Cytochalasin E
new
featured

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

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.


Price and Availability

Size
Price

1mg
USD 225
Size
Price

5mg
USD 470
Size
Price

10mg
USD 788

Cytochalasin E, 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.


Chemical Structure

img

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


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 Key: LAJXCUNOQSHRJO-KGDUIROVSA-N

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


Technical Data

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).

Harmonized System Code:
2934.99.90.01


References

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.