Synonym
Cyclotriazadisulfonamide; CADA
IUPAC/Chemical Name
9-Benzyl-3-methylene-1,5-bis(p-tolylsulfonyl)-1,5,9-triazacyclododecane
InChi Key
SRJIECKMPIRMJJ-UHFFFAOYSA-N
InChi Code
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
SMILES Code
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
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
581.79
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
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.
