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Exploring the Solid State Properties of Enzymatic Poly(amine-co-ester) Terpolymers to Expand their Applications in Gene Transfection.
RSC Adv 2014; 4(18):8953-8961RA

Abstract

Polymers bearing amino functional groups are an important class of materials capable of serving as non-viral carriers for DNA delivery to living cells. In this work biodegradable poly(amine-co-ester) terpolymers were synthesized via ring-opening and polycondensation copolymerization of lactone (ε-caprolactone (CL), ω-dodecalactone, ω-pentadecalactone (PDL), and ω-hexadecalactone) with diethyl sebacate (DES) and N-methyldiethanolamine (MDEA) in diphenyl ether, catalyzed by Candida antarctica lipase B (CALB). All lactone-DES-MDEA terpolymers had random distributions of lactone, sebacate, MDEA repeat units in the polymer chains. PDL-DES-MDEA terpolymers were studied in the composition range from 21 mol% to 90 mol% PDL whereas the terpolymers with other lactones were investigated at a single composition (80 mol% lactone). DSC and WAXS analyses showed that all investigated terpolymers crystallize in their respective homopolylactone crystal lattice. Terpolymers with large lactones and a high lactone content melt well above room temperature and are hard solids, whereas terpolymers with small lactones (e.g. CL) or with a low lactone content melt below/around ambient temperature and are waxy/gluey materials. Given the importance of hydrophobicity in influencing gene delivery, water contact angle measurements were carried out on lactone-DES-MDEA terpolymers showing that it is possible to tune the hydrophilic-to-hydrophobic balance by varying polymer composition and size of lactone units. To demonstrate the feasibility of using solid terpolymers as nanocarriers for DNA delivery, PDL-DES-MDEA copolymers with 65-90% PDL were successfully transformed into free-standing nanoparticles with average particle size ranging from 163 to 175 nm. Our preliminary results showed that LucDNA-loaded nanoparticles of the terpolymer with 65% PDL were effective for luciferase gene transfection of HEK293 cells.

Authors+Show Affiliations

University of Bologna, Department of Chemistry "G. Ciamician" and INSTM UdR Bologna, via Selmi 2, 40126 Bologna, Italy.University of Bologna, Department of Chemistry "G. Ciamician" and INSTM UdR Bologna, via Selmi 2, 40126 Bologna, Italy.Department of Chemical and Environmental Engineering, Yale University, 55 Prospect Street, New Haven, Connecticut 06511, USA.Molecular Innovations Center, Yale University, 600 West Campus Drive, West Haven, Connecticut 06516, USA.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

24683469

Citation

Voevodina, Irina, et al. "Exploring the Solid State Properties of Enzymatic Poly(amine-co-ester) Terpolymers to Expand Their Applications in Gene Transfection." RSC Advances, vol. 4, no. 18, 2014, pp. 8953-8961.
Voevodina I, Scandola M, Zhang J, et al. Exploring the Solid State Properties of Enzymatic Poly(amine-co-ester) Terpolymers to Expand their Applications in Gene Transfection. RSC Adv. 2014;4(18):8953-8961.
Voevodina, I., Scandola, M., Zhang, J., & Jiang, Z. (2014). Exploring the Solid State Properties of Enzymatic Poly(amine-co-ester) Terpolymers to Expand their Applications in Gene Transfection. RSC Advances, 4(18), pp. 8953-8961.
Voevodina I, et al. Exploring the Solid State Properties of Enzymatic Poly(amine-co-ester) Terpolymers to Expand Their Applications in Gene Transfection. RSC Adv. 2014 Jan 1;4(18):8953-8961. PubMed PMID: 24683469.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Exploring the Solid State Properties of Enzymatic Poly(amine-co-ester) Terpolymers to Expand their Applications in Gene Transfection. AU - Voevodina,Irina, AU - Scandola,Mariastella, AU - Zhang,Junwei, AU - Jiang,Zhaozhong, PY - 2014/4/1/entrez PY - 2014/4/1/pubmed PY - 2014/4/1/medline SP - 8953 EP - 8961 JF - RSC advances JO - RSC Adv VL - 4 IS - 18 N2 - Polymers bearing amino functional groups are an important class of materials capable of serving as non-viral carriers for DNA delivery to living cells. In this work biodegradable poly(amine-co-ester) terpolymers were synthesized via ring-opening and polycondensation copolymerization of lactone (ε-caprolactone (CL), ω-dodecalactone, ω-pentadecalactone (PDL), and ω-hexadecalactone) with diethyl sebacate (DES) and N-methyldiethanolamine (MDEA) in diphenyl ether, catalyzed by Candida antarctica lipase B (CALB). All lactone-DES-MDEA terpolymers had random distributions of lactone, sebacate, MDEA repeat units in the polymer chains. PDL-DES-MDEA terpolymers were studied in the composition range from 21 mol% to 90 mol% PDL whereas the terpolymers with other lactones were investigated at a single composition (80 mol% lactone). DSC and WAXS analyses showed that all investigated terpolymers crystallize in their respective homopolylactone crystal lattice. Terpolymers with large lactones and a high lactone content melt well above room temperature and are hard solids, whereas terpolymers with small lactones (e.g. CL) or with a low lactone content melt below/around ambient temperature and are waxy/gluey materials. Given the importance of hydrophobicity in influencing gene delivery, water contact angle measurements were carried out on lactone-DES-MDEA terpolymers showing that it is possible to tune the hydrophilic-to-hydrophobic balance by varying polymer composition and size of lactone units. To demonstrate the feasibility of using solid terpolymers as nanocarriers for DNA delivery, PDL-DES-MDEA copolymers with 65-90% PDL were successfully transformed into free-standing nanoparticles with average particle size ranging from 163 to 175 nm. Our preliminary results showed that LucDNA-loaded nanoparticles of the terpolymer with 65% PDL were effective for luciferase gene transfection of HEK293 cells. SN - 2046-2069 UR - https://www.unboundmedicine.com/medline/citation/24683469/Exploring_the_Solid_State_Properties_of_Enzymatic_Poly_amine_co_ester__Terpolymers_to_Expand_their_Applications_in_Gene_Transfection_ L2 - https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/24683469/ DB - PRIME DP - Unbound Medicine ER -