BB-Cl-Amidine

Last updated

BB-Cl-Amidine
BB-Cl-Amidine structure.png
Identifiers
  • N-[(1S)-4-[(1-amino-2-chloroethylidene)amino]-1-(1H-benzimidazol-2-yl)butyl]-4-phenylbenzamide
CAS Number
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
Formula C26H26ClN5O
Molar mass 459.98 g·mol−1
3D model (JSmol)
  • C1=CC=C(C=C1)C2=CC=C(C=C2)C(=O)N[C@@H](CCCN=C(CCl)N)C3=NC4=CC=CC=C4N3
  • InChI=1S/C26H26ClN5O/c27-17-24(28)29-16-6-11-23(25-30-21-9-4-5-10-22(21)31-25)32-26(33)20-14-12-19(13-15-20)18-7-2-1-3-8-18/h1-5,7-10,12-15,23H,6,11,16-17H2,(H2,28,29)(H,30,31)(H,32,33)/t23-/m0/s1
  • Key:YDOAWJHYHGBQFI-QHCPKHFHSA-N

BB-Cl-Amidine is an experimental drug which acts as a non-subtype selective, irreversible inhibitor of the enzyme peptidylarginine deiminase (PAD). It has anti-cancer effects and is useful for various inflammatory conditions such as arthritis, and while it may be unlikely to be developed for human use due to toxicity concerns, it is widely used in scientific research. [1] [2] [3] [4] [5] [6] [7] [8] As well as its activity as a PAD inhibitor, BB-Cl-Amidine also inhibits the action of the Stimulator of interferon genes (STING) protein by preventing STING oligomerization and thereby terminating the signalling pathway. [9]

See also

References

  1. ↑ Knight JS, Subramanian V, O'Dell AA, Yalavarthi S, Zhao W, Smith CK, et al. (December 2015). "Peptidylarginine deiminase inhibition disrupts NET formation and protects against kidney, skin and vascular disease in lupus-prone MRL/lpr mice". Annals of the Rheumatic Diseases. 74 (12): 2199–2206. doi:10.1136/annrheumdis-2014-205365. PMC   4320672 . PMID   25104775.
  2. ↑ Kawalkowska J, Quirke AM, Ghari F, Davis S, Subramanian V, Thompson PR, et al. (May 2016). "Abrogation of collagen-induced arthritis by a peptidyl arginine deiminase inhibitor is associated with modulation of T cell-mediated immune responses". Scientific Reports. 6 26430. Bibcode:2016NatSR...626430K. doi:10.1038/srep26430. PMC   4876390 . PMID   27210478.
  3. ↑ Elliott W, Guda MR, Asuthkar S, Teluguakula N, Prasad DV, Tsung AJ, et al. (December 2021). "PAD Inhibitors as a Potential Treatment for SARS-CoV-2 Immunothrombosis". Biomedicines. 9 (12): 1867. doi: 10.3390/biomedicines9121867 . PMC   8698348 . PMID   34944683.
  4. ↑ Ai P, Pan H, Chen K, Zheng J, Gao Z, Jin G (August 2021). "Viral mimetic poly(I:C) induces neutrophil extracellular traps via PAD4 to promote inflammation and thrombosis". Biochemical and Biophysical Research Communications. 565: 64–71. Bibcode:2021BBRC..565...64A. doi:10.1016/j.bbrc.2021.05.091. PMID   34098313.
  5. ↑ Mansouri P, Mansouri P, Behmard E, Najafipour S, Kouhpayeh SA, Farjadfar A (October 2024). "Peptidylarginine deiminase (PAD): A promising target for chronic diseases treatment". International Journal of Biological Macromolecules. 278 (Pt 3) 134576. doi:10.1016/j.ijbiomac.2024.134576. PMID   39127273.
  6. ↑ Ciesielski O, Pirola L, Balcerczyk A (February 2024). "Peptidylarginine Deiminases Inhibitors Decrease Endothelial Cells Angiogenic Potential by Affecting Akt Signaling and the Expression and Secretion of Angiogenic Factors". Cellular Physiology and Biochemistry. 58 (1): 63–82. doi: 10.33594/000000683 . PMID   38374715.
  7. ↑ Sadiq A, Chen P, Fert-Bober J (January 2025). "Silencing PADI-2 induces antitumor effects by downregulating NF-κB, Nrf2/HO-1 and AKT1 in A549 lung cancer cells". International Immunopharmacology. 146 113830. doi: 10.1016/j.intimp.2024.113830 . PMID   39700962.
  8. ↑ Seol SI, Oh SA, Davaanyam D, Lee JK (February 2025). "Blocking peptidyl arginine deiminase 4 confers neuroprotective effect in the post-ischemic brain through both NETosis-dependent and -independent mechanisms". Acta Neuropathologica Communications. 13 (1) 33. doi: 10.1186/s40478-025-01951-y . PMC   11834679 . PMID   39966968.
  9. ↑ Humphries F, Shmuel-Galia L, Jiang Z, Zhou JY, Barasa L, Mondal S, et al. (August 2023). "Targeting STING oligomerization with small-molecule inhibitors". Proceedings of the National Academy of Sciences of the United States of America. 120 (33) e2305420120. Bibcode:2023PNAS..12005420H. doi: 10.1073/pnas.2305420120 . PMC   10434303 . PMID   37549268.
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