Yue Zan ◽  
Tianyu Ni ◽  
...  
Keyword(s):  
Hyaluronic Acid ◽  
Osteogenic Differentiation ◽  
Click Reaction ◽  
Diels Alder ◽  
Bioorthogonal Reaction ◽  
Inverse Electron Demand ◽  
Electron Demand

An injectable in situ fast-forming hydrogel was fabricated to encapsulate BMSCs for osteogenic differentiation through the inverse electron demand Diels–Alder click reaction between trans-cyclooctene-modified PEG and tetrazine-modified hyaluronic acid.

Versatile method for AFM-tip functionalization with biomolecules: fishing a ligand by means of an in situ click reaction

Nanoscale ◽  
2015 ◽  
Vol 7 (15) ◽  
pp. 6599-6606 ◽  
Author(s):  
Rakesh Kumar ◽  
Shivaprakash N. Ramakrishna ◽  
Vikrant V. Naik ◽  
Zonglin Chu ◽  
Michael E. Drew ◽  
...  
Keyword(s):  
Click Chemistry ◽  
Click Reaction ◽  
Force Spectroscopy ◽  
Chemical Force

A method for AFM-tip functionalization is described using click chemistry between pre-immobilized tripod–acetylene on the tip and azide-connected biomolecules. It has been successfully applied to chemical force spectroscopy.

scholarly journals Selective colorimetric NO(g) detection based on the use of modified gold nanoparticles using click chemistry

2015 ◽  
Vol 51 (15) ◽  
pp. 3077-3079 ◽  
Author(s):  
Almudena Martí ◽  
Ana M. Costero ◽  
Pablo Gaviña ◽  
Margarita Parra
Keyword(s):  
Gold Nanoparticles ◽  
Click Chemistry ◽  
Click Reaction ◽  
Colorimetric Probe ◽  
Functionalized Gold Nanoparticles

A new colorimetric probe for the detection of NO(g) based on the use of functionalized gold nanoparticles is described. The sensing protocol is based on a click reaction catalized by Cu(i) which is generated in situ from the reduction of Cu(ii) by NO(g).

scholarly journals Nucleoside macrocycles formed by intramolecular click reaction: efficient cyclization of pyrimidine nucleosides decorated with 5'-azido residues and 5-octadiynyl side chains

2018 ◽  
Vol 14 ◽  
pp. 2404-2410 ◽  
Author(s):  
Jiang Liu ◽  
Peter Leonard ◽  
Sebastian L Müller ◽  
Constantin Daniliuc ◽  
Frank Seela
Keyword(s):  
Click Reaction ◽  
Coupling Constants ◽  
Protecting Groups ◽  
Side Chains ◽  
X Ray ◽  
Pyrimidine Nucleosides ◽  
H Nmr ◽  
High Yields ◽  
Very High ◽  
Sugar Conformation

Copper(I)-promoted "click" cyclization in the presence of TBTA afforded nucleoside macrocycles in very high yields (≈70%) without using protecting groups. To this end, dU and dC derivatives functionalized at the 5-position of the nucleobase with octadiynyl side chains and with azido groups at the 5’-position of the sugar moieties were synthesized. The macrocycles display freely accessible Watson–Crick recognition sites. The conformation of the 16-membered macrocycle was deduced from X-ray analysis and 1H,1H-NMR coupling constants. The sugar conformation (N vs S) was different in solution as compared to the solid state.

scholarly journals Accelerated SuFEx Click Chemistry for Modular Synthesis

2021 ◽  
Author(s):  
Christopher J. Smedley ◽  
Timothy Gialelis ◽  
John Moses
Keyword(s):  
Click Chemistry ◽  
Click Reaction ◽  
Reaction Times ◽  
Catalyst Loading ◽  
Silyl Ether ◽  
Reduced Pressure ◽  
Shortening Reaction ◽  
Thermodynamic Driving Force ◽  
Efficient Coupling

Click chemistry is a method for the rapid synthesis of functional molecules with desirable properties. We report the development of accelerated SuFEx, a powerful click reaction for the efficient coupling of aryl and alkyl alcohols directly with SuFExable hubs catalyzed by 2-<i>tert</i>-butyl-1,1,3,3-tetramethylguanidine (BTMG, Barton's base). The new method circumvents the need to synthesize silyl ether substrates while allowing the use of sub-stoichiometric catalyst loadings. This is made possible through a synergistic effect between BTMG and hexamethyldisilazane (HMDS) additive. The powerful combination drives the <i>in situ</i> formation of reactive TMS-ether intermediates while exploiting the silicon-fluoride bond formation's thermodynamic driving force. Comparatively, the required BTMG base's catalyst loading is generally low (1.0–20 mol%) compared to the dominant SuFEx catalyst, DBU (10–30 mol%). In line with click chemistry principles, the scalable reaction only requires simple evaporation of the volatile side products (NH<sub>3</sub>, Me<sub>3</sub>Si-F, TMS-OH, BTMG) under reduced pressure instead of extensive purification. The new SuFEx protocol is tolerant of a wide selection of functional groups and meets all the demands of a click reaction, thereby dramatically shortening reaction times and delivering products in excellent yield.

scholarly journals Accelerated SuFEx Click Chemistry for Modular Synthesis

2021 ◽  
Author(s):  
Christopher J. Smedley ◽  
Timothy Gialelis ◽  
John Moses
Keyword(s):  
Click Chemistry ◽  
Click Reaction ◽  
Reaction Times ◽  
Catalyst Loading ◽  
Silyl Ether ◽  
Reduced Pressure ◽  
Shortening Reaction ◽  
Thermodynamic Driving Force ◽  
Efficient Coupling

Click chemistry is a method for the rapid synthesis of functional molecules with desirable properties. We report the development of accelerated SuFEx, a powerful click reaction for the efficient coupling of aryl and alkyl alcohols directly with SuFExable hubs catalyzed by 2-<i>tert</i>-butyl-1,1,3,3-tetramethylguanidine (BTMG, Barton's base). The new method circumvents the need to synthesize silyl ether substrates while allowing the use of sub-stoichiometric catalyst loadings. This is made possible through a synergistic effect between BTMG and hexamethyldisilazane (HMDS) additive. The powerful combination drives the <i>in situ</i> formation of reactive TMS-ether intermediates while exploiting the silicon-fluoride bond formation's thermodynamic driving force. Comparatively, the required BTMG base's catalyst loading is generally low (1.0–20 mol%) compared to the dominant SuFEx catalyst, DBU (10–30 mol%). In line with click chemistry principles, the scalable reaction only requires simple evaporation of the volatile side products (NH<sub>3</sub>, Me<sub>3</sub>Si-F, TMS-OH, BTMG) under reduced pressure instead of extensive purification. The new SuFEx protocol is tolerant of a wide selection of functional groups and meets all the demands of a click reaction, thereby dramatically shortening reaction times and delivering products in excellent yield.

Sign in / Sign up

Export Citation Format

Share Document