Ortiz-Aldaco María Guadalupe, Estévez Miriam, España-Sánchez Beatriz Liliana, Bonilla-Cruz José, Rodríguez-deLeón Eloy, Báez José E
Department of Chemistry, University of Guanajuato (UG) Noria Alta S/N 36050 Guanajuato Gto Mexico
Centro de Fisica Aplicada y Tecnología Avanzada (CFATA), UNAM Juriquilla Qro. Mexico.
RSC Adv. 2025 Jan 2;15(1):276-288. doi: 10.1039/d4ra08104h.
Linear aliphatic oligoesters derived from ε-caprolactone (CL) were synthesized by ring-opening polymerization (ROP) using terpene alcohols that have antibacterial activity as initiators (nerol, geraniol, β-citronellol and farnesol). Ammonium decamolybdate (NH)[MoO] was used as a catalyst. From previous oligoesters, monodisperse species of monomers, dimers, and trimers were isolated by flash column chromatography (FCC). Poly(ε-caprolactone) (PCL) oligoesters [oligo(CLs)] and monodisperse oligomeric species were characterized by different analytical techniques, such as nuclear magnetic resonance (NMR) spectroscopy, electrospray ionization quadrupole time-of-flight mass spectrometry (ESI/MS-QTOF), and Fourier-transform infrared (FTIR) spectroscopy to determine the chemical nature of the samples. The thermal properties were analyzed by differential scanning calorimetry (DSC), which showed significant differences between the olefin and alkyl terminal groups. The end-groups affected crystalline domains according to the crystallization temperatures ( ), melting temperatures ( ), and glass transition temperature ( ) of the oligo(CLs) and monodisperse oligomeric species. In addition, the results of thermogravimetric analysis (TGA) suggest that the thermal degradation in the case of the monomer and dimer species with olefin terminal groups is similar compared to that with the alkyl terminal group. Due to the antimicrobial properties of olefinic initiators, microbiological tests were carried out on the monodisperse oligomeric species through studies of the minimum inhibitory concentration (MIC), minimum bactericidal concentration (MBC), and antibiograms. This is the first time in the literature that monodisperse oligomers derived from PCL functionalized with terpenes and alkyl end-groups were tested in terms of their antibacterial properties. The results indicated that these monodisperse species could lead to new antibiotic compounds with potential applications.
以具有抗菌活性的萜烯醇（橙花醇、香叶醇、β-香茅醇和法尼醇）为引发剂，通过开环聚合（ROP）合成了源自ε-己内酯（CL）的线性脂肪族低聚酯。使用十钼酸铵（NH₄）₂[Mo₁₀O₃₂]作为催化剂。从先前的低聚酯中，通过快速柱色谱法（FCC）分离出单分散的单体、二聚体和三聚体物种。聚（ε-己内酯）（PCL）低聚酯[低聚（CLs）]和单分散低聚物种通过不同的分析技术进行表征，如核磁共振（NMR）光谱、电喷雾电离四极杆飞行时间质谱（ESI/MS-QTOF）和傅里叶变换红外（FTIR）光谱，以确定样品的化学性质。通过差示扫描量热法（DSC）分析热性能，结果表明烯烃端基和烷基端基之间存在显著差异。端基根据低聚（CLs）和单分散低聚物种的结晶温度（Tc）、熔点（Tm）和玻璃化转变温度（Tg）影响结晶区域。此外，热重分析（TGA）结果表明，与具有烷基端基的单体和二聚体物种相比，具有烯烃端基的单体和二聚体物种的热降解情况相似。由于烯烃引发剂的抗菌特性，通过最小抑菌浓度（MIC）、最小杀菌浓度（MBC）和抗菌谱研究，对单分散低聚物种进行了微生物测试。这是文献中首次对用萜烯和烷基端基官能化的PCL衍生的单分散低聚物的抗菌性能进行测试。结果表明，这些单分散物种可能会产生具有潜在应用价值的新型抗生素化合物。
