Synonym
ML-264; ML264; ML 264; CID-51003603; SID 117686865, and SR-03000002171.
IUPAC/Chemical Name
(E)-3-(3-chlorophenyl)-N-(2-((1,1-dioxidotetrahydro-2H-thiopyran-4-yl)(methyl)amino)-2-oxoethyl)acrylamide
InChi Key
AJCDZIDKYKCOMZ-AATRIKPKSA-N
InChi Code
InChI=1S/C17H21ClN2O4S/c1-20(15-7-9-25(23,24)10-8-15)17(22)12-19-16(21)6-5-13-3-2-4-14(18)11-13/h2-6,11,15H,7-10,12H2,1H3,(H,19,21)/b6-5+
SMILES Code
O=C(NCC(N(C(CC1)CCS1(=O)=O)C)=O)/C=C/C2=CC=CC(Cl)=C2
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, not in water
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
Biological target:
ML264 is an antitumor agent that potently and selectively inhibits Krüppel-like factor five (KLF5) expression.
In vitro activity:
As ML264 inhibited cell proliferation without an effect on apoptosis, its ability to induce cell cycle arrest was investigated. The distribution of 143B and U2OS cells in the different cell cycle phases following a 24‐hours incubation with ML264 (20 or 40 μmol/L) was assessed. ML264 treatment increased the proportion of G0/G1 phase cells while decreasing the number of G2/M and S phase cells (Figure 2A,B). To delineate the mechanisms mediating ML264‐induced cell cycle arrest, the expression of cell cyclerelated proteins were examined. ML264 decreased the expression levels of cyclin E1, cyclin D1 and cyclin‐dependent kinase (CDK) 4 in both a dose‐ and time‐dependent manner (Figure 2C), and mRNA expressions were approximately similar to the proteins (Figure 2D). The above results indicate that ML264 therapy could down‐regulate the expression of proteins associated with G0/G1 cell cycle regulation in osteosarcoma cells, thereby inducing G0/G1 phase arrest.
Reference: J Cell Mol Med. 2020 May; 24(10): 5652–5664. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7214147/
In vivo activity:
This study evaluated the effectiveness of ML264 in inhibiting growth of tumor xenografts in nude mice. In these experiments, DLD-1 cells were subcutaneously injected into nude mice until a tumor volume of approximately 100 mm3 was achieved. The mice were then injected intraperitoneally (IP) for ten days with ML264 according to the following regimens: 10 mg/kg (once per day), 10 mg/kg (twice per day) and 25 mg/kg (twice per day). As shown in Figure 5A, single daily injections of ML264 at 10 mg/kg did not significantly affect tumor growth. However, twice daily injections of ML264 at 10 mg/kg or 25 mg/kg resulted in significant reductions in tumor growth (Figs. 5B and 5C), and this effect could be detected as early as two days after the first injection. The data also show that there is a concentration-dependent effect of ML264 on the tumor volume. Statistical analysis of tumor growth revealed significant tumor size reduction in mice treated twice daily with ML264 compared to those receiving only vehicle at day 5 and 10. It is noteworthy that none of the treatment regimens affected the weight of the mice (Figs. 5D–5F). The photographs shown in Figure 5G clearly demonstrate the dose-dependent differences in tumor size resulting from ML264 treatment as compared to controls. Our results demonstrate that ML264 significantly inhibits the growth of CRCs, cellular proliferation, and mitosis in particular, in vivo systems.
Reference: Mol Cancer Ther. 2016 Jan; 15(1): 72–83. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4707060/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMSO |
64.0 |
166.63 |
|
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
384.88
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 |
Formulation protocol:
1. Huang H, Han Y, Chen Z, Pan X, Yuan P, Zhao X, Zhu H, Wang J, Sun X, Shi P. ML264 inhibits osteosarcoma growth and metastasis via inhibition of JAK2/STAT3 and WNT/β-catenin signalling pathways. J Cell Mol Med. 2020 May;24(10):5652-5664. doi: 10.1111/jcmm.15226. Epub 2020 Apr 13. PMID: 32285603; PMCID: PMC7214147. 2. Ruiz de Sabando A, Wang C, He Y, García-Barros M, Kim J, Shroyer KR, Bannister TD, Yang VW, Bialkowska AB. ML264, A Novel Small-Molecule Compound That Potently Inhibits Growth of Colorectal Cancer. Mol Cancer Ther. 2016 Jan;15(1):72-83. doi: 10.1158/1535-7163.MCT-15-0600. Epub 2015 Nov 30. PMID: 26621868; PMCID: PMC4707060. In
In vitro protocol:
1. Huang H, Han Y, Chen Z, Pan X, Yuan P, Zhao X, Zhu H, Wang J, Sun X, Shi P. ML264 inhibits osteosarcoma growth and metastasis via inhibition of JAK2/STAT3 and WNT/β-catenin signalling pathways. J Cell Mol Med. 2020 May;24(10):5652-5664. doi: 10.1111/jcmm.15226. Epub 2020 Apr 13. PMID: 32285603; PMCID: PMC7214147. 2. Ruiz de Sabando A, Wang C, He Y, García-Barros M, Kim J, Shroyer KR, Bannister TD, Yang VW, Bialkowska AB. ML264, A Novel Small-Molecule Compound That Potently Inhibits Growth of Colorectal Cancer. Mol Cancer Ther. 2016 Jan;15(1):72-83. doi: 10.1158/1535-7163.MCT-15-0600. Epub 2015 Nov 30. PMID: 26621868; PMCID: PMC4707060. In
In vivo protocol:
1. Huang H, Han Y, Chen Z, Pan X, Yuan P, Zhao X, Zhu H, Wang J, Sun X, Shi P. ML264 inhibits osteosarcoma growth and metastasis via inhibition of JAK2/STAT3 and WNT/β-catenin signalling pathways. J Cell Mol Med. 2020 May;24(10):5652-5664. doi: 10.1111/jcmm.15226. Epub 2020 Apr 13. PMID: 32285603; PMCID: PMC7214147. 2. Ruiz de Sabando A, Wang C, He Y, García-Barros M, Kim J, Shroyer KR, Bannister TD, Yang VW, Bialkowska AB. ML264, A Novel Small-Molecule Compound That Potently Inhibits Growth of Colorectal Cancer. Mol Cancer Ther. 2016 Jan;15(1):72-83. doi: 10.1158/1535-7163.MCT-15-0600. Epub 2015 Nov 30. PMID: 26621868; PMCID: PMC4707060. In
1: Ruiz de Sabando A, Wang C, He Y, García-Barros M, Kim J, Shroyer KR, Bannister
TD, Yang VW, Bialkowska AB. ML264, A Novel Small-Molecule Compound That Potently
Inhibits Growth of Colorectal Cancer. Mol Cancer Ther. 2016 Jan;15(1):72-83. doi:
10.1158/1535-7163.MCT-15-0600. Epub 2015 Nov 30. PubMed PMID: 26621868; PubMed
Central PMCID: PMC4707060.
2: Bialkowska A, Crisp M, Madoux F, Spicer T, Knapinska A, Mercer B, Bannister
TD, He Y, Chowdhury S, Cameron M, Yang VW, Hodder P. ML264: An Antitumor Agent
that Potently and Selectively Inhibits Krüppel-like Factor Five (KLF5)
Expression: A Probe for Studying Colon Cancer Development and Progression. 2011
Oct 31 [updated 2013 Mar 7]. Probe Reports from the NIH Molecular Libraries
Program [Internet]. Bethesda (MD): National Center for Biotechnology Information
(US); 2010-. Available from http://www.ncbi.nlm.nih.gov/books/NBK143546/
PubMed PMID: 23762940.
