Design of S–S bond containing maleimide-conjugated closo-dodecaborate (SSMID): identification of unique modification sites on albumin and investigation of intracellular uptake

Satomu Ishii; Shinichi Sato; Hiroya Asami; Tomoko Hasegawa; Jun-Ya Kohno; Hiroyuki Nakamura

doi:10.1039/C9OB00584F

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Design of S–S bond containing maleimide-conjugated closo-dodecaborate (SSMID): identification of unique modification sites on albumin and investigation of intracellular uptake†

Satomu Ishii,^ab Shinichi Sato,

^a Hiroya Asami,^c Tomoko Hasegawa,^c Jun-Ya Kohno^c and Hiroyuki Nakamura

*^a

Author affiliations

* Corresponding authors

^a Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology, R1-13, 4259, Nagatsuta-cho, Midori-ku, Yokohama, Japan
E-mail: hiro@res.titech.ac.jp

^b School of Life Science and Technology, Tokyo Institute of Technology, 4259, Nagatsuta-cho, Midori-ku, Yokohama, Japan

^c Department of Chemistry, Facility of Science, Gakushuin University, 1-5-1 Mejiro, Toshima-ku, Tokyo 171-8588, Japan

Abstract

An S–S bond containing maleimide-conjugated closo-dodecaborate (SSMID) was synthesised for identification of albumin binding sites. Three Lys residues, Lys221, Lys413 and Lys431, were identified as SSMID modification sites in addition to Cys34 in bovin serum albumin (BSA). Fluorescent-labelled MID-BSA was found to be accumulated in the cytosol of HeLa cells.

This article is part of the themed collection: Chemical Biology in OBC

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Article information

DOI: https://doi.org/10.1039/C9OB00584F
Article type: Communication
Submitted: 12 Mar 2019
Accepted: 01 Apr 2019
First published: 03 Apr 2019

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Org. Biomol. Chem., 2019,17, 5496-5499

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Design of S–S bond containing maleimide-conjugated closo-dodecaborate (SSMID): identification of unique modification sites on albumin and investigation of intracellular uptake

S. Ishii, S. Sato, H. Asami, T. Hasegawa, J. Kohno and H. Nakamura, Org. Biomol. Chem., 2019, 17, 5496 DOI: 10.1039/C9OB00584F

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Organic & Biomolecular Chemistry

Design of S–S bond containing maleimide-conjugated closo-dodecaborate (SSMID): identification of unique modification sites on albumin and investigation of intracellular uptake†

Abstract

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Design of S–S bond containing maleimide-conjugated closo-dodecaborate (SSMID): identification of unique modification sites on albumin and investigation of intracellular uptake

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