PMID- 25614935
OWN - NLM
STAT- MEDLINE
DCOM- 20151106
LR  - 20161125
IS  - 1520-4812 (Electronic)
IS  - 1043-1802 (Linking)
VI  - 26
IP  - 2
DP  - 2015 Feb 18
TI  - CBTF: new amine-to-thiol coupling reagent for preparation of antibody conjugates 
      with increased plasma stability.
PG  - 197-200
LID - 10.1021/bc500610g [doi]
AB  - 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 recently 
      revealed to have limited stability in blood circulation, which can compromise 
      therapeutic efficacy of the conjugate. To address this issue, we have developed a 
      heterobifunctional reagent, sodium 
      4-((4-(cyanoethynyl)benzoyl)oxy)-2,3,5,6-tetrafluorobenzenesulfonate (CBTF), for 
      amine-to-thiol coupling. It comprises a recently described 3-arylpropionitrile 
      (APN) function in replacement of maleimide and allows for the preparation of 
      remarkably stable conjugates. A series of antibody-dye conjugates have been 
      prepared using this reagent and shown superior stability in human blood plasma 
      compared to maleimide-derived conjugates.
FAU - Kolodych, Sergii
AU  - Kolodych S
AD  - Laboratory of Functional ChemoSystems (UMR 7199), Labex Medalis, University of 
      Strasbourg , 67081 Strasbourg, France.
FAU - Koniev, Oleksandr
AU  - Koniev O
FAU - Baatarkhuu, Zoljargal
AU  - Baatarkhuu Z
FAU - Bonnefoy, Jean-Yves
AU  - Bonnefoy JY
FAU - Debaene, Francois
AU  - Debaene F
FAU - Cianferani, Sarah
AU  - Cianferani S
FAU - Van Dorsselaer, Alain
AU  - Van Dorsselaer A
FAU - Wagner, Alain
AU  - Wagner A
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
DEP - 20150123
PL  - United States
TA  - Bioconjug Chem
JT  - Bioconjugate chemistry
JID - 9010319
RN  - 0 (Amines)
RN  - 0 (Benzene Derivatives)
RN  - 0 (Cross-Linking Reagents)
RN  - 0 (Immunoconjugates)
RN  - 0 (Maleimides)
RN  - 0 (Sulfhydryl Compounds)
RN  - 2519R1UGP8 (maleimide)
SB  - IM
MH  - Amines/*chemistry
MH  - Benzene Derivatives/*chemistry
MH  - Cell Line
MH  - Cross-Linking Reagents/*chemistry
MH  - Halogenation
MH  - Humans
MH  - Immunoconjugates/blood/*chemistry
MH  - Maleimides/chemistry
MH  - Sulfhydryl Compounds/*chemistry
EDAT- 2015/01/24 06:00
MHDA- 2015/11/07 06:00
CRDT- 2015/01/24 06:00
PHST- 2015/01/24 06:00 [entrez]
PHST- 2015/01/24 06:00 [pubmed]
PHST- 2015/11/07 06:00 [medline]
AID - 10.1021/bc500610g [doi]
PST - ppublish
SO  - Bioconjug Chem. 2015 Feb 18;26(2):197-200. doi: 10.1021/bc500610g. Epub 2015 Jan 
      23.