Cytochalasin E

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MedKoo CAT#: 565438

CAS#: 36011-19-5

Description: Cytochalasin E is a natural autophagy inhibitor which enhances chemotherapy-induced cell death. Cytochalasin E is an epoxide-containing analog of Cytochalasin B which potently and selectively inhibits the growth of endothelial cells, thereby impairing angiogenesis and tumor growth. Unlike Cytochalasin A and Cytochalasin B, it does not inhibit glucose transport.

Chemical Structure

Cytochalasin E
CAS# 36011-19-5

Theoretical Analysis

MedKoo Cat#: 565438
Name: Cytochalasin E
CAS#: 36011-19-5
Chemical Formula: C30H37NO7
Exact Mass: 523.257
Molecular Weight: 523.63
Elemental Analysis: C, 68.81; H, 7.12; N, 2.68; O, 21.39

Price and Availability

Size Price Availability Quantity
1.0mg USD 225.0 2 Weeks
5.0mg USD 470.0 2 Weeks
10.0mg USD 788.0 2 Weeks
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Synonym: NSC-175151; NSC 175151; NSC175151; Cytochalasin E

IUPAC/Chemical Name: (1E,4S,6R,7E,14S,14aS,15S,15aR,16aS,16bS)-14-benzyl-6-hydroxy-4,6,15,15a-tetramethyl-3,13,14,14a,15,15a,16a,16b-octahydro-[1,3]dioxacyclotridecino[4,5-d]oxireno[2,3-f]isoindole-5,10,12(4H,6H)-trione


InChi Code: InChI=1S/C28H33NO7/c1-16-9-8-12-19-23-27(4,35-23)17(2)21-20(15-18-10-6-5-7-11-18)29-24(31)28(19,21)36-25(32)34-14-13-26(3,33)22(16)30/h5-8,10-14,16-17,19-21,23,33H,9,15H2,1-4H3,(H,29,31)/b12-8+,14-13+/t16-,17-,19-,20-,21-,23-,26+,27+,28?/m0/s1

SMILES Code: O=C(O/C=C/[C@@](O)(C1=O)C)OC23[C@@]([H])(/C=C/C[C@@]1(C)[H])[C@H]4[C@](O4)([C@H]([C@]2([C@@H](NC3=O)CC5=CC=CC=C5)[H])C)C

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: >3 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 523.63 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

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1: Han WB, Zhai YJ, Gao Y, Zhou HY, Xiao J, Pescitelli G, Gao JM. Cytochalasins and an Abietane-Type Diterpenoid with Allelopathic Activities from the Endophytic Fungus Xylaria Species. J Agric Food Chem. 2019 Apr 3;67(13):3643-3650. doi: 10.1021/acs.jafc.9b00273. Epub 2019 Mar 22. PubMed PMID: 30875204.

2: Mendes G, Baltazar LM, Souza DG, Sá NP, Rosa LH, Rosa CA, Souza-Fagundes EM, Ramos JP, Alves-Silva J, Cota BB, Johann S. Effects of cytochalasin E on Paracoccidioides brasiliensis. J Appl Microbiol. 2018 Nov;125(5):1296-1307. doi: 10.1111/jam.14053. Epub 2018 Sep 19. PubMed PMID: 30053334.

3: Takanezawa Y, Nakamura R, Kojima Y, Sone Y, Uraguchi S, Kiyono M. Cytochalasin E increased the sensitivity of human lung cancer A549 cells to bortezomib via inhibition of autophagy. Biochem Biophys Res Commun. 2018 Apr 6;498(3):603-608. doi: 10.1016/j.bbrc.2018.03.029. Epub 2018 Mar 9. PubMed PMID: 29524420.

4: Delebassée S, Mambu L, Pinault E, Champavier Y, Liagre B, Millot M. Cytochalasin E in the lichen Pleurosticta acetabulum. Anti-proliferative activity against human HT-29 colorectal cancer cells and quantitative variability. Fitoterapia. 2017 Sep;121:146-151. doi: 10.1016/j.fitote.2017.07.006. Epub 2017 Jul 10. PubMed PMID: 28705509.

5: Reifenberger MS, Yu L, Bao HF, Duke BJ, Liu BC, Ma HP, Alli AA, Eaton DC, Alli AA. Cytochalasin E alters the cytoskeleton and decreases ENaC activity in Xenopus 2F3 cells. Am J Physiol Renal Physiol. 2014 Jul 1;307(1):F86-95. doi: 10.1152/ajprenal.00251.2013. Epub 2014 May 14. PubMed PMID: 24829507; PubMed Central PMCID: PMC4080154.

6: Xiao L, Liu H, Wu N, Liu M, Wei J, Zhang Y, Lin X. Characterization of the high cytochalasin E and rosellichalasin producing-Aspergillus sp. nov. F1 isolated from marine solar saltern in China. World J Microbiol Biotechnol. 2013 Jan;29(1):11-7. doi: 10.1007/s11274-012-1152-9. Epub 2012 Aug 22. PubMed PMID: 22910972.

7: Ikewaki N, Yamada A, Inoko H. Depolymerization of actin filament by cytochalasin E induces interleukin-8 production and up-regulates CD54 in the HeLa epithelial cell line. Microbiol Immunol. 2003;47(10):775-83. PubMed PMID: 14605444.

8: Hansson KM, Tengvall P, Lundström I, Rånby M, Lindahl TL. Comparative studies with surface plasmon resonance and free oscillation rheometry on the inhibition of platelets with cytochalasin E and monoclonal antibodies towards GPIIb/IIIa. Biosens Bioelectron. 2002 Sep;17(9):761-71. PubMed PMID: 12191924.

9: Udagawa T, Yuan J, Panigrahy D, Chang YH, Shah J, D'Amato RJ. Cytochalasin E, an epoxide containing Aspergillus-derived fungal metabolite, inhibits angiogenesis and tumor growth. J Pharmacol Exp Ther. 2000 Aug;294(2):421-7. PubMed PMID: 10900214.

10: Díez-Sampedro A, Urdaneta E, Lostao MP, Barber A. Galactose transport inhibition by cytochalasin E in rat intestine in vitro. Can J Physiol Pharmacol. 1999 Feb;77(2):96-101. PubMed PMID: 10535699.

11: Gan Y, Au JL, Lu J, Wientjes MG. Antiproliferative and cytotoxic effects of geldanamycin, cytochalasin E, suramin and thiacetazone in human prostate xenograft tumor histocultures. Pharm Res. 1998 Nov;15(11):1760-6. PubMed PMID: 9834000.

12: Lopez-Diaz TM, Flannigan B. Mycotoxins of Aspergillus clavatus: Toxicity of Cytochalasin E, Patulin, and Extracts of Contaminated Barley Malt. J Food Prot. 1997 Nov;60(11):1381-1385. doi: 10.4315/0362-028X-60.11.1381. PubMed PMID: 31207790.

13: Lopez-Diaz TM, Flannigan B. Production of patulin and cytochalasin E by Aspergillus clavatus during malting of barley and wheat. Int J Food Microbiol. 1997 Apr 1;35(2):129-36. PubMed PMID: 9105920.

14: Tsukamoto M, Yamamoto M, Tanabe S, Kamada T. Cytochalasin-E-Resistant Mutants of Coprinus cinereus: Isolation and Genetic, Biochemical, and Cytological Analyses. Fungal Genet Biol. 1996 Mar;20(1):52-8. PubMed PMID: 8812286.

15: Kajimoto T, Imamura Y, Yamashita M, Takahashi K, Shibata M, Nohara T. Nuclear magnetic resonance studies of cytochalasin E and its decomposition product. Chem Pharm Bull (Tokyo). 1989 Aug;37(8):2212-3. PubMed PMID: 2598324.

16: Cox AC. Cytochalasin E enhances the protein kinase C-dependent process of secretion. Biochem Biophys Res Commun. 1988 Jan 29;150(2):745-51. PubMed PMID: 3342046.

17: Glinsukon T, Suvitayawat W, Sahaphong S, Piyachaturawat P. Effects of cytochalasin E on H+ and volume secretion in gastric fistula rats. Toxicol Lett. 1987 Mar;36(1):95-103. PubMed PMID: 3564075.

18: Piyachaturawat P, Suvitayawat W, Glinsukon T. Stimulation of gastric mucus and protein secretion by cytochalasin E in rats. Cell Biol Int Rep. 1986 Sep;10(9):707-16. PubMed PMID: 3757065.

19: Sriurairatana S, Glinsukon T. Ultrastructural changes in mouse dermal capillaries induced by cytochalasin E. Res Commun Chem Pathol Pharmacol. 1984 Sep;45(3):379-87. PubMed PMID: 6505378.

20: Mookerjee BK, Jung CY. Effects of cytochalasins on lymphocytes: some distinctive features of cytochalasin-E. J Immunopharmacol. 1984;6(3):185-203. PubMed PMID: 6491312.

21: Glinsukon T, Kongsuktrakoon B, Toskulkao C, Sophasan S. Cytochalasin E: inhibition of intestinal glucose absorption in the mouse. Toxicol Lett. 1983 Mar;15(4):341-8. PubMed PMID: 6836602.