Synthesis and Crosslinking of <scp>L</scp>‐DOPA Containing Polypeptide Vesicles

Holowka, Eric P.; Deming, Timothy J.

doi:10.1002/mabi.200900390

Cited by 50 publications

(34 citation statements)

References 23 publications

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“…In 2010, Deming's lab reported the preparation of lysinedihydroxyphenylalanine (i.e. K 60 DOPA 20 ) based vesicles, where the hydrophobic DOPA segments have the added feature of being sensitive toward oxidation [95]. DOPA residues are found naturally in mussel byssus and are important components in the ability of byssal threads to adhere underwater and to crosslink into rigid networks [96].…”

Section: Insert Figurementioning

confidence: 99%

Synthesis and Self-Assembly of Well-Defined Block Copolypeptides via Controlled NCA Polymerization

Deming

2013

Hierarchical Macromolecular Structures: 60 Years After the Staudinger Nobel Prize II

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Section: Insert Figurementioning

confidence: 99%

Synthesis and Self-Assembly of Well-Defined Block Copolypeptides via Controlled NCA Polymerization

Deming

2013

Hierarchical Macromolecular Structures: 60 Years After the Staudinger Nobel Prize II

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“…In the early 2000s, Lecommandoux et al 38 and Deming et al [39][40][41] reported on the successful preparation of vesicles from self-assembling, amphiphilic, polypeptide-based block copolymers.…”

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Cisplatin-Induced Formation of Biocompatible and Biodegradable Polypeptide-Based Vesicles for Targeted Anticancer Drug Delivery

Shirbin

Ladewig

et al. 2015

Biomacromolecules

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Novel cisplatin (CDDP)-loaded, polypeptide-based vesicles for the targeted delivery of cisplatin to cancer cells have been prepared. These vesicles were formed from biocompatible and biodegradable maleimide-poly(ethylene oxide)114-b-poly(L-glutamic acid)12 (Mal-PEG114-b-PLG12) block copolymers upon conjugation with the drug itself. CDDP conjugation forms a short, rigid, cross-linked, drug-loaded, hydrophobic block in the copolymer, and subsequently induces self-assembly into hollow vesicle structures with average hydrodynamic diameters (Dh) of ∼ 270 nm. CDDP conjugation is critical to the formation of the vesicles. The reactive maleimide-PEG moieties that form the corona and inner layer of the vesicles were protected via formation of a reversible Diels-Alder (DA) adduct throughout the block copolymer synthesis so as to maintain their integrity. Drug release studies demonstrated a low and sustained drug release profile in systemic conditions (pH = 7.4, [Cl(-)] = 140 mM) with a higher "burst-like" release rate being observed under late endosomal/lysosomal conditions (pH = 5.2, [Cl(-)] = 35 mM). Further, the peripheral maleimide functionalities on the vesicle corona were conjugated to thiol-functionalized folic acid (FA) (via in situ reduction of a novel bis-FA disulfide, FA-SS-FA) to form an active targeting drug delivery system. These targeting vesicles exhibited significantly higher cellular binding/uptake into and dose-dependent cytotoxicity toward cancer cells (HeLa) compared to noncancerous cells (NIH-3T3), which show high and low folic acid receptor (FR) expression, respectively. This work thus demonstrates a novel approach to polypeptide-based vesicle assembly and a promising strategy for targeted, effective CDDP anticancer drug delivery.

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“…However, these surfactants consist of amino acids polymerized into polydisperse blocks and then appended to make copolymers. Different amino acids have been blended into each block with set average composition, but the precise sequence of amino acids in each block could not be controlled (8). Amino acid copolymerization prevents the direct incorporation of specific peptide sequences, which are required for recognition and targeting in biology.…”

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Self-assembly of tunable protein suprastructures from recombinant oleosin

Vargo

Parthasarathy

Hammer

2012

Proc. Natl. Acad. Sci. U.S.A.

104

130

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Using recombinant amphiphilic proteins to self-assemble suprastructures would allow precise control over surfactant chemistry and the facile incorporation of biological functionality. We used cryo-TEM to confirm self-assembled structures from recombinantly produced mutants of the naturally occurring sunflower protein, oleosin. We studied the phase behavior of protein self-assembly as a function of solution ionic strength and protein hydrophilic fraction, observing nanometric fibers, sheets, and vesicles. Vesicle membrane thickness correlated with increasing hydrophilic fraction for a fixed hydrophobic domain length. The existence of a bilayer membrane was corroborated in giant vesicles through the localized encapsulation of hydrophobic Nile red and hydrophilic calcein. Circular dichroism revealed that changes in nanostructural morphology in this family of mutants was unrelated to changes in secondary structure. Ultimately, we envision the use of recombinant techniques to introduce novel functionality into these materials for biological applications.protein surfactants | self-assembled suprastructure | cryogenic transmission microscopy

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Synthesis and Crosslinking of L‐DOPA Containing Polypeptide Vesicles

Cited by 50 publications

References 23 publications

Synthesis and Self-Assembly of Well-Defined Block Copolypeptides via Controlled NCA Polymerization

Synthesis and Self-Assembly of Well-Defined Block Copolypeptides via Controlled NCA Polymerization

Cisplatin-Induced Formation of Biocompatible and Biodegradable Polypeptide-Based Vesicles for Targeted Anticancer Drug Delivery

Self-assembly of tunable protein suprastructures from recombinant oleosin

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