Synonym
Eggmanone; Egm; NSC805543; NSC 805543; NSC-805543;
IUPAC/Chemical Name
3-(2-Methylallyl)-2-((2-oxo-2-(thiophen-2-yl)ethyl)thio)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidine-4(3H)-one
InChi Key
XAKJIQPEGSCYIP-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H20N2O2S3/c1-12(2)10-22-19(24)17-13-6-3-4-7-15(13)27-18(17)21-20(22)26-11-14(23)16-8-5-9-25-16/h5,8-9H,1,3-4,6-7,10-11H2,2H3
SMILES Code
O=C1C(C2=C(CCCC2)S3)=C3N=C(SCC(C4=CC=CS4)=O)N1CC(C)=C
Purity
>95% (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
416.57
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: Xie C, Lin PJ, Hao J. Eggmanone Effectively Overcomes Prostate Cancer Cell Chemoresistance. Biomedicines. 2021 May 12;9(5):538. doi: 10.3390/biomedicines9050538. PMID: 34066000; PMCID: PMC8151738.
2: Haycook CP, Balsamo JA, Glass EB, Williams CH, Hong CC, Major AS, Giorgio TD. PEGylated PLGA Nanoparticle Delivery of Eggmanone for T Cell Modulation: Applications in Rheumatic Autoimmunity. Int J Nanomedicine. 2020 Feb 19;15:1215-1228. doi: 10.2147/IJN.S234850. PMID: 32110018; PMCID: PMC7036983.
3: Xie C, Ramirez A, Wang Z, Chow MSS, Hao J. A simple and sensitive HPLC-MS/MS method for quantification of eggmanone in rat plasma and its application to pharmacokinetics. J Pharm Biomed Anal. 2018 May 10;153:37-43. doi: 10.1016/j.jpba.2018.01.009. Epub 2018 Feb 11. PMID: 29459234.
4: Williams CH, Hempel JE, Hao J, Frist AY, Williams MM, Fleming JT, Sulikowski GA, Cooper MK, Chiang C, Hong CC. An in vivo chemical genetic screen identifies phosphodiesterase 4 as a pharmacological target for hedgehog signaling inhibition. Cell Rep. 2015 Apr 7;11(1):43-50. doi: 10.1016/j.celrep.2015.03.001. Epub 2015 Mar 26. PMID: 25818300; PMCID: PMC4394042.
5: Hempel JE, Cadar AG, Hong CC. Development of thieno- and benzopyrimidinone inhibitors of the Hedgehog signaling pathway reveals PDE4-dependent and PDE4-independent mechanisms of action. Bioorg Med Chem Lett. 2016 Apr 15;26(8):1947-53. doi: 10.1016/j.bmcl.2016.03.013. Epub 2016 Mar 7. PMID: 26976215; PMCID: PMC5147493.
6: Kan C, Chen L, Hu Y, Ding N, Li Y, McGuire TL, Lu H, Kessler JA, Kan L. Gli1-labeled adult mesenchymal stem/progenitor cells and hedgehog signaling contribute to endochondral heterotopic ossification. Bone. 2018 Apr;109:71-79. doi: 10.1016/j.bone.2017.06.014. Epub 2017 Jun 21. PMID: 28645539; PMCID: PMC5801258.
