IUPAC/Chemical Name
(2E)-3-(5-Methoxy-2-methyl-1H-indol-3-yl)-1-(4-pyridinyl)-2-propen-1-one
InChi Key
UPJCYXIOWHZRLU-GQCTYLIASA-N
InChi Code
InChI=1S/C18H16N2O2/c1-12-15(4-6-18(21)13-7-9-19-10-8-13)16-11-14(22-2)3-5-17(16)20-12/h3-11,20H,1-2H3/b6-4+
SMILES Code
O=C(C1=CC=NC=C1)/C=C/C2=C(C)NC3=C2C=C(OC)C=C3
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
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
292.33
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: Shah KN, Ditto AJ, Crowder DC, Overmeyer JH, Tavana H, Maltese WA, Yun YH. Receptor-Mediated Attachment and Uptake of Hyaluronan Conjugates by Breast Cancer Cells. Mol Pharm. 2017 Nov 6;14(11):3968-3977. doi: 10.1021/acs.molpharmaceut.7b00636. Epub 2017 Oct 19. PubMed PMID: 28981299.
2: Mbah NE, Overmeyer JH, Maltese WA. Disruption of endolysosomal trafficking pathways in glioma cells by methuosis-inducing indole-based chalcones. Cell Biol Toxicol. 2017 Jun;33(3):263-282. doi: 10.1007/s10565-016-9369-2. Epub 2016 Nov 7. PubMed PMID: 27822587; PubMed Central PMCID: PMC5420496.
3: Trabbic CJ, Overmeyer JH, Alexander EM, Crissman EJ, Kvale HM, Smith MA, Erhardt PW, Maltese WA. Synthesis and biological evaluation of indolyl-pyridinyl-propenones having either methuosis or microtubule disruption activity. J Med Chem. 2015 Mar 12;58(5):2489-512. doi: 10.1021/jm501997q. Epub 2015 Feb 19. PubMed PMID: 25654321; PubMed Central PMCID: PMC4360382.
4: Trabbic CJ, Dietsch HM, Alexander EM, Nagy PI, Robinson MW, Overmeyer JH, Maltese WA, Erhardt PW. Differential Induction of Cytoplasmic Vacuolization and Methuosis by Novel 2-Indolyl-Substituted Pyridinylpropenones. ACS Med Chem Lett. 2014 Jan 9;5(1):73-77. PubMed PMID: 24527179; PubMed Central PMCID: PMC3918887.
5: Robinson MW, Overmeyer JH, Young AM, Erhardt PW, Maltese WA. Synthesis and evaluation of indole-based chalcones as inducers of methuosis, a novel type of nonapoptotic cell death. J Med Chem. 2012 Mar 8;55(5):1940-56. doi: 10.1021/jm201006x. Epub 2012 Feb 28. PubMed PMID: 22335538; PubMed Central PMCID: PMC3314534.
