ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

The synthesis and characterization of novel lawsone derivative molecules: their influence on cell lysis in ovarian granulosa cells in vitro

Mehmet Emin Cakmak, Kiymet Berkil Akar, Caglar Berkel, Oguz Özbek, and Meliha Burcu Gürdere

Department of Molecular Biology and Genetics, Faculty of Science and Arts, Tokat Gaziosmanpaşa University, Tokat, Turkey

E-mail: kiymet.berkilakar@gop.edu.tr

Received: 26 February 2026  Accepted: 19 April 2026

Abstract:

In the present study, five novel lawsone derivative molecules (3a–e) containing a 2-phenylthiazole unit were synthesized for the first time, and the structures of these compounds were confirmed based on their spectral data (¹H–NMR, ¹³C–NMR and FT–IR). Besides, the influence of these new lawsone derivative molecules on cell lysis (plasma membrane rupture) were studied in ovarian granulosa cells (KGN cell line) by comparing the levels of LDH (lactate dehydrogenase) released from these cells in vitro. LDH release is widely used as a quantitative marker of plasma membrane damage and lytic cell death, allowing the reliable assessment of cytotoxic or cytoprotective effects. We found that molecule 3b slightly increased cell lysis by ~ 8%, whereas molecule 3e decreased cell lysis by ~ 10% in granulosa cells, suggesting that some of these lawsone derivative molecules might be able to modulate plasma membrane rupture in these cells in vitro. These findings indicate that small structural variations among the lawsone derivatives may lead to distinct biological responses. Further studies are needed to determine molecular mechanisms by which these new lawsone derivative molecules influence plasma membrane rupture and lytic cell death in ovarian granulosa cells. Comprehensive mechanistic studies are required in order to identify their potential biological significance and therapeutic relevance.

Keywords: Lawsone; Granulosa cells; Lytic cell death; Plasma membrane rupture; Ovarian cells; Inflammation

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-026-04930-2

Chemical Papers 80 (8) 8969–8976 (2026)