DBCO-(CH2)2-NH2-CO-(CH2)3COOH-NHS CAS#: 1393350-27-0

DBCO-(CH2)2-NH2-CO-(CH2)3COOH-NHS Basic information

Product Name:

DBCO-(CH2)2-NH2-CO-(CH2)3COOH-NHS

Synonyms:

DBCO-(CH2)2-NH2-CO-(CH2)3COOH-NHS
DBCO-NHS ester 3 (DIBAC-NHS)
DBCO-NHS ester 3
Dibenz[b,?f]azocine-5(6H)-pentanoic acid, 11,?12-didehydro-δ-oxo-, 2,5-dioxo-1-pyrrolidinyl ester
(2,5-Dioxopyrrolidin-1-yl) 5-(2-azatricyclo[10.4.0.04,9]hexadeca-1(16),4,6,8,12,14-hexaen-10-yn-2-yl)-5-oxopentanoate
DBCO-C5-NHS-ester
2,5-Dioxo-1-pyrrolidinyl 11,12-didehydro-δ-oxodibenz[b,f]azocine-5(6H)-pentanoate

CAS:

1393350-27-0

MF:

C24H20N2O5

MW:

416.43

Product Categories:

ADC LINKER

Mol File:

1393350-27-0.mol

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DBCO-(CH2)2-NH2-CO-(CH2)3COOH-NHS Chemical Properties

Boiling point:: 679.2±65.0 °C(Predicted)
Density: 1.40±0.1 g/cm3(Predicted)
form: Solid
pka: -0.19±0.20(Predicted)
color: White to off-white
InChI: InChI=1S/C24H20N2O5/c27-21(10-5-11-24(30)31-26-22(28)14-15-23(26)29)25-16-19-8-2-1-6-17(19)12-13-18-7-3-4-9-20(18)25/h1-4,6-9H,5,10-11,14-16H2
InChIKey: CFQHVJJWCDJMLI-UHFFFAOYSA-N
SMILES: C(N1CC2=CC=CC=C2C#CC2=CC=CC=C12)(=O)CCCC(=O)ON1C(CCC1=O)=O

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DBCO-(CH2)2-NH2-CO-(CH2)3COOH-NHS Usage And Synthesis

Uses

DBCO-NHS ester 3 (Compound 12) is a cleavable linker that is used for making antibody-drug conjugate (ADC). DBCO-NHS ester 3 is a derivative of Dibenzylcyclooctyne (DBCO) obtained by activation of N-hydroxysuccinimide by the carboxylic acid moiety of both methyl-oxanorbornadiene (MeOND) and dibenzoazacyclooctyne (DIBAC)[1][2]. DBCO-NHS ester 3 is a click chemistry reagent, it contains a DBCO group that can undergo strain-promoted alkyne-azide cycloaddition (SPAAC) with molecules containing Azide groups.

IC 50

Cleavable Linker

References

[1] Silvie A. Meeuwissen, et al. Copper-free click chemistry on polymersomes: pre- vs. post-self-assembly functionalization. Polymer Chemistry. 2012, 3: 1783-1795.
[2] Tang F, et al. Chemoenzymatic synthesis of glycoengineered IgG antibodies and glycosite-specific antibody-drug conjugates. Nat Protoc. 2017 Aug;12(8):1702-1721. DOI:10.1038/nprot.2017.058

DBCO-(CH2)2-NH2-CO-(CH2)3COOH-NHSSupplier

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