Maltitol-based biodegradable polyesters with tailored degradation and controlled release for bone regeneration

Abstract

Despite extensive research performed in the area of drug delivery and tissue engineering, the search for a perfect biomaterial remains an ongoing process. In an effort to find this material, novel maltitol-based polyesters using three different dicarboxylic acids (DCAs; adipic acid, dodecanedioic acid and suberic acid) were synthesized and their properties were investigated. The chemical structure of the polymers was confirmed using Fourier transform infrared and proton nuclear magnetic resonance spectroscopies.Thermal characterization revealed that the polymers were amorphous and that the glass transition temperature decreased with an increase in the chain length and molar ratio of maltitol : DCAs.Mechanical studies showed that the moduli of these polymers were comparable to those of the components of the skeletal system. Contact angle goniometry confirmed that the hydrophobicity of the polymers increased with increase in chain length and the molar ratio of maltitol : DCAs. The polymer degradation followed first order kinetics whereas dye release from these polymers followed zero order kinetics. Both the degradation and dye release studies demonstrated that the degradation and release decreased with increase in chain length and molar ratio of maltitol : DCA. The degradation and dye release can be modulated based on the chain length and the molar ratio of acids. Preliminary cytocompatibility studies showed that these polymers were cytocompatible. Mineralization studies revealed that these polymers showed increased mineralization when compared to results obtained with controls. Thus, this family of polyesters can serve as effective biomaterials for bone tissue engineering with tunable degradation and controlled release properties.Scheme 1 Reaction scheme for the synthesis of the polyesters in the molar ratio of 1 : 1. Red dots near the -OH groups indicate that these groups may also be involved in esterification because it is a random polymerization.40542 | RSC Adv., 2016, 6, 40539-40551This journal is

Review on the Impact of Polyols on the Properties of Bio-Based Polyesters

“…Natarajan et al reacted maltitol with various dicarboxylic acids (adipic acid, dodecanedioic acid, and suberic acid) with variation in the comonomer stoichiometry ( Figure 6 ) [ 106 ]. Prepolymer synthesis was performed by a simple melt condensation at 180 °C for 2 h with continuous nitrogen purging.…”

“… Reaction scheme for the synthesis of poly(maltitol- co -adipate), poly(maltitol- co -suberate), and poly(maltitol- co -dodecanedioate) where R groups are either esters or free hydroxyl moieties [ 106 ]. …”

A broad scope of aliphatic polyesters prepared by elimination of small molecules from sustainable 1,3-dioxolan-4-ones

“…Biodegradable polyesters remain at the forefront of research into sustainable polymers, with the readily synthesised poly (lactic acid) now realising the commercial potential of green plastics. [1][2][3][4] Accessing a broader scope of these aliphatic polyesters remains a challenge, especially when retaining the simple syntheses required for commercial applications. We thus target a family of monomers that are easily prepared from inexpensive, sustainable feedstocks and polymerise to form a range of structurally-diverse polyesters.…”

“…1, B). 1,2 The latter is preferred due to control over molecular weights and dispersity (Đ) and thus polymer properties, 3,4 with ROP driven by release of ring strain. 5,6 While the ROP of lactide (R = CH 3 ) and glycolide (R = H) are commonplace, especially in biomedicine 7 and food packaging, 8 broadening this strategy to other cyclic esters is difficult.…”

A Highly Elastic and Autofluorescent Poly(xylitol-dodecanedioic Acid) for Tissue Engineering

“…Polyester is one kind of these polymer biomaterials that have many applications in tissue engineering due to their biocompatibility and biodegradability . Most of these polyester polymers degrade without any dramatic structural changes during the hydrolytic degradation because of surface and bulk erosion mechanisms. ,− Poly­(lactic acid) (PLA), poly­(caprolactone) (PCL), and poly­(lactic- co -glycolic acid) (PLGA) are examples of these polyesters in the family which have been approved by the FDA and widely used in different biomedical fields like tissue engineering and drug delivery. , However, their applications in soft tissue regeneration are limited by their high stiffness and low elasticity that do not mimic the extracellular matrix (ECM) of soft tissues. − The synthesis routes for these polyester polymers also have several disadvantages, such as complex and costly procedures, toxic catalysts or a large amount of organic solvents required, and nonrenewable resources. These significant drawbacks have led researchers to synthesize new polyester materials with higher elasticity and adjustable mechanical properties to meet the specific needs for soft tissue applications such as in tendons, heart valves, skin, wound dressing, nerves, and blood vessels. ,, Additionally, using renewable resources for the synthesis of a polyester polymer at a low cost will bring new potentials for biomedical applications. − Therefore, an ideal polymer for soft tissue regeneration should be soft and elastic, which is synthesized from biocompatible monomers with a simple and inexpensive synthetic route, without using any toxic solvents or excess amount of catalysts.…”