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MedKoo Cat#: 565130 | Name: Ascofuranone

Description:

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

Ascofuranone is an inhibitor of the ubiquinol oxidase activity of Trypanosoma brucei mitochondrial alternative oxidase (TAO), as well as an inhibitor of HsDHODH.

Chemical Structure

Ascofuranone
Ascofuranone
CAS#38462-04-3

Theoretical Analysis

MedKoo Cat#: 565130

Name: Ascofuranone

CAS#: 38462-04-3

Chemical Formula: C23H29ClO5

Exact Mass: 420.1704

Molecular Weight: 420.93

Elemental Analysis: C, 65.63; H, 6.94; Cl, 8.42; O, 19.00

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Synonym
Ascofuranone; Ascofuranon; (-)-ascofuranone; (S)-ascofuranone
IUPAC/Chemical Name
5-Chloro-3-[(2E,6E)-7-[(2S)-5,5-dimethyl-4-oxooxolan-2-yl]-3-methylocta-2,6-dienyl]-2,4-dihydroxy-6-methylbenzaldehyde
InChi Key
VGYPZLGWVQQOST-JUERRSSISA-N
InChi Code
InChI=1S/C23H29ClO5/c1-13(7-6-8-14(2)18-11-19(26)23(4,5)29-18)9-10-16-21(27)17(12-25)15(3)20(24)22(16)28/h8-9,12,18,27-28H,6-7,10-11H2,1-5H3/b13-9+,14-8+/t18-/m0/s1
SMILES Code
O=CC1=C(C)C(Cl)=C(O)C(C/C=C(C)/CC/C=C([C@H](C2)OC(C)(C)C2=O)\C)=C1O
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 420.93 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: Araki Y, Shinohara Y, Hara S, Sato A, Sakaue R, Gomi K, Kita K, Ito K. Heterologous production of ascofuranone and ilicicolin A in Aspergillus sojae. J Gen Appl Microbiol. 2022 Jun 20;68(1):10-16. doi: 10.2323/jgam.2021.08.001. Epub 2022 Apr 13. PMID: 35418536. 2: Kim HW, Jeong YJ, Hwang SK, Park YY, Choi YH, Kim CH, Magae J, Chang YC. Ascofuranone inhibits epidermal growth factor-induced cell migration by blocking epithelial-mesenchymal transition in lung cancer cells. Eur J Pharmacol. 2020 Aug 5;880:173199. doi: 10.1016/j.ejphar.2020.173199. Epub 2020 May 18. PMID: 32439259. 3: Jeong YJ, Hwang SK, Magae J, Chang YC. Ascofuranone suppresses invasion and F-actin cytoskeleton organization in cancer cells by inhibiting the mTOR complex 1 signaling pathway. Cell Oncol (Dordr). 2020 Oct;43(5):793-805. doi: 10.1007/s13402-020-00520-w. Epub 2020 Jun 2. PMID: 32488849. 4: Jeong YJ, Cho HJ, Magae J, Lee IK, Park KG, Chang YC. Ascofuranone suppresses EGF-induced HIF-1α protein synthesis by inhibition of the Akt/mTOR/p70S6K pathway in MDA-MB-231 breast cancer cells. Toxicol Appl Pharmacol. 2013 Dec 15;273(3):542-50. doi: 10.1016/j.taap.2013.09.027. Epub 2013 Oct 3. PMID: 24096035. 5: Hwang SL, Chang HW, Lee IK, Yang BK, Magae J, Chang YC. Ascofuranone prevents ER stress-induced insulin resistance via activation of AMP-activated protein kinase in L6 myotube cells. Biochem Biophys Res Commun. 2010 Jun 11;396(4):967-72. doi: 10.1016/j.bbrc.2010.05.034. Epub 2010 May 9. PMID: 20460103. 6: Chang YC, Cho HJ. Ascofuranone stimulates expression of adiponectin and peroxisome proliferator activated receptor through the modulation of mitogen activated protein kinase family members in 3T3-L1, murine pre-adipocyte cell line. Biochem Biophys Res Commun. 2012 Jun 8;422(3):423-8. doi: 10.1016/j.bbrc.2012.05.008. Epub 2012 May 9. PMID: 22580003. 7: Cho HJ, Kang JH, Kwak JY, Lee TS, Lee IS, Park NG, Nakajima H, Magae J, Chang YC. Ascofuranone suppresses PMA-mediated matrix metalloproteinase-9 gene activation through the Ras/Raf/MEK/ERK- and Ap1-dependent mechanisms. Carcinogenesis. 2007 May;28(5):1104-10. doi: 10.1093/carcin/bgl217. Epub 2006 Nov 17. PMID: 17114644. 8: Yabu Y, Yoshida A, Suzuki T, Nihei C, Kawai K, Minagawa N, Hosokawa T, Nagai K, Kita K, Ohta N. The efficacy of ascofuranone in a consecutive treatment on Trypanosoma brucei brucei in mice. Parasitol Int. 2003 Jun;52(2):155-64. doi: 10.1016/s1383-5769(03)00012-6. PMID: 12798927. 9: Magae J, Hayasaki J, Matsuda Y, Hotta M, Hosokawa T, Suzuki S, Nagai K, Ando K, Tamura G. Antitumor and antimetastatic activity of an antibiotic, ascofuranone, and activation of phagocytes. J Antibiot (Tokyo). 1988 Jul;41(7):959-65. doi: 10.7164/antibiotics.41.959. PMID: 3417568. 10: Araki Y, Awakawa T, Matsuzaki M, Cho R, Matsuda Y, Hoshino S, Shinohara Y, Yamamoto M, Kido Y, Inaoka DK, Nagamune K, Ito K, Abe I, Kita K. Complete biosynthetic pathways of ascofuranone and ascochlorin in Acremonium egyptiacum. Proc Natl Acad Sci U S A. 2019 Apr 23;116(17):8269-8274. doi: 10.1073/pnas.1819254116. Epub 2019 Apr 5. PMID: 30952781; PMCID: PMC6486709. 11: Park JY, Chung TW, Jeong YJ, Kwak CH, Ha SH, Kwon KM, Abekura F, Cho SH, Lee YC, Ha KT, Magae J, Chang YC, Kim CH. Ascofuranone inhibits lipopolysaccharide- induced inflammatory response via NF-kappaB and AP-1, p-ERK, TNF-α, IL-6 and IL-1β in RAW 264.7 macrophages. PLoS One. 2017 Feb 16;12(2):e0171322. doi: 10.1371/journal.pone.0171322. PMID: 28207754; PMCID: PMC5313137. 12: Cardinale V, Alvaro D. Ascofuranone: a possible therapeutic tool for autosomal dominant polycystic kidney disease? Mol Cancer Ther. 2010 Nov;9(11):3100; author reply 3101. doi: 10.1158/1535-7163.MCT-10-0741. Epub 2010 Oct 26. PMID: 20978157. 13: Jeong JH, Kang SS, Park KK, Chang HW, Magae J, Chang YC. p53-independent induction of G1 arrest and p21WAF1/CIP1 expression by ascofuranone, an isoprenoid antibiotic, through downregulation of c-Myc. Mol Cancer Ther. 2010 Jul;9(7):2102-13. doi: 10.1158/1535-7163.MCT-09-1159. Epub 2010 Jun 29. PMID: 20587660. 14: Hijikawa Y, Matsuzaki M, Suzuki S, Inaoka DK, Tatsumi R, Kido Y, Kita K. Re- identification of the ascofuranone-producing fungus Ascochyta viciae as Acremonium sclerotigenum. J Antibiot (Tokyo). 2017 Mar;70(3):304-307. doi: 10.1038/ja.2016.132. Epub 2016 Nov 2. PMID: 27804952. 15: Barra L, Abe I. Chemistry of fungal meroterpenoid cyclases. Nat Prod Rep. 2021 Mar 1;38(3):566-585. doi: 10.1039/d0np00056f. Epub 2020 Oct 1. PMID: 33000846. 16: Saimoto H, Kido Y, Haga Y, Sakamoto K, Kita K. Pharmacophore identification of ascofuranone, potent inhibitor of cyanide-insensitive alternative oxidase of Trypanosoma brucei. J Biochem. 2013 Mar;153(3):267-73. doi: 10.1093/jb/mvs135. Epub 2012 Nov 23. PMID: 23180806. 17: Cho HJ, Kang JH, Kim T, Park KK, Kim CH, Lee IS, Min KS, Magae J, Nakajima H, Bae YS, Chang YC. Suppression of PAI-1 expression through inhibition of the EGFR-mediated signaling cascade in rat kidney fibroblast by ascofuranone. J Cell Biochem. 2009 May 15;107(2):335-44. doi: 10.1002/jcb.22130. PMID: 19306296. 18: Minagawa N, Yabu Y, Kita K, Nagai K, Ohta N, Meguro K, Sakajo S, Yoshimoto A. An antibiotic, ascofuranone, specifically inhibits respiration and in vitro growth of long slender bloodstream forms of Trypanosoma brucei brucei. Mol Biochem Parasitol. 1996 Oct 30;81(2):127-36. doi: 10.1016/0166-6851(96)02665-5. Corrected and republished in: Mol Biochem Parasitol. 1997 Feb;84(2):271-80. PMID: 8898329. 19: Fukai Y, Amino H, Hirawake H, Yabu Y, Ohta N, Minagawa N, Sakajo S, Yoshimoto A, Nagai K, Takamiya S, Kojima S, Kita K. Functional expression of the ascofuranone-sensitive Trypanosoma brucei brucei alternative oxidase in the cytoplasmic membrane of Escherichia coli. Comp Biochem Physiol C Pharmacol Toxicol Endocrinol. 1999 Oct;124(2):141-8. doi: 10.1016/s0742-8413(99)00040-7. PMID: 10622429. 20: Magae J, Hosokawa T, Matsuda Y, Hotta M, Hayasaki J, Nagai K, Ando K, Yamasaki M, Tamura G. Suppression of hypertriglyceridemia of Ehrlich carcinoma- bearing mice by an antibiotic, ascofuranone. Cancer Res. 1987 Jan 1;47(1):96-9. PMID: 3791222.

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Cosalane