J.Technology and Education, Vol.32, No.1, pp.19-24 (2025)
研究論文

糖鎖を有するフタロシアニンの合成と質量分析法の確立

 

小山 紗佳，松井 栄樹^*

福井工業高等専門学校　物質工学科　（〒916-8507　福井県鯖江市下司町）

*eiki@fukui-nct.ac.jp

 

Synthesis of phthalocyanines bearing sugar chains and their identification by mass spectrometry

 

Suzuka KOYAMA and Eiki MATSUI*

Department of Chemistry and Biology, National Institute of Technology, Fukui College

(Geshi, Sabae, Fukui 916-8507, Japan)

 

(Received March 15, 2025; Accepted May 1, 2025)

 

The synthesis and characterization of new functionalized phthalocyanines with directly appended sugar chains are described. These phthalocyanine compounds (Pcs) contain four deprotected sugar chains, and there is no metal in the center (free base). The synthesis of Pcs was carried out in three stages, and the formation of Pcs was confirmed by MALDI?MS, IR, and UV?Vis measurements. The design strategy of the Pcs contributes to the development of phthalocyanine-based cancer photodynamic therapy (PDT) using dicyano derivatives with sugar chains synthesized by a substitution reaction. MALDI?MS spectra of Pcs measured in the negative mode also confirmed the formation of phthalocyanines with four deprotected sugar chains, and UV?Vis measurements revealed the Soret and Q bands of the phthalocyanine skeleton.

Key words: phthalocyanine, sugar chain, oxidative coupling, MALDI?MS, negative mode, deprotection