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Steady-migration retention characteristics of peptides under gradient elution： application towards a dynamic separation method for minor-adjustments of the retention of peptides in RPLC

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Science China Chemistry 2017年第6期60卷 829-836页

作者： Min Li Yongjun Lu Yicong Yang Jianjun Li Lili Wang Wei Tuo Xiaohui Ning Xin-Du Geng Institute of Modern Separation Science Shaanxi Provincial Key Laboratory Northwest University Xi'an 710069 China Xi'an Aolan Science and Technology Development Company Xi 'an 710075 China Xi'an Shiyou University Xi'an 710065 China

Minor-adjustment of the retention of peptides, induced by varying the mobile phase flow-rate(MPF-R), is a new dynamic separation method for simultaneously and rapidly identifying and improving the selectivity of hidden and overlapping peptide peaks. It can also-stabilize the reverse elution order of some pair-peaks under gradient elution in reverse phase liquid chromatography. The retention characteristics of peptides under gradient elution in RPLC was firstly found to be dominated by two variables of the steady region(SR) and migration region(MR). The changes in peptide retention induced by varying the MPF-R can be attributed to changes in the rate of bond breaking of multiple molecular interactions of peptides from the SR and of the mass transfer of peptides from the stationary phase to the mobile phase in the MR. The two dynamic variables were also found to independently depend on the type of peptide. Desirable results were obtained using six standard oligopeptides and a real sample of trypsin-digested *** is expected that the quality control of peptide drugs, high dispersion of peptide peaks in peptide mapping and "bottom-up MS"in proteomics will be improved by this method, even enabling peptide purification on a preparative scale in industry.

关键词： steady-migration retention liquid chromatography peptides dynamic separation minor-adjustment of retention elution orders

Neuroprotective effect of immunomodulatory peptides in rats with traumatic spinal cord injury

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Neural Regeneration Research 2021年第7期16卷 1273-1280页

作者： Dulce Parra-Villamar Liliana Blancas-Espinoza Elisa Garcia-Vences Juan Herrera-García Adrian Flores-Romero Alberto Toscano-Zapien Jonathan Vilchis Villa Rodríguez Barrera-Roxana Soria Zavala Karla Antonio Ibarra Raúl Silva-García Unidad de Investigación Médica en Inmunología Hospital de PediatríaCentro Médico Nacional Siglo XXI/Instituto Mexicano del Seguro Social/Ciudad de MéxicoMéxico Centro de Investigación en Ciencias de la Salud(CICSA) Facultad de Ciencias de la SaludUniversidad Anáhuac MéxicoCampus NorteHuixquilucanEdo de MéxicoMéxico Centro de Investigación del Proyecto Camina A.C Ciudad de MéxicoMéxico

Several therapies have shown obvious effects on structural conservation contributing to motor functional recovery after spinal cord injury(SCI).Nevertheless, neither strategy has achieved a convincing *** purposed a combined therapy of immunomodulatory peptides that individually have shown significant effects on motor functional recovery in rats with *** objective of this study was to investigate the effects of the combined therapy of monocyte locomotion inhibitor factor(MLIF), A91 peptide, and glutathione monoethyl ester(GSH-MEE) on chronic-stage spinal cord *** Sprague-Dawley rats underwent a laminectomy of the T9 vertebra and a moderate *** groups were included: sham, PBS, MLIF + A91, MLIF + GSH-MEE, A91 + GSH-MEE, and MLIF + A91 + *** months after injury, motor functional recovery was evaluated using the open field *** and white matter preservation was evaluated using hematoxylin & eosin staining and Luxol Fast Blue staining, *** number of motoneurons in the ventral horn and the number of axonal fibers were determined using hematoxylin & eosin staining and immunohistochemistry, *** deposition was evaluated using Masson's trichrome *** combined therapy of MLIF, A91, and GSH-MEE greatly contributed to motor functional recovery and preservation of the medullary parenchyma, white matter, motoneurons, and axonal fibres, and reduced the deposition of collagen in the lesioned *** combined therapy of MLIF, A91, and GSH-MEE preserved spinal cord tissue integrity and promoted motor functional recovery of rats after *** study was approved by the National Commission for Scientific Research on Bioethics and Biosafety of the Instituto Mexicano del Seguro Social under registration number R-2015-785-116(approval date November 30, 2015) and R-2017-3603-33(approval date June 5, 2017).

关键词： glutathione monoethyl ester monocyte locomotion inhibitor factor motor functional recovery neuroprotection neurorestoration peptides protective autoimmunity spinal cord injury

Electrochemical chemoselective thiocarbamylation of late-stage Tyr-containing drugs and peptides

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Science China Chemistry 2024年第10期67卷 3382-3388页

作者： Wan-Jie Wei Xin-Yu Wang Hai-Tao Tang Fei-Hu Cui Yun-Qi Wu Ying-Ming Pan State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources(Ministry of Education of China)Collaborative Innovation Center for Guangxi Ethnic MedicineSchool of Chemistry and Pharmaceutical SciencesGuangxi Normal UniversityGuilin 541004China

The synthesis and modification of peptides occupy a unique position in the field of drug development,and the functionalization of amino acids is a valuable strategy as an alternative to peptide ***,the development of tyrosine(Tyr)as a target amino acid is a major challenge in the field of ***,we report an electrochemical radical coupling reaction of labeling tyrosine-containing active drugs and peptides with thiocarbamate derivatives for the first *** tri-component,onepot reaction can be performed smoothly under simple,gentle,and clean electrochemical conditions and is suitable for the functionalization of various Tyr-containing drug molecular derivatives and peptides.

关键词： tyrosine electrochemical radical coupling chemical modification peptides

Purifi cation and identification of anti-inflammatory peptides from sturgeon (Acipenser schrenckii) cartilage

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Food Science and Human Wellness 2023年第6期12卷 2175-2183页

作者： Li Yuan Qian Chu Bei Yang Wei Zhang Quancai Sun Ruichang Gao School of Food and Biological Engineering Jiangsu UniversityZhenjiang 212013China Bio-resources Key Laboratory of Shaanxi Province School of Biological Science and EngineeringShaanxi University of TechnologyHanzhong 723001China

Cartilage is a nonedible byproduct with little saleable ***,previous studies have proposed the possibility of producing peptides from cartilage with immune function modulation *** current study aimed to investigate the potential anti-inflammatory activity of peptides derived from sturgeon(Acipenser schrenckii)cartilage in lipopolysaccharide(LPS)-stimulated RAW264.7 *** peptide sequences,including four novel peptides,were identified from ethanol-soluble cartilage *** these five peptides,LTGP,LLLE,LLEL and VGPAGPAGP reduced the production of nitric oxide(NO)and interleukin-6(IL-6)while increasing interleukin-10(IL-10)*** analysis suggested the inhibition of activated mitogen-activated protein kinase(MAPK)and interleukin-17(IL-17)signaling pathways after LLEL ***,which is involved in the IL-17 signaling pathway,was further proved to be blocked by downregulating the phosphorylation of p38,extracellular-signal regulated protein kinase(ERK),and c-jun N-terminal kinase(JNK).This novel peptide offers an attractive approach to develop functional foods.

关键词： Sturgeon cartilage peptides Anti-inflammatory Mitogen-activated protein kinase

Identification and the molecular mechanism of novel duck liver-derived anti-inflammatory peptides in lipopolysaccharide-induced RAW264.7 cell model

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Food Science and Human Wellness 2024年第6期13卷 3595-3605页

作者： Xiankang Fan Laidi Zhang Yangying Sun Changyu Zhou Qiang Xia Lihui Du Zhen Wu Daodong Pan State Key Laboratory for Managing Biotic and Chemical Threats to the Quality and Safety of Agro-products Ningbo UniversityNingbo 315211China Key Laboratory of Animal Protein Food Processing Technology of Zhejiang Province College of Food and Pharmaceutical SciencesNingbo UniversityNingbo 315832China

In this study,10 novel anti-inflammatory peptides were identified from duck liver,and their molecular mechanism was demonstrated based on machine learning and molecular *** Sephadex G-15 gel chromatography separation,reversed-phase high-performance liquid chromatography purification,liquid chromatography-tandem mass spectrometry identification,and BIOPEP database comparison,10 novel antiinflammatory peptides were initially *** splendid angiotensin-converting enzyme(ACE)inhibition and anti-inflammatory properties were confirmed by machine *** binding energies less than–20.93 kJ/mol,molecular docking revealed that they could efficiently bind to the active pockets of tumor necrosis factorα(TNF-α),interleukin 6(IL-6),cyclooxygenase 2(COX-2),and nuclear factorκB(NF-κB)proteins with efficiency,indicating that the compounds can spontaneously form complexes through hydrogen bonding and hydrophobic interactions with the protein binding *** the lipopolysaccharide-induced RAW264.7 cell model,the release of NO,TNF-α,and IL-6 and the mRNA expression of inflammatory factors(TNF-α,IL-6,COX-2,and NF-κB)were significantly inhibited by these *** concluded it might be due to their anti-inflammatory effects by inhibiting the protein phosphorylation of inhibitor of NF-κB(IκBα)in the cytoplasm and preventing the translocation of NF-κB p65 in the cytoplasm to the nucleus,thereby regulating the NF-κB signaling *** study is essential for the screening of anti-inflammatory peptides and the investigation of the mechanism of action.

关键词： peptides Machine learning Molecular docking Infl ammation Liquid chromatography-tandem mass spectrometry

Mitochondria-targeted cancer therapy based on functional peptides

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Chinese Chemical Letters 2023年第5期34卷 104-110页

作者： Yuhan Sun He Zhang Guangzhao Lu Huan Wang Ying Lu Li Fan Department of Pharmaceutical Sciences School of PharmacyNaval Medical UniversityShanghai 200433China

Mitochondria are critical for tumor growth and metastasis.A number of traditional antitumor drugs have poor water solubility and must penetrate multiple cellular barriers to reach the *** mitochondria have a unique transmembrane potential and an inner membrane with a low permeability,it is difficult for most drugs to enter *** recent years,mitochondria-targeted delivery systems that use functional peptides to modify drugs have received increasing *** functional peptides can change the original physicochemical properties of drugs and actively target *** peptide-drug conjugates(PDCs,peptide-drug conjugates)can decompose and release drugs over time or due to certain stimuli in *** preserves the biological activity of the drug while increasing intratumor uptake through the enhanced permeability and retention effect(EPR,the enhanced permeability and retention effect).In this review,we focus on the direction of cancer therapy and review the application of different functional peptides in the mitochondria-targeted tumor treatments reported in recent years.

关键词： peptides Mitochondria Cancer therapy Targeting Cell uptake

Multifunctional oral delivery systems for enhanced bioavailability of therapeutic peptides/proteins

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Acta Pharmaceutica Sinica B 2019年第5期9卷 902-922页

作者： Ying Han Zhonggao Gao Liqing Chen Lin Kang Wei Huang Mingji Jin Qiming Wang You Han Bae State Key Laboratory of Bioactive Substance and Function of Natural Medicines Department of PharmaceuticsInstitute of Materia MedicaChinese Academy of Medical Sciences and Peking Union Medical CollegeBeijing100050China Department of Pharmaceutics and Pharmaceutical Chemistry the University of UtahSalt Lake CityUT84108USA

In last few years, therapeutic peptides/proteins are rapidly growing in drug market considering their higher efficiency and lower toxicity than chemical drugs. However, the administration of therapeutic peptides/proteins is mainly limited in parenteral approach. Oral therapy which was hampered by harsh gastrointestinal environment and poorly penetrating epithelial barriers often results in low bioavailability(less than 1%–2%). Therefore, delivery systems that are rationally designed to overcome these challenges in gastrointestinal tract and ameliorate the oral bioavailability of therapeutic peptides/proteins are seriously promising. In this review, we summarized various multifunctional delivery systems, including lipid-based particles, polysaccharide-based particles, inorganic particles, and synthetic multifunctional particles that achieved effective oral delivery of therapeutic peptides/proteins.

关键词： Multifunctional delivery systems Oral Bioavailability Macromolecules peptides and proteins Gastrointestinal environment Epithelial barriers Nanoparticles

Cytological evaluation by Caco-2 and KU812 of non-allergenic peptides from simulated digestion of infant formula in vitro

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Food Science and Human Wellness 2023年第3期12卷 817-824页

作者： Zihao Xu Hao Bai Xin Ma Yong Wu Zhihua Wu Anshu Yang Weixiang Mao Xin Li Hongbing Chen State Key Laboratory Food Science and Technology Nanchang UniversityNanchang 330047China School of food science and Technology Nanchang UniversityNanchang 330047China Sino-German Joint Research Institute Nanchang UniversityNanchang 330047China Jiangxi Province Key Laboratory of Food Allergy Nanchang UniversityNanchang 330047China Jiangxi Institute of Quality and Standardization Nanchang 330046China

Milk allergy is a common allergic reaction found in infants and young children,most of them appear tolerance after growing *** this study,infant formula was digested by simulated in vitro digestion *** potential non-allergenic peptides were further screened from undigested products by exclusion of the known epitopes fromβ-lactoglobulin(BLG)andα-lactalbumin(ALA).These potential non-allergenic peptides were synthesized and their transferability were determined by Caco-2 cell monolayer ***,the potential allergenicity were evaluated by KU812 cell degranulation *** results showed that 7 peptides were screened as non-allergenic sequences,among which were 3 from ALA and 4 from *** Caco-2 cell model showed that all the synthetic peptides were absorbed and transported ***,only peptide BLG_(107-118)showed potential allegencity by KU812 *** conclusion,6 peptides,including ALA_(29-51),ALA_(80-90),ALA_(94-103),BLG_(1-20),BLG_(24-50),and BLG_(123-139)were evaluated as hypoallergenic peptides,which could be used for candidates of peptides inducing immune tolerance for persons with milk allergy.

关键词： Milk allergy Epitopes peptides Hypoallergenic Immune tolerance

The application of sulfur-containing peptides in drug discovery

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Chinese Chemical Letters 2018年第7期29卷 1079-1087页

作者： Jiaoyan Zhao Xuefeng Jiang Shanghai Key Laboratory of Green Chemistry and Chemical Process School of Chemistry and Molecular EngineeringEast China Normal University State Key Laboratory of Elemento-organic Chemistry Nankai University

In recent decades, peptides as potential drugs were more and more explored with the development of non-oral medicine. There into, sulfur-containing peptide is one of the most popular aspects in peptide drugs due to the introduction of sulfur atoms leading unique *** purpose of the present review is to focus on the discovery of various sulfur-containing peptides with particular emphasis on their pharmacological mechanisms. This review is organized according to the structures of the sulfurcontaining peptides.

关键词： peptides Disulfide Thioether Thiazole Drug discovery