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Molecular Assembly of Peptide based Materials towards Biomedical Application.

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Plenary lecture given by Prof. Junbai Li (Chinese Academy of Sciences) at the XVII B-MRS Meeting, in Natal (Brazil), on September 17, 2018.

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Molecular Assembly of Peptide based Materials towards Biomedical Application.

  1. 1. INSTITUTE OF CHEMISTRY CHINESE ACADEMY OF SCIENCE 中 国 科 学 院 化 学 研 究 所 Molecular Assembly of Peptide based Materials towards Biomedical Application Junbai Li Institute of Chemistry Chinese Academy of Sciences, Beijing
  2. 2. Institute of Chemistry, Chinese Academy of Sciences (CAS) Research Characteristic Multidisciplinary Interdisciplinary Comprehensive Polymer Chemistry Green Printing Advanced Polymer Material Polymer Physics/Chemistry Engineering Plastics Analytical Chemistry Analytical Chemistry for living biosystems Physical ChemistryColloid , Interface Sciences Chemistry Thermodynamics Molecular Nanostructure Organic Solid Reaction Dynamics Organic Chemistry Molecular Recognition Organic Solid Photochemistry Nanoscience Molecular Nanostructure Nanotechnology Numbers of SCI Publication SCI Citation ranks No. 1 in Chinese institutions on Chemistry
  3. 3. Molecular Assembly Self-assembly Hydrogen bonds Aromatic interactions van der Waals interactions …… Self-assembly Electrostatic interactions Hydrophobic interactions Coordination interactions …… Building Blocks Supermolecular Assembly Adler-Abramovich L, Gazit E. Chem. Soc. Rev. 2014, 43, 6881.
  4. 4. lipid peptide protein Cell cell membrane microtubule motor protein E. Coil chloroplast mitochondria Organism contains various scales of hierarchical assembly structures and relies on their collection to implement each process of life
  5. 5. Biomolecule-based Assemblies Layer-by-layer (LbL) assembly LbL Assembled Micro/Nanostructures and their biomedical applications lipid peptide protein
  6. 6. Biomedical Application LbL Assembled Micro/Nanostructures Layer-by-layer (LbL) assembly LbL Assembled Micro/Nanostructures and their biomedical applications Blood Substitutes Drug Carriers
  7. 7. Biomolecule-based Complex Assemblies as Artificial Cell Structure pH or light-driven ATP BiosynthesisRotary Motor—ATPase Linear Motor—Kinesin Kinesin-driven Cargo Delivery
  8. 8. Super Resolution Fluorescence Microscopy (STORM) to Observe Biomolecule-based Complex Assemblies Distribution of gelatin in CaCO3 crystal Tubular compartments in NIH3T3 cellsInteraction between FF and liposomes Interactions between the tube DNA origami and lysosomes
  9. 9. Angew. Chem. Int. Ed. 2018, 57, 1903 Angew. Chem. Int. Ed. 2018, 57, 7759 Angew. Chem. Int. Ed. 2018, 57, 6049 Angew. Chem. Int. Ed., 2018, 57, 11404 Angew. Chem. Int. Ed. 2018, 57, 6532 Angew. Chem. Int. Ed. 2017, 56, 12903 Angew. Chem. Int. Ed. 2017, 56, 2660 Angew. Chem. Int. Ed. 2016, 55, 13538 Angew. Chem. Int. Ed., 2016, 55, 908 Angew. Chem. Int. Ed. 2015, 54, 12782 Angew. Chem. Int. Ed. 2014, 53, 2366 Angew. Chem. Int. Ed. 2011, 50, 11186 Angew. Chem. Int. Ed. 2007, 46, 6996 Adv. Mater., 2016, 28, 1251 Adv. Mater., 2016, 28, 1302 Adv. Mater., 2016, 28, 1312 Chem. Rev. 2015, 115, 1597 Adv. Funct. Mater., 2018, 28, 1706557 Adv. Funct. Mater., 2016, 26, 2651 Adv. Funct. Mater. 2015, 25, 1193 Adv. Funct. Mater. 2012, 22, 2673 Adv. Funct. Mater. 2012, 22, 1446 ACS Nano, 2018, 12, 1445 ACS Nano 2018, 12, 1934 ACS Nano 2017, 11, 10489 ACS Nano, 2017, 11, 10175 ACS Nano, 2017, 11, 7349 ACS Nano, 2016, 10, 556 ACS Nano 2015, 9, 2689 ACS Nano 2014, 8, 8529 ACS Nano 2012, 6, 10910 ACS Nano 2012, 6, 6897 Representative Work
  10. 10. Biological inspired aromatic dipeptide (FF) NH2-DAEFR HDSGY EVHHQ KLVFF AEDVG SNKGA IIGLM VGGVV IA-COOH Alzheimer’s amyloid β-peptide motif: Aβ(1-42) L-Phe-L-Phe(FF) Amyloid Precursor Protein (APP) Aβ(1-42) Reches, M., Gazit, E., Science 2003, 300, 625; C. H. Görbitz, Chem. Eur. J. 2001, 7,5153. L-Phe-L-Phe(FF) H2O
  11. 11. Peptide-based Molecular Assembly Cation-diphenylalanine (CDP) Diphenylalanine (FF) Yan. et al., Chem. Soc. Rev., 39 (2010) 1877-1890
  12. 12. Cation-diphenylalanine (CDP) Diphenylalanine (FF) Glutaraldehyde (GA) 12 Glutaraldehyde (GA) mediated assembly of dipeptide Schiff Base -C=N- Peptide-based Molecular Assembly Y. Jia, J. Li*, Chem. Rev., 115 (2015) 1597
  13. 13. GA/FF Nanoparticles——Enzyme Carrier water pH=5.0 pH=6.5 pH=7.2 pH=8.1 The pH-triggered fast disassembly of FF nanoparticles
  14. 14. Adsorption of different small molecules into FF nanoparticles, and their adsorption efficiency (AE) and loading efficiency (LE) The release of ibuprofen (IBU) Burst release within 5 s Turbidity change pH-responsive UV–vis spectra J. Fei, H. Zhang, A. Wang, C. Qin, H. Xue, J. Li*, Adv. Healthcare Mater. 2017, 6, 1601198
  15. 15. Thrombin-FF nanoparticles sprayed into different PBS solutions in vitro clotting measurement using different sprays J. Fei, H. Zhang, A. Wang, C. Qin, H. Xue, J. Li*, Adv. Healthcare Mater. 2017, 6, 1601198 in vivo clotting measurement using different sprays
  16. 16. GA/CDP Nanoparticles——Drug Carrier Glutaraldehyde (GA) Cation-diphenylalanine (CDP) H. Zhang, J. Fei, X. Yan,* A. Wang, J. Li*, Adv. Funct. Mater., 2015, 25, 1193 CDP Nanocarriers (CDPNCs)
  17. 17. CDPNCs co-incubated with trypsin in PBS 0 days 5 days 1 days 10 days CDPNCs degraded in HeLa cells over time Good Biodegradability of CDPNCs
  18. 18. The loading and release of DOX from CDPNCs Drug release from CDP-DOX nanoparticles Cytotoxicity of CDPNCs-DOX for HeLa cells Gradually release 18 H. Zhang, J. Fei, X. Yan,* A. Wang, J. Li*, Adv. Funct. Mater., 2015, 25, 1193
  19. 19. Co-encapsulated two-photon fluorescent dye bis(pyrene) (BP) and a photosensitizer rose bengal (RB) in CDP/GA nanoparticles 400 450 500 550 600 650 700 0 1000 2000 3000 BP-CDPNP BP-CDPNP-RB CDPNP-RB Two-photonFL Intensity Wavelength/nm Two-photon excitation fluorescence spectra B. Sun, L. Wang, Q. Li, P. He, H. Liu, H. Wang, Y. Yang*, J. Li*, Biomacromolecules, 2017, 18, 3506-3513 450 500 550 600 650 0.0 0.4 0.8 1.2 RB BP Emission spectra of BP and absorption spectra of RB Normalized Intensity Wavelength/nm BP-GA/CDP-RB Nanoparticles
  20. 20. CDP/Genipin Nanospheres——Photodynamic Therapy X. Yang, J. Fei, Q. Li, J. Li*, Chem. Eur. J., 2016, 22, 6477 Characterization of dipeptide-genipin nanospheres (DPGNSs) The assembly of dipeptide-genipin nanospheres and their application as intrinsic photosensitizers in PDT
  21. 21. FTIR, UV/Vis spectra, fluorescence emission spectrum and CLSM image of dipeptide-genipin nanospheres The photosensitivity of nanospheres Under irradiation, DPGNSs can generate 1O2 and therefore they could serve as a new efficient intrinsic photosensitizer for PDT.
  22. 22. 3D-CLSM image of the MCF-7 cells endocytosing DPGNSs Relative content of cellular ROS Cell viability with increased concentrations of DPGNS 22 X. Yang, J. Fei, Q. Li, J. Li*, Chem. Eur. J., 2016, 22, 6477
  23. 23. 23 Optical Property of Peptide-based Assembly C. Wu, Z. X. Wang, H. X. Lei, W. Zhang, Y. Duan, J. Am. Chem. Soc. 2007, 129, 1225-1232 Cation-diphenylalanine (CDP) CPABS HPABS MO Sulfonic-azobenzene is the analog of Congo red, which is an important medical molecule for the detection and therapy of Alzheimer’s disease Congo red
  24. 24. urchin-like structures flower-like structures plate-like structures
  25. 25. urchin-like structures CPABS flower-like structures HPABS plate-like structures MO CDP FTIR XRD pattern urchin-like structures flower-like structures plate-like structures H. Ma, J. Fei, Y. Cui, J. Zhao, A. Wang, J. Li*, Chem. Commun., 2013, 49, 9956
  26. 26. urchin-like structures flower-like structures plate-like structures H. Ma, J. Fei, Y. Cui, J. Zhao, A. Wang, J. Li*, Chem. Commun., 2013, 49, 9956 increasing the amount of CDP would induce morphology change 26
  27. 27. UV Vis Cation-diphenylalanine (CDP) Photoswitchable sulfonicazobenzene to optically manipulate the self-assembly of CDP Photo-induced reversible structural transition of CDP self-assembly H. Ma , J. Fei , Q. Li , J. Li *, Small, 2015, 11, 1787-1791
  28. 28. branched nanostructures with elongated nanoplates and helical nanobelts trans-cis isomerization
  29. 29. trans cis photo-induced structural transition H. Ma , J. Fei , Q. Li , J. Li *, Small, 2015, 11, 1787-1791
  30. 30. X. Liu, et al., Angew Chem. Int. Ed. 2017, 56, 2660 The transition of a dipeptide-based organogel into a hexagonal crystal under extremely cold conditions (77 K) SEM images of FF–toluene organogels after different numbers of cryogenic treatments
  31. 31. Cross-polarized microscopy images of the assembly at different angles Photoluminescence emission spectra of FF solution and FF–toluene gel at room temperature. after cryogenic treatment X. Liu, J. Fei, A. Wang, W. Cui, P. Zhu, J. Li*, Angew Chem. Int. Ed. 2017, 56, 2660
  32. 32. The self-assembly of FF crystals from molecules in NH4OH solution withdrawal speed of 2.0 μm/s withdrawal speed of 4.6 μm/s Self-Assembly of Ultralong Aligned Dipeptide Single Crystals
  33. 33. FF single crystal imaged in reflection with crossed polarizersCharacterization of the FF single crystals B. Sun, Q. Li, H. Riegler, S. Eickelmann, L. Dai, Y. Yang, R. Perez-Garcia, Y. Jia, G. Chen, J. Fei, K. Holmberg, J. Li*, ACS Nano, 2017, 11, 10489
  34. 34. Solubility of FF pH The change of concentration of FF (CFF) in the NH OH solution as NH and H O evaporate. Aligned FF single crystals formed under different NH4OH concentration and temperature 38 oC,0.1% 75 oC,0.1% 75 oC,28%75 oC,5% The “gradient single crystals” at a silicon wafer (positions 1,2,3,4) obtained with different withdrawal speeds 2.0 μm/s 2.0 μm/s 4.6 μm/s 4.6 μm/s
  35. 35. Proposed assembly mechanism of the aligned FF single crystal growth process 35 B. Sun, Q. Li, H. Riegler, S. Eickelmann, L. Dai, Y. Yang, R. Perez-Garcia, Y. Jia, G. Chen, J. Fei, K. Holmberg, J. Li*, ACS Nano, 2017, 11, 10489
  36. 36. Optical waveguide properties of aligned FF single crystals 5 µm Optical waveguiding property B. Sun, Q. Li, H. Riegler, S. Eickelmann, L. Dai, Y. Yang, R. Perez-Garcia, Y. Jia, G. Chen, J. Fei, K. Holmberg, J. Li*, ACS Nano, 2017, 11, 10489
  37. 37. GA/FF crystalline platelet——Active Optical Waveguiding X. Yan, Y. Su, J. Li ,* J. Früh, H. Möhwald,, Angew. Chem. Int. Ed., 2011, 50, 11186 toluene solution
  38. 38. Optical Waveguiding of Peptide Crystals
  39. 39. Optical Waveguiding of Peptide Crystals
  40. 40. K. Tao, et al., Nature Comm. 2018 in press Optical Waveguiding of Peptide Crystals
  41. 41. Conclusions 1. Taking dipeptide diphenylalanine and its derivatives as building block, we have constructed a series of assemblies with 1D, 2D and 3D structures via molecular assembly. 2. Controlled assembly and disassembly of diphenylalanine peptides can be easily tuned by changing physicochemical parameters or assembly conditions, such as concentration, solvents and introducing small molecules to assembly systems. 3. These peptide-based assemblies possess good biodegradability, pH-responsivity and physiological environment-responsivity, thus they may be potentially applied in drug carriers, fast blood clotting and other biomedical applications. 4. The peptide-based fibrils possess good crystalline structures and demonstrate excellent optical properties, they may be potentially applied in optical waveguiding.
  42. 42. Acknowledgements  Contributors: Q. LiH. Zhang X. K. Yang X. C. Liu W. G. Dong J. L. Li Y. Jia J. R. Xia J. B. Fei G. L. Li H. C. Ma X. B. LiT. T. YuanB. B. Sun ¥¥¥¥¥:

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