5840-76-6Relevant academic research and scientific papers
Poly(Sarcosine) Surface Modification Imparts Stealth-Like Properties to Liposomes
Bleher, Stefan,Buck, Jonas,Muhl, Christian,Sieber, Sandro,Barnert, Sabine,Witzigmann, Dominik,Huwyler, J?rg,Barz, Matthias,Süss, Regine
, (2019)
Circulation lifetime is a crucial parameter for a successful therapy with nanoparticles. Reduction and alteration of opsonization profiles by surface modification of nanoparticles is the main strategy to achieve this objective. In clinical settings, PEGylation is the most relevant strategy to enhance blood circulation, yet it has drawbacks, including hypersensitivity reactions in some patients treated with PEGylated nanoparticles, which fuel the search for alternative strategies. In this work, lipopolysarcosine derivatives (BA-pSar, bisalkyl polysarcosine) with precise chain lengths and low polydispersity indices are synthesized, characterized, and incorporated into the bilayer of preformed liposomes via a post insertion technique. Successful incorporation of BA-pSar can be realized in a clinically relevant liposomal formulation. Furthermore, BA-pSar provides excellent surface charge shielding potential for charged liposomes and renders their surface neutral. Pharmacokinetic investigations in a zebrafish model show enhanced circulation properties and reduction in macrophage recognition, matching the behavior of PEGylated liposomes. Moreover, complement activation, which is a key factor in hypersensitivity reactions caused by PEGylated liposomes, can be reduced by modifying the surface of liposomes with an acetylated BA-pSar derivative. Hence, this study presents an alternative surface modification strategy with similar benefits as the established PEGylation of nanoparticles, but with the potential of reducing its drawbacks.
Mapping the supramolecular assembly space of poly(sarcosine)-: B-poly(propylene sulfide) using a combinatorial copolymer library
Frey, Molly,Vincent, Michael,Bobbala, Sharan,Burt, Rajan,Scott, Evan,Scott, Evan
, p. 6644 - 6647 (2020)
A combinatorial copolymer library was created to rapidly screen the landscape of self-assembled nanostructure morphologies formed by block copolymers composed of hydrophilic peptoid polysarcosine (PSarc) and hydrophobic poly(propylene sulfide) (PPS) block
Thermo-Induced Aggregation and Crystallization of Block Copolypeptoids in Water
Secker, Christian,V?lkel, Antje,Tiersch, Brigitte,Koetz, Joachim,Schlaad, Helmut
, p. 979 - 985 (2016)
Block copolypeptoids comprising a thermosensitive, crystallizable poly(N-(n-propyl)glycine) block and a water-soluble poly(N-methylglycine) block, P70My (y = 23, 42, 76, 153, and 290), were synthesized by ring-opening polymerization of the corresponding N-alkylglycine N-carboxyanhydrides (NCAs) and examined according to their thermo-induced aggregation and crystallization in water by turbidimetry, micro-differential scanning calorimetry (micro-DSC), cryogenic scanning electron microscopy (cryo-SEM), analytical ultracentrifugation (AUC), and static light scattering (SLS). At a temperature above the cloud point temperature, the initially formed micellar aggregates started to crystallize and grow into larger complex assemblies of about 100-500 nm, exhibiting flower-like (P70M23), ellipsoidal (P70M42 and P70M72), or irregular shapes (P70M153 and P70M290).
Cyclic Poly(α-peptoid)s by Lithium bis(trimethylsilyl)amide (LiHMDS)-Mediated Ring-Expansion Polymerization: Simple Access to Bioactive Backbones
Salas-Ambrosio, Pedro,Tronnet, Antoine,Since, Marc,Bourgeade-Delmas, Sandra,Stigliani, Jean-Luc,Vax, Amelie,Lecommandoux, Sébastien,Dupuy, Bruno,Verhaeghe, Pierre,Bonduelle, Colin
supporting information, p. 3697 - 3702 (2021/04/07)
Cyclic polymers display unique physicochemical and biological properties. However, their development is often limited by their challenging preparation. In this work, we present a simple route to cyclic poly(α-peptoids) from N-alkylated-N-carboxyanhydrides (NNCA) using LiHMDS promoted ring-expansion polymerization (REP) in DMF. This new method allows the unprecedented use of lysine-like monomers in REP to design bioactive macrocycles bearing pharmaceutical potential against Clostridioides difficile, a bacterium responsible for nosocomial infections.
Alkali-metal hexamethyldisilazide initiated polymerization on alpha-amino acid N-substituted N-carboxyanhydrides for facile polypeptoid synthesis
Wu, Yueming,Zhou, Min,Chen, Kang,Chen, Sheng,Xiao, Ximian,Ji, Zhemin,Zou, Jingcheng,Liu, Runhui
supporting information, p. 1675 - 1678 (2021/03/15)
Polypeptoids have been explored as mimics of polypeptides, owing to polypeptoids’ superior stability upon proteolysis. Polypeptoids can be synthesized from one-pot ring-opening polymerization of amino acid N-substituted N-carboxyanhydrides (NNCAs). However, the speed of polymerization of NNCAs can be very slow, especially for NNCAs bearing a bulky N-substitution group. This hindered the exploration on polypeptoids with more diverse structures and functions. Therefore, it is in great need to develop advanced strategies that can accelerate the polymerization on inactive NNCAs. Hereby, we report that lithium/sodium/potassium hexamethyldisilazide (Li/Na/KHMDS) initiates a substantially faster polymerization on NNCAs than do commonly used amine initiators, especially for NNCAs with bulky N-substitution group. This fast NNCA polymerization will increase the structure diversity and application of polypeptoids as synthetic mimics of polypeptides.
Superfast and Water-Insensitive Polymerization on α-Amino Acid N-Carboxyanhydrides to Prepare Polypeptides Using Tetraalkylammonium Carboxylate as the Initiator
Chen, Jiacheng,Chen, Kang,Ding, Yun,Ji, Zhemin,Liu, Longqiang,Liu, Runhui,Liu, Shiqi,Shao, Ning,Wu, Xue,Wu, Yueming,Zhang, Weiwei,Zhou, Min,Zhu, Minghui
supporting information, p. 26063 - 26071 (2021/11/12)
We design the tetraalkylammonium carboxylate-initiated superfast polymerization on α-amino acid N-carboxyanhydrides (NCA) for efficient synthesis of polypeptides. Carboxylates, as a new class of initiator for NCA polymerization, can initiate the superfast NCA polymerization without the need of extra catalysts and the polymerization can be operated in open vessels at ambient condition without the use of glove box. Tetraalkylammonium carboxylate-initiated polymerization on NCA easily affords block copolymers with at least 15 blocks. Moreover, this method avoids tedious purification steps and enables direct polymerization on crude NCAs in aqueous environments to prepare polypeptides and one-pot synthesis of polypeptide nanoparticles. These advantages and the mild polymerization condition of tetraalkylammonium carboxylate-initiated NCA polymerization imply its great potential in functional exploration and application of polypeptides.
METHOD OF SYNTHESIZING N-CARBOXYANHYDRIDE USING FLOW REACTOR
-
Paragraph 0092-0096; 0113-0114, (2020/03/26)
PROBLEM TO BE SOLVED: To provide a synthesis method that allows high-yield continuous production of a compound of interest in synthesis and production of N-carboxyanhydride (NCA) and the like using a flow reactor. SOLUTION: In a synthesis method using a flow reactor 100, a basic solution adjusted in advance to a pH of 7-14 becomes acidic with a pH of 0-7, or an acidic solution adjusted in advance to a pH of 0-7 becomes basic with a pH of 7-14, within 60 seconds after the start of mixture of at least two ingredient solutions. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2020,JPOandINPIT
METHOD FOR PRODUCING AMINO ACID-N-CARBOXYLIC ACID ANHYDRIDE
-
Paragraph 0084, (2020/08/07)
PROBLEM TO BE SOLVED: To provide: a method for safely and efficiently producing amino acid-N-carboxylic acid anhydride; and a method for producing peptide by using the obtained amino acid-N-carboxylic acid anhydride. SOLUTION: The method for producing an amino acid-N-carboxylic acid anhydride according to the present invention is characterized in that the amino acid-N-carboxylic acid anhydride is represented by the following formula (II), and a step of irradiating a composition containing a halogenated methane and an amino acid compound represented by the following formula (I) with high energy light in the presence of oxygen is included. [In the formula, R1 represents an amino acid side chain group in which the reactive group is protected, and R2 represents H or the like.]. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT
POLYPEPT(O)ID-BASED GRAFT COPOLYMERS FOR IN VIVO IMAGING BY TETRAZINE TRANSCYCLOOCTENE CLICK CHEMISTRY
-
Page/Page column 8-9, (2020/01/24)
There is provided novel polypeptide-based carrier systems, which make it possible to label polymeric nanoparticles in the living organism. This enables new approaches in tumor diagnostics (high signal to background ratio) and radiotherapy (radiotherapy of solid tumors). The polypeptide-based carrier system comprises a polypept(o)idic comb (graft) copolymer, and one or more tetrazine bioorthogonal functional groups each linked to a diagnostic agent.
SURFACE-MODIFIED POLYMERIC SUBSTRATES GRAFTED WITH A PROPERTIES-IMPARTING COMPOUND USING CLIP CHEMISTRY
-
Paragraph 0358-0359, (2019/08/27)
The present invention relates to an efficient method for grafting a properties-imparting compound onto a polymeric substrate containing carbon-hydrogen (C—H) bonds using clip chemistry. The method of the invention includes coating the substrate with the properties-imparting compound and irradiating it with a reactive light source, and repeating this sequence at least once. The present invention further relates to surface-modified polymeric substrates grafted with a properties-imparting compound, in particular obtained with the method of the invention, medical devices comprising same, and non-medical of said surface-modified polymeric substrates.
