Chemists developed a way to synthesize complex molecules called oligocyclotryptamines, originally found in plants, which could hold potential as antibiotics, analgesics, or anticancer drugs.
MIT chemists have developed a new way to synthesize complex molecules that were originally isolated from plants and could hold potential as antibiotics, analgesics, or cancer drugs.
In addition to allowing scientists to synthesize oligocyclotryptamines found in plants, this approach could also be used to generate new variants that may have even better medicinal properties, or molecular probes that can help to reveal their mechanism of action.Oligocyclotryptamines belong to a class of molecules called alkaloids -- nitrogen-containing organic compounds produced mainly by plants.
When the researchers shine certain wavelengths of light on the substrate containing the two fragments linked via the two nitrogen atoms, it causes the two atoms of nitrogen to break away as nitrogen gas, leaving behind two very reactive carbon radicals in close proximity that join together almost immediately. This type of bond formation has also allowed the researchers to control the molecules' stereochemistry.
"The reason why we're excited about this is that this single solution allowed us to go after multiple targets," Movassaghi says."That same route provides us a solution to multiple members of the natural product family because by extending the iteration one more cycle, your solution is now applied to a new natural product."Using this approach, the researchers were able to create molecules with six or seven cyclotryptamine rings, which has never been done before.
They should also be able to create novel compounds by switching in slightly different cyclotryptamine subunits, Movassaghi says.
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