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SML1396

Sigma-Aldrich

Heclin

≥98% (HPLC)

Synonym(s):

N-(4-Acetylphenyl)-3-(5-ethyl-2-furanyl)-2-propenamide

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About This Item

Empirical Formula (Hill Notation):
C17H17NO3
CAS Number:
890605-54-6
Molecular Weight:
283.32
UNSPSC Code:
12352200
PubChem Substance ID:
329825844
NACRES:
NA.77
Pricing and availability is not currently available.

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

2-8°C

SMILES string

CC(C1=CC=C(NC(/C=C/C2=CC=C(CC)O2)=O)C=C1)=O

InChI

1S/C17H17NO3/c1-3-15-8-9-16(21-15)10-11-17(20)18-14-6-4-13(5-7-14)12(2)19/h4-11H,3H2,1-2H3,(H,18,20)/b11-10+

InChI key

SPTWXRJNCFIDRQ-ZHACJKMWSA-N

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Millex™ polyethersulfone inline filter pore size 0.22 μm, diam. 50 mm, sterile, hydrophilic, 1/4-1/2 in. hose barb

SLGP05010

Millex™ polyethersulfone inline filter

Millex™ polyethersulfone inline filter pore size 0.22 μm, diam. 50 mm, sterile, hydrophilic, 1/4-1/2 in. hose barb with outlet bell

SLGPB5010

Millex™ polyethersulfone inline filter

Millex™ hydrophobic PTFE syringe filter pore size 0.2 μm, diam. 25 mm, sterile, male Luer-Lok® outlet

SLFGL25BS

Millex™ hydrophobic PTFE syringe filter

Millex™ hydrophobic PTFE syringe filter pore size 0.2 μm, diam. 25 mm, non-sterile, sterilization compatible with autoclavable

SLFG02550

Millex™ hydrophobic PTFE syringe filter

material

methacrylate-butadiene-styrene (MBS) housing, polyethersulfone membrane

material

methacrylate-butadiene-styrene (MBS) housing, polyethersulfone membrane

material

PTFE membrane, blue PVC housing

material

PTFE membrane, polypropylene housing

pore size

0.22 μm

pore size

0.22 μm

pore size

0.2 μm

pore size

0.2 μm

diam.

50 mm

diam.

50 mm

diam.

25 mm

diam.

25 mm

manufacturer/tradename

Millex™

manufacturer/tradename

Millex™

manufacturer/tradename

Millex™

manufacturer/tradename

Millex™

fitting

inlet/outlet hose barb (1/4-1/2 in., with Female Luer slip interior)

fitting

inlet stepped hose barb (1/4-1/2 in, with Female Luer slip interior), outlet filling bell

fitting

female Luer-Lok® inlet, male Luer-Lok® outlet

fitting

female Luer-Lok® inlet, male Luer outlet slip

sterility

γ-irradiated, sterile

sterility

γ-irradiated, sterile

sterility

ethylene oxide treated, sterile

sterility

non-sterile

Application

Heclin has been used as a HECT-type ubiquitin E3 ligase inhibitor in human embryonic kidney (HEK293) cells.[1] It has also been used to test its effect on dandelion-induced chloride channel protein (ClC-Ka) inhibition in HEK293 cells [2] and fibroblast-like COS-7 cell line.[3]

Biochem/physiol Actions

HECT E3 ubiquitin ligase inhibitor
Heclin is a selective reversible inihbitor of HECT E3 ubiquitin ligases. Heclin inhibited Nedd4, Smurf2 and WWP1 with IC50 values of 6.3 μM, 6.8 μM and 6.9 μM, respectively, and inhibited autoubiquitination of the Smurf2 HECT domain in vivo with an IC50 value of 9 μM. Heclin had no effect on the auto-ubiquitination of the RING domain ligase Mdm2.
Heclin is not effective in inhibiting E1 or E2 proteins.[4]

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
126M4607V
075M4623V

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O2-dependent protein internalization underlies astrocytic sensing of acute hypoxia by restricting multimodal TRPA1 channel responses
Uchiyama M, et al.
Current Biology, 30(17), 3378-3396 (2020)
Thomas Mund et al.
Proceedings of the National Academy of Sciences of the United States of America, 111(47), 16736-16741 (2014-11-12)
The human genome encodes several hundred E3 ubiquitin ligases containing RING domains, and around 28 containing HECT domains. These enzymes catalyze the transfer of ubiquitin from E2 enzyme thioesters to a huge range of substrates and play crucial roles in
Jadier Redondo et al.
Neurobiology of learning and memory, 167, 107135-107135 (2019-12-11)
Ubiquitination is involved in synaptic plasticity and memory, but the involvement of HECT E3 ligases in these processes has not yet been established. Here, we bilaterally infused heclin, a specific inhibitor of some of these ligases, into the dorsal hippocampus
Zeming Zhang et al.
Journal of immunology (Baltimore, Md. : 1950), 204(7), 1904-1918 (2020-02-23)
IFN regulatory factor 3 (IRF3) is critical for the transcription of type I IFNs in defensing virus and promoting inflammatory responses. Although several kinds of posttranslational modifications have been identified to modulate the activity of IRF3, whether atypical ubiquitination participates
Ke Wang et al.
Oncogene (2023-02-12)
The IGF1 signal pathway is highly activated in some subtype of gastric cancer(GC) that exhibits poor survival and chemotherapy resistance. Although the results of clinical trials of anti-IGF1R monoclonal antibodies and IGF-1R inhibitors have been mostly disappointing in unselected cancer
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