Synonym
ND-322 HCl; ND 322 HCl; ND322 HCl; ND-322 Hydrochloride; ND 322 Hydrochloride; ND322 Hydrochloride;
IUPAC/Chemical Name
4-(4-((thiiran-2-ylmethyl)sulfonyl)phenoxy)aniline hydrochloride
InChi Key
FOCZQHBXIUOIJR-UHFFFAOYSA-N
InChi Code
InChI=1S/C15H15NO3S2.ClH/c16-11-1-3-12(4-2-11)19-13-5-7-15(8-6-13)21(17,18)10-14-9-20-14;/h1-8,14H,9-10,16H2;1H
SMILES Code
NC1=CC=C(OC2=CC=C(S(=O)(CC3SC3)=O)C=C2)C=C1.[H]Cl
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
>2 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
357.86
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: Meisel JE, Chang M. Selective small-molecule inhibitors as chemical tools to define the roles of matrix metalloproteinases in disease. Biochim Biophys Acta. 2017 Nov;1864(11 Pt A):2001-2014. doi: 10.1016/j.bbamcr.2017.04.011. Epub 2017 Apr 20. Review. PubMed PMID: 28435009.
2: Marusak C, Bayles I, Ma J, Gooyit M, Gao M, Chang M, Bedogni B. The thiirane-based selective MT1-MMP/MMP2 inhibitor ND-322 reduces melanoma tumor growth and delays metastatic dissemination. Pharmacol Res. 2016 Nov;113(Pt A):515-520. doi: 10.1016/j.phrs.2016.09.033. Epub 2016 Sep 26. PubMed PMID: 27687955; PubMed Central PMCID: PMC5107128.
3: Yan Y, Chen X, Yang X, Zhang J, Xu W, Zhang Y. Synthesis of chiral ND-322, ND-364 and ND-364 derivatives as selective inhibitors of human gelatinase. Bioorg Med Chem. 2015 Oct 15;23(20):6632-40. doi: 10.1016/j.bmc.2015.09.013. Epub 2015 Sep 7. PubMed PMID: 26386821.
4: Song W, Peng Z, Gooyit M, Suckow MA, Schroeder VA, Wolter WR, Lee M, Ikejiri M, Cui J, Gu Z, Chang M. Water-soluble mmp-9 inhibitor prodrug generates active metabolites that cross the blood-brain barrier. ACS Chem Neurosci. 2013 Aug 21;4(8):1168-73. doi: 10.1021/cn400077d. Epub 2013 May 30. PubMed PMID: 23687970; PubMed Central PMCID: PMC3750675.
5: Gooyit M, Lee M, Schroeder VA, Ikejiri M, Suckow MA, Mobashery S, Chang M. Selective water-soluble gelatinase inhibitor prodrugs. J Med Chem. 2011 Oct 13;54(19):6676-90. doi: 10.1021/jm200566e. Epub 2011 Sep 6. PubMed PMID: 21866961; PubMed Central PMCID: PMC3190643.
