TokeOni Analog - seMpai: Properties and Applications

Introduction

Bioluminescence imaging (BLI) has been an indispensable technique for noninvasive and highly sensitive observation of biological events in living tissues1-3. Firefly luciferase (Fluc) and D-luciferin have been a standard bioluminescence system for noninvasive small animal imaging. This bioluminescence system generates light signals within visible wavelength (λmax = 560 nm) where light is highly absorbed by hemoglobin and melanin4,5. This fact motivated us to develop a bioluminescence system generating near-infrared light that could penetrate living tissues deeply. Maki et al. evaluated synthetic substrate TokeOni (aka AkaLumine-HCl) (Product No. 808350) that emits near-infrared (λmax = 677 nm) in the reaction with native Fluc6. BLI imaging with TokeOni successfully achieved highly sensitive imaging of deep tissues7. However, poor solubility (< 1 mM) of TokeOni in neutral-buffered aqueous media limits its applications in some biological experiments.

Highly soluble TokeOni analog: seMpai for highly sensitivity deep tissue imaging in neutral buffer conditions

We are now introducing a newly synthesized substrate, seMpai (Product No: 902268), a TokeOni analog that emits near-infrared bioluminescence in the reaction with Fluc, similar to TokeOni (Figure 1). In addition, seMpai offers high solubility (> 60 mM) in neutral-buffered aqueous media and is stable for several months under -80 ˚C.

sempai

Figure 1.Chemical structures and bioluminescent spectrums of SeMpai, D-luciferin and TokeOni.

Detection of lung metastasis in mice demonstrated that the detection sensitivity of seMpai is higher than that of D-luciferin (Figure 2) and is comparable with that of TokeOni8.

imaging-of-lung-metastasis-with-sempa

Figure 2.Highly-sensitive noninvasive imaging of lung metastasis with seMpai. The murine lung metastasis was established 2 weeks after intravenous injection of LLC/Fluc cells into B6 albino mice. The bioluminescence images were acquired 15 minutes after intraperitoneal administration of D-luciferin or seMpai (120 μMol / kg).

Summary

Overall results suggest that seMpai is a suitable substrate of near-infrared BLI for many biological experiments. Its high solubility in neutral buffer conditions further extends the bioluminescent application of TokeOni derivatives.

Materials
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References

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Kuchimaru T, Iwano S, Kiyama M, Mitsumata S, Kadonosono T, Niwa H, Maki S, Kizaka-Kondoh S. 2016. A luciferin analogue generating near-infrared bioluminescence achieves highly sensitive deep-tissue imaging. Nat Commun. 7(1): http://dx.doi.org/10.1038/ncomms11856
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