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
Instruction

Theoretical Analysis

MedKoo Cat#: 406335
Name: Deguelin
CAS#: 522-17-8
Chemical Formula: C23H22O6
Exact Mass: 394.14
Molecular Weight: 394.417
Elemental Analysis: C, 70.04; H, 5.62; O, 24.34

Price and Availability

Size Price Availability Quantity
10mg USD 285
25mg USD 425
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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

More Info:         

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 394.42 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Tuli HS, Mittal S, Loka M, Aggarwal V, Aggarwal D, Masurkar A, Kaur G, Varol M, Sak K, Kumar M, Sethi G, Bishayee A. Deguelin targets multiple oncogenic signaling pathways to combat human malignancies. Pharmacol Res. 2021 Apr;166:105487. doi: 10.1016/j.phrs.2021.105487. Epub 2021 Feb 11. PMID: 33581287.


2: Boyd J, Han A. Deguelin and Its Role in Chronic Diseases. Adv Exp Med Biol. 2016;929:363-375. doi: 10.1007/978-3-319-41342-6_16. PMID: 27771933.


3: Varughese RS, Lam WS, Marican AABH, Viganeshwari SH, Bhave AS, Syn NL, Wang J, Wong AL, Kumar AP, Lobie PE, Lee SC, Sethi G, Goh BC, Wang L. Biopharmacological considerations for accelerating drug development of deguelin, a rotenoid with potent chemotherapeutic and chemopreventive potential. Cancer. 2019 Jun 1;125(11):1789-1798. doi: 10.1002/cncr.32069. Epub 2019 Apr 1. PMID: 30933320.


4: Wang Y, Ma W, Zheng W. Deguelin, a novel anti-tumorigenic agent targeting apoptosis, cell cycle arrest and anti-angiogenesis for cancer chemoprevention. Mol Clin Oncol. 2013 Mar;1(2):215-219. doi: 10.3892/mco.2012.36. Epub 2012 Oct 18. PMID: 24649149; PMCID: PMC3956259.


5: Lin ZY, Yun QZ, Wu L, Zhang TW, Yao TZ. Pharmacological basis and new insights of deguelin concerning its anticancer effects. Pharmacol Res. 2021 Dec;174:105935. doi: 10.1016/j.phrs.2021.105935. Epub 2021 Oct 10. PMID: 34644595.


6: Lu G, Yao Y, Zhang X, Cui D, Zhou J. Deguelin Attenuates Non-Small-Cell Lung Cancer Cell Metastasis by Upregulating PTEN/KLF4/EMT Signaling Pathway. Dis Markers. 2022 May 21;2022:4090346. doi: 10.1155/2022/4090346. PMID: 35637651; PMCID: PMC9148257.


7: Ranieri R, Pianigiani G, Sciabolacci S, Perriello VM, Marra A, Cardinali V, Pierangeli S, Milano F, Gionfriddo I, Brunetti L, Martelli MP, Falini B. Current status and future perspectives in targeted therapy of NPM1-mutated AML. Leukemia. 2022 Oct;36(10):2351-2367. doi: 10.1038/s41375-022-01666-2. Epub 2022 Aug 25. PMID: 36008542; PMCID: PMC9522592.


8: Liao W, Liu X, Yang Q, Liu H, Liang B, Jiang J, Huang J, Ning C, Zang N, Zhou B, Liao Y, Chen J, Tian L, Ho W, Abdullah AS, Kong L, Liang H, Chen H, Ye L. Deguelin inhibits HCV replication through suppressing cellular autophagy via down regulation of Beclin1 expression in human hepatoma cells. Antiviral Res. 2020 Feb;174:104704. doi: 10.1016/j.antiviral.2020.104704. Epub 2020 Jan 7. PMID: 31917237.


9: Li M, Yu X, Li W, Liu T, Deng G, Liu W, Liu H, Gao F. Deguelin suppresses angiogenesis in human hepatocellular carcinoma by targeting HGF-c-Met pathway. Oncotarget. 2017 Oct 26;9(1):152-166. doi: 10.18632/oncotarget.22077. PMID: 29416603; PMCID: PMC5787453.


10: Chen L, Jiang K, Chen H, Tang Y, Zhou X, Tan Y, Yuan Y, Xiao Q, Ding K. Deguelin induces apoptosis in colorectal cancer cells by activating the p38 MAPK pathway. Cancer Manag Res. 2018 Dec 20;11:95-105. doi: 10.2147/CMAR.S169476. PMID: 30588113; PMCID: PMC6305136.


11: Li W, Gao F, Ma X, Wang R, Dong X, Wang W. Deguelin inhibits non-small cell lung cancer via down-regulating Hexokinases II-mediated glycolysis. Oncotarget. 2017 May 16;8(20):32586-32599. doi: 10.18632/oncotarget.15937. PMID: 28427230; PMCID: PMC5464811.


12: Preston S, Korhonen PK, Mouchiroud L, Cornaglia M, McGee SL, Young ND, Davis RA, Crawford S, Nowell C, Ansell BRE, Fisher GM, Andrews KT, Chang BCH, Gijs MAM, Sternberg PW, Auwerx J, Baell J, Hofmann A, Jabbar A, Gasser RB. Deguelin exerts potent nematocidal activity via the mitochondrial respiratory chain. FASEB J. 2017 Oct;31(10):4515-4532. doi: 10.1096/fj.201700288R. Epub 2017 Jul 7. PMID: 28687609.


13: Bao Z, Zhang P, Yao Y, Lu G, Tong Z, Yan B, Tu L, Yang G, Zhou J. Deguelin Attenuates Allergic Airway Inflammation via Inhibition of NF-κb Pathway in Mice. Int J Biol Sci. 2017 Apr 8;13(4):492-504. doi: 10.7150/ijbs.17238. PMID: 28529457; PMCID: PMC5436569.


14: Zhang P, Zhang M, Mellich TA, Pearson BJ, Chen J, Zhang Z. Variation in Rotenone and Deguelin Contents among Strains across Four Tephrosia Species and Their Activities against Aphids and Whiteflies. Toxins (Basel). 2022 May 13;14(5):339. doi: 10.3390/toxins14050339. PMID: 35622585; PMCID: PMC9146100.


15: Boreddy SR, Srivastava SK. Deguelin suppresses pancreatic tumor growth and metastasis by inhibiting epithelial-to-mesenchymal transition in an orthotopic model. Oncogene. 2013 Aug 22;32(34):3980-91. doi: 10.1038/onc.2012.413. Epub 2012 Sep 17. PMID: 22986522; PMCID: PMC3530646.


16: Lee H, Lee JH, Jung KH, Hong SS. Deguelin promotes apoptosis and inhibits angiogenesis of gastric cancer. Oncol Rep. 2010 Oct;24(4):957-63. doi: 10.3892/or.2010.957. PMID: 20811676.


17: Gao F, Yu X, Li M, Zhou L, Liu W, Li W, Liu H. Deguelin suppresses non-small cell lung cancer by inhibiting EGFR signaling and promoting GSK3β/FBW7-mediated Mcl-1 destabilization. Cell Death Dis. 2020 Feb 21;11(2):143. doi: 10.1038/s41419-020-2344-0. PMID: 32081857; PMCID: PMC7035355.


18: Li W, Yu X, Ma X, Xie L, Xia Z, Liu L, Yu X, Wang J, Zhou H, Zhou X, Yang Y, Liu H. Deguelin attenuates non-small cell lung cancer cell metastasis through inhibiting the CtsZ/FAK signaling pathway. Cell Signal. 2018 Oct;50:131-141. doi: 10.1016/j.cellsig.2018.07.001. Epub 2018 Jul 7. PMID: 30018008.


19: Wang A, Wang W, Chen Y, Ma F, Wei X, Bi Y. Deguelin induces PUMA-mediated apoptosis and promotes sensitivity of lung cancer cells (LCCs) to doxorubicin (Dox). Mol Cell Biochem. 2018 May;442(1-2):177-186. doi: 10.1007/s11010-017-3202-y. Epub 2017 Oct 13. PMID: 29030732.


20: Zhao D, Han W, Liu X, Cui D, Chen Y. Deguelin inhibits epithelial-to- mesenchymal transition and metastasis of human non-small cell lung cancer cells by regulating NIMA-related kinase 2. Thorac Cancer. 2017 Jul;8(4):320-327. doi: 10.1111/1759-7714.12444. Epub 2017 May 16. PMID: 28509438; PMCID: PMC5494456.