Control of in vivo blood clearance time of polymeric micelle by stereochemistry of amphiphilic polydepsipeptides

Makino, Akihiro; Hara, Eri; Hara, Isao; Yamahara, Ryo; Kurihara, Kensuke; Ozeki, Eiichi; Yamamoto, Fujio; Kimura, Shunsaku

doi:10.1016/j.jconrel.2012.05.006

Cited by 41 publications

(31 citation statements)

References 21 publications

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“…44,46,48,54,55 Amphiphilic block copolymers comprised of hydrophilic polypeptoid segments have also been investigated for biomedical applications such as drug carriers. 56–58 …”

Section: Introductionmentioning

confidence: 99%

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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“…44,46,48,54,55 Amphiphilic block copolymers comprised of hydrophilic polypeptoid segments have also been investigated for biomedical applications such as drug carriers. 56–58 …”

Section: Introductionmentioning

confidence: 99%

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

et al. 2016

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“…AB-type lactosomes persist in the bloodstream for a long time. [13] However, AB-type lactosomes exhibit a drawback in multiple in vivo administrations,[14] in which they accumulate in solid tumors after the first administration, but accumulate only slightly after the second administration. To compensate for this drawback, a lactosome composed of (PSar) 3 -block-PLLA (A 3 B-type) has recently been developed.…”

Section: Introductionmentioning

confidence: 99%

Enhanced cellular uptake of lactosomes using cell-penetrating peptides

Akahoshi

Matsuura

Ozeki

et al. 2016

Science and Technology of Advanced Materials

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Polymeric micelles that are composed of synthetic polymers are generally size controllable and can be easily modified for various applications. Lactosomes (A3B-type) are biodegradable polymeric micelles composed of an amphipathic polymer, including three poly(sarcosine) blocks and a poly(l-lactic acid) block. Lactosomes accumulate in tumors in vivo through the enhanced permeability and retention (EPR) effect, even on frequently administering them. However, lactosomes cannot be efficiently internalized by cells. To improve cellular uptake of lactosomes, cell-penetrating peptide (CPP)-modified lactosomes were prepared. Seven CPPs (including EB1 and Pep1) were used, and most of them improved the cellular uptake efficiency of lactosomes. In particular, EB1- and Pep1-modified lactosomes were efficiently internalized by cells. In addition, by using CPP-modified and photosensitizer-loaded lactosomes, we demonstrated the photoinduced killing of mammalian cells, including human cancer cells. Accumulation of the EB1-modified lactosomes in NCI-N87 tumors was shown by in vivo imaging. Thus, this study demonstrated that the CPP-modified lactosome is a promising drug carrier.

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“…One polymeric micelle and three kinds of vesicles were prepared from AB‐type amphiphilic block polymers having commonly a hydrophilic block of poly(sarcosine) and a helical hydrophobic block of poly(lactic acid) or Aib‐based peptides (Figure ). The degree of polymerization of poly(lactic acid) is 30, which length is long enough to take a helical structure . Aib‐based peptides have alternating sequences of Leu or Val and Aib residues, which also take α‐helical conformation .…”

Section: Resultsmentioning

confidence: 99%

Modulation of immunogenicity of poly(sarcosine) displayed on various nanoparticle surfaces due to different physical properties

Kim

Hara

Watabe

et al. 2017

Journal of Peptide Science

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Poly(sarcosine) displayed on polymeric micelle is reported to trigger a T cell-independent type2 reaction with B1a cells in the mice to produce IgM and IgG3 antibodies. In addition to polymeric micelle, three kinds of vesicles displaying poly(sarcosine) on surface were prepared here to evaluate the amounts and avidities of IgM and IgG3, which were produced in mice, to correlate them with physical properties of the molecular assemblies. The largest amount of IgM was produced after twice administrations of a polymeric micelle of 35 nm diameter (G1). On the other hand, the production amount of IgG3 became the largest after twice administrations of G3 (vesicle of 229 nm diameter) or G4 (vesicle of 85 nm diameter). The augmented avidity of IgG3 after the twice administrations compared with that at the single administration was the highest with G3. These differences in immune responses are discussed in terms of surface density of poly(sarcosine) chains, nanoparticle size, hydrophobic component of poly(L-lactic acid) or (Leu- or Val-Aib) , and membrane elasticity of the nanoparticles. Copyright © 2017 European Peptide Society and John Wiley & Sons, Ltd.

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Control of in vivo blood clearance time of polymeric micelle by stereochemistry of amphiphilic polydepsipeptides

Cited by 41 publications

References 21 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

Enhanced cellular uptake of lactosomes using cell-penetrating peptides

Modulation of immunogenicity of poly(sarcosine) displayed on various nanoparticle surfaces due to different physical properties

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