The generation of stabilized supramolecular nanorods from star-shaped polyglutamates

Zagorodko, Oleksandr; Nebot, Vicent J.; Vicent, Marı́a J.

doi:10.1039/c9py01442j

Cited by 10 publications

(7 citation statements)

References 31 publications

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“…6A), most probably consisting of doublehelical fibers, similar to a previously reported compound with an FFF core and ten glutamic residues per arm. 29 At pH 3.0, we observed various distinct morphologies, including separate fibers, parallel fiber doublets, short flat objects, and twisted nanoribbons consisting of multiple interacting fibers (Fig. 6B).…”

Section: Nanoribbon Formationmentioning

confidence: 89%

“…Recent studies have reported that, upon closer examination, at least some nanofibers in aqueous solutions comprise two smaller fibers, either twisted or parallel. 28,29 Furthermore, several studies have reported the formation of more complicated structures (e.g., nanoribbons or triple helices) during the self-assembly of BTAbased molecules in organic solvents or their mixtures with water. [30][31][32] In water, stepwise self-assembly into clearly defined double helical nanorods was reported only for BTA-based Aucontaining metalloamphiphiles.…”

Section: Introductionmentioning

confidence: 99%

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Higher-order interfiber interactions in the self-assembly of benzene-1,3,5-tricarboxamide-based peptides in water

et al. 2021

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Section: Nanoribbon Formationmentioning

confidence: 89%

Section: Introductionmentioning

confidence: 99%

Higher-order interfiber interactions in the self-assembly of benzene-1,3,5-tricarboxamide-based peptides in water

et al. 2021

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“…Inspired by a recent report of Zagorodko et al., who reported the formation of SPBs based on the BTP motif with three amino acid units per arm, we further increased the number of H‐bonds to identify the critical step for the formation of SPBs in our system. [ 35 ] For this purpose, we synthesized compound 2 comprising two leucine units per arm (Schemes S3 and S5, Supporting Information). We deliberately chose leucine in this case due to its sufficient hydrophobicity to shield the core H‐bonds compared to alanine.…”

Section: Methodsmentioning

confidence: 99%

Overcoming the Necessity of a Lateral Aggregation in the Formation of Supramolecular Polymer Bottlebrushes in Water

Klein

Ulrich

Gruschwitz

et al. 2020

Macromol. Rapid Commun.

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The assembly of supramolecular polymer bottlebrushes in aqueous systems is, in most cases, associated with a lateral aggregation of the supramolecular building blocks in addition to their axial stacking. Here, it is demonstrated that this limitation can be overcome by attaching three polymer chains to a central supramolecular unit that possesses a sufficiently high number of hydrogen bonding units to compensate for the increased steric strain. Therefore, a 1,3,5‐benzenetrisurea‐polyethylene oxide conjugate is modified with different peptide units located next to the urea groups which should facilitate self‐assembly in water. For a single amino acid per arm, spherical micelles are obtained for all three tested amino acids (alanine, leucine, and phenylalanine) featuring different hydrophobicities. Only a slight increase in size and solution stability of spherical micelles is observed with increasing hydrophobicity of amino acid unit. In contrast, introducing two amino acid units per arm and thus increasing the number of hydrogen bonds per unimer molecule results in the formation of cylindrical structures, that is, supramolecular polymer bottlebrushes, despite a suppressed lateral aggregation. Consequently, it can be concluded that the number of hydrogen bonds has a more profound impact on the resulting solution morphology than the hydrophobicity of the amino acid unit.

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“…Finally, the solvent was removed under reduced pressure yielding a highly viscous yellowish polymer. Yield: 995.3 mg (71%); 1 H-NMR (300 MHz, CDCl 3 , δ): 1.43 (s, 9H), 3.01 (br, 2H), 3.28 (br, 2H), 3.51 (br, 4H), 3.58 (br, 4H), 5.50 ppm (br, 1H); 31 carbamate)phosphazene and formation of the macroinitiator P1 was performed according to adapted literature procedure. [29,30] Briefly, the polymer (304.4 mg, 0.5641 mmol, 1 equiv.)…”

Section: Synthesis Of Poly(tert-butyl N-(2-[2-(2-aminoethoxy)ethoxy]e...mentioning

confidence: 99%

“…Vicent et al improved this aspect in the form of star‐branched PGAs, showing increased plasma half‐life time ( t 1/2 ) and cell uptake enhancement. [ 30 ] This has led to the development of different nanostructures, for example, self‐assembled nanorods [ 31 ] and sphere‐like cross‐linked nanocarriers. [ 32 ] These structures, alongside their linear analogues, have been broadly investigated for various applications in biomedicine.…”

Section: Introductionmentioning

confidence: 99%

Degradable Bottlebrush Polypeptides and the Impact of their Architecture on Cell Uptake, Pharmacokinetics, and Biodistribution In Vivo

Strasser

Montsch

Weiss

et al. 2023

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Bottlebrush polymers are highly promising as unimolecular nanomedicines due to their unique control over the critical parameters of size, shape and chemical function. However, since they are prepared from biopersistent carbon backbones, most known bottlebrush polymers are non‐degradable and thus unsuitable for systemic therapeutic administration. Herein, we report the design and synthesis of novel poly(organo)phosphazene‐g‐poly(α‐glutamate) (PPz‐g‐PGA) bottlebrush polymers with exceptional control over their structure and molecular dimensions (Dh ≈ 15–50 nm). These single macromolecules show outstanding aqueous solubility, ultra‐high multivalency and biodegradability, making them ideal as nanomedicines. While well‐established in polymer therapeutics, it has hitherto not been possible to prepare defined single macromolecules of PGA in these nanosized dimensions. A direct correlation was observed between the macromolecular dimensions of the bottlebrush polymers and their intracellular uptake in CT26 colon cancer cells. Furthermore, the bottlebrush macromolecular structure visibly enhanced the pharmacokinetics by reducing renal clearance and extending plasma half‐lives. Real‐time analysis of the biodistribution dynamics showed architecture‐driven organ distribution and enhanced tumor accumulation. This work, therefore, introduces a robust, controlled synthesis route to bottlebrush polypeptides, overcoming limitations of current polymer‐based nanomedicines and, in doing so, offers valuable insights into the influence of architecture on the in vivo performance of nanomedicines.

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The generation of stabilized supramolecular nanorods from star-shaped polyglutamates

Abstract: We developed a new strategy of polyglutamate nanorod preparation based on supramolecular polymers stabilized with hydrophobic drugs.

Cited by 10 publications

References 31 publications

Higher-order interfiber interactions in the self-assembly of benzene-1,3,5-tricarboxamide-based peptides in water

Higher-order interfiber interactions in the self-assembly of benzene-1,3,5-tricarboxamide-based peptides in water

Overcoming the Necessity of a Lateral Aggregation in the Formation of Supramolecular Polymer Bottlebrushes in Water

Degradable Bottlebrush Polypeptides and the Impact of their Architecture on Cell Uptake, Pharmacokinetics, and Biodistribution In Vivo

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