CADA

• CAT Number: I023949
• CAS Number: 182316-44-5
• Molecular Formula: C31H39N3O4S2
• Molecular Weight: 581.79
• Purity: ≥95%
• Synonyms: Cyclotriazadisulfonamide; CADA
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4℃ for short term (days to weeks) or -20℃ for long term (months to years).
• IUPAC Name: 9-Benzyl-3-methylene-1,5-bis(p-tolylsulfonyl)-1,5,9-triazacyclododecane
• InChI: InChI=1S/C31H39N3O4S2/c1-26-11-15-30(16-12-26)39(35,36)33-21-7-19-32(25-29-9-5-4-6-10-29)20-8-22-34(24-28(3)23-33)40(37,38)31-17-13-27(2)14-18-31/h4-6,9-18H,3,7-8,19-25H2,1-2H3
• InChIKey: SRJIECKMPIRMJJ-UHFFFAOYSA-N
• SMILES: O=S(N1CC(CN(S(=O)(C2=CC=C(C)C=C2)=O)CCCN(CC3=CC=CC=C3)CCC1)=C)(C4=CC=C(C)C=C4)=O

CADA (Cat.No:I023949), also known as Cyclotriazadisulfonamide, is an inhibitor of CD4 biosynthesis at Sec61α, most likely by preventing a reorientation step of the signal sequence in the protein-conducting channel.

Reference

1: Van Puyenbroeck V, Claeys E, Schols D, Bell TW, Vermeire K. A Proteomic Survey Indicates Sortilin as a Secondary Substrate of the ER Translocation Inhibitor Cyclotriazadisulfonamide (CADA). Mol Cell Proteomics. 2017 Feb;16(2):157-167. doi: 10.1074/mcp.M116.061051. Epub 2016 Dec 20. PubMed PMID: 27998951; PubMed Central PMCID: PMC5294205.
2: Chawla R, Van Puyenbroeck V, Pflug NC, Sama A, Ali R, Schols D, Vermeire K, Bell TW. Tuning Side Arm Electronics in Unsymmetrical Cyclotriazadisulfonamide (CADA) Endoplasmic Reticulum (ER) Translocation Inhibitors to Improve their Human Cluster of Differentiation 4 (CD4) Receptor Down-Modulating Potencies. J Med Chem. 2016 Mar 24;59(6):2633-47. doi: 10.1021/acs.jmedchem.5b01832. Epub 2016 Mar 14. PubMed PMID: 26974263.
3: Demillo VG, Goulinet-Mateo F, Kim J, Schols D, Vermeire K, Bell TW. Unsymmetrical cyclotriazadisulfonamide (CADA) compounds as human CD4 receptor down-modulating agents. J Med Chem. 2011 Aug 25;54(16):5712-21. doi: 10.1021/jm2002603. Epub 2011 Jul 29. PubMed PMID: 21800875.
4: Vermeire K, Van Laethem K, Janssens W, Bell TW, Schols D. Human immunodeficiency virus type 1 escape from cyclotriazadisulfonamide-induced CD4-targeted entry inhibition is associated with increased neutralizing antibody susceptibility. J Virol. 2009 Sep;83(18):9577-83. doi: 10.1128/JVI.00648-09. Epub 2009 Jul 1. PubMed PMID: 19570853; PubMed Central PMCID: PMC2738218.
5: Pinheiro JR, Bitencourt M, da Cunha EF, Ramalho TC, Freitas MP. Novel anti-HIV cyclotriazadisulfonamide derivatives as modeled by ligand- and receptor-based approaches. Bioorg Med Chem. 2008 Feb 15;16(4):1683-90. Epub 2007 Nov 13. PubMed PMID: 18053727.
6: Bell TW, Anugu S, Bailey P, Catalano VJ, Dey K, Drew MG, Duffy NH, Jin Q, Samala MF, Sodoma A, Welch WH, Schols D, Vermeire K. Synthesis and structure-activity relationship studies of CD4 down-modulating cyclotriazadisulfonamide (CADA) analogues. J Med Chem. 2006 Feb 23;49(4):1291-312. PubMed PMID: 16480266.
7: Vermeire K, Bell TW, Choi HJ, Jin Q, Samala MF, Sodoma A, De Clercq E, Schols D. The Anti-HIV potency of cyclotriazadisulfonamide analogs is directly correlated with their ability to down-modulate the CD4 receptor. Mol Pharmacol. 2003 Jan;63(1):203-10. PubMed PMID: 12488553.