Thiol-reactive thiosulfonate group containing copolymers: facile entry to disulfide-mediated polymer conjugation and redox-responsive functionalizable networks

2020 ◽  
Vol 11 (10) ◽  
pp. 1763-1773 ◽  
Author(s):  
Mehmet Arslan ◽  
Rana Sanyal ◽  
Amitav Sanyal
Keyword(s):  
Synthetic Approach ◽  
Side Chains ◽  
Reactive Polymers ◽  
Disulfide Linkages ◽  
Redox Responsive ◽  
Polymer Conjugation

Herein, we report a synthetic approach to thiol-reactive polymers containing methanethiosulfonate groups as side chains, and demonstrate their application in post-polymerization functionalization through reversible disulfide linkages.

scholarly journals Tuning Paclitaxel Release Behavior Using Dually-Responsive Nanomicellar Assemblies with Multiple Diselenide/Disulfide Linkages

2021 ◽  
Author(s):  
Jingwen Xu ◽  
Xiangji Yan ◽  
Yue Zhang ◽  
Kangsheng Tu ◽  
Wen Shen ◽  
...  
Keyword(s):  
Disulfide Bonds ◽  
Slow Release ◽  
Gel Permeation Chromatography ◽  
Mass Ratio ◽  
Drug Bioavailability ◽  
Chemical Structures ◽  
Disulfide Linkages ◽  
Vis Spectroscopy ◽  
Redox Responsive

Abstract Background: There are many reasons that lead to the failure of cancer chemotherapy, such as uncontrolled drug release, low drug utilization, and severe side effects. Methods: To overcome these obstacles, we designed two kinds of copolymers with thermal and redox-responsive properties containing multiple diselenide/disulfide bonds polyethylene glycol -alt- diselenodipropionate/disulfhydryldipropionate-b-poly(N-isopropylacrylamide) (abbreviated as PEG-alt-DSeDP-b-PNIPAM and PEG-alt-DSDP-b-PNIPAM) by alternative esterification and following atom transfer radical polymerization. Afterward, these prepared copolymers were mixed with the mass ratio of 8:0, 5:3, 3:5, 0:8 (denoted as S1, S2, S3, and S4, respectively), and self-assembled with paclitaxel (PTX) to obtain PTX-loaded S1, S2, S3, and S4 nanomicellar assemblies, aiming to realize PTX controlled and on-demand release. Results: The chemical structures of these two copolymers were characterized by gel permeation chromatography (GPC), indicating eight diselenide/disulfide linkages and eight PEG units were contained in these copolymers. Moreover, the thermal-responsive property was detected by UV-vis spectroscopy, meanwhile, the redox-responsive property was observed by TEM in the presence of 10 mM glutathione (GSH). We found that 76.90% of PTX was released from S1 nanomicelles within 23 h. In contrast, this percentage decreased to 64.53% for S4 nanomicelles even the incubation time prolonged to 82 h, indicating explosive and slow release behaviors of S1 and S4 nanomicelles, respectively. In addition, gradually decreased fluorescence intensity around the cellular nucleus was occurred from S1 to S4 orderly, which was consistent with cellular uptake and in vivo anti-tumor experiments. Conclusion: This work not only provides a strategy for the controlled and effective release of PTX, but also improves drug bioavailability in cancer treatment.

scholarly journals Controlling the mode of operation of organic transistors through side-chain engineering

2016 ◽  
Vol 113 (43) ◽  
pp. 12017-12022 ◽  
Author(s):  
Alexander Giovannitti ◽  
Dan-Tiberiu Sbircea ◽  
Sahika Inal ◽  
Christian B. Nielsen ◽  
Enrico Bandiello ◽  
...  
Keyword(s):  
Operation Mode ◽  
Triethylene Glycol ◽  
Organic Transistors ◽  
Synthetic Approach ◽  
Side Chains ◽  
Semiconductor Interface ◽  
Transistor Channel ◽  
Fast Switching ◽  
Electrochemical Transistor ◽  
Mode Of Operation

Electrolyte-gated organic transistors offer low bias operation facilitated by direct contact of the transistor channel with an electrolyte. Their operation mode is generally defined by the dimensionality of charge transport, where a field-effect transistor allows for electrostatic charge accumulation at the electrolyte/semiconductor interface, whereas an organic electrochemical transistor (OECT) facilitates penetration of ions into the bulk of the channel, considered a slow process, leading to volumetric doping and electronic transport. Conducting polymer OECTs allow for fast switching and high currents through incorporation of excess, hygroscopic ionic phases, but operate in depletion mode. Here, we show that the use of glycolated side chains on a thiophene backbone can result in accumulation mode OECTs with high currents, transconductance, and sharp subthreshold switching, while maintaining fast switching speeds. Compared with alkylated analogs of the same backbone, the triethylene glycol side chains shift the mode of operation of aqueous electrolyte-gated transistors from interfacial to bulk doping/transport and show complete and reversible electrochromism and high volumetric capacitance at low operating biases. We propose that the glycol side chains facilitate hydration and ion penetration, without compromising electronic mobility, and suggest that this synthetic approach can be used to guide the design of organic mixed conductors.

Biodegradable thermal- and redox-responsive poly(l-glutamate) with Y-shaped oligo(ethylene glycol) side-chain and tunable phase transition temperature

RSC Advances ◽  
2016 ◽  
Vol 6 (74) ◽  
pp. 70243-70250 ◽  
Author(s):  
Xiaohui Fu ◽  
Yinan Ma ◽  
Jing Sun ◽  
Zhibo Li
Keyword(s):  
Phase Transition ◽  
Transition Temperature ◽  
Ethylene Glycol ◽  
Phase Transition Temperature ◽  
Side Chain ◽  
Side Chains ◽  
Redox Responsive

A series of poly(l-glutamate) bearing Y-shaped oligo(ethylene glycol)x side-chains were synthesized via a combination of ROP and thiol–yne photoaddition. The polypeptides showed dual thermal and redox-responsive properties.

scholarly journals General approach to prepare polymers bearing pendant isocyanate groups

2020 ◽  
Vol 11 (32) ◽  
pp. 5140-5146
Author(s):  
Rodrigo Navarro ◽  
Carolina García ◽  
Juan Rodríguez-Hernández ◽  
Carlos Elvira ◽  
Angel Marcos-Fernández ◽  
...  
Keyword(s):  
Synthetic Approach ◽  
Side Chains ◽  
Linear Polymers ◽  
Reaction Conditions

A versatile synthetic approach for the easy preparation, under smooth reaction conditions, of diverse classes of linear polymers bearing aliphatic or aromatic isocyanate groups in the side chains is described.

A Synthetic Approach for the Incorporation of Highly Efficient, Thermally Stable Second Order Nonlinear Optical Chromophores Into Side-Chain Polymers

1993 ◽  
Vol 328 ◽  
Author(s):  
Kevin J. Drost ◽  
Alex K-Y. Jen ◽  
V. Pushkara Rao ◽  
R. M. Mininni
Keyword(s):  
Nonlinear Optical ◽  
Second Order ◽  
Side Chain ◽  
Synthetic Approach ◽  
Synthetic Method ◽  
Side Chains ◽  
Thermally Stable ◽  
Highly Efficient ◽  
Nonlinear Optical Chromophores ◽  
Optical Chromophores

ABSTRACTA new synthetic method is developed to incorporate efficient nonlinear optical chromophores containing thiophene conjugating units and tricyanovinyl acceptors into side-chain polymers. This approach emphasizes the incorporation of the tricyanovinyl groups into the pendant side chains after the desired polymer is formed.

Expedient Synthesis of Gonadotropin Releasing Hormone (GnRH) Through a Combined Chemical-Enzymatic Approach

1992 ◽  
Vol 47 (10) ◽  
pp. 1424-1430
Author(s):  
Urszula Słomczyńska ◽  
Tomasz Leplawy ◽  
Mirosław T. Leplawy
Keyword(s):  
Amino Acids ◽  
Scaling Up ◽  
Gonadotropin Releasing Hormone ◽  
Synthetic Approach ◽  
Side Chains ◽  
Chemical Methods ◽  
Peptide Bonds ◽  
Releasing Hormone ◽  
Protection Strategy

We have developed a chemical-enzymatic synthetic approach to gonadotropin releasing hormone Glp1–His-2–Trp3–Ser4–Tyr5–Gly6–Leu7–Arg8—Pro9–Gly10–NH2 (GnRH) which enables one to perform the synthesis efficiently according to minimal protection strategy with all reactive side chains of amino acids unprotected. Five peptide bonds His2–Trp3, Tyr5–Gly6, Leu7–Arg8 and Trp3–Ser4, Ser4–Tyr5 were formed by means of a-chymotrypsin and papain, respectively. The remaining four bonds Glp1–His2, Gly6–Leu7, Arg8—Pro9, Pro9—Gly10 were formed by chemical methods. The synthesis is simple to carry out and there are no problems in scaling up as demonstrated by the final coupling on 2 g scale affording highly pure GnRH in the yield of 84-90%.

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