Ipomoeassin F (Synonyms: Ipom-F)

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Ipomoeassin F is a potent and selective endoplasmic reticulum (ER) protein-translocation inhibitor by targeting the pore-forming subunit of the Sec61 complex (Sec61α) at the ER membrane. Ipomoeassin F selectively inhibits the ER membrane translocation of SARS-CoV-2 proteins. Ipomoeassin F block the ER translocation of secretory proteins and type I transmembrane proteins (TMPs), but not type III TMPs.

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Ipomoeassin F Chemical Structure

CAS No. : 915392-44-8

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References
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Description

Cellular Effect

Cell Line	Type	Value	Description	References
A2780	IC₅₀	36 nM Compound: Ipomoeassin F	Cytotoxicity against human A2780 cells after 72 hrs Cytotoxicity against human A2780 cells after 72 hrs	[PMID: 29291442]
HeLa	IC₅₀	16.4 nM Compound: 188	Cytotoxicity against human HeLa cells assessed as cell growth inhibition incubated for 3 days by MTT assay Cytotoxicity against human HeLa cells assessed as cell growth inhibition incubated for 3 days by MTT assay	[PMID: 29126728]
HT-29	IC₅₀	4.2 nM Compound: Ipomoeassin F	Cytotoxicity against human HT-29 cells after 72 hrs Cytotoxicity against human HT-29 cells after 72 hrs	[PMID: 29291442]
Jurkat	IC₅₀	6.1 nM Compound: 188	Cytotoxicity against human Jurkat cells assessed as cell growth inhibition incubated for 3 days by MTT assay Cytotoxicity against human Jurkat cells assessed as cell growth inhibition incubated for 3 days by MTT assay	[PMID: 29126728]
L929	IC₅₀	7.4 nM Compound: Ipomoeassin F	Cytotoxicity against mouse L929 cells after 72 hrs Cytotoxicity against mouse L929 cells after 72 hrs	[PMID: 29291442]
MCF-10A	IC₅₀	5.1 nM Compound: Ipomoeassin F	Cytotoxicity against human MCF10A cells assessed as reduction in cell viability after 72 hrs by Alamar Blue assay Cytotoxicity against human MCF10A cells assessed as reduction in cell viability after 72 hrs by Alamar Blue assay	[PMID: 29291442]
MCF-10A	IC₅₀	5.4 nM Compound: 188	Cytotoxicity against human MCF-10A cells assessed as cell growth inhibition incubated for 3 days by MTT assay Cytotoxicity against human MCF-10A cells assessed as cell growth inhibition incubated for 3 days by MTT assay	[PMID: 29126728]
MCF7	IC₅₀	36.4 nM Compound: Ipomoeassin F	Cytotoxicity against human MCF7 cells assessed as reduction in cell viability after 72 hrs by MTT assay Cytotoxicity against human MCF7 cells assessed as reduction in cell viability after 72 hrs by MTT assay	[PMID: 29291442]
MCF7	IC₅₀	43.7 nM Compound: 188	Cytotoxicity against human MCF7 cells assessed as cell growth inhibition incubated for 3 days by MTT assay Cytotoxicity against human MCF7 cells assessed as cell growth inhibition incubated for 3 days by MTT assay	[PMID: 29126728]
MCF7	IC₅₀	43.7 nM Compound: Ipomoeassin F	Antiproliferative activity against human MCF7 cells after 72 hrs by MTT assay Antiproliferative activity against human MCF7 cells after 72 hrs by MTT assay	[PMID: 28465102]
MDA-MB-231	IC₅₀	6.5 nM Compound: 188	Cytotoxicity against human MDA-MB-231 cells assessed as cell growth inhibition incubated for 3 days by MTT assay Cytotoxicity against human MDA-MB-231 cells assessed as cell growth inhibition incubated for 3 days by MTT assay	[PMID: 29126728]
MDA-MB-231	IC₅₀	6.5 nM Compound: Ipomoeassin F	Antiproliferative activity against human MDA-MB-231 cells after 72 hrs by alamarBlue assay Antiproliferative activity against human MDA-MB-231 cells after 72 hrs by alamarBlue assay	[PMID: 28465102]
MDA-MB-231	IC₅₀	7.7 nM Compound: Ipomoeassin F	Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viability after 72 hrs by Alamar Blue assay Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viability after 72 hrs by Alamar Blue assay	[PMID: 29291442]
MDA-MB-435	IC₅₀	9.4 nM Compound: Ipomoeassin F	Cytotoxicity against human MDA-MB-435 cells after 72 hrs Cytotoxicity against human MDA-MB-435 cells after 72 hrs	[PMID: 29291442]
NIH3T3	IC₅₀	16.8 nM Compound: 188	Cytotoxicity against mouse NIH/3T3 cells assessed as cell growth inhibition incubated for 3 days by MTT assay Cytotoxicity against mouse NIH/3T3 cells assessed as cell growth inhibition incubated for 3 days by MTT assay	[PMID: 29126728]
Panel NCI-60 cells	GI₅₀	30 nM Compound: Ipomoeassin F	Growth inhibition of human NCI60 cells after 48 hrs by SRB assay Growth inhibition of human NCI60 cells after 48 hrs by SRB assay	[PMID: 29291442]
U-937	IC₅₀	2.6 nM Compound: Ipomoeassin F	Cytotoxicity against human U937 cells after 72 hrs Cytotoxicity against human U937 cells after 72 hrs	[PMID: 29291442]
U-937	IC₅₀	5.4 nM Compound: 188	Cytotoxicity against human U-937 cells assessed as cell growth inhibition incubated for 3 days by MTT assay Cytotoxicity against human U-937 cells assessed as cell growth inhibition incubated for 3 days by MTT assay	[PMID: 29126728]

In Vitro

Ipomoeassin F (1-500 nM; 24 h) potently inhibits α1AT translocation into the ER^[1].
Ipomoeassin F is strongly active in the A2780 (human ovarian cancer cell line) assay with an IC₅₀ value of 0.036 μM^[2].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Western Blot Analysis^[1]

Cell Line:	HepG2 cells
Concentration:	1, 5, 10, 25, 50, 75, 100, 250, 500 nM
Incubation Time:	24 h
Result:	Downregulated cellular ATP levels and inhibited Sec61-mediated protein translocation with comparable potency.

Molecular Weight

830.95

Formula

C₄₄H₆₂O₁₅

CAS No.

915392-44-8

SMILES

O=C(/C=C/C1=CC=CC=C1)O[C@H]([C@](COC(CCC(CCCCCC2)=O)=O)([H])O[C@](O[C@@]([C@@H](O)[C@H]3OC(C)=O)([H])[C@](O[C@@H]3C)([H])O[C@H]2CCCCC)([H])[C@@H]4O)[C@@H]4OC(/C(C)=C/C)=O

Structure Classification

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Initial Source

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Room temperature in continental US; may vary elsewhere.

Storage

Please store the product under the recommended conditions in the Certificate of Analysis.

Purity & Documentation

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References

[1]. Peristera Roboti, et al.Ipomoeassin-F disrupts multiple aspects of secretory protein biogenesis. Sci Rep. 2021 Jun 2;11(1):11562. [Content Brief]

[2]. Shugeng Cao, et al. Ipomoeassin F, a new cytotoxic macrocyclic glycoresin from the leaves of Ipomoea squamosa from the Suriname rainforest.Nat Prod Res. 2007 Aug;21(10):872-6. [Content Brief]

[3]. Sarah O'Keefe, et al. Ipomoeassin-F inhibits the in vitro biogenesis of the SARS-CoV-2 spike protein and its host cell membrane receptor. J Cell Sci. 2021 Feb 19;134(4):jcs257758. [Content Brief]

Ipomoeassin F Related Classifications

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Help & FAQs

Do most proteins show cross-species activity?
Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

Keywords:

Ipomoeassin F915392-44-8Ipom-FSARS-CoVSARS coronavirusendoplasmic reticulumERprotein-translocationSec61Sec61αSARS-CoV-2secretory proteintransmembrane proteinsTMPInhibitorinhibitorinhibit

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