Lipophilic Prodrug Charge Masking strategy for novel oxytocin prodrugs production

Gitlin-Domagalska, Agata; Ptaszyńska, Natalia; Olejnik, Anna; Ruczyński, Jaroslaw; Glavaš, Mladena; Dębowski, Dawid; Helbik-Maciejewska, Aleksandra; Łęgowska, Anna; Gilon, Chaim; Rolka, Krzysztof (2024) Lipophilic Prodrug Charge Masking strategy for novel oxytocin prodrugs production. In: Rovero, Paolo; Chorev, Michael; Cavelier, Florine; Li, Xuechen; Matsuzaki, Katsumi; Wade, John, (eds.) EPS 2024: Book of Abstracts. United Kingdom, John Wiley & Sons, pp. 213-214 .

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Abstract

Lipophilic Prodrug Charge Masking strategy is based on the introduction of transient charge masking group that would increase lipophilicity, and thus enhance peptide drug permeability. After permeation, enzymes (e.g. esterases) present throughout the body would bioconvert the prodrug to parent peptide with its original hydrophilic properties and activity. Masking groups used in this project are alkoxycarbonyl groups with general formula R-O-C. They vary in the alkyl chain length, i.e. from 2 to 12 C atoms. Oxytocin (OT) is a nona peptide neurohormone produced in the hypothalamus, well characterized for its involvement in labor and lactation, but also social behavior, as well as affection. We synthesized seriesof OT prodrugs where charge on the N-terminus was masked with alkoxycarbonyl groups with various alkyl chain lengths from 2 to 12 carbon atoms.

Item Type:	Conference or workshop item published in conference proceedings (UNSPECIFIED)
Uncontrolled Keywords:	Lipophilic Prodrug Charge Masking; peptides; PAMPA test
Subjects:	NATURAL SCIENCES > Chemistry > Organic Chemistry NATURAL SCIENCES > Biology > Biochemistry and Molecular Biology
Divisions:	NMR Center
Projects:	Project title Project leader Project code Project type Lipophilic Prodrug Charge Masking (LPCM) as a novel strategy to enhance oral bioavailability of charged active peptides. Optimization and generalization of the method Agata Gitlin-Domagalska UMO-2019/35/D/NZ7/00174 NCS Poland
Depositing User:	Mladena Glavaš
Date Deposited:	18 Dec 2025 14:48
URI:	http://fulir.irb.hr/id/eprint/10590

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