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Key Documents

807664

Sigma-Aldrich

CBTF

Synonyme(s) :

APN-TFS ester, Sodium 4-((4-(cyanoethynyl)benzoyl)oxy)-2,3,5,6-tetrafluorobenzenesulfonate

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About This Item

Formule empirique (notation de Hill):
C16H4F4NNaO5S
Poids moléculaire :
421.26
Code UNSPSC :
12352200
ID de substance PubChem :
Nomenclature NACRES :
NA.22

Forme

powder

Niveau de qualité

Pertinence de la réaction

reagent type: cross-linking reagent

Groupe fonctionnel

ester

Température de stockage

−20°C

Chaîne SMILES 

O=C(OC1=C(F)C(F)=C(S(=O)(O[Na])=O)C(F)=C1F)C2=CC=C(C#CC#N)C=C2

InChI

1S/C16H5F4NO5S.Na/c17-10-12(19)15(27(23,24)25)13(20)11(18)14(10)26-16(22)9-5-3-8(4-6-9)2-1-7-21;/h3-6H,(H,23,24,25);/q;+1/p-1

Clé InChI

YFJYSJRZDOWXDH-UHFFFAOYSA-M

Description générale

CBTF (Sodium 4-((4-(cyanoethynyl)benzoyl)oxy)-2,3,5,6-tetrafluorobenzenesulfonate) is a heterobifunctional reagent. It bears a 3-arylpropionitrile (APN) group. CBTF can be prepared from 4-iodobenzoic acid. It participates in various amine-to-thiol coupling reactions. It participates in the synthesis of various antibody-dye conjugates. CBTF is widely used for antibody conjugation.

Application

CBTF is a bifunctional crosslinker for amine-to-thiol coupling. The coupling can be performed with high selectivity in biological medium using mild reaction conditions. CBTF readily reacts with organic amines in basic conditions to produce APN-probes suitable for cysteine labeling.

Autres remarques

Standard protein labeling procedure (lysine labeling):
  • Dissolve the protein in an appropriate buffer* with pH 7.5-9.0 (e.g. PBS) at 1-10mg/mL concentration.
  • Apply the appropriate amount of the stock solution of the reagent (1-5 molar eq. per lysine residue).
  • Incubate at room temperature for 2 hours.
  • If necessary, purify the protein-APN conjugate using size exclusion chromatography or ultrafiltration.
  • The conjugate can be readily coupled with thiol-containing substrates by incubating the components in aqueous buffer (pH 6.5-9.0) at ambient temperature for 2 hours.



Standard protein labeling procedure (cysteine labeling):

Dissolve the protein in the appropriate buffer* with pH 6.5-9.0 (e.g. PBS) at 1-10mg/mL concentration.
Apply the appropriate amount of the stock solution of the APN-labeled molecule (1-5 molar eq. per free cysteine residue).
Incubate at room temperature for 2 hours.
If necessary, purify the protein conjugate using size exclusion chromatography or ultrafiltration.

*Note: avoid amine- and thiol-containing buffers.

Pictogrammes

Skull and crossbones

Mention d'avertissement

Danger

Mentions de danger

Conseils de prudence

Classification des risques

Acute Tox. 3 Oral

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable


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Consulter la Bibliothèque de documents

Houzong Yao et al.
International journal of molecular sciences, 17(2), doi:10-doi:10 (2016-02-06)
Antibody-drug conjugates (ADCs) have become a promising targeted therapy strategy that combines the specificity, favorable pharmacokinetics and biodistributions of antibodies with the destructive potential of highly potent drugs. One of the biggest challenges in the development of ADCs is the
Construction of homogeneous antibody-drug conjugates using site-selective protein chemistry.
Akkapeddi P, et al.
Chemical Science, 7(5), 2954-2963 (2016)
Sergii Kolodych et al.
Bioconjugate chemistry, 26(2), 197-200 (2015-01-24)
Amine-to-thiol coupling is the most common route for the preparation of antibody-drug conjugates (ADC). It is usually achieved by using heterobifunctional reagents possessing an activated ester at one end and a maleimide group at the other. However, maleimide-based conjugates were

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