Synthesis of .alpha.,.beta.-poly [(2-hydroxyethyl)-DL-aspartamide], a newplasma expander

Neri, Paolo; Antoni, G.; Benvenuti, Franco; Cocola, Francesco; Gazzei, G

doi:10.1021/jm00266a006

Cited by 223 publications

(117 citation statements)

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“…The two polymer classes chosen, both featuring linear polyamide-type main chains, were (1) polyaspartamides derived from polysuccinimide by nucleophilic ring-opening steps, and (2) polyamidoamines obtained by Michael addition polymerization of bisacrylamides with primary and/or secondary amine comonomers. The polyaspartamides were pioneered in the 'Seventies by Neri and Antoni [54,55] and others [56][57][58], whereas Ferruti's laboratory [59,60] initiated and promoted work on the polyamidoamines. Subsequently, the two carrier classes were further developed by our group [61,62].…”

Section: Resultsmentioning

confidence: 99%

Macromolecular Antiproliferative Agents Featuring Dicarboxylato-Chelated Platinum

Komane

Mukaya

Neuse

et al. 2007

J Inorg Organomet Polym

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Cancerous diseases, together with cardiac afflictions, account for the predominant causes of death among the adult population of the Western world. The classical platinum drugs, with cisplatin as their parent, have established themselves for years as leading components in the oncologist's arsenal of antitumor agents. As with most other antineoplastic drugs, however, incisive pharmacological deficiencies, notably excessive systemic toxicity and induction of drug resistance, have severely curtailed their overall efficaciousness. With the objective of overcoming these counterproductive deficiencies, the technique of polymer-drug conjugation, representing an advanced modality of drug delivery, has been developed in recent years to high standards worldwide. In a drug conjugate, water-soluble macromolecular carrier constructs designed in compliance with stringent pharmacological specifications are covalently, yet bioreversibly, interconnected with the bioactive agent. As a macromolecule following a pharmacokinetic pathway different from that of non-polymeric compounds, the conjugate acts as a pro-drug favorably transporting the agent through the various body compartments to, and into, the target cell, where the agent is enzymatically or hydrolytically separated from the carrier for its biological action. In the authors' laboratories the conjugation strategy has been adopted as the primary tool for drug efficacy enhancement. The present paper describes a special type of platinum complex carrier-bound via dicarboxymetal chelation, synthesized from carboxyl-functionalized polyamide-type carriers by platination with trans-1,2-diaminocyclohexanediaquaplatinum(II) dinitrate. In a series of in vitro tests antiproliferative activities have been determined against several human cancer cell lines. Whereas no improvements are observed in tests against a colorectal cancer, outstanding findings of the screening program include a 10-to 100-fold increase in cell-killing performance of the conjugates relative to the (non-polymeric) cisplatin standard against the HeLa adenocarcinoma, and distinctly reduced resistance factors (again, relative to cisplatin) in tests against the A2780 and A2780-cis pair of ovarian cell lines. These findings augur well for future developments of this class of platinum drugs. This article is dedicated to Professor Astruc.

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Section: Resultsmentioning

confidence: 99%

Macromolecular Antiproliferative Agents Featuring Dicarboxylato-Chelated Platinum

Komane

Mukaya

Neuse

et al. 2007

J Inorg Organomet Polym

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“…The product was finally dried at 70°C in vacuum for 3 days to obtain PSI in a white powder form. The molecular weight was estimated to be approximately 130 000 Da, as calculated from an empirical equation relating the solution viscosity to the molecular weight [40].…”

Section: Synthesis Of Polysuccinimide (Psi)mentioning

confidence: 99%

Mussel-mimetic self-healing polyaspartamide derivative gel via boron-catechol interactions

Wang¹,

Jeon²,

Park³

et al. 2015

Express Polym. Lett.

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Abstract. The catechol group from catechol of 3,4-dihydroxyphenethylamine (DOP, dopamine) has the ability to interact with metal ions to form non-covalent bonds in polymer chains. In this study, a novel kind of mussel-inspired copolymer, dopamine-conjugated poly(hydroxyethyl aspartamide), polyAspAm(DOP/EA), was synthesized and its interaction with boric acid (H 3 BO 3 ) to form a cross-linked gel via boron-catechol coordinative binding was investigated. The copolymer was designed to contain a pH responsive adhesive catechol group, which reversibly underwent gelation through the metalcatechol binding, as proved by UV-Vis spectroscopy. When the pH is increased from acidic conditions to a specified pH (pH > 9), the B(OH) 3 is considered to have a functionality of two to bind catechols, leading to bis-complexes. In addition, the reversibility of the boron-catechol bonds provides self-healing characteristics to the polyAspAm gels. The rheological results showed that boron-catechol coordination could lead to quick and full recovery after the fracture of a gel specimen. This novel pH-responsive and self-healing gel system has potential in various applications including smart hydrogels, medical adhesives, and sealants.

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“…8,14 The polymer possessed a reduced viscosity of 38 mL/g in DMF. The molecular weight was estimated to be about 120,000 Da, as calculated from an empirical equation relating the solution viscosity to the molecular weight.…”

Section: Preparation and Characterization Of Crosslinked Gelsmentioning

confidence: 99%

“…[3][4][5] Poly(amino acid)s, which have protein-like linkages, are known to be biodegradable and have been investigated in various biomedical applications including drug delivery systems. Poly(aspartic acid), PASP, is one of synthetic water-soluble and biodegradable polymer, which can be produced from the hydrolysis of polysuccinimide (PSI), [6][7][8] the thermal condensation polymer of aspartic acid monomer. PASP has been commercialized as a biodegradable polymeric dispersant, and also investigated as a biodegradable superabsorbent in the crosslinked form or as a polymeric drug carrier.…”

mentioning

confidence: 99%

“…9,10 ,-Poly(N-2-hydroxyethyl-DL-aspartamide), PHEA, is another important polymer, derived by coupling PSI with ethanolamine, which has been proposed as a potential plasma extender and carrier for macromolecular prodrugs. 8,11,12 The presence of hydroxyl groups in the side chain provides the possibility of forming a covalent linkage between the polymer and drug molecules with or without proper spacer group. This polymer has been demonstrated to possess suitable physico-chemical characteristics for development of macromolecular prodrugs, including biodegradability, high water solubility, excellent biocompatibility, and low cost.…”

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confidence: 99%

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Preparation and Properties of PHEA/Chitosan Composite Hydrogel

Kim

Sim

Lee

et al. 2004

Polym J

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ABSTRACT:Biodegradable hydrogels based on synthetic PHEA and IPN type composite hydrogel with chitosan, a natural carbohydrate polymer, were prepared by crosslinking using glutaraldehyde in aqueous mixture. Relatively strong hydrogels were formed in a shaped mold. Preparation of crosslinked gels and their swelling behavior depending on the composition, medium, and pH of solution are investigated. The porous morphology of scaffolds, obtained by freeze-drying method, was observed by scanning electron microscopy. Also preliminary results on hydrolytic degradation and cytotoxicity test of the hydrogel are included.

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Synthesis of .alpha.,.beta.-poly [(2-hydroxyethyl)-DL-aspartamide], a newplasma expander

Cited by 223 publications

References 1 publication

Macromolecular Antiproliferative Agents Featuring Dicarboxylato-Chelated Platinum

Macromolecular Antiproliferative Agents Featuring Dicarboxylato-Chelated Platinum

Mussel-mimetic self-healing polyaspartamide derivative gel via boron-catechol interactions

Preparation and Properties of PHEA/Chitosan Composite Hydrogel

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