Biocatalytic synthesis of poly[ε-caprolactone-co-(12-hydroxystearate)] copolymer for sorafenib nanoformulation useful in drug delivery

Kántor, Izolda; Aparaschivei, Diana; Todea, Anamaria; Biró, Emese; Babos, György; Szerényi, Dóra; Kakasi, Balázs; Péter, Fráncisc; Şişu, Eugen; Feczkó, Tivadar

doi:10.1016/j.cattod.2020.05.005

Cited by 6 publications

(8 citation statements)

References 31 publications

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“…Lipases are particularly valuable for the ROP reactions of lactones [16], allowing the synthesis of polymers/oligomers and copolymers/co-oligomers in controlled reaction conditions and suited for biomedical applications, avoiding the toxicity effects of trace amounts of the metal catalyst, e.g., PCL-b-PEG-b-PCL triblock copolymers with polyethylene glycol [17]. The previous works of our group demonstrated the synthetic possibilities towards various co-oligomers of ECL with δ-gluconolactone [18][19][20], 5-hydroxymethyl-2-furancarboxylic acid [21], and fatty hydroxy acids [22][23][24]. The importance of copolymers derived from ECL is emphasized by novel reports on the possibilities to obtain this monomer from phenol by a chemoenzymatic process [25].…”

Section: Introductionmentioning

confidence: 90%

Biocatalytic Approach for Novel Functional Oligoesters of ε-Caprolactone and Malic Acid

et al. 2021

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Biocatalysis has developed in the last decades as a major tool for green polymer synthesis. The particular ability of lipases to catalyze the synthesis of novel polymeric materials has been demonstrated for a large range of substrates. In this work, novel functional oligoesters were synthesized from ε-caprolactone and D,L/L-malic acid by a green and sustainable route, using two commercially available immobilized lipases as catalysts. The reactions were carried out at different molar ratios of the comonomers in organic solvents, but the best results were obtained in solvent-free systems. Linear and cyclic oligomeric products with average molecular weights of about 1500 Da were synthesized, and the formed oligoesters were identified by matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF MS) analysis. The oligoester synthesis was not enantioselective in the studied reaction conditions. The operational stability of both biocatalysts (Novozyme 435 and GF-CalB-IM) was excellent after reutilization in 13 batch reaction cycles. The thermal properties of the reaction products were investigated by thermogravimetric (TG) and differential scanning calorimetry (DSC) analysis. The presence of polar pendant groups in the structure of these oligomers could widen the possible applications compared to the oligomers of ε-caprolactone or allow the conversion to other functional materials.

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Section: Introductionmentioning

confidence: 90%

Biocatalytic Approach for Novel Functional Oligoesters of ε-Caprolactone and Malic Acid

et al. 2021

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“…ε-Caprolactone-12-hydroxystearic acid copolymer (12CL) polyester was synthesised biocatalytically in our previous work [ 25 ]. Polyvinyl alcohol (PVA, Mw = 30,000–70,000 g/mol, 87–90% hydrolysed), dichloromethane (DCM), 1-ethyl-3(3-dimethylaminopropyl) carbodiimide (EDC), N-hydroxy succinimide (NHS), N,N-dicyclohexylcarbodiimide (DCC), acetone, dimethyl sulfoxide (DMSO), sodium azide, sodium acetate, iRGD, sodium dodecyl sulfate (SDS), 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) and Dulbecco’s Modified Eagle’s medium (DMEM (high glucose)), 12-hydroxystearic acid (98%), ε-caprolactone, trans-2-[3-(4-t-butyl-phenyl)-2-methyl-2-propenylidene]malononitrile (DCTB), and potassium trifluoroacetate (KTFA), were obtained from Sigma–Aldrich (St. Louis, MO, USA).…”

Section: Methodsmentioning

confidence: 99%

“…The aim of this work was to prepare anticancer drug-loaded polymeric nanoparticles from a biodegradable and biocompatible oligomer, co-encapsulating sorafenib and cisplatin, which can become effective sustained and targeted drug delivery devices. The oligomer was obtained through a green biocatalytic route, from ε-caprolactone and 12-hydroxystearic acid using a microbial lipase, as previously reported [ 24 ], and was proved to be efficient for the nanoencapsulation of sorafenib [ 25 ]. It belongs to a new class of biobased oligomers of hydroxy acids, which are increasingly considered for biomedical and cosmetic applications [ 26 ].…”

Section: Introductionmentioning

confidence: 99%

Co-Entrapment of Sorafenib and Cisplatin Drugs and iRGD Tumour Homing Peptide by Poly[ε-caprolactone-co-(12-hydroxystearate)] Copolymer

et al. 2021

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The drug-loaded nanocarriers have overcome various challenges compared with the pure chemotherapeutic drug, such as limited bioavailability, multiple drug resistance, poor patient compliance, and adverse drug reactions, offering advantages such as protection from degradation in the blood stream, better drug solubility, and improved drug stability. One promising group of controlled and targeted drug delivery systems is polymer-based nanoparticles that can sustain the release of the active agent by diffusion and their degradation. Sorafenib is the only drug that can prolong the life of patients suffering from hepatocellular carcinoma. Cisplatin remains one of the most widely used broad-spectrum anticancer drugs for the treatment of a variety of solid tumours. Nanoformulations can exert a synergistic effect by entrapping two drugs with different modes of action, such as sorafenib and cisplatin. In our study, polymeric nanoparticles were prepared with a good production yield by an improved double emulsion solvent evaporation method using the copolymer of 12-hydroxystearic acid with ε-caprolactone (12CL), a biocatalytically synthesised biocompatible and biodegradable carrier, for the co-entrapment of sorafenib and cisplatin in nanotherapeutics. A bovine serum albumin (BSA) model compound was used to increase the cisplatin incorporation; then, it was successfully substituted by a iRGD tumour penetrating peptide that might provide a targeting function of the nanoparticles.

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“…Recently, the enzymatically synthesized oligoesters containing ε-caprolactone and 12-hydroxystearic acid were used for preparation of sorafenib-loaded polymeric nanocomposites. The resulting nanoparticles showed promising drug release profile and cytotoxic effect in vitro in HepG2 hepatocellular cells [37].…”

Section: Trends In the Lipase-catalyzed Synthesis Of Polyesters And Co-polyesters Of ε-Caprolactonementioning

confidence: 99%

“…Biocatalytic strategies using lipases have become important bio-based alternatives to conventional polymerization methods, since several drawbacks related to the presence of metal catalyst traces, toxicity and higher temperatures could be avoided [16]. Moreover, functionalization of polymers such as polylactic acid [35] or polycaprolactone [36,37] can be accomplished using lipases, allowing improved drug delivery properties in systems needing higher hydrophilicity.…”

Section: Introductionmentioning

confidence: 99%

Achievements and Trends in Biocatalytic Synthesis of Specialty Polymers from Biomass-Derived Monomers Using Lipases

et al. 2021

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New technologies for the conversion of biomass into high-value chemicals, including polymers and plastics, is a must and a challenge. The development of green processes in the last decade involved a continuous increase of the interest towards the synthesis of polymers using in vitro biocatalysis. Among the remarkable diversity of new bio-based polymeric products meeting the criteria of sustainability, biocompatibility, and eco-friendliness, a wide range of polyesters with shorter chain length were obtained and characterized, targeting biomedical and cosmetic applications. In this review, selected examples of such specialty polymers are presented, highlighting the recent developments concerning the use of lipases, mostly in immobilized form, for the green synthesis of e-caprolactone co-polymers, polyesters with itaconate or furan units, estolides, and polyesteramides. The significant process parameters influencing the average molecular weights and other characteristics are discussed, revealing the advantages and limitations of biocatalytic processes for the synthesis of these bio-based polymers.

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Biocatalytic synthesis of poly[ε-caprolactone-co-(12-hydroxystearate)] copolymer for sorafenib nanoformulation useful in drug delivery

Cited by 6 publications

References 31 publications

Biocatalytic Approach for Novel Functional Oligoesters of ε-Caprolactone and Malic Acid

Biocatalytic Approach for Novel Functional Oligoesters of ε-Caprolactone and Malic Acid

Co-Entrapment of Sorafenib and Cisplatin Drugs and iRGD Tumour Homing Peptide by Poly[ε-caprolactone-co-(12-hydroxystearate)] Copolymer

Achievements and Trends in Biocatalytic Synthesis of Specialty Polymers from Biomass-Derived Monomers Using Lipases

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