A3134

3-Aminopropionitrile fumarate salt

Name: 3-Aminopropionitrile fumarate salt
Brand: SIGMA

synthetic (organic), ≥98% (TLC), irreversible inhibitor of lysyl oxidase, powder

Synonyme(s) :

β-Alaninenitrile

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About This Item

Formule linéaire :

NH₂CH₂CH₂CN · ½ (HO₂CCH=CHCO₂H)

Numéro CAS:

2079-89-2

Poids moléculaire :

128.13

MDL number:

MFCD00013142

UNSPSC Code:

12352202

PubChem Substance ID:

24278224

NACRES:

NA.77

EC Number:

218-208-7

Beilstein/REAXYS Number:

3573532

Nom du produit

3-Aminopropionitrile fumarate salt, metabolite

SMILES string

NCCC#N.NCCC#N.OC(=O)\C=C\C(O)=O

InChI

1S/C4H4O4.2C3H6N2/c5-3(6)1-2-4(7)8;2*4-2-1-3-5/h1-2H,(H,5,6)(H,7,8);2*1-2,4H2/b2-1+;;

InChI key

NYMXYZMHOZAPHQ-SEPHDYHBSA-N

biological source

synthetic (organic)

assay

≥98% (TLC)

form

powder

mp

177 °C (dec.) (lit.)

solubility

water: 50 mg/mL, clear, colorless to faintly yellow

Quality Level

200

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Catégories apparentées

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

Application

3-Aminopropionitrile fumarate salt has been used as a lysyl oxidase (LOX) inhibitor:

to inhibit collagen cross-linking during microtissue formation and culture
in LIM domain only 1 (LMO1)- or vector-expressing BE2C neuroblastoma cell line in transwell migration and invasion assay
in lysyl oxidase (LOX) activity assay
to study requirement of LOX activity for inducing hypoxia-inducible factor (HIF)2A-dependent stiffness in mouse organoids

Biochem/physiol Actions

3-Aminopropionitrile (β-Aminopropionitrile (BAPN)) functions as an irreversible inhibitor of lysyl oxidase (LOX), an enzyme involved in collagen cross-linking.

In mammals, metabolism of 3-aminopropionitrile leads to release of cyanide ions. Metabolic activity is localized in the microsomal fraction of the liver, and is believed to proceed through a free-radical pathway.

pictograms

GHS08

signalword

Danger

hcodes

H360FD

pcodes

P201 - P202 - P280 - P308 + P313 - P405 - P501

Hazard Classifications

Repr. 1B

Classe de stockage

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

ppe

Eyeshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificats d'analyse (COA)

Lot/Batch Number

0000502374

0000496532

0000490992

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Consulter la Bibliothèque de documents

Force-driven evolution of mesoscale structure in engineered 3D microtissues and the modulation of tissue stiffening

Zhao R, et al.

Biomaterials, 35(19), 5056-5064 (2014)

LMO1 synergizes with MYCN to promote neuroblastoma initiation and metastasis

Zhu Shizhen, et al.

Cancer Cell, 32(3), 310-323 (2017)

Transforming growth factor-beta2 induces expression of biologically active bone morphogenetic protein-1 in human trabecular meshwork cells

Tovar-Vidales T, et al.

Investigative Ophthalmology & Visual Science, 54(7), 4741-4748 (2013)

HIF2A--LOX Pathway Promotes Fibrotic Tissue Remodeling in Thyroid-Associated Orbitopathy

Hikage F, et al.

Endocrinology, 160(1) (2018)

Intraductal xenografts show lobular carcinoma cells rely on their own extracellular matrix and LOXL1.

George Sflomos et al.

EMBO molecular medicine, 13(3), e13180-e13180 (2021-02-23)

Invasive lobular carcinoma (ILC) is the most frequent special histological subtype of breast cancer, typically characterized by loss of E-cadherin. It has clinical features distinct from other estrogen receptor-positive (ER+ ) breast cancers but the molecular mechanisms underlying its characteristic

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