» Articles » PMID: 23976793

Effect of Linker Structure on Salicylic Acid-Derived Poly(anhydride-esters)

Overview
Journal Macromolecules
Date 2013 Aug 27
PMID 23976793
Citations 27
Authors
Affiliations
Soon will be listed here.
Abstract

A series of salicylic acid-derived poly(anhydride-esters) were synthesized by melt polym erization methods, in which the structures of the molecule ("linker") linking together the two salicylic acids were varied. To determine the relationship between the linker and the physical properties of the corresponding poly(anhydride-ester), several linkers were evaluated including linear aliphatic, aromatic, and aliphatic branched structures. For the linear aliphatic linkers, higher molecular weights were obtained with longer linear alkyl chains. The most sterically hindered linkers yielded lower molecular weight polymers. The thermal decomposition temperature increased with the alkyl chain length, but the glass transition temperature decreased, due to the enhanced flexibility of the polymer. The highest glass transition temperatures were obtained by using aromatic linkers as a result of increased π-π interactions. Water contact angles determined the relative hydrophobicity of the polymers, which correlated to hydrolytic degradation rates; i.e., the highest contact angle values yielded the slowest degrading polymers.

Citing Articles

Polymer-prodrug conjugates as candidates for degradable, long-acting implants, releasing the water-soluble nucleoside reverse-transcriptase inhibitor emtricitabine.

Liu C, Hern F, Shakil A, Temburnikar K, Chambon P, Liptrott N J Mater Chem B. 2023; 11(48):11532-11543.

PMID: 37955203 PMC: 10718295. DOI: 10.1039/d3tb02268d.


Linear and branched polymer prodrugs of the water-soluble nucleoside reverse-transcriptase inhibitor emtricitabine as structural materials for long-acting implants.

Shakil A, Hern F, Liu C, Temburnikar K, Chambon P, Liptrott N J Mater Chem B. 2022; 10(23):4395-4404.

PMID: 35604111 PMC: 9199480. DOI: 10.1039/d2tb00825d.


Novel polymeric derivatives of betulin with anticancer activity.

Niewolik D, Krukiewicz K, Bednarczyk-Cwynar B, Ruszkowski P, Jaszcz K RSC Adv. 2022; 9(36):20892-20900.

PMID: 35515533 PMC: 9065995. DOI: 10.1039/c9ra03326b.


Degradable Polymer Films Made from Poly(salicylic-acid--sebacic acid) and Poly(sebacic anhydride)/Poly(adipic anhydride) Blends: Degradation Kinetics and Use as Sacrificial Layers for Polymer Multilayer Systems.

Deng Z, Riga E, Lienkamp K Macromol Chem Phys. 2021; 221(12).

PMID: 34646086 PMC: 7611817. DOI: 10.1002/macp.202000106.


Inhibition of BMP9 Induced Bone Formation by Salicylic-acid Polymer Capping.

Acri T, Laird N, Hong L, Chakka J, Shin K, Elangovan S MRS Adv. 2021; 4(64):3505-3512.

PMID: 33912355 PMC: 8078835. DOI: 10.1557/adv.2020.61.


References
1.
Leong K, Kost J, Mathiowitz E, Langer R . Polyanhydrides for controlled release of bioactive agents. Biomaterials. 1986; 7(5):364-71. DOI: 10.1016/0142-9612(86)90007-4. View

2.
Elvira C, San Roman J . Complexation of polymeric drugs based on polyacrylic chains with aminosalicylic acid side groups. J Mater Sci Mater Med. 2004; 8(12):743-6. DOI: 10.1023/a:1018504410878. View

3.
Sato H, Kojima J, Nakajima A, Morita T, Noishiki Y, Gu Z . Study on antithrombogenicity of poly[beta-(acetylsalicylyloxy)ethyl methacrylate] relative to poly(hydroxyethyl methacrylate). J Biomater Sci Polym Ed. 1991; 2(1):1-13. DOI: 10.1163/156856291x00016. View

4.
Gopferich A . Mechanisms of polymer degradation and erosion. Biomaterials. 1996; 17(2):103-14. DOI: 10.1016/0142-9612(96)85755-3. View

5.
Leong K, DAmore P, Marletta M, Langer R . Bioerodible polyanhydrides as drug-carrier matrices. II. Biocompatibility and chemical reactivity. J Biomed Mater Res. 1986; 20(1):51-64. DOI: 10.1002/jbm.820200106. View