Biotin-C5-NHS Ester

Names

[ CAS No. ]:
72040-63-2

[ Name ]:
Biotin-C5-NHS Ester

[Synonym ]:
(2,5-dioxopyrrolidin-1-yl) 6-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]hexanoate
N-{6-[(2,5-dioxopyrrolidin-1-yl)oxy]-6-oxohexyl}-5-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanamide
MFCD00065502
N-{6-[(2,5-Dioxo-1-pyrrolidinyl)oxy]-6-oxohexyl}-5-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanamide
1H-Thieno[3,4-d]imidazole-4-pentanamide, N-[6-[(2,5-dioxo-1-pyrrolidinyl)oxy]-6-oxohexyl]hexahydro-2-oxo-, (3aS,4S,6aR)-

Biological Activity

[Description]:

Biotin-C5-NHS Ester is an alkyl/ether-based PROTAC linker that can be used in the synthesis of PROTACs[1].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> PROTAC >> PROTAC Linker

[Target]

Alkyl/ether

[In Vitro]

PROTACs contain two different ligands connected by a linker; one is a ligand for an E3 ubiquitin ligase and the other is for the target protein. PROTACs exploit the intracellular ubiquitin-proteasome system to selectively degrade target proteins[1].

[References]

[1]. An S, et al. Small-molecule PROTACs: An emerging and promising approach for the development of targeted therapy drugs. EBioMedicine. 2018 Oct;36:553-562.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Melting Point ]:
169-171 °C

[ Molecular Formula ]:
C₂₀H₃₀N₄O₆S

[ Molecular Weight ]:
454.540

[ Exact Mass ]:
454.188599

[ PSA ]:
159.21000

[ LogP ]:
-1.62

[ Index of Refraction ]:
1.591

[ Storage condition ]:
−20°C

[ Stability ]:
Moisture Sensitive

[ Water Solubility ]:
H2O: ≤2 mg/mL with sonication

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Avidin binding of carboxyl-substituted biotin and analogues.

Biochemistry 21 , 978-984, (1982)

Ligation of major histocompatability complex (MHC) class I molecules on human T cells induces cell death through PI-3 kinase-induced c-Jun NH2-terminal kinase activity: a novel apoptotic pathway distinct from Fas-induced apoptosis.

J. Cell Biol. 139 , 1523-1531, (1997)

Ligation of major histocompatability complex class I (MHC-I) molecules expressed on T cells leads to both growth arrest and apoptosis. The aim of the current study was to investigate the intracellular...

ATM-dependent phosphorylation of Mdm2 on serine 395: role in p53 activation by DNA damage.

Genes Dev. 15 , 1067-1077, (2001)

The p53 tumor suppressor protein, a key regulator of cellular responses to genotoxic stress, is stabilized and activated after DNA damage. The rapid activation of p53 by ionizing radiation and radiomi...