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Poly(anhydride-esters) comprised exclusively of naturally occurring antimicrobials and EDTA: antioxidant and antibacterial activities.

Carbone-Howell AL, Stebbins ND, Uhrich KE - Biomacromolecules (2014)

Bottom Line: The resulting polymers were characterized to confirm their chemical composition and understand their thermal properties and molecular weight.In vitro release studies demonstrated that polymer hydrolytic degradation was complete after 16 days, resulting in the release of free antimicrobials and EDTA.Antioxidant and antibacterial assays determined that polymer release media exhibited bioactivity similar to that of free compound, demonstrating that polymer incorporation and subsequent release had no effect on activity.

View Article: PubMed Central - PubMed

ABSTRACT
Carvacrol, thymol, and eugenol are naturally occurring phenolic compounds known to possess antimicrobial activity against a range of bacteria, as well as antioxidant activity. Biodegradable poly(anhydride-esters) composed of an ethylenediaminetetraacetic acid (EDTA) backbone and antimicrobial pendant groups (i.e., carvacrol, thymol, or eugenol) were synthesized via solution polymerization. The resulting polymers were characterized to confirm their chemical composition and understand their thermal properties and molecular weight. In vitro release studies demonstrated that polymer hydrolytic degradation was complete after 16 days, resulting in the release of free antimicrobials and EDTA. Antioxidant and antibacterial assays determined that polymer release media exhibited bioactivity similar to that of free compound, demonstrating that polymer incorporation and subsequent release had no effect on activity. These polymers completely degrade into components that are biologically relevant and have the capability to promote preservation of consumer products in the food and personal care industries via antimicrobial and antioxidant pathways.

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FTIR spectra of thymol-containing diacid 3a (A, top)and polymer 4a (B, bottom).
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fig2: FTIR spectra of thymol-containing diacid 3a (A, top)and polymer 4a (B, bottom).

Mentions: The phenolic antimicrobials(1) are reacted with EDTA dianhydride (2) in the presence of triethylamine to yield diacid (3) via a ring-opening transesterification (Scheme 1). The diacids, 3, were successfully preparedin high yields (76–85%) with only minor purification necessary.Diacid structures were confirmed by 1H NMR and FT-IR spectra,while DSC, MS, and elemental analysis were used for melting point,molecular weight, and chemical composition determination, respectively.In the 1H NMR spectrum of 3a, which is providedas an example (Figure 1), the disappearanceof the phenol signal of 1a at 9.02 ppm and the appearanceof EDTA linker peaks at 4.15, 3,77, and 3.13 ppm demonstrate successfulring-opening esterification to generate 3a. The diacids 3 were polymerized via solution polymerization techniques,33,34 using triphosgene as the coupling reagent in the presence of triethylamineat 0 °C. Solution polymerization was chosen instead of melt-condensationto prevent potential ring closure and regeneration of the EDTA dianhydride, 5.34 Polymers were characterizedby 1H NMR to confirm structure. Additionally, FT-IR (Figure 2) confirmed the synthesis of a poly(anhydride-ester)through the disappearance of the carboxylic acid stretch at 1712 cm–1 in diacid 4 and the appearance of theC=O anhydride stretches at 1815 and 1745 cm–1 in polymer 5.


Poly(anhydride-esters) comprised exclusively of naturally occurring antimicrobials and EDTA: antioxidant and antibacterial activities.

Carbone-Howell AL, Stebbins ND, Uhrich KE - Biomacromolecules (2014)

FTIR spectra of thymol-containing diacid 3a (A, top)and polymer 4a (B, bottom).
© Copyright Policy
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4020595&req=5

fig2: FTIR spectra of thymol-containing diacid 3a (A, top)and polymer 4a (B, bottom).
Mentions: The phenolic antimicrobials(1) are reacted with EDTA dianhydride (2) in the presence of triethylamine to yield diacid (3) via a ring-opening transesterification (Scheme 1). The diacids, 3, were successfully preparedin high yields (76–85%) with only minor purification necessary.Diacid structures were confirmed by 1H NMR and FT-IR spectra,while DSC, MS, and elemental analysis were used for melting point,molecular weight, and chemical composition determination, respectively.In the 1H NMR spectrum of 3a, which is providedas an example (Figure 1), the disappearanceof the phenol signal of 1a at 9.02 ppm and the appearanceof EDTA linker peaks at 4.15, 3,77, and 3.13 ppm demonstrate successfulring-opening esterification to generate 3a. The diacids 3 were polymerized via solution polymerization techniques,33,34 using triphosgene as the coupling reagent in the presence of triethylamineat 0 °C. Solution polymerization was chosen instead of melt-condensationto prevent potential ring closure and regeneration of the EDTA dianhydride, 5.34 Polymers were characterizedby 1H NMR to confirm structure. Additionally, FT-IR (Figure 2) confirmed the synthesis of a poly(anhydride-ester)through the disappearance of the carboxylic acid stretch at 1712 cm–1 in diacid 4 and the appearance of theC=O anhydride stretches at 1815 and 1745 cm–1 in polymer 5.

Bottom Line: The resulting polymers were characterized to confirm their chemical composition and understand their thermal properties and molecular weight.In vitro release studies demonstrated that polymer hydrolytic degradation was complete after 16 days, resulting in the release of free antimicrobials and EDTA.Antioxidant and antibacterial assays determined that polymer release media exhibited bioactivity similar to that of free compound, demonstrating that polymer incorporation and subsequent release had no effect on activity.

View Article: PubMed Central - PubMed

ABSTRACT
Carvacrol, thymol, and eugenol are naturally occurring phenolic compounds known to possess antimicrobial activity against a range of bacteria, as well as antioxidant activity. Biodegradable poly(anhydride-esters) composed of an ethylenediaminetetraacetic acid (EDTA) backbone and antimicrobial pendant groups (i.e., carvacrol, thymol, or eugenol) were synthesized via solution polymerization. The resulting polymers were characterized to confirm their chemical composition and understand their thermal properties and molecular weight. In vitro release studies demonstrated that polymer hydrolytic degradation was complete after 16 days, resulting in the release of free antimicrobials and EDTA. Antioxidant and antibacterial assays determined that polymer release media exhibited bioactivity similar to that of free compound, demonstrating that polymer incorporation and subsequent release had no effect on activity. These polymers completely degrade into components that are biologically relevant and have the capability to promote preservation of consumer products in the food and personal care industries via antimicrobial and antioxidant pathways.

Show MeSH