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MedKoo Cat#: 208177 | Name: Andrographolide analogue 3A.1

Description:

WARNING: This product is for research use only, not for human or veterinary use.

The andrographolide analog, 19-tert-butyldiphenylsilyl-8,7-epoxy andrographolide (3A.1), has shown anticancer activity against various cancers. The andrographolide analogue, 19-tert-butyldiphenylsilyl-8,7-epoxy andrographolide (3A.1), showed anticancer activity against metastatic castration-resistant and neuroendocrine variant prostate cancers (mCRPC/NEPC). Additionally, 3A.1 exhibited synergistic anticancer effect in combination with standard chemotherapy drugs docetaxel and cabazitaxel in mCRPC/NEPC. Post-treatment gene expression studies revealed that heat shock proteins (Hsp70, Hsp40, Hsp27, and Hsp90) and MAT2A are important in the mechanism of 3A.1 action and drug response.

Chemical Structure

Andrographolide analogue 3A.1
Andrographolide analogue 3A.1
CAS#unknown

Theoretical Analysis

MedKoo Cat#: 208177

Name: Andrographolide analogue 3A.1

CAS#: unknown

Chemical Formula: C36H48O6Si

Exact Mass: 604.3220

Molecular Weight: 604.86

Elemental Analysis: C, 71.49; H, 8.00; O, 15.87; Si, 4.64

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Andrographolide analogue 3A.1, Andrographolide analogue 3A.1
IUPAC/Chemical Name
19-tert-Butyldiphenylsilyl-8,7-epoxy andrographolide; (4S,E)-3-(2-((1S,2S,5R,6R,8aR)-5-(((tert-Butyldiphenylsilyl)oxy)methyl)-6-hydroxy-5,8a-dimethyloctahydro-1H-spiro[naphthalene-2,2'-oxiran]-1-yl)ethylidene)-4-hydroxydihydrofuran-2(3H)-one
InChi Key
FZWGASFAISTFMO-LAOZKMBUSA-N
InChi Code
InChI=1S/C36H48O6Si/c1-33(2,3)43(25-12-8-6-9-13-25,26-14-10-7-11-15-26)42-23-35(5)29-18-21-36(24-41-36)30(34(29,4)20-19-31(35)38)17-16-27-28(37)22-40-32(27)39/h6-16,28-31,37-38H,17-24H2,1-5H3/b27-16+/t28-,29?,30+,31-,34-,35+,36-/m1/s1
SMILES Code
CC(C)(C)[Si](C1=CC=CC=C1)(OC[C@@]2(C)C(CC[C@@]3(CO3)[C@H]4C/C=C5[C@H](O)COC\5=O)[C@@]4(C)CC[C@H]2O)C6=CC=CC=C6
Appearance
Solid powder
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 604.86 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.

Recalculate based on batch purity %
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: Mitra Ghosh T, Kansom T, Mazumder S, Davis J, Alnaim AS, Jasper SL, Zhang C, Bird A, Opanasopit P, Mitra AK, Arnold RD. The Andrographolide Analogue 3A.1 Synergizes with Taxane Derivatives in Aggressive Metastatic Prostate Cancers by Upregulation of Heat Shock Proteins and Downregulation of MAT2A-Mediated Cell Migration and Invasion. J Pharmacol Exp Ther. 2022 Mar;380(3):180-201. doi: 10.1124/jpet.121.000898. Epub 2021 Dec 23. PMID: 34949650. 2: Kansom T, Sajomsang W, Saeeng R, Charoensuksai P, Opanasopit P, Tonglairoum P. Apoptosis Induction and Antimigratory Activity of Andrographolide Analog (3A.1)-Incorporated Self-Assembled Nanoparticles in Cancer Cells. AAPS PharmSciTech. 2018 Oct;19(7):3123-3133. doi: 10.1208/s12249-018-1139-4. Epub 2018 Aug 16. PMID: 30117042. 3: Reabroi S, Chairoungdua A, Saeeng R, Kasemsuk T, Saengsawang W, Zhu W, Piyachaturawat P. A silyl andrographolide analogue suppresses Wnt/β-catenin signaling pathway in colon cancer. Biomed Pharmacother. 2018 May;101:414-421. doi: 10.1016/j.biopha.2018.02.119. Epub 2018 Mar 22. PMID: 29501763. 4: Nateewattana J, Dutta S, Reabroi S, Saeeng R, Kasemsook S, Chairoungdua A, Weerachayaphorn J, Wongkham S, Piyachaturawat P. Induction of apoptosis in cholangiocarcinoma by an andrographolide analogue is mediated through topoisomerase II alpha inhibition. Eur J Pharmacol. 2014 Jan 15;723:148-55. doi: 10.1016/j.ejphar.2013.12.002. Epub 2013 Dec 17. PMID: 24360936. 5: Nateewattana J, Saeeng R, Kasemsook S, Suksen K, Dutta S, Jariyawat S, Chairoungdua A, Suksamrarn A, Piyachaturawat P. Inhibition of topoisomerase II α activity and induction of apoptosis in mammalian cells by semi-synthetic andrographolide analogues. Invest New Drugs. 2013 Apr;31(2):320-32. doi: 10.1007/s10637-012-9868-9. Epub 2012 Aug 17. PMID: 22899371.