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]

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IMCTA-C14

Identifiers
3D model (JSmol)	Interactive image
PubChem CID	170915881
InChI InChI=1S/C26H51NO10/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-27-19-17(15-28)35-25(23(33)21(19)31)37-26-24(34)22(32)20(30)18(16-29)36-26/h17-34H,2-16H2,1H3/t17-,18-,19-,20-,21+,22+,23-,24-,25-,26-/m1/s1 Key: CBNACTPWHANYMM-PCIRLDFKSA-N
SMILES C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)O)NCCCCCCCCCCCCCC)O
Properties
Chemical formula	C26H51NO10
Molar mass	537.691 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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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]