SM-102
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| Names | |
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| Preferred IUPAC name
9-Heptadecanyl 8-{(2-hydroxyethyl)[6-oxo-6-(undecyloxy)hexyl]amino}octanoate | |
| Other names
1-Octylnonyl 8-[(2-hydroxyethyl)[6-oxo-6-(undecyloxy)hexyl]amino]octanoate
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| Identifiers | |
3D model (
JSmol ) |
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| ChemSpider | |
PubChem CID
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| UNII | |
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| Properties | |
| C44H87NO5 | |
| Molar mass | 710.182 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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SM-102 is a synthetic amino
lipid nanoparticles.[1] These are used for the delivery of mRNA-based vaccines,[2][3][4] and in particular SM-102 forms part of the drug delivery system for the Moderna COVID-19 vaccine.[5][6][7]
Lipid nanoparticles are an extension of earlier
RNA transfection methods such as cationic liposomes.[8] Such systems are needed to protect the delicate mRNA molecules and shuttle them into cells without the immune system destroying them first. The nanoparticles enter the cells by triggering receptor-mediated endocytosis
.
Ionisable lipids like SM-102 hold a relatively (/ close to) neutral charge at
phospholipids and cholesterol molecules that contribute to the particle’s structure.[8]
SM-102 is also used for non-invasive bioluminescence imaging when SM-102 containing luciferase-encoding mRNA is used for in-vivo luciferase expression in animal models.[9][10][11]
Synthesis
The preparation of SM-102 was first described in a patent application to lipid nanoparticles by Moderna in 2017.[12]: 139–142 The final step is an alkylation reaction in which a secondary amine is combined with a lipid bromo ester.
- HO(CH2)2NH(CH2)7CO2CH(C8H17)2 + Br(CH2)5CO2C11H23 → SM-102
See also
- Moderna COVID-19 vaccine nanoparticle ingredients
References
- PMID 30785039.
- ^ Safety and Immunogenicity Study of 2019-nCoV Vaccine (mRNA-1273) for Prophylaxis of SARS-CoV-2 Infection (COVID-19), clinicaltrials.gov (US NIH/NLM), identifier NCT04283461. Accessed Jan. 17, 2021.
- ^ Clinical study protocol mRNA-1273-P301 Archived 2021-05-22 at the Wayback Machine, Amendment 6, ModernaTX, Inc., Dec. 23, 2020; accessed on line Jan. 17, 2021.
- ^ COVID-19 Vaccines: Update on Allergic Reactions, Contraindications, and Precautions, Clinician Outreach and Communication Activity (COCA) Webinar, Wednesday, December 30, 2020, CDC (US HHS); accessed on line Jan. 17, 2021.
- ^ Fact Sheet for Healthcare Providers Administering Vaccine (PDF). U.S. Food and Drug Administration (FDA) (Report). Moderna.
- ^ "Moderna COVID-19 Vaccine Standing Orders for Administering Vaccine to Persons 18 Years of Age and Older" (PDF). U.S. Centers for Disease Control and Prevention (CDC).
- PMID 33376248.
- ^ a b Cross R. "Without these lipid shells, there would be no mRNA vaccines for COVID-19". Chemical & Engineering News. Retrieved 30 June 2021.
- PMID 33478109.
- PMID 20628357. Retrieved 21 October 2021.
- ^ "SM-102 (CAS 2089251-47-6)". www.caymanchem.com. Retrieved 21 October 2021.
- ^ WO application 2017049245, Benenato K.E.; Kumarasinghe E.S. & Cornebise M., "Compounds and compositions for intracellular delivery of therapeutic agents", published 2017-03-23, assigned to ModernaTX, Inc.