A new bifunctional chelator enables facile biocoupling and radiolabeling as the basis for a bioconjugation kit
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A new bifunctional chelator enables facile biocoupling and radiolabeling as the basis for a bioconjugation kit. / Barandov, Ali; Grünstein, Dan; Apostolova, Ivalaya; Buchert, Ralph; Roger, Michel; Brenner, Winfried; Abram, Ulrich; Seeberger, Peter H.
in: CHEMBIOCHEM, Jahrgang 15, Nr. 7, 05.05.2014, S. 986-94.Publikationen: SCORING: Beitrag in Fachzeitschrift/Zeitung › SCORING: Zeitschriftenaufsatz › Forschung › Begutachtung
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TY - JOUR
T1 - A new bifunctional chelator enables facile biocoupling and radiolabeling as the basis for a bioconjugation kit
AU - Barandov, Ali
AU - Grünstein, Dan
AU - Apostolova, Ivalaya
AU - Buchert, Ralph
AU - Roger, Michel
AU - Brenner, Winfried
AU - Abram, Ulrich
AU - Seeberger, Peter H
N1 - © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
PY - 2014/5/5
Y1 - 2014/5/5
N2 - A new tridentate bifunctional chelator, N-(-2-picolyl)(-4-hydroxy)(-3-amino)benzoic acid (PHAB), was designed to efficiently coordinate the [(99m)Tc(CO)3](+) core and facilitate coupling reactions to biomolecules. The chelator can be procured in the form of the corresponding benzotriazole ester (PHAB-OBT), which can be stored and used as a bioconjugation kit. PHAB-OBT reacts with modified carbohydrates with high selectivity and efficiency in a single step in both aqueous and organic media. As is desirable for a kit, no complicated chemical bench work is required. Glycoconjugate postlabeling resulted in neutral radiolabeled glycans with high radiochemical yields. Prelabeling approaches were assessed by successive reaction of PHAB-OBT with the [(99m)Tc(CO)3](+) core and a modified galactose model. The radiolabeled galactose was obtained in 84% yield as defined by HPLC analysis. Biodistribution of the radioactive (99m)Tc-labeled chelator, as well as the glycoconjugates, were examined in mice. Noticeably different biodistribution patterns were observed that reflect trends in the uptake of carbohydrate analogues by various organs.
AB - A new tridentate bifunctional chelator, N-(-2-picolyl)(-4-hydroxy)(-3-amino)benzoic acid (PHAB), was designed to efficiently coordinate the [(99m)Tc(CO)3](+) core and facilitate coupling reactions to biomolecules. The chelator can be procured in the form of the corresponding benzotriazole ester (PHAB-OBT), which can be stored and used as a bioconjugation kit. PHAB-OBT reacts with modified carbohydrates with high selectivity and efficiency in a single step in both aqueous and organic media. As is desirable for a kit, no complicated chemical bench work is required. Glycoconjugate postlabeling resulted in neutral radiolabeled glycans with high radiochemical yields. Prelabeling approaches were assessed by successive reaction of PHAB-OBT with the [(99m)Tc(CO)3](+) core and a modified galactose model. The radiolabeled galactose was obtained in 84% yield as defined by HPLC analysis. Biodistribution of the radioactive (99m)Tc-labeled chelator, as well as the glycoconjugates, were examined in mice. Noticeably different biodistribution patterns were observed that reflect trends in the uptake of carbohydrate analogues by various organs.
KW - Animals
KW - Chelating Agents
KW - Crystallography, X-Ray
KW - Galactose
KW - Glycoconjugates
KW - Isotope Labeling
KW - Mice
KW - Mice, Inbred BALB C
KW - Molecular Conformation
KW - Organotechnetium Compounds
KW - Solvents
KW - Tissue Distribution
KW - Tomography, Emission-Computed, Single-Photon
KW - Triazoles
KW - Journal Article
KW - Research Support, Non-U.S. Gov't
U2 - 10.1002/cbic.201400001
DO - 10.1002/cbic.201400001
M3 - SCORING: Journal article
C2 - 24723504
VL - 15
SP - 986
EP - 994
JO - CHEMBIOCHEM
JF - CHEMBIOCHEM
SN - 1439-4227
IS - 7
ER -
