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Interactions that influence the binding of synthetic heparan sulfate based disaccharides to fibroblast growth factor-2.

Li YC, Ho IH, Ku CC, Zhong YQ, Hu YP, Chen ZG, Chen CY, Lin WC, Zulueta MM, Hung SC, Lin MG, Wang CC, Hsiao CD
ACS Chem Biol 9 1712-7 (2014)
Related entries: 4oee, 4oef

Cited: 15 times
EuropePMC logo PMID: 24959968

Abstract

Heparan sulfate (HS) is a linear sulfated polysaccharide that mediates protein activities at the cell-extracellular interface. Its interactions with proteins depend on the complex patterns of sulfonations and sugar residues. Previously, we synthesized all 48 potential disaccharides found in HS and used them for affinity screening and X-ray structural analysis with fibroblast growth factor-1 (FGF1). Herein, we evaluated the affinities of the same sugars against FGF2 and determined the crystal structures of FGF2 in complex with three disaccharides carrying N-sulfonated glucosamine and 2-O-sulfonated iduronic acid as basic backbones. The crystal structures show that water molecules mediate different interactions between the 3-O-sulfonate group and Lys125. Moreover, the 6-O-sulfonate group forms intermolecular interactions with another FGF2 unit apart from the main binding site. These findings suggest that the water-mediated interactions and the intermolecular interactions influence the binding affinity of different disaccharides with FGF2, correlating with their respective dissociation constants in solution.

Reviews citing this publication (2)

  1. Heparin-Mimicking Polymers: Synthesis and Biological Applications. Paluck SJ, Nguyen TH, Maynard HD. Biomacromolecules 17 3417-3440 (2016)
  2. Current structural biology of the heparin interactome. Pomin VH, Mulloy B. Curr Opin Struct Biol 34 17-25 (2015)

Articles citing this publication (13)

  1. Sulfated glycopeptide nanostructures for multipotent protein activation. Lee SS, Fyrner T, Chen F, Álvarez Z, Sleep E, Chun DS, Weiner JA, Cook RW, Freshman RD, Schallmo MS, Katchko KM, Schneider AD, Smith JT, Yun C, Singh G, Hashmi SZ, McClendon MT, Yu Z, Stock SR, Hsu WK, Hsu EL, Stupp SI. Nat Nanotechnol 12 821-829 (2017)
  2. Making the longest sugars: a chemical synthesis of heparin-related [4] n oligosaccharides from 16-mer to 40-mer. Hansen SU, Miller GJ, Cliff MJ, Jayson GC, Gardiner JM. Chem Sci 6 6158-6164 (2015)
  3. Fully Synthetic Heparan Sulfate-Based Neural Tissue Construct That Maintains the Undifferentiated State of Neural Stem Cells. Chopra P, Logun MT, White EM, Lu W, Locklin J, Karumbaiah L, Boons GJ. ACS Chem Biol 14 1921-1929 (2019)
  4. A cyclic peptide retards the proliferation of DU145 prostate cancer cells in vitro and in vivo through inhibition of FGFR2. Zhang Y, Ouyang M, Wang H, Zhang B, Guang W, Liu R, Li X, Shih TC, Li Z, Cao J, Meng Q, Su Z, Ye J, Liu F, Hong A, Chen X. MedComm (2020) 1 362-375 (2020)
  5. Chemical synthesis of human syndecan-4 glycopeptide bearing O-, N-sulfation and multiple aspartic acids for probing impacts of the glycan chain and the core peptide on biological functions. Yang W, Eken Y, Zhang J, Cole LE, Ramadan S, Xu Y, Zhang Z, Liu J, Wilson AK, Huang X. Chem Sci 11 6393-6404 (2020)
  6. Modular synthesis of heparin-related tetra-, hexa- and octasaccharides with differential o-6 protections: programming for regiodefined 6-o-modifications. Baráth M, Hansen SU, Dalton CE, Jayson GC, Miller GJ, Gardiner JM. Molecules 20 6167-6180 (2015)
  7. Expedient Synthesis of a Library of Heparan Sulfate-Like "Head-to-Tail" Linked Multimers for Structure and Activity Relationship Studies. Zhang J, Liang L, Yang W, Ramadan S, Baryal K, Huo CX, Bernard JJ, Liu J, Hsieh-Wilson L, Zhang F, Linhardt RJ, Huang X. Angew Chem Int Ed Engl 61 e202209730 (2022)
  8. Automated Solid Phase Assisted Synthesis of a Heparan Sulfate Disaccharide Library. Ramadan S, Su G, Baryal K, Hsieh-Wilson LC, Liu J, Huang X. Org Chem Front 9 2910-2920 (2022)
  9. Fine epitope mapping of a human disulphide-stabilized diabody against fibroblast growth factor-2. Zhong J, Zhang S, Zhang L, Cai Y, Deng Y, Zheng Q, Deng N. J Biochem 165 487-495 (2019)
  10. Evaluation of wound healing effect of Mallotus philippensis (Lam.) Mull. Arg. by in silico multitargets directed for multiligand approach. Bodas KS, Bagul CD, Shinde VM. In Silico Pharmacol 10 19 (2022)
  11. Synthesis of a Systematic 64-Membered Heparan Sulfate Tetrasaccharide Library. Baryal KN, Ramadan S, Su G, Huo C, Zhao Y, Liu J, Hsieh-Wilson LC, Huang X. Angew Chem Int Ed Engl 62 e202211985 (2023)
  12. Synthetic Heparan Sulfate Hydrogels Regulate Neurotrophic Factor Signaling and Neuronal Network Activity. Latchoumane CV, Chopra P, Sun L, Ahmed A, Palmieri F, Wu HF, Guerreso R, Thorne K, Zeltner N, Boons GJ, Karumbaiah L. ACS Appl Mater Interfaces 14 28476-28488 (2022)
  13. Single-Step Per-O-Sulfonation of Sugar Oligomers with Concomitant 1,6-Anhydro Bridge Formation for Binding Fibroblast Growth Factors. Yeh CJ, Ku CC, Lin WC, Fan CY, Zulueta MML, Manabe Y, Fukase K, Li YK, Hung SC. Chembiochem 20 237-240 (2019)


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