DBCO-Acid Property

Melting point:

118-125 °C

Boiling point:

622.0±55.0 °C(Predicted)

Density 

1.34±0.1 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

Soluble in dimethyl sulfoxide and dimethyl formamide.

pka

4.47±0.17(Predicted)

form 

Solid

color 

Off-white to Gray

InChI

InChI=1S/C19H15NO3/c21-18(11-12-19(22)23)20-13-16-7-2-1-5-14(16)9-10-15-6-3-4-8-17(15)20/h1-8H,11-13H2,(H,22,23)

InChIKey

NDLOVDOICXITOK-UHFFFAOYSA-N

SMILES

O=C(C([H])([H])C([H])([H])C(=O)O[H])N1C2=C([H])C([H])=C([H])C([H])=C2C#CC2=C([H])C([H])=C([H])C([H])=C2C1([H])[H]

Safety

HS Code 

29339900

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

DBCO-Acid Chemical Properties,Usage,Production

Description

DBCO-Acid is a non-activated building block and adds minimal spacer to modified molecules. In the presence of activators such as EDC or HATU, this reagent can be used to derivatize amine-containing molecules through a stable amide bond. DBCO is commonly used for copper-free Click Chemistry reactions.

Uses

DBCO-Acid is a reactant in the synthesis of high-generation polyester dendrimers. Also used in the preparation of modular, plasmin sensitive, clickable poly(ethylene glycol)-heparin-laminin microsphere systems for creating growth factor gradients in peripheral nerve regeneration.

Application

DBCO-acid (11,12-Didehydro-gamma-oxodibenz[b,f]azocine-5(6H)-butanoic acid) is a cleavable antibody-drug conjugate (ADC) linker used in the synthesis of ADC linkers DBCO-NHS ester (HY-115524 and HY-115545) and drug-linker conjugates DBCO-PEG-MMAE (HY-111012 and HY-126690). DBCO-acid is also a click chemistry reagent that contains a DBCO group in its structure and can undergo strain-promoted alkyne-azide cycloaddition (SPAAC) with molecules containing an azide group.

General Description

Acid functionalized cyclooctyne derivative. Cyclooctynes are useful in strain-promoted copper-free azide-alkyne click chemistry reactions. This azadibenzocyclooctyne will react with azide functionalized compounds or biomolecules without the need for a Cu(I) catalyst to result in a stable triazole linkage.