Encapsulation of synthesized purpurin-18-N-aminoimide methyl ester in lipid nanovesicles for use as agents in photodynamic cancer therapy

Sooho Yeo; Huiqiang Wu; Young Kyu Song; Il Yoon; Woo Kyoung Lee

doi:10.1016/j.xphs.2025.01.001

Encapsulation of synthesized purpurin-18-N-aminoimide methyl ester in lipid nanovesicles for use as agents in photodynamic cancer therapy

J Pharm Sci. 2025 Jan 19:S0022-3549(25)00003-6. doi: 10.1016/j.xphs.2025.01.001. Online ahead of print.

Authors

Sooho Yeo¹, Huiqiang Wu², Young Kyu Song³, Il Yoon⁴, Woo Kyoung Lee⁵

Affiliations

¹ College of Pharmacy & Yonsei Institute of Pharmaceutical Sciences, Yonsei University, 85 Songdogwahak-ro, Yeonsu-gu, Incheon, 21983, Republic of Korea; Center for Nano Manufacturing and Department of Nanoscience and Engineering, Inje University, Gimhae 50834, Republic of Korea. Electronic address: sooho32@yonsei.ac.kr.
² Center for Nano Manufacturing and Department of Nanoscience and Engineering, Inje University, Gimhae 50834, Republic of Korea.
³ Research Center of Dr. i&B Co., DaeJeon, Republic of Korea.
⁴ Center for Nano Manufacturing and Department of Nanoscience and Engineering, Inje University, Gimhae 50834, Republic of Korea. Electronic address: yoonil71@inje.ac.kr.
⁵ Center for Nano Manufacturing and Department of Nanoscience and Engineering, Inje University, Gimhae 50834, Republic of Korea. Electronic address: wlee@inje.ac.kr.

PMID: 39832621
DOI: 10.1016/j.xphs.2025.01.001

Abstract

This study aimed to synthesize purpurin-18-N-aminoimide methyl ester (P18 N AI ME) and encapsulate it into lipid nanovesicles (LNVs) for potential application as photodynamic therapy (PDT) agents in cancer therapy. PDT, a light-induced treatment, offers several advantages over conventional cancer treatments, such as minimal invasiveness and localized action. P18 N AI ME, a chlorine class photosensitizer model drug, was synthesized in an attempt to treat tumor in deeper tissues by interacting long-wavelength light. LNVs were introduced to improve anticancer effect and photostability of P18 N AI ME. LNVs using glycerol monostearate demonstrated smaller particle sizes and more sustained release profiles than those using lauric acid. In photocytotoxicity against HeLa (human cervical carcinoma) and A549 (human lung carcinoma) cell lines, P18 N AI ME-LNVs demonstrated safety under dark conditions and enhanced anticancer effects under light conditions compared to P18 N AI ME alone. The inhibitory concentration values (IC₅₀) were 0.86 μM (P18 N AI ME) and 0.68 μM (LNVs) in HeLa cell line and 0.85 μM (P18 N AI ME) and 0.64 μM (LNVs) in A549 cell line. These findings suggest that P18 N AI ME-LNVs hold promise as PDT agents in cancer therapy.

Keywords: Lipid nanovesicles; Photodynamic cancer therapy; Photosensitizer; Photostability; Purpurin-18-N-aminoimide methyl ester.