Oxidative Cyclization at ortho-Position of Phenol: Improved Total Synthesis of 3-(Phenethylamino)demethyl(oxy)aaptamine

Nakatani, Yôichi; Kimura, Ryoji; Kimata, Toshihiko; Kotoku, Naoyuki

doi:10.3390/md21050311

Cited by 2 publications

References 26 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

A preformulation study of marine alkaloid aaptamine: Physicochemical properties investigation and liposomal formulation development toward hepatocellular carcinoma treatment

Geng,

Xue,

Kong

et al. 2024

Euro J Lipid Sci & Tech

View full text Add to dashboard Cite

Hepatocellular carcinoma (HCC) is a global health concern with high prevalence and mortality. A marine alkaloid, AP‐427, has been reported to show potential for HCC treatment. However, its use is limited by low solubility and high toxicity. We aimed to investigate the preformulation parameters and develop AP‐427 liposomes to improve its clinical suitability. A stability‐indicating HPLC assay was established, and the physicochemical properties of AP‐427 were analyzed. Afterward, AP‐427 liposomes were prepared and characterized, and their cytotoxicity was evaluated. AP‐427 had a low solubility at physiological pH, a LogD of 2.56 ± 0.03, and a basic pKa of 3.24 ± 0.12. An entrapment efficiency of 52.71 ± 3.2% was achieved after optimization. The resulting AP‐427 liposomes were 147.2 ± 3.4 nm and stable up to three months when stored in a pellet form at 4°C. The crystallization of AP‐427 in liposomes became less ordered, and AP‐427 liposomes exhibited a controlled release fitted in Korsmeyer–Peppas model, indicating the release was driven by diffusion. Furthermore, AP‐427 liposomes showed a 3.6 times reduced cytotoxicity against HepG2 cells compared with free AP‐427, potentially enhancing its antitumor efficacy. In conclusion, the precise preformulation parameters advanced the AP‐427 liposomal formulation development, which showed potential for HCC treatment.Practical Applications: The aaptamine derivative AP‐427 has shown cytotoxic effects against hepatocellular carcinoma. However, the low solubility and high toxicity limit its clinical application. The present study aims to prepare liposomal formulation to solve the current problems. Results obtained from this study shed light on challenges related to drug solubility and have paved the way for the development of an effective AP‐427 liposomal formulation with promising application in hepatocellular carcinoma therapy.

show abstract

A preformulation study of marine alkaloid aaptamine: Physicochemical properties investigation and liposomal formulation development toward hepatocellular carcinoma treatment

Geng,

Xue,

Kong

et al. 2024

Euro J Lipid Sci & Tech

View full text Add to dashboard Cite

show abstract

Theoretical and practical aspects of indirect spin–spin couplings

Jaźwiński

2024

Nuclear Magnetic Resonance

View full text Add to dashboard Cite

The review gathers the most important works on SSCC, considering their practical and theoretical aspects. These chapters deal with the improvement of calculation methods, benchmark calculations using large sets of compounds, measurements of coupling constants in individual compounds, and application of coupling to the exploration of the conformations as well as couplings through unusual chemical bonds. Finally, examples of natural compounds were provided in which J(H,H) and J(C,H) were helpful in determining their structure. This review covers the period from May 2023 to April 2024.

show abstract

Oxidative Cyclization at ortho-Position of Phenol: Improved Total Synthesis of 3-(Phenethylamino)demethyl(oxy)aaptamine

Cited by 2 publications

References 26 publications

A preformulation study of marine alkaloid aaptamine: Physicochemical properties investigation and liposomal formulation development toward hepatocellular carcinoma treatment

A preformulation study of marine alkaloid aaptamine: Physicochemical properties investigation and liposomal formulation development toward hepatocellular carcinoma treatment

Theoretical and practical aspects of indirect spin–spin couplings

Contact Info

Product

Resources

About