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Merck
CN

S4562

β-Secretase inhibitor

≥97% (HPLC), powder

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About This Item

Empirical Formula (Hill Notation):
C73H118N16O27
Molecular Weight:
1651.81
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD02683580

Key Documents

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Product Name

β-Secretase inhibitor, ≥97% (HPLC), powder

SMILES string

N([C@H]([C@@H](O)CC(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](Cc1ccccc1)C(=O)O)CC(C)C)C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](N)CCCCN)[C@H](O)C)CCC(=O)O)C

InChI

1S/C73H118N16O27/c1-11-37(8)59(88-66(108)45(23-27-56(101)102)79-63(105)43(21-25-54(97)98)81-72(114)60(39(10)91)89-62(104)41(75)19-15-16-28-74)71(113)85-49(33-90)68(110)80-44(22-26-55(99)100)65(107)87-58(36(6)7)70(112)83-47(31-51(76)93)67(109)82-46(29-34(2

InChI key

CQTBDEGWLSDJEP-JMAXQNTPSA-N

biological source

synthetic (organic)

assay

≥97% (HPLC)

form

powder

mol wt

~_1.65 kDa

color

white

mp

200 °C

solubility

DMSO: soluble

shipped in

dry ice

storage temp.

−20°C

Quality Level

200

Related Categories

Application

β-Secretase inhibitor has been used as β-site amyloid precursor protein (APP) cleaving enzyme-1 (BACE1) inhibitor in BACE1 inhibitor assay.(2)
β-Secretase inhibitor may be used to inhibit BACE1 in studies related to AD.

Biochem/physiol Actions

β-Site amyloid precursor protein (APP) cleaving enzyme-1 (BACE1) is a β-secretase that initiates the production of amyloid protein in Alzheimer′s dieases (AD) patients. β-Secretase inhibitors decrease the generation of β amyloid and formation of amyloid plaques typical of AD.

General description

β-Site amyloid precursor protein (APP) cleaving enzyme-1 (BACE1), an aspartic protease belongs to the protease family of enzymes comprises of six luminal cysteine residues. These residues help in the formation of three intermolecular disulfide bonds and N-linked glycosylation sites.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
SLBZ0604
SLBX6274
SLBT2813
SLBP1431V
SLBM3424V

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Hans Hilpert et al.
Journal of medicinal chemistry, 56(10), 3980-3995 (2013-04-18)
An extensive fluorine scan of 1,3-oxazines revealed the power of fluorine(s) to lower the pKa and thereby dramatically change the pharmacological profile of this class of BACE1 inhibitors. The CF3 substituted oxazine 89, a potent and highly brain penetrant BACE1
B J Baranowski et al.
Physiological reports, 12(16), e70001-e70001 (2024-08-20)
Brain-derived neurotrophic factor (BDNF) content and signaling has been identified as one potential regulator of amyloid precursor protein (APP) processing. Recently published work has demonstrated that BDNF reduces BACE1 activity while also elevating the inhibition of GSK3β in the prefrontal
Jungmi Lee et al.
Analytica chimica acta, 1022, 89-95 (2018-05-08)
Amyloid-β (Aβ) is generated by proteolytic processing of amyloid precursor protein (APP) by beta-secretase (BACE-1) and gamma-secretase. Amyloid-β is responsible for the formation of senile plaques in Alzheimer's disease (AD). Consequently, inhibition of β-secretase (BACE-1), a rate-limiting enzyme in the
beta-secretase inhibitor; a promising novel therapeutic drug in Alzheimer?s disease
Menting KW, et al.
Frontiers in Aging Neuroscience, 6, 165-165 (2014)
S Sinha et al.
Nature, 402(6761), 537-540 (1999-12-11)
Proteolytic processing of the amyloid precursor protein (APP) generates amyloid beta (Abeta) peptide, which is thought to be causal for the pathology and subsequent cognitive decline in Alzheimer's disease. Cleavage by beta-secretase at the amino terminus of the Abeta peptide
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