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Spy-LHP

Item # Unit Size
S343-10
1 mg

For Research Use Only Products

Application: Phospholipid peroxidase detection
                       Selective to lipid hydroperoxidase

Fluometric detection
MSDS
Chemical Name: 2-(4-Diphenylphosphanyl-phenyl)-9-(1-hexyl-heptyl)-anthra[2,1,9-def,6,5,10-d’e’f’]diisoquinoline-1,3,8,10-tetraone

Appearance: Reddish black crystalline powder or solid
Purity: ≥90.0% (HPLC)
MW: 832.96, C55H49N2O4P

Storage Condition: ambient temperature, protect from light
Shipping Condition:
ambient temperature

Product Description
Spy-LHP is a newly developed fluorescent probe for live cell imaging of phospholipid peroxide. There are several detection methods available for lipid peroxides, such as iodide titration method, colorimetric method, or chemiluminometric method to determine malondialdehyde or 4-hydroxynonenal. Malondialdehyde and 4-hydroxynonenal are derivatives from lipid hydroperoxide prepared by oxidation with reactive oxygen species. Thiobarbituriic acid and 1-Methyl-2-phenylindole are used for deriving malondialdehyde for the colorimetric or fluorometric analysis.

Spy-LHP is a low-fluorescent compound, but is oxidized with lipid hydroperoxide to become a high fluorescent compound as indicated in Fig. 1. A similar product, DPPP, is oxidized by a lipid hydroperoxide and becomes a fluorescence compound that can be excited at 352 nm to emit fluorescence at 380 nm. However, the UV excitation for DPPP significantly damages a live cell. Since the oxidized Spy-LHP emits
strong fluorescence (quantum yield: ~1) with maximum wavelength at 535 nm when excited at 524 nm, damage to live cells is very small. Spy-LHP has two alkyl chains to improve the affinity to the lipid bilayer. Spy-LHP is highly selective to lipid hydroperoxide and does not react with hydrogen peroxide, hydroxy radicals, superoxide anion, nitric oxides, peroxynitrite, and alkylperoxy radicals.


Fig. 1 Reaction of Spy-LHP with lipid hydroperoxide


References
1. N. Soh, et al., Novel fluorescent probe for detecting hydroperoxides with strong emission in the visible range. Bioorg Med Chem Lett. 2006;16:2943-2946.
2. N. Soh, et al., Swallow-tailed perylene derivative: a new tool for fluorescent imaging of lipid hydroperoxides. Org Biomol Chem. 2007;5:3762-3768.
B. Nowicka, B. Pluciński, P. Kuczyńska, J. Kruk, Physiological characterization of Chlamydomonas reinhardtii acclimated to chronic stress induced by Ag, Cd, Cr, Cu and Hg ions, Ecotoxicology and Environmental Safety 2016 130:133-145.

B. Nowicka, B. Pluciński, P. Kuczyńska, J. Kruk , Prenyllipid antioxidants participate in response to acute stress induced by heavy metals in green microalga Chlamydomonas reinhardtii, Environmental and Experimental Botany 2016 123:98–107.