IMCTA-C14 is an ''N''- tetradecyl (C14) derivative of

trehalosamine Trehalosamines are amino sugars in which a hydroxyl group of trehalose is replaced with an amino group. While 2-, 3-, and 4-trehalosamine derived from actinomycetes have been reported as natural compounds, 6-trehalosamine has been reported as a s ...

, a bacterial metabolite. It was synthesized as a sugar-based

surfactant Surfactants are chemical compounds that decrease the surface tension or interfacial tension between two liquids, a liquid and a gas, or a liquid and a solid. The word ''surfactant'' is a Blend word, blend of "surface-active agent", coined in ...

containing a trehalose substructure from the condensation of 4-

and tetradecanal. Its surfactant properties are not very different from those of other sugar-based surfactant with aliphatic chains of similar length. However, IMCTA-C14 shows similar biological activity to trehalose at low concentrations. For the induction of

autophagy Autophagy (or autophagocytosis; from the Greek language, Greek , , meaning "self-devouring" and , , meaning "hollow") is the natural, conserved degradation of the cell that removes unnecessary or dysfunctional components through a lysosome-depe ...

in cultured cells, trehalose is required at a high concentration of about 10-100 mM. In contrast, IMCTA-C14 shows similar activity at about 1/3000 of that concentration. To illustrate this, expression of the metabolic clock gene, ''Period'' 1, was induced more strongly in cultured hepatocytes at a concentration 1/1000 that of trehalose. The reason for its strong biological activity is thought to be that it has a fatty chain length similar to that of the phospholipids that make up the cell membrane, and a highly basic secondary

amine In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of elec ...

. This gives it a strong affinity for the cell membrane, thereby enhancing its proximity to and effect on the

glucose transporter Glucose transporters are a wide group of membrane proteins that facilitate the transport of glucose across the plasma membrane, a process known as facilitated diffusion. Because glucose is a vital source of energy for all life, these transporte ...

and sweet taste receptor, membrane proteins, the functions of which are modulated by trehalose and other

carbohydrate A carbohydrate () is a biomolecule composed of carbon (C), hydrogen (H), and oxygen (O) atoms. The typical hydrogen-to-oxygen atomic ratio is 2:1, analogous to that of water, and is represented by the empirical formula (where ''m'' and ''n'' ...

References

{{Reflist Disaccharides Surfactants