Development of the Second Generation of Caged Compounds toward to New Cell Sorters

2015 Fiscal Year Final Research Report

• Project/Area Number: 25560404
• Research Category: Grant-in-Aid for Challenging Exploratory Research
• Allocation Type: Multi-year Fund
• Research Field: Biomolecular chemistry
• Research Institution: Nara Institute of Science and Technology
• Principal Investigator: Kakiuchi Kiyomi 奈良先端科学技術大学院大学, 物質創成科学研究科, 教授 (60152592)
• Co-Investigator(Renkei-kenkyūsha): HOSOKAWA YOUICHIRO 奈良先端科学技術大学院大学, 物質創成科学研究科, 准教授 (20448088)
• Project Period (FY): 2013-04-01 – 2016-03-31
• Keywords: ケージド化合物 / ホタルルシフェリン / ルシフェリン－ルシフェラーゼ反応 / チオクロモン / 蛍光 / 核酸 / アンチセンス分子 / アンケージング

Outline of Final Research Achievements

In this research, we tried to apply our novel photolabile protecting group to caged compounds. A firefly luciferin was selected as a target bioactive compound, and we examined the Photodeprotection reaction of the synthesized caged firefly luciferin in water. After photoirradiation, the original firefly luciferin was released from caged compounds with increasing the irradiation time. In in vivo experiment, however, the enzyme in the cell dissociates the chemical bond (ester bond) between a firefly luciferin and a photolabile protecting group. Next, we selected thymidine as a new target compound, and synthesized caged thymidine with ether bond to suppress the bond dissociation by the enzyme. After photoirradiation to the synthesized caged thymidine, we confirmed the regeneration of thymidine. In addition, we applied caged thymidine to the caged antisense oligomer. This caged antisense oligomer enabled to recover the original function as antisense oligomer after photoirradiation.

Free Research Field

光生物化学