SM-102
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Hodoodo CAT#: H464358

CAS#: 2089251-47-6

Description: SM-102 is an ionizable amino lipid that has been used in combination with other lipids in the formation of lipid nanoparticles. Administration of luciferase mRNA in SM-102-containing lipid nanoparticles induces hepatic luciferase expression in mice. Formulations containing SM-102 have been used in the development of lipid nanoparticles for delivery of mRNA-based vaccines.


Chemical Structure

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SM-102
CAS# 2089251-47-6

Theoretical Analysis

Hodoodo Cat#: H464358
Name: SM-102
CAS#: 2089251-47-6
Chemical Formula: C44H87NO5
Exact Mass: 709.66
Molecular Weight: 710.180
Elemental Analysis: C, 74.42; H, 12.35; N, 1.97; O, 11.26

Price and Availability

Size Price Availability Quantity
10mg USD 90 Ready to ship
25mg USD 150 Ready to ship
50mg USD 250 Ready to ship
100mg USD 450 Ready to ship
200mg USD 650 Ready to ship
500mg USD 1350 Ready to Ship
500mg USD 1350 Ready to ship
1g USD 2150 Ready to Ship
2g USD 3850 Ready to Ship
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Synonym: SM-102; SM102; SM 102;

IUPAC/Chemical Name: heptadecan-9-yl 8-((2-hydroxyethyl)(6-oxo-6-(undecyloxy)hexyl)amino)octanoate

InChi Key: BGNVBNJYBVCBJH-UHFFFAOYSA-N

InChi Code: 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

SMILES Code: OCCN(CCCCCC(OCCCCCCCCCCC)=O)CCCCCCCC(OC(CCCCCCCC)CCCCCCCC)=O

Appearance: Oily liquid

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target: SM-102 is an ionizable cationic amino lipid that has been used in combination with other lipids to form lipid nanoparticles (LNPs).
In vitro activity: SM-102 may influence cellular activities by inhibiting specific ionic currents. In endocrine cells (GH3 and MA-10) and microglial cells (BV2), SM-102 concentration-dependently blocked hyperpolarization-activated K+ currents, impacting their functional activities. The IC50 for SM-102 inhibition of GH3 cells was 108 μM, similar to its KD value of 134 μM for deactivation time constant accentuation. Reference: Biomedicines. 2021 Oct 1;9(10):1367. https://pubmed.ncbi.nlm.nih.gov/34680484/
In vivo activity: SM-102-based CRISPR LNPs show promise as a therapeutic strategy against hepatitis B virus (HBV) infection. CRISPR nanoparticle treatment decreased the levels of HBcAg, HBsAg and cccDNA in AAV-HBV1.04 transduced mouse liver by 53%, 73% and 64% respectively. In HBV infected tree shrews, the treatment achieved 70% reduction of viral RNA and 35% reduction of cccDNA. In HBV transgenic mouse, 90% inhibition of HBV RNA and 95% inhibition of DNA were observed. Reference: Antiviral Res. 2023 Jul;215:105618. https://pubmed.ncbi.nlm.nih.gov/37142191/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Chloroform 100.0 140.80
DMSO 100.0 140.80
Ethanol 100.0 140.80

Preparing Stock Solutions

The following data is based on the product molecular weight 710.18 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Reinhart AG, Osterwald A, Ringler P, Leiser Y, Lauer ME, Martin RE, Ullmer C, Schumacher F, Korn C, Keller M. Investigations into mRNA Lipid Nanoparticles Shelf-Life Stability under Nonfrozen Conditions. Mol Pharm. 2023 Dec 4;20(12):6492-6503. doi: 10.1021/acs.molpharmaceut.3c00956. Epub 2023 Nov 17. PMID: 37975733. 2. Cho HY, Chuang TH, Wu SN. 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. 2021 Oct 1;9(10):1367. doi: 10.3390/biomedicines9101367. PMID: 34680484; PMCID: PMC8533363. 3. Yi J, Lei X, Guo F, Chen Q, Chen X, Zhao K, Zhu C, Cheng X, Lin J, Yin H, Xia Y. Co-delivery of Cas9 mRNA and guide RNAs edits hepatitis B virus episomal and integration DNA in mouse and tree shrew models. Antiviral Res. 2023 Jul;215:105618. doi: 10.1016/j.antiviral.2023.105618. Epub 2023 May 2. PMID: 37142191. 4. Wang W, Feng S, Ye Z, Gao H, Lin J, Ouyang D. Prediction of lipid nanoparticles for mRNA vaccines by the machine learning algorithm. Acta Pharm Sin B. 2022 Jun;12(6):2950-2962. doi: 10.1016/j.apsb.2021.11.021. Epub 2021 Dec 2. PMID: 35755271; PMCID: PMC9214321.
In vitro protocol: 1. Reinhart AG, Osterwald A, Ringler P, Leiser Y, Lauer ME, Martin RE, Ullmer C, Schumacher F, Korn C, Keller M. Investigations into mRNA Lipid Nanoparticles Shelf-Life Stability under Nonfrozen Conditions. Mol Pharm. 2023 Dec 4;20(12):6492-6503. doi: 10.1021/acs.molpharmaceut.3c00956. Epub 2023 Nov 17. PMID: 37975733. 2. Cho HY, Chuang TH, Wu SN. 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. 2021 Oct 1;9(10):1367. doi: 10.3390/biomedicines9101367. PMID: 34680484; PMCID: PMC8533363.
In vivo protocol: 1. Yi J, Lei X, Guo F, Chen Q, Chen X, Zhao K, Zhu C, Cheng X, Lin J, Yin H, Xia Y. Co-delivery of Cas9 mRNA and guide RNAs edits hepatitis B virus episomal and integration DNA in mouse and tree shrew models. Antiviral Res. 2023 Jul;215:105618. doi: 10.1016/j.antiviral.2023.105618. Epub 2023 May 2. PMID: 37142191. 2. Wang W, Feng S, Ye Z, Gao H, Lin J, Ouyang D. Prediction of lipid nanoparticles for mRNA vaccines by the machine learning algorithm. Acta Pharm Sin B. 2022 Jun;12(6):2950-2962. doi: 10.1016/j.apsb.2021.11.021. Epub 2021 Dec 2. PMID: 35755271; PMCID: PMC9214321.

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1. Xue Y, Zhang Y, Zhong Y, Du S, Hou X, Li W, Li H, Wang S, Wang C, Yan J, Kang DD, Deng B, McComb DW, Irvine DJ, Weiss R, Dong Y. LNP-RNA-engineered adipose stem cells for accelerated diabetic wound healing. Nat Commun. 2024 Jan 25;15(1):739. doi: 10.1038/s41467-024-45094-5. PMID: 38272900; PMCID: PMC10811230.

2. Zhang W, Pfeifle A, Lansdell C, Frahm G, Cecillon J, Tamming L, Gravel C, Gao J, Thulasi Raman SN, Wang L, Sauve S, Rosu-Myles M, Li X, Johnston MJW. The Expression Kinetics and Immunogenicity of Lipid Nanoparticles Delivering Plasmid DNA and mRNA in Mice. Vaccines (Basel). 2023 Oct 11;11(10):1580. doi: 10.3390/vaccines11101580. PMID: 37896985; PMCID: PMC10610642.