Novel Amphoteric Cystine-Based Poly(amidoamine)s Responsive to Redox Stimuli

Emilitri, Elisa; Ferruti, Paolo; Annunziata, Rita; Ranucci, Elisabetta; Rossi, Manuela; Falciola, L.; Mussini, Patrizia R.; Chiellini, Emo; Bartoli, Cristina

doi:10.1021/ma062115e

Cited by 33 publications

(26 citation statements)

References 26 publications

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“…Alternatively, an example for the synthesis of polydisulfides via conjugate Michael‐type addition polymerization is given with the reaction of diverse nucleophiles (i.e., Michael donors) and cysteine derivative as Michael acceptor (Scheme C and Scheme ) . The reaction is remarkably specific and leads to a large variety of polymer structures.…”

Section: Chemistrymentioning

confidence: 99%

Sulfur Chemistry in Polymer and Materials Science

Mutlu

Ceper

et al. 2018

Macromol. Rapid Commun.

255

220

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The ORCID identification number(s) for the author(s) of this article can be found under https://doi.org/10.1002/marc.201800650. ChemistryBefore moving to the recent advances within the last 5 years in the diverse applications of sulfur chemistry in polymer and Sulfur-Containing PolymersSulfur and its functional groups are major players in an area of exciting research taking place in modern polymer and materials science, both in academia and industry. In fact, manifold sulfur-based reactions that are both exceptionally versatile as well as tremendously useful have been implemented, and further utilized for the design and preparation of polymeric materials that lead to a plethora of applications ranging from medicine to optics and nanotechnology to separation science. Hence, within this review, an overview of strategies and developments used over the last 5 years to reinforce the importance of the sulfur functional group in modern polymer and materials science is presented. In particular, many important references in the primary literature of sulfur chemistry are referred to, including thiol-ene, thiol-yne, thiol-Michael addition, disulfide cross-linking, and thiol-disulfide exchange, among others, by explaining and illustrating the important principles. Last but not least, the grand aim to underpin the importance of sulfur in modern polymer and materials science is achieved by presenting selected examples in diverse fields and postulating the respective potential for real-world applications. he is now a full professor at KIT.sulfur atoms, and tetraphenylethene-bearing di(alkyl bromide) (Scheme 3). The yield of the polymerization was dependent on the di(alkyl bromide) monomer; the longer spacer between the aromatic moiety and the reactive bromide end groups Scheme 1. The discussion henceforth focuses on the synthesis of polymers possessing the depicted sulfur functional groups. Scheme 2.Representative examples of polythioethers prepared via A) the nucleophilic substitution reaction between an electrophilic dihalide with nucleophilic derivatives of dithiols under alkaline conditions; B) the thiol-ene/yne addition reaction between AA and BB type monomers (i.e., dithiols and dienes/diynes); and C) radical or ionic ring-opening of sulfurcontaining strained rings.Scheme 3. The thiol-bromo polymerization of conformationally fixed monomers to provide multifunctional polymers. [19] Macromol. Rapid Commun. 2019, 40, 1800650 Scheme 4. The regioselective selective nucleophilic aromatic substitution between thiol and fluorinated aromatic compounds, the para-fluorothiol reaction (PFTR).Scheme 5. Synthesis of a linear polymer via PFTR-reaction. [21]

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Section: Chemistrymentioning

confidence: 99%

Sulfur Chemistry in Polymer and Materials Science

Mutlu

Ceper

et al. 2018

Macromol. Rapid Commun.

255

220

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“…Moreover, disulfide reduction allows for rapid polymer degradation into small non-toxic fragments. The incorporation of bioreducible disulfide linkages in polymers for gene and drug delivery has been favorably exploited by us and several other groups [21][22][23][24].…”

Section: Introductionmentioning

confidence: 99%

Effects of branched or linear architecture of bioreducible poly(amido amine)s on their in vitro gene delivery properties

Martello

Piest

Engbersen

et al. 2012

Journal of Controlled Release

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In this study, the gene delivery properties of new hyperbranched poly(amido amine)s (PAAs) with disulfide linkages in the main chain were investigated in comparison with their linear analogs. Eight different bioreducible PAAs were prepared by Michael addition of N,N'-bisacryloylpiperazine (BP) with cystamine (CYST) or N,N'-dimethylcystamine (DMC) and of N,N'-cystaminebisacrylamide (CBA) with N,N'-ethylenediamine (EDA) or N,N'-dimethylethylenediamine (DMEDA). In order to study the effect of terminal groups on the transfection efficiency, each polymer was terminated with 4-aminobutanol (ABOL) or with 2-aminoethanol (ETA). The hyperbranched and the linear PAAs generally formed polyplexes with plasmid DNA with sizes around 200nm and positive zeta potentials ranging from +10 to +22mV at polymer/DNA weight ratios equal or higher than 3/1. Remarkably low or no cytotoxicity was observed for both hyperbranched and linear PAAs. Hyperbranched CBA-containing PAAs showed higher gene expression in DNA transfection tests with COS-7 cells than their linear analogs and up to two times higher than linear PEI that was used as the reference polymer. Transfection efficiencies of the branched PAAs were generally enhanced by the presence of serum, which is a promising property for future in vivo studies with these hyperbranched PAAs. In this study the ease of synthetic modification of both linear and hyperbranched poly(amido amide)s and the versatility of hyperbranched PAAs in regulating DNA transfection and cytotoxicity are demonstrated. The results show the large possibilities for this class of polymers to provide polymeric vectors with controllable properties for gene therapy applications.

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“…A different class of stimuli responsive polymers based on α-amino acids, named polyamidoamino acids (PAACs), has been obtained by the Michael-type polyaddition of α-amino acids with bisacrylamides, as for instance N,N'-methylenebisacrylamide [24][25][26][27][28][29][30], 2,2'-bis(acrylamidoacetic) acid [29][30][31], and 1,4-bis(acryloyl)piperazine [32]. In particular, the PAAC named L-ARGO7 was obtained from N,N'-methylenebisacrylamide and L-arginine [24].…”

Section: Introductionmentioning

confidence: 99%

pH-Dependent Chiral Recognition of D- and L-Arginine Derived Polyamidoamino Acids by Self-Assembled Sodium Deoxycholate

et al. 2020

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D- and L-arginine-based polyamidoamino acids, called D- and L-ARGO7, retain the chirality and acid/base properties of the parent α-amino acids and show pH-dependent self-structuring in water. The ability of the ARGO7 chiral isomers to selectively interact with chiral biomolecules and/or surfaces was studied by choosing sodium deoxycholate (NaDC) as a model chiral biomolecule for its ability to self-assembly into globular micelles, showing enantio-selectivity. To this purpose, mixtures of NaDC with D-, L- or D,L-ARGO7, respectively, in water were analysed by circular dichroism (CD) spectroscopy and small-angle neutron scattering (SANS) at different levels of acidity expressed in terms of pD and concentrations. Differences in the CD spectra indicated chiral discrimination for NaDC/ARGO7 mixtures in the gel phase (pD 7.30) but not in the solution phase (pD 9.06). SANS measurements confirmed large scale structural perturbation induced by this chiral discrimination in the gel phase yet no modulation of the structure in the solution phase. Together, these techniques shed light on the mechanism by which ARGO7 stereoisomers modify the morphology of NaDC micelles as a function of pH. This work demonstrates chirality-dependent interactions that drive structural evolution and phase behaviour of NaDC, opening the way for designing novel smart drug delivery systems.

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Novel Amphoteric Cystine-Based Poly(amidoamine)s Responsive to Redox Stimuli

Cited by 33 publications

References 26 publications

Sulfur Chemistry in Polymer and Materials Science

Sulfur Chemistry in Polymer and Materials Science

Effects of branched or linear architecture of bioreducible poly(amido amine)s on their in vitro gene delivery properties

pH-Dependent Chiral Recognition of D- and L-Arginine Derived Polyamidoamino Acids by Self-Assembled Sodium Deoxycholate

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