Chemistry:IMCTA-C14
IMCTA-C14 is an N-tetradecyl (C14) derivative of trehalosamine, a bacterial metabolite. It was synthesized as a sugar-based surfactant containing a trehalose substructure from the condensation of 4-trehalosamine and tetradecanal.[1] Its surfactant properties are not very different from those of other sugar-based surfactant with aliphatic chains of similar length.[1] However, IMCTA-C14 shows similar biological activity to trehalose at low concentrations.[1][2]
For the induction of autophagy 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.[1] 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.[2] 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. This gives it a strong affinity for the cell membrane, thereby enhancing its proximity to and effect on the glucose transporter[3][4] and sweet taste receptor,[5] membrane proteins, the functions of which are modulated by trehalose and other carbohydrates.[1]
References
- ↑ 1.0 1.1 1.2 1.3 1.4 "Rediscovery of 4-Trehalosamine as a Biologically Stable, Mass-Producible, and Chemically Modifiable Trehalose Analog". Advanced Biology 6 (6). June 2022. doi:10.1002/adbi.202101309. PMID 35297567.
- ↑ 2.0 2.1 "Hepatocyte Period 1 dictates oxidative substrate selection independent of the core circadian clock". Cell Reports 43 (10). October 2024. doi:10.1016/j.celrep.2024.114865. PMID 39412985.
- ↑ "Trehalose inhibits solute carrier 2A (SLC2A) proteins to induce autophagy and prevent hepatic steatosis". Science Signaling 9 (416): ra21. February 2016. doi:10.1126/scisignal.aac5472. PMID 26905426.
- ↑ "SLC2A8 (GLUT8) is a mammalian trehalose transporter required for trehalose-induced autophagy". Scientific Reports 6 (1). December 2016. doi:10.1038/srep38586. PMID 27922102. Bibcode: 2016NatSR...638586M.
- ↑ "Sweet taste receptor agonists attenuate macrophage IL-1β expression and eosinophilic inflammation linked to autophagy deficiency in myeloid cells". Clinical and Translational Medicine 12 (8). August 2022. doi:10.1002/ctm2.1021. PMID 35988262.
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