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Hydrogen-bonding regulated supramolecular chirality with controllable biostability

Nano Research 2022年第3期15卷 2226-2234页

作者： Jinying Liu Yu Zhao Changli Zhao Xiaoqiu Dou Xiaoyu Ma Shaokang Guan Yu Jia Chuanliang Feng State Key Lab of Metal Matrix Composites School of Materials Science and EngineeringShanghai Jiao Tong UniversityShanghai 200240China Key Laboratory for Special Functional Materials of Ministry of Education School of Materials Science and EngineeringHenan UniversityKaifeng 475004China School of Materials Science and Engineering Zhengzhou UniversityZhengzhou 450001China International Laboratory for Quantum Functional Materials of Henan and School of PhysicsZhengzhou UniversityZhengzhou 450001China

The regulation of natural helical nanostructures is principally supported and actuated by hydrogen bonds(H-bonds)formed from hydrogen-bonding groups(peptide bonds and base pairs)to realize biological activities and specific biofunctional transformations.However,studying the role of H-bonding patterns on the handedness of supramolecular assemblies is still challenging,since supramolecular assemblies will be disassembled or destabilized with slightly varying H-bonding groups for most supramolecules.To circumvent this issue,herein,two types of self-assembled C2-symmetric phenylalanine derivatives differed by a single H-bonding group(ester or amide)are systematically designed for deciphering the role of H-bonding pattern on the chirality of supramolecular assemblies and their related biostability.Opposite handedness nanofibrous structures with tailorable diameter and helical pitch are achieved with the transition from ester to amide groups in the gelators.Experimental and theoretical evidence suggests that helical orientation of ester-containing gelators ascribes to intermolecular H-bonds.In contrast,the helical direction for the amide-counterparts is mainly due to intra-and intermolecular H-bonds.Moreover,these H-bonding groups greatly influence their stability,as revealed by in vitro and in vivo degradation experiments and the left-handed assemblies are more stable than the right-handed ones.Thus,the study offers a feasible model to have valuable insight into understanding the role of H-bonding patterns in biological folding.

关键词： supramolecular chirality Helical structures hydrogen-bonding group hydrogen-bonding pattern biostability

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Modulation of Conformational Transition of Polypeptides under Slightly Acidic Environment

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Chinese Journal of Chemistry 2022年第24期40卷 2981-2987,I0002页

作者： Jie Li Jiajie Zhang Qi Long Weisheng Guo Menghua Xiong Guangzhou First People's Hospital School of Biomedical Sciences and EngineeringSouth China University of TechnologyGuangzhou International CampusGuangzhouGuangdong511442 China National Engineering Research Center for Tissue Restoration and Reconstruction South China University of TechnologyGuangzhouGuangdong510006 China Translational Medicine Center Key Laboratory of Molecular TargetClinical PharmacologySchool of Pharmaceutical SciencesThe Second Affiliated HospitalGuangzhou Medical UniversityGuangzhouGuangdong510260 China Key Laboratory of Biomedical Engineering of Guangdong Province and Innovation Center for Tissue Restoration and ReconstructionSouth China University of TechnologyGuangzhouGuangdong510006 China Key Laboratory of Biomedical Materials and Engineering of the Ministry of Education South China University of TechnologyGuangzhouGuangdong510006 China

Controlling the conformational transition of polypeptides under slightly acidic environment is challenging.Herein,we report a class of pH-responsive helix-to-coil conformationally transitionable polypeptides(pCTPs)by simply conjugating tertiary amine groups(TAs)to polylysine.Their conformation is highly dependent on the charge state of TAs,showing a helical structure when most TAs are deprotonated and a non-helical structure when majority of TAs are protonated.The conformational transition pH can be modulated by tuning the hydrophobicity of TAs and the incorporation of hydrophobic monomers at a pH range of 7.2 to 6.0.Such pCTP showed a vesicle-to-micelle transition when their conformation transformed from helix to coil,facilitating controlled drug release.Our study provided an approach to control the conformational transition of polypeptides under slightly acidic condition.

关键词： Peptides Conformational transition Helical structures pH responsiveness Drug delivery

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α/Sulfono-γ-AA peptide hybrids agonist of GLP-1R with prolonged action both in vitro and in vivo

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Acta Pharmaceutica Sinica B 2023年第4期13卷 1648-1659页

作者： Yan Shi Candy Lee Peng Sang Zaid Amso David Huang Weixia Zhong Meng Gu Lulu Wei Vân T.B.Nguyen-Tran Jingyao Zhang Weijun Shen Jianfeng Cai Department of Chemistry University of South FloridaTampaFL 33620USA Calibr at Scripps Research La JollaCA 92037USA

Peptides are increasingly important resources for biological and therapeutic development,however,their intrinsic susceptibility to proteolytic degradation represents a big hurdle.As a natural agonist for GLP-1R,glucagon-like peptide 1(GLP-1)is of significant clinical interest for the treatment of type-2 diabetes mellitus,but its in vivo instability and short half-life have largely prevented its therapeutic application.Here,we describe the rational design of a series of a/sulfono-γ-AA peptide hybrid analogues of GLP-1 as the GLP-1R agonists.Certain GLP-1 hybrid analogues exhibited enhanced stability(t_(1/2)>14 days)compared to t_(1/2)(<1 day)of GLP-1 in the blood plasma and in vivo.These newly developed peptide hybrids may be viable alternative of semaglutide for type-2 diabetes treatment.Additionally,our findings suggest that sulfono-γ-AA residues could be adopted to substitute canonical amino acids residues to improve the pharmacological activity of peptide-based drugs.

关键词： GLP-1 Peptidomimetics Helical structures Stability Type-2 diabetes treatments Rational design GLP-1R agonists Pharmacological activity

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Hierarchical Microphase Behaviors of Chiral Block Copolymers under Kinetic and Thermodynamic Control

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CCS Chemistry 2022年第7期4卷 2460-2468页

作者： Zhen Geng Huiying Wang Seon-Mi Jin Xinghao Yan Min Ren Bijin Xiong Ke Wang Renhua Deng Senbin Chen Eunji Lee Lianbin Zhang Jintao Zhu Zhenzhong Yang State Key Laboratory of Materials Processing and Die&Mould Technology Key Laboratory of Materials Chemistry for Energy Conversion and Storage of Ministry of EducationSchool of Chemistry and Chemical EngineeringHuazhong University of Science and TechnologyWuhan 430074 School of Materials Science and Engineering Gwangju Institute of Science and Technology(GIST)Gwangju 61005 Institute of Polymer Science and Engineering Department of Chemical EngineeringTsinghua UniversityBeijing 100084

Chiral superstructures in confined spaces are subtly affected by the complex interplay among various noncovalent interactions,details of which are still in adequately understood.Herein,we report the threedimensional confined assembly of the chiral block copolymers of polystyrene-block-poly(D-lactide)andits enantiomer in emulsion droplets and demonstrate unprecedented successive microphase transformations from single helices to double helices with inverted helicity,and then to twisted cylinders in the constructedcolloidal particles.Theabovehierarchical structural transformations of chiral microphases are kinetically dependent and can further transform into thermodynamically stable achiral cylinders with saddle-shaped topology upon solvent annealing.The formation and subsequent structural transformations as well as thefinal degeneration of chiral architectures provide guidance to understand the chiral evolution at different length scales within spherical confined space and to fabricate biomimetic systems.

关键词： chiral block copolymers Helical structures confined assembly kinetic control mesoporous chiral nanochannels

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Novel 1D Copper（ll） helical Chain Formed by Weak Coordination-driven Self-assembly： Synthesis, Structure, and Magnetic Property

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Chinese Journal of Chemistry 2012年第5期30卷 1052-1056页

作者：黄婉云陈自卢邹华红刘冬成梁福沛 State Key Laboratory of Coordination Chemistry Coordination Chemistry InstituteSchool of Chemistry and Chemical EngineeringNanjing UniversityNanjingJiangsu 210093China Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources(Ministry of Education of China)School of Chemistry and Chemical Engineering Guangxi Normal UniversityGuilinGuangxi 541004China

A novel 1D copper（II） helical chain is constructed through the connection of tetranuclear copper（ll） units [Cu4（L）（Py）4] （H8L=N,N＇-（BINOL-3,3＇-dicarboxyl）-disalicylhydrazide, where BINOL is 1,l＇-binaphthalenyl-2,2＇- diol, py=pyridine） by weak coordination-driven self-assembly, and characterized by IR, single crystal X-ray dif- fraction, thermogravimetric analysis, and X-ray power diffraction analysis. Interestingly, the helical chains are packed in an alternating left-（M） and right-handed （P） chirality, the orientation of the helices was determined by the axial chirality of the ligand. The complex shows antiferromagnetic interactions between the copper centers.

关键词： Helical structures copper weak coordination-driven axial chirality magnetic property

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Structure of Coordination Polymer, 〔Zn(bipy)(H2O)3SO4〕·2H2O (bipy=4,4'-bipyridine)

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Chinese Journal of Structural Chemistry 2000年第2期19卷 103-106页

作者： MA Jian Fang a LIU Jing Fu a XING Yan b JIA Heng Qing b LIN Yong Hua b a (Department of Chemistry, Northeast Normal University, Changchun, 130024) b (Changchun Institute of Applied Chemistry, the Chinese Academy of Sciences, Changchu 西北师范大学甘肃长春 1 3 0 0 2 中科院长春应用化学所吉林长春 1 3 0 0 2

The crystal of the title compound (C 10 H 18 N 2O 9SZn M r =407.69) belongs to the hexagonal system, space group P6 5 with cell parameters: a=11.411(2), c=20.908(4), V=2357.7(7) 3, Z=6, D c =1.723g/cm 3, F(000)=1260, μ (Mo Kα )=1 743mm -1 . The final R and wR factors are 0.072 and 0.178 respectively for 1335 observed reflections. In the structure, zinc ions are bridged by 4,4’ bipyridine to form infinite chains. The sheets containing parallel chains stack along a 6 5 screw axis to give a helical staircase motif. The helical structure is mainly controlled by the hydrogen bonds.

关键词： zinc 4 4’ bipyridine coordination polymer Helical structures

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