Radiosynthesis and initial evaluation of 18F labeled nanocarrier composed of poly(L-lactic acid)-block-poly(sarcosine) amphiphilic polydepsipeptide

Yamamoto, Fujio; Yamahara, Ryo; Makino, Akihiro; Kurihara, Kensuke; Tsukada, Hideo; Hara, Eri; Hara, Isao; Kizaka‐Kondoh, Shinae; Ohkubo, Yasuhito; Ozeki, Eiichi; Kimura, Shunsaku

doi:10.1016/j.nucmedbio.2012.12.008

Cited by 37 publications

(34 citation statements)

References 29 publications

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“…HRP was encapsulated in the A 92 M 94 D 12 hydrogel (sample 2, Table 1) at 37 °C for up to 7 d, over which period the enzymatic activity was examined and quantified. 57 The HRP encapsulated in hydrogels do not exhibit any appreciable changes in the specific enzymatic activity in the first 24 h of encapsulation (Figure 12). The activities are comparable to the control sets (no gel, Figure 12), where the HRP was kept in PBS buffer at 37 °C for the same duration.…”

Section: Resultsmentioning

confidence: 98%

Thermoreversible and Injectable ABC Polypeptoid Hydrogels: Controlling the Hydrogel Properties through Molecular Design

et al. 2016

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A series of ABC triblock copolypeptoids [i.e., poly(N-allyl glycine)-b-poly(N-methyl glycine)-b-poly(N-decyl glycine) (AMD)] with well-defined structure and varying composition have been synthesized by sequential primary amine-initiated ring-opening polymerization of the corresponding N-substituted N-carboxyanhydride monomers (Al-NCA, Me-NCA, and De-NCA). The ABC block copolypeptoids undergo sol-to-gel transitions with increasing temperature in water and biological media at low concentrations (2.5–10 wt %). The sol–gel transition is rapid and fully reversible with a narrow transition window, evidenced by the rheological measurements. The gelation temperature (Tgel) and mechanical stiffness of the hydrogels are highly tunable: Tgel in the 26.2–60.0 °C range, the storage modulus (G′) and Young’s modulus (E) in the 0.2–780 Pa and 0.5–2346 Pa range, respectively, at the physiological temperature (37 °C) can be readily accessed by controlling the block copolypeptoid composition and the polymer solution concentration. The hydrogel is injectable through a 24 gauge syringe needle and maintains their shape upon in contact with surfaces or water baths that are kept above the sol–gel transition temperature. The hydrogels exhibit minimal cytotoxicity toward human adipose derived stem cells (hASCs), evidenced from both alamarBlue and PicoGreen assays. Furthermore, quantitative PCR analysis revealed significant up-regulation of the Col2a1 gene and down-regulation of ANGPT1 gene, suggesting that the hydrogel exhibit biological activity in inducing chondrogenesis of hASCs. It was also demonstrated that the hydrogel can be used to quantitatively encapsulate water-soluble enzymes (e.g., horseradish peroxidase) by manipulating the sol–gel transition. The enzymatic activity of HRP remain unperturbed after encapsulation at 37 °C for up to 7 d, suggesting that the hydrogel does not adversely affect the enzyme structure and thereby the enzymatic activity. These results suggest that the polypeptoid hydrogel a promising synthetic platform for tissue engineering or protein storage applications.

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Section: Resultsmentioning

confidence: 98%

Thermoreversible and Injectable ABC Polypeptoid Hydrogels: Controlling the Hydrogel Properties through Molecular Design

et al. 2016

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“…This suggests that these polymers should be excellently suited as drug carriers. Indeed, in initial and more recent reports, Kimura and coworkers have reported very good biocompatibility and biodistribution after single injection with prolonged circulation of drug delivery systems (polymer micelles and polymersomes) comprising polysarcosine as the hydrophilic moiety . Interestingly, the biodistribution of nanoparticles of block copolymers of polysarcosine and polylactide depended on the stereochemistry of the hydrophobic component, polylactide .…”

Section: Properties Of Polypeptoidsmentioning

confidence: 99%

Polypeptoids: A perfect match for molecular definition and macromolecular engineering?

Luxenhofer

Fetsch

Grossmann

2013

J. Polym. Sci. Part A: Polym. Chem.

112

131

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Precision synthesis of polymers has been a hot topic in recent years. While this is notoriously difficult to address for polymers with a CAC backbone, Merrifield has discovered a way many decades ago for polypeptides. Using a similar approach, N-substituted polypeptides, so-called polypeptoids have been synthesized and studied for about 20 years. In contrast, the living ring-opening polymerization (ROP) of N-substituted N-carboxyanhydrides was among the first living polymerizations to be discovered. More recently, a surge in new synthetic approaches led to the efficient synthesis of cyclic or linear multiblock copolypeptoids. Thus, polypeptoids can be synthesized either by solid phase synthesis to yield complex and exactly defined oligo-and small polymers or by ROP of appropriately N-substituted N-carboxyanhydrides (NNCA) to give linear, cyclic, or star-like polymers. Together with an excellent biocompatibility, this polymer family may have a bright future ahead as biomaterials.

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“…[38,39] Kimura and co-workers have studied PSar-block-PAla and PSar-block-PLA copolymers. [40][41][42] Aditionally, Zuckermann and co-workers have performed excellent work on solid phase synthesis of PSar. [43] But in all these reports sarcosine was kept at a low degree of polymerization of 20-30.…”

Section: Introductionmentioning

confidence: 99%

Introducing PeptoPlexes: Polylysine‐block‐Polysarcosine Based Polyplexes for Transfection of HEK 293T Cells

Heller

Birke

Huesmann

et al. 2014

Macromolecular Bioscience

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A series of well-defined polypeptide-polypeptoid block copolymers based on the body's own amino acids sarcosine and lysine are prepared by ring opening polymerization of N-carboxyanhydrides. Block lengths were varied between 200-300 for the shielding polysarcosine block and 20-70 for the complexing polylysine block. Dispersity indexes ranged from 1.05 to 1.18. Polylysine is polymerized with benzyloxycarbonyl as well as trifluoroacetyl protecting groups at the ϵ-amine group and optimized deprotection protocols for both groups are reported. The obtained block ionomers are used to complex pDNA resulting in the formation of polyplexes (PeptoPlexes). The PeptoPlexes can be successfully applied in the transfection of HEK 293T cells and are able to transfect up to 50% of cells in vitro (FACS assay), while causing no detectable toxicity in an Annexin V assay. These findings are a first indication that PeptoPlexes may be a suitable alternative to PEG based non-viral transfection systems.

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Radiosynthesis and initial evaluation of 18F labeled nanocarrier composed of poly(L-lactic acid)-block-poly(sarcosine) amphiphilic polydepsipeptide

Cited by 37 publications

References 29 publications

Thermoreversible and Injectable ABC Polypeptoid Hydrogels: Controlling the Hydrogel Properties through Molecular Design

Thermoreversible and Injectable ABC Polypeptoid Hydrogels: Controlling the Hydrogel Properties through Molecular Design

Polypeptoids: A perfect match for molecular definition and macromolecular engineering?

Introducing PeptoPlexes: Polylysine‐block‐Polysarcosine Based Polyplexes for Transfection of HEK 293T Cells

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