Deguelin
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MedKoo CAT#: 406335

CAS#: 522-17-8

Description: Deguelin is a naturally occurring rotenoid, is known to be an Akt inhibitor and to have an anti-tumor effect on several cancers. Deguelin displays anti-cancer activity by inhibiting the growth of pre-cancerous and cancerous cells - particularly for lung cancer. So far the compound has shown no toxic effects on normal cells. However, high doses of deguelin are suspected of having negative effects on the heart, lungs and nerves. The molecular mechanisms include the induction of apoptosis, mediatated through AKT/PKB signaling pathways in malignant and premaligant human bronchial epithelia (HBE) cells, with only minimal effects on normal HBE cells. Deguelin inhibits AKT by both Phosphoinositol-3-phosphate kinase (PI3K)-dependent and PI3K-independent pathways. (http://en.wikipedia.org/wiki/Deguelin).


Chemical Structure

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Deguelin
CAS# 522-17-8

Theoretical Analysis

MedKoo Cat#: 406335
Name: Deguelin
CAS#: 522-17-8
Chemical Formula: C23H22O6
Exact Mass: 394.14164
Molecular Weight: 394.41718
Elemental Analysis: C, 70.04; H, 5.62; O, 24.34

Size Price Shipping out time Quantity
10mg USD 285 2 Weeks
25mg USD 425 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2021-02-26. Prices are subject to change without notice.

Deguelin, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.

Synonym: Deguelin

IUPAC/Chemical Name: (7aS,13aS)-9,10-dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-pyrano[2,3-c:6,5-f']dichromen-7(7aH)-one.

InChi Key: ORDAZKGHSNRHTD-UXHICEINSA-N

InChi Code: InChI=1S/C23H22O6/c1-23(2)8-7-12-15(29-23)6-5-13-21(24)20-14-9-17(25-3)18(26-4)10-16(14)27-11-19(20)28-22(12)13/h5-10,19-20H,11H2,1-4H3/t19-,20+/m1/s1

SMILES Code: O=C1[C@]2([H])[C@](COC3=CC(OC)=C(OC)C=C32)([H])OC4=C5C=CC(C)(C)OC5=CC=C14

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, 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

Handling Instructions:

Preparing Stock Solutions

The following data is based on the product molecular weight 394.41718 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.

Select a batch to recalculate based on the batch molecular weight:
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

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1: Farmer RL, Scheidt KA. A Concise Enantioselective Synthesis and Cytotoxic Evaluation of the Anticancer Rotenoid Deguelin Enabled by a Tandem Knoevenagel/Conjugate Addition/Decarboxylation Sequence. Chem Sci. 2013 Aug;4(8):3304-3309. PubMed PMID: 24101971; PubMed Central PMCID: PMC3790643.

2: Vrana JA, Boggs N, Currie HN, Boyd J. Amelioration of an undesired action of deguelin. Toxicon. 2013 Nov;74:83-91. doi: 10.1016/j.toxicon.2013.07.028. Epub 2013 Aug 7. PubMed PMID: 23933198; PubMed Central PMCID: PMC3790265.

3: Xiong JR, Liu HL. Regulatory effects of deguelin on proliferation and cell cycle of Raji cells. J Huazhong Univ Sci Technolog Med Sci. 2013 Aug;33(4):491-5. doi: 10.1007/s11596-013-1147-2. Epub 2013 Aug 1. PubMed PMID: 23904366.

4: Chen HB, Hu XH, Jiang KH, Zhu SL, Zhao CX, Yuan W, Lan Y, Chen S, Yuan HG, Song XF, Wang YL. [Inhibitory effect of Akt inhibitor deguelin on the growth of PC-3 prostate cancer cells]. Zhonghua Nan Ke Xue. 2013 Jun;19(6):501-5. Chinese. PubMed PMID: 23862226.

5: Mehta R, Katta H, Alimirah F, Patel R, Murillo G, Peng X, Muzzio M, Mehta RG. Deguelin action involves c-Met and EGFR signaling pathways in triple negative breast cancer cells. PLoS One. 2013 Jun 10;8(6):e65113. doi: 10.1371/journal.pone.0065113. Print 2013. PubMed PMID: 23762292; PubMed Central PMCID: PMC3677900.

6: Mehta RR, Katta H, Kalra A, Patel R, Gupta A, Alimirah F, Murillo G, Peng X, Unni A, Muzzio M, Mehta RG. Efficacy and mechanism of action of Deguelin in suppressing metastasis of 4T1 cells. Clin Exp Metastasis. 2013 May 5. [Epub ahead of print] PubMed PMID: 23645347; PubMed Central PMCID: PMC3796171.

7: Yang YL, Ji C, Bi ZG, Lu CC, Wang R, Gu B, Cheng L. Deguelin induces both apoptosis and autophagy in cultured head and neck squamous cell carcinoma cells. PLoS One. 2013;8(1):e54736. doi: 10.1371/journal.pone.0054736. Epub 2013 Jan 23. PubMed PMID: 23372762; PubMed Central PMCID: PMC3553079.

8: Suh YA, Kim JH, Sung MA, Boo HJ, Yun HJ, Lee SH, Lee HJ, Min HY, Suh YG, Kim KW, Lee HY. A novel antitumor activity of deguelin targeting the insulin-like growth factor (IGF) receptor pathway via up-regulation of IGF-binding protein-3 expression in breast cancer. Cancer Lett. 2013 May 10;332(1):102-9. doi: 10.1016/j.canlet.2013.01.022. Epub 2013 Jan 21. Erratum in: Cancer Lett. 2013 Sep 28;338(2):328. PubMed PMID: 23348700; PubMed Central PMCID: PMC3638119.

9: Li Z, Wu J, Wu C, Jiang J, Zheng X, Xu B, Li M. Deguelin, a natural rotenoid, inhibits mouse myeloma cell growth in vitro via induction of apoptosis. Oncol Lett. 2012 Oct;4(4):677-681. Epub 2012 Jul 6. PubMed PMID: 23226790; PubMed Central PMCID: PMC3506627.

10: Chang DJ, An H, Kim KS, Kim HH, Jung J, Lee JM, Kim NJ, Han YT, Yun H, Lee S, Lee G, Lee S, Lee JS, Cha JH, Park JH, Park JW, Lee SC, Kim SG, Kim JH, Lee HY, Kim KW, Suh YG. Design, synthesis, and biological evaluation of novel deguelin-based heat shock protein 90 (HSP90) inhibitors targeting proliferation and angiogenesis. J Med Chem. 2012 Dec 27;55(24):10863-84. doi: 10.1021/jm301488q. Epub 2012 Dec 7. PubMed PMID: 23186287.



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