All Photos(1)
Synonym(s):
APN-TFS ester, Sodium 4-((4-(cyanoethynyl)benzoyl)oxy)-2,3,5,6-tetrafluorobenzenesulfonate
Empirical Formula (Hill Notation):
C16H4F4NNaO5S
Recommended Products
form
powder
Quality Level
reaction suitability
reagent type: cross-linking reagent
functional group
ester
storage temp.
−20°C
SMILES string
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
InChI key
YFJYSJRZDOWXDH-UHFFFAOYSA-M
Related Categories
General description
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.
Other Notes
Standard protein labeling procedure (lysine labeling):
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.
- 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.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 3 Oral
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Certificates of Analysis (COA)
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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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