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Protein Recognition by Functionalized Sulfonatocalix[4]arenes.

Doolan AM, Rennie ML, Crowley PB
Chemistry 24 984-991 (2018)
Related entries: 5kpf, 5t8w

Cited: 15 times
EuropePMC logo PMID: 29125201

Abstract

The interactions of two mono-functionalized sulfonatocalix[4]arenes with cytochrome c were investigated by structural and thermodynamic methods. The replacement of a single sulfonate with either a bromo or a phenyl substituent resulted in altered recognition of cytochrome c as evidenced by X-ray crystallography. The bromo-substituted ligand yielded a new binding mode in which a self-encapsulated calixarene dimer contributed to crystal packing. This ligand also formed a weak halogen bond with the protein. The phenyl-substituted ligand was bound to Lys4 of cytochrome c, in a 1.7 Å resolution crystal structure. A dimeric packing arrangement mediated by ligand-ligand contacts in the crystal suggested a possible assembly mechanism. The different protein recognition properties of these calixarenes are discussed.

Reviews - 5lft mentioned but not cited (1)

  1. Atomic Details of Carbon-Based Nanomolecules Interacting with Proteins. Di Costanzo L, Geremia S. Molecules 25 E3555 (2020)

Articles - 5lft mentioned but not cited (1)

  1. Protein-Calixarene Complexation: From Recognition to Assembly. Crowley PB. Acc Chem Res 55 2019-2032 (2022)


Reviews citing this publication (2)

  1. Synthetic Receptors for the Recognition and Discrimination of Post-Translationally Methylated Lysines. Gruber T. Chembiochem 19 2324-2340 (2018)
  2. NMR Spectroscopy of supramolecular chemistry on protein surfaces. Bayer P, Matena A, Beuck C. Beilstein J Org Chem 16 2505-2522 (2020)

Articles citing this publication (11)

  1. Auto-regulated Protein Assembly on a Supramolecular Scaffold. Rennie ML, Fox GC, Pérez J, Crowley PB. Angew Chem Int Ed Engl 57 13764-13769 (2018)
  2. Photo-Controlled Reversible Microtubule Assembly Mediated by Paclitaxel-Modified Cyclodextrin. Zhang YM, Zhang NY, Xiao K, Yu Q, Liu Y. Angew Chem Int Ed Engl 57 8649-8653 (2018)
  3. Cucurbit[7]uril-Dimethyllysine Recognition in a Model Protein. Guagnini F, Antonik PM, Rennie ML, O'Byrne P, Khan AR, Pinalli R, Dalcanale E, Crowley PB. Angew Chem Int Ed Engl 57 7126-7130 (2018)
  4. Reversible Click Chemistry for Ultrafast and Quantitative Formation of Protein-Polymer Nanoassembly and Intracellular Protein Delivery. Liu B, Ianosi-Irimie M, Thayumanavan S. ACS Nano 13 9408-9420 (2019)
  5. Design of a Thiosemicarbazide-Functionalized Calix[4]arene Ligand and Related Transition Metal Complexes: Synthesis, Characterization, and Biological Studies. Bahojb Noruzi E, Kheirkhahi M, Shaabani B, Geremia S, Hickey N, Asaro F, Nitti P, Kafil HS. Front Chem 7 663 (2019)
  6. Molecular Tweezers with Additional Recognition Sites. Heid C, Sowislok A, Schaller T, Niemeyer F, Klärner FG, Schrader T. Chemistry 24 11332-11343 (2018)
  7. A Thermodynamic Model of Auto-regulated Protein Assembly by a Supramolecular Scaffold. Rennie ML, Crowley PB. Chemphyschem 20 1011-1017 (2019)
  8. Complexation of chiral amines by resorcin[4]arene sulfonic acids in polar media - circular dichroism and diffusion studies of chirality transfer and solvent dependence. Setner B, Szumna A. Beilstein J Org Chem 15 1913-1924 (2019)
  9. Noncovalent Protein-Pseudorotaxane Assembly Incorporating an Extended Arm Calix[8]arene with α-Helical Recognition Properties. Mockler NM, Ramberg KO, Guagnini F, Raston CL, Crowley PB. Cryst Growth Des 21 1424-1427 (2021)
  10. Unveiling the Binding Modes of the Crystallophore, a Terbium-based Nucleating and Phasing Molecular Agent for Protein Crystallography. Engilberge S, Riobé F, Wagner T, Di Pietro S, Breyton C, Franzetti B, Shima S, Girard E, Dumont E, Maury O. Chemistry 24 9739-9746 (2018)
  11. Complex Formation between Cytochrome c and a Tetra-alanino-calix[4]arene. Volpi S, Doolan A, Baldini L, Casnati A, Crowley PB, Sansone F. Int J Mol Sci 23 15391 (2022)


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