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Synthesis of oxytocin derivatives lipidated via a carbonate or carbamate linkage as a long-acting therapeutic agent for social impairment-like behaviors.

Abstract：

:In the course of our studies of hydrophobic oxytocin (OT) analogues, we newly synthesized lipidated OT (LOT-4a-c and LOT-5a-c), in which a long alkyl chain (C14-C16) is conjugated via a carbonate or carbamate linkage at the Tyr-2 phenolic hydroxy group and a palmitoyl group at the terminal amino group of Cys-1. These LOTs did not activate OT and vasopressin receptors. Among the LOTs, however, LOT-4c, having a C16-chain via a carbonate linkage at the phenolic hydroxyl group of the Tyr-2, showed very long-lasting action for the recovery of impaired social behavior in CD38 knockout mice, a rodent model of autistic phenotypes, whereas the effect of OT itself rapidly diminished. These results indicate that LOT-4c may serve as a potential prodrug in mice.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Cherepanov SM,Miura R,Shabalova AA,Ichinose W,Yokoyama S,Fukuda H,Watanabe M,Higashida H,Shuto S

doi

10.1016/j.bmc.2019.06.018

subject

Has Abstract

pub_date

2019-08-01 00:00:00

pages

3358-3363

issue

15

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(19)30808-9

journal_volume

27

pub_type

杂志文章

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