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depsipeptide
Frontiers of Chemical Science and Engineering · 2011 ·Vol. 5 ·期 4 ·409-415 · IF 0

Synthesis of depsipeptides from L-amino acids and lactones

Cao Hongfei,Feng Yakai,Wang Heyun,Zhang Li,Khan Musammir,Guo Jintang

By using the corresponding L -amino acid sodium as initiator, ɛ -caprolactone-depsipeptides CL-Ala and CL-Leu were prepared by the reactions of ɛ -caprolactone (CL) with L -alanine and L -leucine, respectively, and p -dioxanone-depsipeptide (PDO-Leu) was prepared by the reaction of p -dioxanone (PDO) with L leucine. Two poly( ɛ -caprolactone) oligomers (PCL-Ala and PCL-Leu) of different molecular weights with depsipeptide unit were synthesized by controlling the feed ratio of L -amino acid sodium and CL. The presence of the depsipeptide structure in these obtained products was confirmed by 1 H NMR spectra and the molecular weight of the poly( ɛ -caprolactone) oligomers was measured by gel permeation chromatography (GPC). These products contain a hydroxyl group and a carboxyl group in one molecule, which means they could act as bifunctional monomers for further polymerization to prepare high molecular weight polymers. By this way, the depsipeptide unit could be introduced into the polymers and the biodegradation rates of the novel polymers could be well controlled in vivo by the tailored molecular structures.

研究领域: 有机化学 · 高分子化学 · 生物材料学
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JOURNAL OF ANTIBIOTICS · 2019 ·Vol. 72 ·期 10 ·736-743 · IF 2.446

Two novel cyclic depsipeptides Xenematides F and G from the entomopathogenic bacterium Xenorhabdus budapestensis

Xi Xuedong,Lu Xingzhong,Zhang Xiaodong,Bi Yuhui,Li Xiaochun,Yu Zhiguo

Two novel depsipeptides xenematides F and G ( 1 , 2 ), were isolated from entomopathogenic Xenorhabdus budapestensis SN84 along with a known compound xenematide B. The structures of the two new molecules were elucidated using NMR, MS and Marfey’s method. The xenematide G ( 2 ) contains α-aminoheptanoic acid, a non-protein amino acid that is rarely found in secondary metabolites from entomopathogenic bacteria. Xenematides F and G were tested for antibacterial activity. Xenematide G ( 2 ) exhibited moderate antibacterial activity.

研究领域: 微生物学 · 天然产物化学 · 药物开发
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REACTIVE & FUNCTIONAL POLYMERS · 2013 · IF 2.505

Controlled release of doxorubicin from amphiphilic depsipeptide–PDO–PEG-based copolymer nanosized microspheres

Li Zhang,Yakai Feng,Hong Tian,Changcan Shi,Miao Zhao,Jintang Guo

Novel biodegradable amphiphilic ABA triblock copolymers , i.e. poly(3(S)-methyl-morpholine-2,5-dione- co - p -dioxanone)-block-poly(ethylene glycol)-block-poly(3(S)-methyl-morpholine-2,5-dione- co - p -dioxanone) [P(MMD- co -PDO)- b -PEG- b -P(MMD- co -PDO)], were successfully prepared by ring-opening polymerization of 3(S)-methyl-morpholine-2,5-dione (MMD) and p -dioxanone (PDO) in the presence of poly(ethylene glycol) 6000 as an initiator. These triblock copolymers were characterized by 1 H NMR, 13 C NMR, Fourier transform infrared, gel permeation chromatography and differential scanning calorimetry measurements. P(MMD- co -PDO)- b -PEG- b -P(MMD- co -PDO) could self-assemble into stable nanosized microspheres with critical micellar concentrations of 0.41–0.66   μg/mL. The microspheres showed high hydrolytic degradation. In addition, doxorubicin (DOX) was chosen as a model drug and successfully encapsulated into the microspheres by hydrogen-bond interaction and hydrophobic effect . The transmission electron microscopy and dynamic light scattering measurements revealed that these microspheres were ellipsoidal nanoparticles with diameters ranged from 50 to 100   nm. These copolymer microspheres exhibited high loading capacity (LC), encapsulation efficiency (EE) of DOX and sustained drug release behavior in phosphate buffered solution (PBS). Moreover, the release rate of DOX from those microspheres in pH 4.0 PBS was faster than that in pH 7.4 due to pH sensitivity of the polymer–drug systems and the degradation of the matrix polymers . These amphiphilic depsipeptide multiblock copolymers would be potential promising carriers for anti-tumour drug delivery.

研究领域: 药剂学 · 生物材料 · 肿瘤学
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JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY · 2013 ·Vol. 51 ·期 15 ·3213-3226 · IF 3.543

Amphiphilic depsipeptide-based block copolymers as nanocarriers for controlled release of ibuprofen with doxorubicin

Li Zhang,Yakai Feng,Hong Tian,Miao Zhao,Musammir Khan,Jintang Guo

Well-defined amphiphilic multiblock copolymers PDMAEMA-b-P(IBMD- co -PDO)-b-PEG-b-P(IBMD- co -PDO)-b-PDMAEMA [PDMAEMA-PIBMD-PPDO-PEG], based on poly(2-(dimethylamino)ethyl methacrylate) block (PDMAEMA), poly(3( S )-isobutyl-morpholine-2,5-dione- co-p -dioxanone) block (P(IBMD- co -PDO)), and poly(ethylene glycol) block (PEG) were successfully synthesized by combination of ring-opening polymerization (using 3( S )-isobutyl-morpholine-2,5-dione and p -dioxanone initiated by hydroxyl end of PEG) and atom transfer radical polymerization (ATRP). Furthermore, all these copolymers were characterized by 1 H NMR, 13 C NMR, Fourier transformed-infrared, gel permeation chromatography, differential scanning calorimetry, and thermogravimetric analysis measurements. The degradation experiments showed that the molecular weight of PDMAEMA-PIBMD-PPDO-PEG decreased along with degradation time. In addition, these copolymers could readily self-assemble into nanosized microspheres in phosphate buffered solution. Ibuprofen (IBU) and doxorubicin (DOX) as a kind of combined model drugs were loaded into these microspheres by the combination of ionic interaction and hydrophobic effect. These copolymer microspheres exhibited high loading capacity (LC, up to 26.88%), encapsulation efficiency (EE, up to 61.29%), and sustained release behavior of IBU–DOX in phosphate buffered solution. The results of transmission electron microscopy and dynamic light scattering showed that the microspheres were well-defined uniform spherical particles with average diameter less than 120 nm. Therefore, it can be envisaged that these copolymer systems are promising candidates for controlled release application. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 3213–3226

研究领域: 材料科学 · 药学 · 高分子化学
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REACTIVE & FUNCTIONAL POLYMERS · 2014 · IF 2.822

Biodegradable depsipeptide–PDO–PEG-based block copolymer micelles as nanocarriers for controlled release of doxorubicin

Juan Lv,Li Zhang,Musammir Khan,Xiangkui Ren,Jintang Guo,Yakai Feng

Nowadays, biodegradable amphiphilic block copolymers with stable performance and adjustable structure have attracted the interests of researchers in the field of drug delivery. In this work, the triblock copolymer , P(SBMD- co -PDO)- b -PEG- b -P(SBMD- co -PDO), was successfully synthesized by ring-opening polymerization of 3(S)- sec -butyl-morpholine-2,5-dione (SBMD) and p -dioxanone (PDO) with poly(ethylene glycol) (PEG) as the initiator. In phosphate buffered solution (PBS), these copolymers could self-assemble into nano-sized micelles that have a hydrophobic P(SBMD- co -PDO) core surrounded by a hydrophilic PEG shell. Because of the strong hydrogen bonding and hydrophobic interactions, doxorubicin (DOX) was loaded into the micelles with high loading capacity (LC, up to 28.4%) and encapsulation efficiency (EE, up to 62.5%). The drug-loaded micelles showed sustained-release of DOX along with the hydrolytic degradation of the micelles in PBS. Therefore, these amphiphilic triblock copolymers have potential as drug matrix for controlled release.

研究领域: 药物递送 · 材料科学 · 生物医学工程
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Marine Drugs · 2021 ·Vol. 20 ·期 1 ·16 · IF 5.118

Actinomycin X2, an Antimicrobial Depsipeptide from Marine-Derived Streptomyces cyaneofuscatus Applied as a Good Natural Dye for Silk Fabric

Wei Chen,Kaixiong Ye,Xiaoji Zhu,Huihui Zhang,Ranran Si,Jianing Chen,Zijun Chen,Kaili Song,Zhicheng Yu,Bingnan Han

Actinomycins as clinical medicine have been extensively studied, while few investigations were conducted to discover the feasibility of actinomycins as antimicrobial natural dye contributing to the medical value of the functional fabrics. This study was focused on the application of actinomycin X2 (Ac.X2), a peptide pigment cultured from marine-derivedStreptomyces cyaneofuscatus, in the dyeing and finishing of silk fabric. The dyeing potential of Ac.X2 with silk vs. cotton fabrics was assessed. As a result, the silk fabric exhibited greater uptake and color fastness with Ac.X2. Through Fourier transform infrared spectroscopy (FT-IR), scanning electron microscopy (SEM), and X-ray diffraction (XRD) analyses, some changes of chemical property for the dyed fabric and Ac.X2 were studied. The silk fabric dyed with Ac.X2 exhibited good UV protection ability. The antibacterial properties of dyed and finished silk were also evaluated, which exhibited over 90% antibacterial activity even after 20 washing cycles. In addition, the brine shrimp assay was conducted to evaluate the general toxicity of the tested fabric, and the results indicated that the dyed silk fabrics had a good biological safety property.

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