SM-102 Synthesis
SM-102 (Synonyms: Heptadecan-9-yl 8-((2-hydroxyethyl)(6-oxo-6-(undecyloxy)hexyl)amino)octanoate)
SM-102 is an ionizable cationic lipid (pKa = 6.68) that has been used in the generation of lipid nanoparticles (LNPs) for the delivery of mRNA and plasmid DNA in vitro and in vivo.1,2 It inhibits inward-rectifying potassium currents mediated by human-ether-a-go-go (hERG), also known as Kv11.1, in GH3 rat pituitary cells and MA-10 mouse Leydig cells (IC50s = 108 and 98 µM, respectively).3 Administration of luciferase mRNA in SM-102-containing LNPs induces hepatic luciferase expression in mice.1 LNPs containing SM-102 and Q1-SM-102 (Item No. 41239) as a cationic lipid pair (CLP) and encapsulating a luciferase reporter induce luciferase expression in the lungs and spleen in mice.4 Intramuscular immunization of LNPs containing SM-102 and encapsulating mRNA encoding the severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) spike glycoprotein increases serum SARS-CoV-2 spike glycoprotein-specific IgG titers in mice.5 LNPs containing SM-102 and encapsulating mRNA encoding β-catenin increase bone volume in a mouse model of tibia fracture repair when administered via injection to the fracture callus.6 Formulations containing SM-102 have been used in the development of LNPs for delivery of mRNA-based vaccines.
SM-102
An ionizable cationic lipid
Item No. BA32498
CAS No. 2089251-47-6
Purity: 98%
SM-102 Synthetic Route
1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 12 h / 25 °C / Inert atmosphere
2: trifluoroacetic acid / dichloromethane / 5 h / 25 °C
3: potassium carbonate / N,N-dimethyl-formamide / 5 h / 80 °C
4: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 8 h / 80 °C
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References
1.Current Patent Assignee: SENDA BIOSCIENCES - WO2023/91787, 2023, A1.
2.Sabnis, S., Kumarasinghe , E.S., Salerno, T., et al. A novel amino lipid series for mRNA delivery: Improved endosomal escape and sustained pharmacology and safety in non-human primates. Mol. Ther. 26(6), 1509-1519 (2018).
3.Zhang, W., Pfeifle, A., Lansdell, C., et al. The expression kinetics and immunogenicity of lipid nanoparticles delivering plasmid DNA and mRNA in mice. Vaccines (Basel) 11(10), 1580 (2023).
4.Cho, H.-Y., Chuang, T.-H., and Wu, S.-N. Effective perturbations on the amplitude and hysteresis of Erg-mediated potassium current caused by 1-octylnonyl 8-[(2-hydroxyethyl)[6-oxo-6(undecyloxy)hexyl]amino]-octanoate (SM-102), a cationic Lipid. Biomedicines 9(10), 1367 (2021).
5.Zeng, G., He, Z., Yang, H., et al. Cationic lipid pairs enhance liver-to-lung tropism of lipid nanoparticles for in vivo mRNA delivery. ACS Appl. Mater. Interfaces 16(20), 25698-25709 (2024).
6.Chen, K., Fan, N., Huang, H., et al. mRNA vaccines against SARS-CoV-2 variants delivered by lipid nanoparticles based on novel ionizable lipids. Adv. Funct. Mater. 32(39), (2022).
7.Nelson, A.L., Mancino, C., Gao, X., et al. β-catenin mRNA encapsulated in SM-102 lipid nanoparticles enhances bone formation in a murine tibia fracture repair model. Bioact. Mater. 39, 273-286 (2024).
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