1069020-23-0Relevant academic research and scientific papers
Multicomponent Bioluminescence Imaging with a π-Extended Luciferin
Yao, Zi,Zhang, Brendan S.,Steinhardt, Rachel C.,Mills, Jeremy H.,Prescher, Jennifer A.
, p. 14080 - 14089 (2020)
Bioluminescence imaging with luciferase-luciferin pairs is commonly used for monitoring biological processes in cells and whole organisms. Traditional bioluminescent probes are limited in scope, though, as they cannot be easily distinguished in biological environments, precluding efforts to visualize multicellular processes. Additionally, many luciferase-luciferin pairs emit light that is poorly tissue penetrant, hindering efforts to visualize targets in deep tissues. To address these issues, we synthesized a set of π-extended luciferins that were predicted to be red-shifted luminophores. The scaffolds were designed to be rotationally labile such that they produced light only when paired with luciferases capable of enforcing planarity. A luciferin comprising an intramolecular "lock"was identified as a viable light-emitting probe. Native luciferases were unable to efficiently process the analog, but a complementary luciferase was identified via Rosetta-guided enzyme design. The unique enzyme-substrate pair is red-shifted compared to well-known bioluminescent tools. The probe set is also orthogonal to other luciferase-luciferin probes and can be used for multicomponent imaging. Four substrate-resolved luciferases were imaged in a single session. Collectively, this work provides the first example of Rosetta-guided design in engineering bioluminescent tools and expands the scope of orthogonal imaging probes.
DERIVATIVES OF LUCIFERIN
-
Page/Page column 38, (2014/10/18)
The present invention relates to a compound having the formula (I): wherein ring A is an optionally substituted 5- or 6-membered heterocyclyl, or heteroaiyl ring; ring B is an optionally substituted 5- or 6-membered heterocyclyl, heteroaiyl, or hydrocarbon ring; R1 is hydrogen or an optionally substituted alkyl group; each R2, when present, is a group independently selected from optionally substituted hydroxyl, optionally substituted amino, optionally substituted thiol, optionally substituted alkyl, and optionally substituted aryl; R3 is an optionally substituted acyl group; M is a group selected from O, S, and NR4, wherein R4 is a group selected from hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted heteroaiyl, and optionally substituted heterocyclyl; X is an optionally substituted unsaturated hydrocarbon group or an optionally substituted alkylene carbonyl; and n is 0, 1, 2, or 3. Such compound is a substrate of luciferase enzymes.
