Development of near‐infrared firefly luciferin analogue reacted with wild‐type and mutant luciferases
| Autor: | Shojiro Maki, Kazuma Karube, Takashi Hirano, Rika Obata, Ryohei Saito, Atsushi Miyawaki, Nobuo Kitada, Satoshi Iwano |
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| Rok vydání: | 2020 |
| Předmět: |
Firefly luciferin
Firefly Luciferin 010402 general chemistry 01 natural sciences Catalysis Analytical Chemistry Mice Structure-Activity Relationship near‐infrared bioluminescence chemistry.chemical_compound In vivo TokeOni Drug Discovery Animals luciferin analogues Bioluminescence imaging Bioluminescence Luciferase Luciferases Special Issue: In Honor and Memory of Prof. Koji Nakanishi Spectroscopy Akaluc Pharmacology 010405 organic chemistry Chemistry Organic Chemistry Wild type Special Issue Article luciferin‐luciferase reaction Stereoisomerism Luciferin 0104 chemical sciences Photinus pyralis luciferase Luminescent Measurements mutant luciferase Biophysics |
| Zdroj: | Chirality |
| ISSN: | 1520-636X 0899-0042 |
| Popis: | Interestingly, only the D‐form of firefly luciferin produces light by luciferin–luciferase (L–L) reaction. Certain firefly luciferin analogues with modified structures maintain bioluminescence (BL) activity; however, all L‐form luciferin analogues show no BL activity. To this date, our group has developed luciferin analogues with moderate BL activity that produce light of various wavelengths. For in vivo bioluminescence imaging, one of the important factors for detection sensitivity is tissue permeability of the number of photons emitted by L–L reaction, and the wavelengths of light in the near‐infrared (NIR) range (700–900 nm) are most appropriate for the purpose. Some NIR luciferin analogues by us had performance for in vivo experiments to make it possible to detect photons from deep target tissues in mice with high sensitivity, whereas only a few of them can produce NIR light by the L–L reactions with wild‐type luciferase and/or mutant luciferase. Based on the structure–activity relationships, we designed and synthesized here a luciferin analogue with the 5‐allyl‐6‐dimethylamino‐2‐naphthylethenyl moiety. This analogue exhibited NIR BL emissions with wild‐type luciferase (λ max = 705 nm) and mutant luciferase AlaLuc (λ max = 655 nm). |
| Databáze: | OpenAIRE |
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