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807664

Sigma-Aldrich

CBTF

Sinônimo(s):

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

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About This Item

Fórmula empírica (Notação de Hill):
C16H4F4NNaO5S
Peso molecular:
421.26
Código UNSPSC:
12352200
ID de substância PubChem:
NACRES:
NA.22

forma

powder

Nível de qualidade

adequação da reação

reagent type: cross-linking reagent

grupo funcional

ester

temperatura de armazenamento

−20°C

cadeia de caracteres 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

chave InChI

YFJYSJRZDOWXDH-UHFFFAOYSA-M

Descrição geral

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.

Aplicação

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.

Outras notas

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.

Pictogramas

Skull and crossbones

Palavra indicadora

Danger

Frases de perigo

Declarações de precaução

Classificações de perigo

Acute Tox. 3 Oral

Código de classe de armazenamento

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

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable


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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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