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MedKoo Cat#: 406804 | Name: Silvestrol

Description:

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

Silvestrol, a member of flavagline family of natural products from the genus of Aglaia exhibiting anti-cancer activity in vitro and in vivo. Silvestrol induces early autophagy and apoptosis in human melanoma cells. Silvestrol exhibits direct anti-tumor activity while preserving innate and adaptive immunity against EBV-driven lymphoproliferative disease. Silvestrol exhibits significant in vivo and in vitro antileukemic activities and inhibits FLT3 and miR-155 expressions in acute myeloid leukemia.

Chemical Structure

Silvestrol
Silvestrol
CAS#697235-38-4

Theoretical Analysis

MedKoo Cat#: 406804

Name: Silvestrol

CAS#: 697235-38-4

Chemical Formula: C34H38O13

Exact Mass: 654.2312

Molecular Weight: 654.67

Elemental Analysis: C, 62.38; H, 5.85; O, 31.77

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
Silvestrol
IUPAC/Chemical Name
methyl (1R,2R,3S,3aR,8bS)-6-[[(3R,6R)-6-[(1R)-1,2-dihydroxyethyl]-3-methoxy-1,4-dioxan-2-yl]oxy]-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxylate
InChi Key
GVKXFVCXBFGBCD-YKBYZOLHSA-N
InChi Code
InChI=1S/C34H38O13/c1-40-20-12-10-19(11-13-20)34-27(18-8-6-5-7-9-18)26(30(38)42-3)29(37)33(34,39)28-23(41-2)14-21(15-24(28)47-34)45-32-31(43-4)44-17-25(46-32)22(36)16-35/h5-15,22,25-27,29,31-32,35-37,39H,16-17H2,1-4H3/t22-,25-,26-,27-,29-,31-,32?,33+,34+/m1/s1
SMILES Code
O=C([C@H]([C@H]1C2=CC=CC=C2)[C@@H](O)[C@]3(O)[C@@]1(C4=CC=C(OC)C=C4)OC5=C3C(OC)=CC(OC6O[C@@H]([C@H](O)CO)CO[C@H]6OC)=C5)OC
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
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 654.67 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: Daker M, Yeo JT, Bakar N, Abdul Rahman AS, Ahmad M, Yeo TC, Khoo AS. Inhibition of nasopharyngeal carcinoma cell proliferation and synergism of cisplatin with silvestrol and episilvestrol isolated from Aglaia stellatopilosa. Exp Ther Med. 2016 Jun;11(6):2117-2126. Epub 2016 Mar 29. PubMed PMID: 27284293; PubMed Central PMCID: PMC4887938. 2: Chen WL, Pan L, Kinghorn AD, Swanson SM, Burdette JE. Silvestrol induces early autophagy and apoptosis in human melanoma cells. BMC Cancer. 2016 Jan 13;16:17. doi: 10.1186/s12885-015-1988-0. PubMed PMID: 26762417; PubMed Central PMCID: PMC4712514. 3: Patton JT, Lustberg ME, Lozanski G, Garman SL, Towns WH, Drohan CM, Lehman A, Zhang X, Bolon B, Pan L, Kinghorn AD, Grever MR, Lucas DM, Baiocchi RA. The translation inhibitor silvestrol exhibits direct anti-tumor activity while preserving innate and adaptive immunity against EBV-driven lymphoproliferative disease. Oncotarget. 2015 Feb 20;6(5):2693-708. PubMed PMID: 25393910; PubMed Central PMCID: PMC4413611. 4: Pan L, Woodard JL, Lucas DM, Fuchs JR, Kinghorn AD. Rocaglamide, silvestrol and structurally related bioactive compounds from Aglaia species. Nat Prod Rep. 2014 Jul;31(7):924-39. doi: 10.1039/c4np00006d. Epub 2014 May 2. Review. PubMed PMID: 24788392; PubMed Central PMCID: PMC4091845. 5: Hawkins BC, Lindqvist LM, Nhu D, Sharp PP, Segal D, Powell AK, Campbell M, Ryan E, Chambers JM, White JM, Rizzacasa MA, Lessene G, Huang DC, Burns CJ. Simplified silvestrol analogues with potent cytotoxic activity. ChemMedChem. 2014 Jul;9(7):1556-66. doi: 10.1002/cmdc.201400024. Epub 2014 Mar 27. PubMed PMID: 24677741. 6: Kogure T, Kinghorn AD, Yan I, Bolon B, Lucas DM, Grever MR, Patel T. Therapeutic potential of the translation inhibitor silvestrol in hepatocellular cancer. PLoS One. 2013 Sep 26;8(9):e76136. doi: 10.1371/journal.pone.0076136. eCollection 2013. PubMed PMID: 24086701; PubMed Central PMCID: PMC3784426. 7: Alachkar H, Santhanam R, Harb JG, Lucas DM, Oaks JJ, Hickey CJ, Pan L, Kinghorn AD, Caligiuri MA, Perrotti D, Byrd JC, Garzon R, Grever MR, Marcucci G. Silvestrol exhibits significant in vivo and in vitro antileukemic activities and inhibits FLT3 and miR-155 expressions in acute myeloid leukemia. J Hematol Oncol. 2013 Mar 16;6:21. doi: 10.1186/1756-8722-6-21. PubMed PMID: 23497456; PubMed Central PMCID: PMC3623627. 8: Liu T, Nair SJ, Lescarbeau A, Belani J, Peluso S, Conley J, Tillotson B, O'Hearn P, Smith S, Slocum K, West K, Helble J, Douglas M, Bahadoor A, Ali J, McGovern K, Fritz C, Palombella VJ, Wylie A, Castro AC, Tremblay MR. Synthetic silvestrol analogues as potent and selective protein synthesis inhibitors. J Med Chem. 2012 Oct 25;55(20):8859-78. doi: 10.1021/jm3011542. Epub 2012 Oct 12. PubMed PMID: 23025805. 9: Alinari L, Prince CJ, Edwards RB, Towns WH, Mani R, Lehman A, Zhang X, Jarjoura D, Pan L, Kinghorn AD, Grever MR, Baiocchi RA, Lucas DM. Dual targeting of the cyclin/Rb/E2F and mitochondrial pathways in mantle cell lymphoma with the translation inhibitor silvestrol. Clin Cancer Res. 2012 Sep 1;18(17):4600-11. doi: 10.1158/1078-0432.CCR-12-0839. Epub 2012 Jul 12. PubMed PMID: 22791882; PubMed Central PMCID: PMC3677230. 10: Gupta SV, Sass EJ, Davis ME, Edwards RB, Lozanski G, Heerema NA, Lehman A, Zhang X, Jarjoura D, Byrd JC, Pan L, Chan KK, Kinghorn AD, Phelps MA, Grever MR, Lucas DM. Resistance to the translation initiation inhibitor silvestrol is mediated by ABCB1/P-glycoprotein overexpression in acute lymphoblastic leukemia cells. AAPS J. 2011 Sep;13(3):357-64. doi: 10.1208/s12248-011-9276-7. Epub 2011 May 4. PubMed PMID: 21538216; PubMed Central PMCID: PMC3160166. 11: Saradhi UV, Gupta SV, Chiu M, Wang J, Ling Y, Liu Z, Newman DJ, Covey JM, Kinghorn AD, Marcucci G, Lucas DM, Grever MR, Phelps MA, Chan KK. Characterization of silvestrol pharmacokinetics in mice using liquid chromatography-tandem mass spectrometry. AAPS J. 2011 Sep;13(3):347-56. doi: 10.1208/s12248-011-9273-x. Epub 2011 Apr 16. PubMed PMID: 21499689; PubMed Central PMCID: PMC3160157. 12: Pan L, Kardono LB, Riswan S, Chai H, Carcache de Blanco EJ, Pannell CM, Soejarto DD, McCloud TG, Newman DJ, Kinghorn AD. Isolation and characterization of minor analogues of silvestrol and other constituents from a large-scale re-collection of Aglaia foveolata. J Nat Prod. 2010 Nov 29;73(11):1873-8. doi: 10.1021/np100503q. Epub 2010 Oct 12. PubMed PMID: 20939540; PubMed Central PMCID: PMC2993763. 13: Cencic R, Carrier M, Galicia-Vázquez G, Bordeleau ME, Sukarieh R, Bourdeau A, Brem B, Teodoro JG, Greger H, Tremblay ML, Porco JA Jr, Pelletier J. Antitumor activity and mechanism of action of the cyclopenta[b]benzofuran, silvestrol. PLoS One. 2009;4(4):e5223. doi: 10.1371/journal.pone.0005223. Epub 2009 Apr 29. PubMed PMID: 19401772; PubMed Central PMCID: PMC2671147. 14: Lucas DM, Edwards RB, Lozanski G, West DA, Shin JD, Vargo MA, Davis ME, Rozewski DM, Johnson AJ, Su BN, Goettl VM, Heerema NA, Lin TS, Lehman A, Zhang X, Jarjoura D, Newman DJ, Byrd JC, Kinghorn AD, Grever MR. The novel plant-derived agent silvestrol has B-cell selective activity in chronic lymphocytic leukemia and acute lymphoblastic leukemia in vitro and in vivo. Blood. 2009 May 7;113(19):4656-66. doi: 10.1182/blood-2008-09-175430. Epub 2009 Feb 3. PubMed PMID: 19190247; PubMed Central PMCID: PMC2680369. 15: Adams TE, El Sous M, Hawkins BC, Hirner S, Holloway G, Khoo ML, Owen DJ, Savage GP, Scammells PJ, Rizzacasa MA. Total synthesis of the potent anticancer Aglaia metabolites (-)-silvestrol and (-)-episilvestrol and the active analogue (-)-4'-desmethoxyepisilvestrol. J Am Chem Soc. 2009 Feb 4;131(4):1607-16. doi: 10.1021/ja808402e. PubMed PMID: 19140688. 16: El Sous M, Khoo ML, Holloway G, Owen D, Scammells PJ, Rizzacasa MA. Total synthesis of (-)-episilvestrol and (-)-silvestrol. Angew Chem Int Ed Engl. 2007;46(41):7835-8. PubMed PMID: 17823902. 17: Gerard B, Cencic R, Pelletier J, Porco JA Jr. Enantioselective synthesis of the complex rocaglate (-)-silvestrol. Angew Chem Int Ed Engl. 2007;46(41):7831-4. PubMed PMID: 17806093. 18: Kim S, Hwang BY, Su BN, Chai H, Mi Q, Kinghorn AD, Wild R, Swanson SM. Silvestrol, a potential anticancer rocaglate derivative from Aglaia foveolata, induces apoptosis in LNCaP cells through the mitochondrial/apoptosome pathway without activation of executioner caspase-3 or -7. Anticancer Res. 2007 Jul-Aug;27(4B):2175-83. PubMed PMID: 17695501; PubMed Central PMCID: PMC2787233. 19: Mi Q, Kim S, Hwang BY, Su BN, Chai H, Arbieva ZH, Kinghorn AD, Swanson SM. Silvestrol regulates G2/M checkpoint genes independent of p53 activity. Anticancer Res. 2006 Sep-Oct;26(5A):3349-56. PubMed PMID: 17094452. 20: Hwang BY, Su BN, Chai H, Mi Q, Kardono LB, Afriastini JJ, Riswan S, Santarsiero BD, Mesecar AD, Wild R, Fairchild CR, Vite GD, Rose WC, Farnsworth NR, Cordell GA, Pezzuto JM, Swanson SM, Kinghorn AD. Silvestrol and episilvestrol, potential anticancer rocaglate derivatives from Aglaia silvestris. J Org Chem. 2004 May 14;69(10):3350-8. Erratum in: J Org Chem. 2004 Sep 3;69(18):6156. PubMed PMID: 15132542.