Briciclib (ON-014185)

Alias: Briciclib.; ON-013105; ON014185; ON-014185; ON013105; ON 013105; ON 014185; ON-013105 sodium
Cat No.:V2815 Purity: ≥98%
Briciclib (also known as ON 013105; ON 014185) is an orally bioavailable small molecule and a disodium phosphate ester prodrug of ON 013100 with improved water solubility compared to ON 013100.
Briciclib (ON-014185) Chemical Structure CAS No.: 865783-99-9
Product category: Eukaryotic Initiation Factor
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
10mg
25mg
50mg
100mg
250mg
500mg
Other Sizes

Other Forms of Briciclib (ON-014185):

  • ON-013100
Official Supplier of:
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Briciclib (also known as ON 013105; ON 014185) is an orally bioavailable small molecule and a disodium phosphate ester prodrug of ON 013100 with improved water solubility compared to ON 013100. It is a derivative of benzyl styryl sulfone, which may have anticancer properties and suppress the build-up of cyclin D1 in cancer cells. Briciclib binds to eIF4E, preventing the cap-dependent translation of cyclin D1 and other cancer proteins (c-MYC, VEGF), which results in the death of tumor cells, according to in vitro data. In nonclinical tumor models, briciclib has demonstrated potency and activity when paired with multiple chemotherapeutics. In conclusion, data from both in vitro and in vivo studies show that briciclib has the potential to target eIF4E in solid and hematopoietic cancers, and that an oral form of this exciting therapeutic agent may be developed.

Biological Activity I Assay Protocols (From Reference)
Targets
eIF4
ln Vitro

Briciclib may be used to target eIF4E. Briciclib shows inhibitory activity against the proliferation of mantle cell leukemia (EKO-1 and MINO), breast (MCF7 and MDA-MB-231), gastric (AGS), and esophageal (OE19, OE33, and FLO-1) cancer cell lines with GI50s of 9.8-12.2 nM, and with no toxicity on normal endothelial cells. In 8 hours, biciclib dose-dependently lowers the expression of c-Myc and cyclin D1 in breast and MCL cancer cell lines[1].

ln Vivo

Enzyme Assay
Briciclib is a small molecule that prevents cancer cells from accumulating cyclin D1. Cyclin D1 as the target in vitro At nanomolar concentrations (GI50 = 9.8 - 12.2 nM), briciclib inhibits the growth of malignant cell lines of the breast (MCF7 and MDA-MB-231), gastric (AGS), esophageal (OE19, OE33, and FLO-1), and MCL (JEKO-1 and MINO). Cyclin D1, a protein overexpressed in many tumors, is necessary for normal cell cycle progression. The function of the protein known as eukaryotic initiation factor 4E (eIF4E) is necessary for the process known as cap-dependent translation, which regulates the expression of cyclin D1. According to in vitro data, briciclib binds to eIF4E to prevent cyclin D1 and other cancer proteins (c-MYC, VEGF) from being translated cap-dependently, which results in the death of tumor cells. In nonclinical tumor models, briciclib has demonstrated potency and activity when paired with multiple chemotherapeutics.
Animal Protocol


References

[1]. Abstract 1649: Potent anticancer activity of an orally bioavailable small molecule, ON 013100, and its water soluble derivative, briciclib, a clinical-stage eIF4E-targeted agent. Cancer Research. August 2015, Volume 75, Issue 15.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C₁₉H₂₃O₁₀PS
Molecular Weight
474.42
Exact Mass
474.08
Elemental Analysis
C, 48.10; H, 4.89; O, 33.72; P, 6.53; S, 6.76
CAS #
865783-99-9
Appearance
Solid powder
SMILES
COC1=C(C=C(C=C1)CS(=O)(=O)/C=C/C2=C(C=C(C=C2OC)OC)OC)OP(=O)(O)O
InChi Key
LXENKEWVEVKKGV-BQYQJAHWSA-N
InChi Code
InChI=1S/C19H23O10PS/c1-25-14-10-17(27-3)15(18(11-14)28-4)7-8-31(23,24)12-13-5-6-16(26-2)19(9-13)29-30(20,21)22/h5-11H,12H2,1-4H3,(H2,20,21,22)/b8-7+
Chemical Name
[2-methoxy-5-[[(E)-2-(2,4,6-trimethoxyphenyl)ethenyl]sulfonylmethyl]phenyl] dihydrogen phosphate
Synonyms
Briciclib.; ON-013105; ON014185; ON-014185; ON013105; ON 013105; ON 014185; ON-013105 sodium
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: ≥ 30 mg/mL
Water: N/A
Ethanol: N/A
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.1078 mL 10.5392 mL 21.0784 mL
5 mM 0.4216 mL 2.1078 mL 4.2157 mL
10 mM 0.2108 mL 1.0539 mL 2.1078 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT02168725 Terminated Drug: briciclib Neoplasms
Advanced Solid Tumor
Onconova Therapeutics, Inc. June 2014 Phase 1
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