10289-12-0Relevant academic research and scientific papers
Fluorinated PEG-Polypeptide Polyplex Micelles Have Good Serum-Resistance and Low Cytotoxicity for Gene Delivery
Wu, Ting,Wang, Longhai,Ding, Shenggang,You, Yezi
, (2017)
A novel PEGylation polypeptide, poly(ethylene glycol)-b-poly(l-lysine)-b-poly(l-cysteine) (PEG-PLL-PCys) triblock copolymer is synthesized via the sequential ring-opening polymerization of amino acid N-carboxyanhydrides initiated by methoxypolyethylene gl
α-Helix nucleation constant in copolypeptides of alanine and ornithine or lysine
Yang, Jianxin,Zhao, Kang,Gong, Youxiang,Vologodskii, Alexander,Kallenbach, Neville R.
, p. 10646 - 10652 (1998)
The α-helix is one of a small number of fundamental structural motifs of the peptide backbone that are abundant in native proteins. The forces responsible for its stability have attracted a great deal of theoretical and experimental attention. Helix formation can naturally be considered in terms of two processes, initial nucleation of a helix from a sequence of disordered residues and propagation or growth of helical structure from such a nucleus. Data from a variety of short peptide and polypeptide models have revealed more details about the propagation of helix structure than about helix nucleation. To investigate helix nucleation, we have synthesized two series of high molecular weight polypeptides containing differing ratios of alanine and one of the basic side chains, ornithine or lysine; poly L-alanine is insoluble in water. The CD signals of these copolymers have been analyzed by a program that evaluates the helix content in terms of the experimental chain-length distribution and composition, with the helix nucleation constant (σ value) and the propagation constants (s values) for the amino acids involved. Fitting the CD data allows the determination of the propagation constants for Orn (s = 0.45) and Lys (s = 0.8) in addition to that of the helix nucleation constant once the s value for Ala is specified. The value of σ is sensitive to the dependence of the CD signal on helix length; using the Yang equation, [θ]222 = -41000(n - x)/n, with x = 2.5, the nucleation constant value is σ = 0.004 ± 0.002 at 4 °C in the presence of 1 M salt. This value is consistent with earlier estimates based on analysis of the helix-coil transition in poly(Lys), poly(Glu), and shorter Ala-rich peptides. However, if x is taken to be zero, the resulting σ value is 0.02, considerably larger than the above estimates.
Reduction-sensitive amphiphilic dextran derivatives as theranostic nanocarriers for chemotherapy and MR imaging
Yang, Hui-Kang,Qi, Meng,Mo, Lei,Yang, Rui-Meng,Xu, Xiang-Dong,Bao, Jun-Fang,Tang, Wen-Jie,Lin, Jian-Tao,Zhang, Li-Ming,Jiang, Xin-Qing
, p. 114519 - 114531 (2016)
Reduction-sensitive, amphiphilic dextran derivatives were developed from disulfide-linked dextran-g-poly-(N-ε-carbobenzyloxy-l-lysine) graft polymer (Dex-g-SS-PZLL), and used as theranostic nanocarriers for chemotherapy and MR imaging. Dex-g-SS-PZLLs were
Polypeptoid-block-polypeptide copolymers: Synthesis, characterization, and application of amphiphilic block copolypept(o)ides in drug formulations and miniemulsion techniques
Birke, Alexander,Huesmann, David,Kelsch, Annette,Weilbaecher, Martin,Xie, Jing,Bros, Matthias,Bopp, Tobias,Becker, Christian,Landfester, Katharina,Barz, Matthias
, p. 548 - 557 (2014)
We report the synthesis of polysarcosine-blockpolyglutamic acid benzylester (PSar-block-PGlu(OBn)) and polysarcosine-block-polylysine-ε-N- benzyloxycarbonyl (PSarblock-PLys(Z)) copolymers. The novel polypeptoid- blockpolypeptide copolymers (Copolypept(o)ides) have been synthesized by ring-opening polymerization (ROP) of Ncarboxyanhydrides (NCAs). Polymerization conditions were optimized regarding protecting groups, block sequence and length. While the degree of polymerization of the PSar block length was set to be around 200 or 400, PGlu(OBn) and PLys(Z) block lengths were varied between 20 to 75. The obtained block copolymers had a total degree of polymerization of 220.475 and dispersity indices between 1.1 and 1.2. Having ensured a nontoxic behavior up to a concentration of 3 mg/mL in HEK293 cells, the novel block copolymers have been applied to the synthesis of organic colloids (by miniemulsion polymerization and miniemulsion solvent evaporation process). Colloids of around 100 nm (miniemulsion polymerization) to 200 nm (miniemulsion process) have been prepared. Additionally, PSar-block-PGlu(OBn) copolymers have been used in a drug formulation of an adenylate cyclase inhibitor. Micelles of 28.0 nm (without drug) and 33.0 nm (with drug) diameter have been observed by fluorescence correlation spectroscopy (FCS). The polypeptoid-block-polypeptide formulation increased solubility of the drug and enhances its bioavailability, which leads to a reduction of intracellular cAMP levels in MaMel 91 melanoma cells.
Tandem catalysis: A new approach to polypeptides and cyclic carbonates
Raman, Sumesh K.,Brul, Emilie,Tschan, Mathieu J.-L.,Thomas, Christophe M.
, p. 13773 - 13776 (2014)
A new tandem catalytic system mediates very efficiently and selectively at room temperature two sequential reactions to produce relevant derivatives in one pot. Remarkably, this new concept of catalysis allows the facile synthesis of polypeptides and provides direct access to cyclic carbonates in high yields, through the incorporation of the carbon dioxide released from the initial step, thus achieving full-atom economy.
Synthesis of thiol-clickable and block copolypeptide brushes via nickel-mediated surface initiated polymerization of α-amino acid N-carboxyanhydrides (NCAs)
Sparks, Bradley J.,Ray, Jacob G.,Savin, Daniel A.,Stafford, Christopher M.,Patton, Derek L.
, p. 6245 - 6247 (2011)
We describe the synthesis of homo-, block, and clickable copolypeptide brushes from low surface area substrates using nickel-mediated surface-initiated polymerization of α-amino N-carboxyanhydrides.
On-POM Ring-Opening Polymerisation of N-Carboxyanhydrides
Soria-Carrera, Héctor,Franco-Castillo, Isabel,Romero, Pilar,Martín, Santiago,de la Fuente, Jesús M.,Mitchell, Scott G.,Martín-Rapún, Rafael
, p. 3449 - 3453 (2021)
The ring-opening polymerisation of α-amino acid N-carboxyanhydrides (NCAs) offers a simple and scalable route to polypeptides with predicted and narrow molecular weight distributions. Here we show how polyoxometalates (POMs)—redox-active molecular metal-oxide anions—can serve as inorganic scaffold initiators for such NCA polymerisations. This “On-POM polymerisation” strategy serves as an innovative platform to design hybrid materials with additive or synergistic properties stemming from the inorganic and polypeptide component parts. We have used this synthetic approach to synthesise a library of bactericidal poly(lysine)–POM hybrid derivatives that can be used to prevent biofilm formation. This versatile “On-POM polymerisation” method provides a flexible synthetic approach for combining inorganic scaffolds with amino acids, and the potential to tailor and improve the specificity and performance of hybrid antimicrobial materials.
Effective gene delivery using stimulus-responsive catiomer designed with redox-sensitive disulfide and acid-labile imine linkers
Cai, Xiaojun,Dong, Chunyan,Dong, Haiqing,Wang, Gangmin,Pauletti, Giovanni M.,Pan, Xiaojing,Wen, Huiyun,Mehl, Isaac,Li, Yongyong,Shi, Donglu
, p. 1024 - 1034 (2012)
A dual stimulus-responsive mPEG-SS-PLL15-glutaraldehyde star (mPEG-SS-PLL15-star) catiomer is developed and biologically evaluated. The catiomer system combines redox-sensitive removal of an external PEG shell with acid-induced escape from the endosomal c
High potency and broad-spectrum antimicrobial peptides synthesized via ring-opening polymerization of α-Aminoacid-N-carboxyanhydrides
Zhou, Chuncai,Qi, Xiaobao,Li, Peng,Chen, Wei Ning,Mouad, Lamrani,Chang, Matthew W.,Leong, Susanna Su Jan,Chan-Park, Mary B.
, p. 60 - 67 (2010)
Antimicrobial peptides (AMPs), particularly those effective against methicillin-resistant Staphylococcus aureus (S. aureus) and antibiotic-resistant Pseudomonas aeruginosa (P. aeruginosa), are important alternatives to antibiotics. Typical peptide synthesis methods involving solid-phase sequential synthesis are slow and costly, which are obstacles to their more widespread application. In this paper, we synthesize peptides via ring-opening polymerization of α-amino acid N-carboxyanhydrides (NCA) using a transition metal initiator. This method offers high potential for inexpensive synthesis of substantial quantities of AMPs. Lysine (K) was chosen as the hydrophilic amino acid and alanine (A), phenylalanine (F), and leucine (L) as the hydrophobic amino acids. We synthesized five series of AMPs (i.e., P(KA), P(KL), P(KF), P(KAL), and P(KFL)), varied the hydrophobic amino acid content from 0 to 100%, and determined minimal inhibitory concentrations (MICs) against clinically important Gramnegative and Gram-positive bacteria and fungi (i.e., Escherichia coli (E. coli), P. aeruginosa, Serratia marcescens (S. marcescens), and Candida albicans (C. albicans). We found that P(K10F 7.5L7.5) and P(K10F15) show the broadest activity against all five pathogens and have the lowest MICs against these pathogens. For P(K10F7.5L7.5), the MICs against E. coli, P. aeruginosa, S. marcescens, S. aureus, and C. albicans are 31 μg/mL, 31 μg/mL, 250 μg/mL, 31 μg/mL, and 62.5 μg/mL, while for P(K10F15) the respective MICs are 31 μg/mL, 31 μg/mL, 250 μg/mL, 31 μg/mL, and 125 μg/mL. These are lower than the MICs of many naturally occurring AMPs. The membrane depolarization and SEM assays confirm that the mechanism of microbe killing by P(K10F 7.5L7.5) copeptide includes membrane disruption, which is likely to inhibit rapid induction of AMP-resistance in pathogens.
Biodegradable Poly(ethylene glycol)-co-poly(l-lysine)-g-histidine Multiblock Copolymers for Nonviral Gene Delivery
Bikram, Malavosklish,Ahn, Cheol-Hee,Chae, Su Young,Lee, Minhyung,Yockman, James W.,Kim, Sung Wan
, p. 1903 - 1916 (2004)
The development of biodegradable cationic polymers for use in nonviral gene delivery was discussed. This high molecular weight multiblock copolymer (MBC) consists of repeating units of low molecular weight poly(ethylene glycol) conjugated to low molecular
