# SM-102

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> Markdown URL: https://mediated.wiki/source/SM-102.md
> Source: https://en.wikipedia.org/wiki/SM-102
> Source revision: 1329691002
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{{cs1 config|name-list-style=vanc}}
{{chembox
| Name = SM-102
| ImageFile = SM-102 Structural formula V1.svg
| ImageClass = skin-invert-image
| PIN = <nowiki>9-Heptadecanyl 8-{(2-hydroxyethyl)[6-oxo-6-(undecyloxy)hexyl]amino}octanoate</nowiki>
| OtherNames = 1-Octylnonyl 8-[(2-hydroxyethyl)[6-oxo-6-(undecyloxy)hexyl]amino]octanoate
|Section1={{Chembox Identifiers
| CASNo = 2089251-47-6
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 109107894
| PubChem = 126697616
| SMILES = CCCCCCCCCCCOC(=O)CCCCCN(CCCCCCCC(=O)OC(CCCCCCCC)CCCCCCCC)CCO
| StdInChI=InChI=1S/C44H87NO5/c1-4-7-10-13-16-17-18-24-32-41-49-43(47)35-29-25-31-38-45(39-40-46)37-30-23-19-22-28-36-44(48)50-42(33-26-20-14-11-8-5-2)34-27-21-15-12-9-6-3/h42,46H,4-41H2,1-3H3
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = BGNVBNJYBVCBJH-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| UNII = T7OBQ65G2I

}}
|Section2={{Chembox Properties
| C=44 | H=87 | N=1 | O=5
}}
}}

'''SM-102''' is a synthetic amino [lipid](/source/lipid) which is used in combination with other lipids to form [lipid nanoparticle](/source/lipid_nanoparticle)s.<ref>{{cite journal |last1=Hassett |first1=Kimberly J. |last2=Benenato |first2=Kerry E. |last3=Jacquinet |first3=Eric |last4=Lee |first4=Aisha |last5=Woods |first5=Angela |last6=Yuzhakov |first6=Olga |last7=Himansu |first7=Sunny |last8=Deterling |first8=Jessica |last9=Geilich |first9=Benjamin M. |last10=Ketova |first10=Tatiana |last11=Mihai |first11=Cosmin |last12=Lynn |first12=Andy |last13=McFadyen |first13=Iain |last14=Moore |first14=Melissa J. |last15=Senn |first15=Joseph J. |last16=Stanton |first16=Matthew G. |last17=Almarsson |first17=Örn |last18=Ciaramella |first18=Giuseppe |last19=Brito |first19=Luis A. |title=Optimization of Lipid Nanoparticles for Intramuscular Administration of mRNA Vaccines |journal=Molecular Therapy: Nucleic Acids |date=April 2019 |volume=15 |pages=1–11 |doi=10.1016/j.omtn.2019.01.013 |pmid=30785039 |pmc=6383180 |doi-access=free}}</ref> These are used for the delivery of mRNA-based vaccines,<ref>[https://clinicaltrials.gov/ct2/show/NCT04283461 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.</ref><ref>[https://www.modernatx.com/sites/default/files/content_documents/Final%20mRNA-1273-P301%20Protocol%20Amendment%206%20-%2023Dec2020.pdf Clinical study protocol mRNA-1273-P301] {{Webarchive|url=https://web.archive.org/web/20210522152055/https://www.modernatx.com/sites/default/files/content_documents/Final%20mRNA-1273-P301%20Protocol%20Amendment%206%20-%2023Dec2020.pdf |date=2021-05-22 }}, Amendment 6, ModernaTX, Inc., Dec. 23, 2020; accessed on line Jan. 17, 2021.</ref><ref>[https://emergency.cdc.gov/coca/ppt/2020/dec-30-coca-call.pdf 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.</ref> and in particular SM-102 forms part of the [drug delivery system](/source/Nanoparticle_drug_delivery) for the [Moderna COVID-19 vaccine](/source/Moderna_COVID-19_vaccine).<ref>{{cite report | url=https://www.fda.gov/media/144637/download | archive-url=https://web.archive.org/web/20201219003854/https://www.fda.gov/media/144637/download | url-status=dead | archive-date=December 19, 2020 | format=PDF | title=Fact Sheet for Healthcare Providers Administering Vaccine | publisher=Moderna | website=U.S. [Food and Drug Administration](/source/Food_and_Drug_Administration) (FDA) }}</ref><ref name="CDC standing order">{{cite web | url=https://www.cdc.gov/vaccines/covid-19/info-by-product/moderna/downloads/standing-orders.pdf | title=Moderna COVID-19 Vaccine Standing Orders for Administering Vaccine to Persons 18 Years of Age and Older | publisher=U.S. [Centers for Disease Control and Prevention](/source/Centers_for_Disease_Control_and_Prevention) (CDC)}}</ref><ref>{{cite journal |vauthors= |title=Messengers of hope |journal=Nat Biotechnol |volume=39 |issue=1 |date=January 2021 |pmid=33376248 |pmc=7771724 |doi=10.1038/s41587-020-00807-1 |department=editorial | doi-access=free | title-link=doi |page=1 }}</ref>

Lipid nanoparticles are an extension of earlier [RNA transfection](/source/RNA_transfection) methods such as [cationic liposome](/source/cationic_liposome)s.<ref name=C&E>{{cite web |last1=Cross |first1=Ryan |title=Without these lipid shells, there would be no mRNA vaccines for COVID-19 |url=https://cen.acs.org/pharmaceuticals/drug-delivery/Without-lipid-shells-mRNA-vaccines/99/i8 |website=Chemical & Engineering News |access-date=30 June 2021}}</ref> 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](/source/receptor-mediated_endocytosis).

Ionisable lipids like SM-102 hold a relatively (/ close to) neutral charge at [physiological pH](/source/physiological_pH) but are positively charged within the nanoparticle (the [amine](/source/amine) group is [protonated](/source/protonated) to form an [ammonium](/source/ammonium) cation). This allows them to bind to the negatively charged backbone of mRNA. The rest of the nanoparticle is formed from [PEGylated](/source/PEGylated) lipids, which help stabilize the particle, and [phospholipids](/source/phospholipids) and [cholesterol](/source/cholesterol) molecules that contribute to the particle’s structure.<ref name=C&E />

SM-102 is also used for non-invasive [bioluminescence imaging](/source/bioluminescence_imaging) when SM-102 containing [luciferase](/source/luciferase)-encoding mRNA is used for in-vivo luciferase expression in animal models.<ref>{{cite journal |last1=Buschmann |first1=Michael D. |last2=Carrasco |first2=Manuel J. |last3=Alishetty |first3=Suman |last4=Paige |first4=Mikell |last5=Alameh |first5=Mohamad Gabriel |last6=Weissman |first6=Drew |title=Nanomaterial Delivery Systems for mRNA Vaccines |journal=Vaccines |date=19 January 2021 |volume=9 |issue=1 |page=11 |pmid=33478109 |doi=10.3390/vaccines9010065|pmc=7836001 |doi-access=free |language=en}}</ref><ref>{{cite journal |last1=Tao |first1=Weikang |last2=Davide |first2=Joseph P |last3=Cai |first3=Mingmei |last4=Zhang |first4=Guo-Jun |last5=South |first5=Victoria J |last6=Matter |first6=Andrea |last7=Ng |first7=Bruce |last8=Zhang |first8=Ye |last9=Sepp-Lorenzino |first9=Laura |title=Noninvasive Imaging of Lipid Nanoparticle–Mediated Systemic Delivery of Small-Interfering RNA to the Liver |journal=Molecular Therapy |date=September 2010 |volume=18 |issue=9 |pages=1657–1666 | pmc=2956923|  doi=10.1038/mt.2010.147 |pmid=20628357 |url=https://dx.doi.org/10.1038%2Fmt.2010.147 |access-date=21 October 2021}}</ref><ref>{{cite web |title=SM-102 (CAS 2089251-47-6) |url=https://www.caymanchem.com/product/33474/sm-102#reference61317 |website=www.caymanchem.com |access-date=21 October 2021 |language=en}}</ref>

==Synthesis==
The preparation of SM-102 was first described in a patent application to lipid nanoparticles by [Moderna](/source/Moderna) in 2017.<ref name=WO2017>{{cite patent |country=WO |number=2017049245 |status=application |pubdate=2017-03-23 |fdate=2016-09-16 |pridate=2015-09-17 |invent1 =Benenato K.E. |invent2=Kumarasinghe E.S. |invent3=Cornebise M. |title=Compounds and compositions for intracellular delivery of therapeutic agents |assign1=ModernaTX, Inc.}}</ref>{{rp|139–142}} The final step is an [alkylation](/source/alkylation) reaction in which a [secondary amine](/source/Amine) is combined with a lipid bromo [ester](/source/ester).

:HO(CH<sub>2</sub>)<sub>2</sub>NH(CH<sub>2</sub>)<sub>7</sub>CO<sub>2</sub>CH(C<sub>8</sub>H<sub>17</sub>)<sub>2</sub> + Br(CH<sub>2</sub>)<sub>5</sub>CO<sub>2</sub>C<sub>11</sub>H<sub>23</sub> → SM-102

==See also==
* [ALC-0315](/source/ALC-0315)
;Moderna COVID-19 vaccine nanoparticle ingredients
*[Distearoylphosphatidylcholine](/source/Distearoylphosphatidylcholine)
*[DMG-PEG 2000](/source/DMG-PEG_2000)

==References==
{{reflist}}

Category:Tertiary amines
Category:Lipids
Category:Ethanolamines
Category:Esters

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Adapted from the Wikipedia article [SM-102](https://en.wikipedia.org/wiki/SM-102) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/SM-102?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.