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Exploration of pipecolate sulfonamides as binders of the FK506-binding proteins 51 and 52.

Gopalakrishnan R, Kozany C, Wang Y, Schneider S, Hoogeland B, Bracher A, Hausch F
J Med Chem 55 4123-31 (2012)
Cited: 26 times
EuropePMC logo PMID: 22455398

Abstract

FK506-binding proteins (FKBP) 51 and 52 are cochaperones that modulate the signal transduction of steroid hormone receptors. Single nucleotide polymorphisms in the gene encoding FKBP51 have been associated with a variety of psychiatric disorders. Rapamycin and FK506 are two macrocyclic natural products, which tightly bind to most FKBP family members, including FKBP51 and FKBP52. A bioisosteric replacement of the α-ketoamide moiety of rapamycin and FK506 with a sulfonamide was envisaged with the retention of the conserved hydrogen bonds. A focused solid support-based synthesis protocol was developed, which led to ligands with submicromolar affinity for FKBP51 and FKBP52. The molecular binding mode for one sulfonamide analogue was confirmed by X-ray crystallography.

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Articles - 4drq mentioned but not cited (1)

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Reviews citing this publication (8)

  1. Is the HPA Axis as Target for Depression Outdated, or Is There a New Hope? Menke A. Front Psychiatry 10 101 (2019)
  2. FKBP Ligands-Where We Are and Where to Go? Kolos JM, Voll AM, Bauder M, Hausch F. Front Pharmacol 9 1425 (2018)
  3. The Many Faces of FKBP51. Hähle A, Merz S, Meyners C, Hausch F. Biomolecules 9 E35 (2019)
  4. Functional diversity and pharmacological profiles of the FKBPs and their complexes with small natural ligands. Galat A. Cell Mol Life Sci 70 3243-3275 (2013)
  5. Precision pharmacotherapy: psychiatry's future direction in preventing, diagnosing, and treating mental disorders. Menke A. Pharmgenomics Pers Med 11 211-222 (2018)
  6. Conformational Dynamics in FKBP Domains: Relevance to Molecular Signaling and Drug Design. LeMaster DM, Hernandez G. Curr Mol Pharmacol 9 5-26 (2015)
  7. Development of Non-Immunosuppressive FK506 Derivatives as Antifungal and Neurotrophic Agents. Jung JA, Yoon YJ. J Microbiol Biotechnol 30 1-10 (2020)
  8. Analysis of the Selective Antagonist SAFit2 as a Chemical Probe for the FK506-Binding Protein 51. Buffa V, Knaup FH, Heymann T, Springer M, Schmidt MV, Hausch F. ACS Pharmacol Transl Sci 6 361-371 (2023)

Articles citing this publication (16)

  1. Selective inhibitors of the FK506-binding protein 51 by induced fit. Gaali S, Kirschner A, Cuboni S, Hartmann J, Kozany C, Balsevich G, Namendorf C, Fernandez-Vizarra P, Sippel C, Zannas AS, Draenert R, Binder EB, Almeida OF, Rühter G, Uhr M, Schmidt MV, Touma C, Bracher A, Hausch F. Nat Chem Biol 11 33-37 (2015)
  2. Large FK506-binding proteins shape the pharmacology of rapamycin. März AM, Fabian AK, Kozany C, Bracher A, Hausch F. Mol Cell Biol 33 1357-1367 (2013)
  3. Pharmacological Inhibition of the Psychiatric Risk Factor FKBP51 Has Anxiolytic Properties. Hartmann J, Wagner KV, Gaali S, Kirschner A, Kozany C, Rühter G, Dedic N, Häusl AS, Hoeijmakers L, Westerholz S, Namendorf C, Gerlach T, Uhr M, Chen A, Deussing JM, Holsboer F, Hausch F, Schmidt MV. J Neurosci 35 9007-9016 (2015)
  4. FKBPs and the Akt/mTOR pathway. Hausch F, Kozany C, Theodoropoulou M, Fabian AK. Cell Cycle 12 2366-2370 (2013)
  5. Crystal structures of the free and ligand-bound FK1-FK2 domain segment of FKBP52 reveal a flexible inter-domain hinge. Bracher A, Kozany C, Hähle A, Wild P, Zacharias M, Hausch F. J Mol Biol 425 4134-4144 (2013)
  6. Molecular dynamics simulation, binding free energy calculation and unbinding pathway analysis on selectivity difference between FKBP51 and FKBP52: Insight into the molecular mechanism of isoform selectivity. Shi D, Bai Q, Zhou S, Liu X, Liu H, Yao X. Proteins 86 43-56 (2018)
  7. Ligand-based and structure-based investigation for Alzheimer's disease from traditional chinese medicine. Liao KH, Chen KB, Lee WY, Sun MF, Lee CC, Chen CY. Evid Based Complement Alternat Med 2014 364819 (2014)
  8. Differential conformational dynamics in the closely homologous FK506-binding domains of FKBP51 and FKBP52. Mustafi SM, LeMaster DM, Hernández G. Biochem J 461 115-123 (2014)
  9. Rational design and asymmetric synthesis of potent and neurotrophic ligands for FK506-binding proteins (FKBPs). Pomplun S, Wang Y, Kirschner A, Kozany C, Bracher A, Hausch F. Angew Chem Int Ed Engl 54 345-348 (2015)
  10. Macrocyclic FKBP51 Ligands Define a Transient Binding Mode with Enhanced Selectivity. Voll AM, Meyners C, Taubert MC, Bajaj T, Heymann T, Merz S, Charalampidou A, Kolos J, Purder PL, Geiger TM, Wessig P, Gassen NC, Bracher A, Hausch F. Angew Chem Int Ed Engl 60 13257-13263 (2021)
  11. The seven pillars of molecular pharmacology: GPCR research honored with Nobel Prize for chemistry. Hausch F, Holsboer F. Angew Chem Int Ed Engl 51 12172-12175 (2012)
  12. C-H…O hydrogen bonds in FK506-binding protein-ligand interactions. Rajan S, Baek K, Yoon HS. J Mol Recognit 26 550-555 (2013)
  13. FKBP51 and FKBP12.6-Novel and tight interactors of Glomulin. Hähle A, Geiger TM, Merz S, Meyners C, Tianqi M, Kolos J, Hausch F. PLoS One 14 e0221926 (2019)
  14. Classical force field parameters for two high-affinity ligands of FKBP12. Olivieri L, Gardebien F. J Mol Graph Model 49 118-128 (2014)
  15. Deconstructing Protein Binding of Sulfonamides and Sulfonamide Analogues. Purder PL, Meyners C, Sugiarto WO, Kolos J, Löhr F, Gebel J, Nehls T, Dötsch V, Lermyte F, Hausch F. JACS Au 3 2478-2486 (2023)
  16. Discovery of pentapeptide-inhibitor hits targeting FKBP51 by combining computational modeling and X-ray crystallography. Han JT, Zhu Y, Pan DB, Xue HX, Wang S, Peng Y, Liu H, He YX, Yao X. Comput Struct Biotechnol J 19 4079-4091 (2021)


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