Search

We successfully synthesized new macroporous hydrogel particles consisting of hyperbranched poly(amidoamine)s (HPAMAM) using the Oil-in-Water-in-Oil (O/W/O) suspension polymerization method at both the 50 mL flask scale and the 5 L reactor scale. The pore sizes and particle sizes were easily tuned by controlling the agitation speeds during the polymerization reaction. Since O/W/O suspension polymerization gives porous architecture to the microparticles, synthesized hydrogel particles having abundant amine groups inside polymers exhibited a high CO2 absorption capacity (104 mg/g) and a fast absorption rate in a packed-column test. [ABSTRACT FROM AUTHOR]

We successfully synthesized new macroporous hydrogel particles consisting of hyperbranched poly(amidoamine)s (HPAMAM) using the Oil-in-Water-in-Oil (O/W/O) suspension polymerization method at both the 50 mL flask scale and the 5 L reactor scale. The pore sizes and particle sizes were easily tuned by controlling the agitation speeds during the polymerization reaction. Since O/W/O suspension polymerization gives porous architecture to the microparticles, synthesized hydrogel particles having abundant amine groups inside polymers exhibited a high CO2 absorption capacity (104 mg/g) and a fast absorption rate in a packed-column test.

In this study, we investigated nanoparticles formulated by self-assembly of a biodegradable poly(amidoamine) (PAA) and a fluorescently labeled peptide, in their capacity to internalize in endothelial cells and deliver the peptide, with possible applications for brain drug delivery. The nanoparticles were characterized in terms of size, surface charge, and loading efficiency, and were applied on human cerebral microvascular endothelial cells (hCMEC/D3) and human umbilical vein endothelial cells (Huvec) cells. Cell-internalization and cytotoxicity experiments showed that the PAA-based nanocomplexes were essentially nontoxic, and the peptide was successfully internalized into cells. The results indicate that these PAAs have an excellent property as nontoxic carriers for intracellular protein and peptide delivery, and provide opportunities for novel applications in the delivery of peptides to endothelial cells of the brain. [ABSTRACT FROM AUTHOR]

Poly(amidoamine)s (PAAs) are a family of synthetic polymers obtained by stepwise polyaddition of prim- or sec-amines to bisacrylamides. Nearly all conceivable bisacrylamides and prim- or sec-amines can be employed as monomers endowing PAAs of a structural versatility nearly unique among stepwise polyaddition polymers. PAAs are degradable in aqueous media, including physiological fluids. Many of them are remarkably biocompatible notwithstanding their cationic character. PAAs are per se highly functional polymers and, in addition, can be further functionalized giving rise to an endless variety of polymeric structures meeting the requisites for applications in such apparently disparate fields as inorganic water pollutants scavengers, sensors, drug and protein intracellular carriers, transfection promoters, peptidomimetic antiviral and antimalarial agents. In this review, the unique chemistry of PAAs is discussed and a vast library of PAA structures and PAA applications from the beginning to the present days reported. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 2319-2353 [ABSTRACT FROM AUTHOR]

Traditional precipitation methods for inorganic micropollutant removal from waters are increasingly being replaced by sorption methods based on both natural and synthetic materials. In this context, two novel effective heavy metal ions absorbers are presented. These resins, LYMA and LMT85, were crosslinked poly(amidoamine)s carrying amine and carboxyl groups in their repeating units. In particular, the LYMA-repeating unit contains one carboxyl and two amine groups and is a mimic of L-lysine, whereas LMT85 contains two amine and five carboxyl groups and is a mimic of EDTA. Both resins were prepared at moderate cost by simple eco-friendly procedures. The heavy metal ion set adopted as benchmark was Cu2+, Cd2+, Pb2+, Zn2+, Ni2+, and Co2+. LYMA proved selective for Cu2+ and Ni2+, the other ions tested being negligibly absorbed, whereas LMT85 proved capable of rapidly and quantitatively absorbing all the ions tested either singly or in mixed solution. The absorption process was reversible, and the resins were easily regenerated by acidification. The absorption of several metal ions imparted intense coloring to the resins, a feature possibly exploitable for analytical purposes. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012 [ABSTRACT FROM AUTHOR]

This article reports on a simple and straightforward preparation method of poly(amidoamine)s (PAAs) with hetero-difunctional chain ends as well as of several up to now hardly obtainable PAA derivatives of biotechnological interest, such as for instance PAAs of controlled molecular weight and narrow polydispersity mono-functionalized at one end with an acrylamide group, PAAs with star-like molecular architecture, graft-PAA-protein conjugates, 'tadpole-like' PAA conjugates with hydrophobic moieties able to self assemble into nanoparticles in aqueous media. The key step was to design suitable building blocks consisting of hetero-difunctional dimers (HDDs). In particular, the HDDs considered were the mono-addition products of bis- sec-amines and bisacrylamides expected to give PAAs of proven biomedical potential and were obtained as hydrochlorides or trifluoroacetates. In this form, they could be indefinitely kept dormant at 0-5 °C in the dry state, whereas at room temperature and in aqueous media, they polymerized at pH > 7.5. The preparation of the above-cited PAA derivatives did not necessarily involve the preliminary synthesis of hetero-difunctional PAAs but was directly achieved by one-pot polymerization of HDDs in the presence of the substrates of interest. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012 [ABSTRACT FROM AUTHOR]

Abstract: To improve design processes in the field of nanomedicine, in vitro characterization of nanoparticles with systematically varied properties is of great importance. In this study, surface sensitive analytical techniques were used to evaluate the responsiveness of nano-sized drug-loaded polyelectrolyte complexes when adsorbed to model lipid membranes. Two bioreducible poly(amidoamine)s (PAAs) containing multiple disulfide linkages in the polymer backbone (SS-PAAs) were synthesized and used to form three types of nanocomplexes by self-assembly with human insulin, used as a negatively charged model protein at neutral pH. The resulting nanoparticles collapsed on top of negatively charged model membranes upon adsorption, without disrupting the membrane integrity. These structural rearrangements may occur at a cell surface which would prevent uptake of intact nanoparticles. By the addition of glutathione, the disulfide linkages in the polymer backbone of the SS-PAAs were reduced, resulting in fragmentation of the polymer and dissociation of the adsorbed nanoparticles from the membrane. A decrease in ambient pH also resulted in destabilization of the nanoparticles and desorption from the membrane. These mimics of intracellular environments suggest dissociation of the drug formulation, a process that releases the protein drug load, when the nanocomplexes reaches the interior of a cell. [Copyright &y& Elsevier]

Abstract: A poly(amidoamine) (PAA) copolymer with β-cyclodextrin was obtained by polyaddition reaction of 6-deoxy-6-amino-β-cyclodextrin (β-CD-NH2) and 2-methylpiperazine to 2,2-bis(acrylamido)acetic acid in aqueous medium. This β-CD/PAA copolymer bears β-CD units along the macromolecular chain, is water-soluble and non-cytotoxic. The complexing capacity of β-CD/PAA was determined using an antiviral drug, Acyclovir, as a model of poorly water-soluble drug. Complex formation was confirmed by means of DSC and FTIR analyses. β-CD/PAA can solubilize up to 11% w/w of Acyclovir notably increasing the aqueous solubility of the drug. The in vitro release studies showed the dependence of Acyclovir release rate on the solution pH. The antiviral activity of Acyclovir β-CD/PAA complex was evaluated against herpes simplex virus type I in cell cultures. The Acyclovir β-CD/PAA complex exhibited a higher antiviral activity than the free drug. [Copyright &y& Elsevier]

The polyaddition kinetics of 2-methylpiperazine to 1,4-bis-acryloylpiperazine was determined in water, methanol, ethylene glycol, formamide, and dimethylformamide, respectively. In the protic solvents, the polyaddition proceeded through a two-step mechanism, each step involved one of the two different secondary amino groups; the difference in amine reactivity was ascribed to the different steric hindrance by the neighbouring groups. Each step followed pseudo-second-order kinetics; the kinetic constants included the catalytic protonic species. In the case of dimethylformamide, the polyaddition proceeded through third-order kinetics; this accounted for the autocatalytic activity of the amino groups. The apparent kinetic constants in the protic solvents increased with the increase in the autoprotolysis constant values and decreased with the increase of the dipole moment. [ABSTRACT FROM AUTHOR]

Abstract: The pH-responsive poly(amidoamine)s (PAAs) have been previously described. Whereas ISA23 enhances transfection in vitro and ISA1 promotes the cytosolic delivery of the non-permeant toxins this process shows poor efficiency. The aim of this study was to prepare and evaluate PAA conjugates containing the membrane disrupting peptide melittin (MLT). It was hypothesised that PAA conjugation would reduce the haemolytic activity of MLT at pH 7.4, however, upon delivery to tumours by the EPR effect, the polymer would uncoil in an acidic environment exposing MLT and allowing it to interact with membranes. PAA–MLT conjugates were prepared using MLT as a comonomer together with bis-acryloylpiperazine, 2-methylpiperazine and bis-hydroxyethylethylenediamine (ISA1-like), or bis-acrylamidoacetic acid and 2-methylpiperazine (ISA23-like). The melittin content of the conjugates was 6–19% (w/w). Although ISA1–MLT improved gelonin delivery compared to the parent polymer ISA1 (α 13-fold increase) and showed pH-dependent haemolytic activity at a polymer concentration of 0.05mg/ml, this conjugate also displayed high haemolytic activity at pH 7.4. In contrast, ISA23–MLT like the parent compound ISA23 did not deliver gelonin. However, this conjugate could have potential as a novel polymeric anticancer conjugate due to its lack of haemolytic activity at pH 7.4 and retention of cytotoxicity. [Copyright &y& Elsevier]

A linear amphoteric poly(amidoamino acid), L-ARGO7, is prepared by Michael-type polyaddition of L-arginine with N,N'-methylenebisacrylamide. Chain-extension of acrylamide end-capped L-ARGO7 oligomers with piperazine leads to high-molecular-weight copolymers in which L-arginine maintains its absolute configuration. Acid/base properties of L-ARGO7 polymers show isolectric points of ≈ 10 and positive net average charges per repeating unit at pH = 7.4 from 0.25 to 0.40. These arginine-rich synthetic polymers possibly share some of the unique biological properties of polyarginine cell-permeating peptides. In vitro tests with mouse embryo fibroblasts balb/3T3 clone A31 show that L-ARGO7 polymers are endowed with effective cell internalization ability combined with minimal cytotoxicity., (© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)