Palmitoyl C16 Modification

Bio-Synthesis offer Palmitoyl C16 Modification services. Contact us for Palmitoyl C16 modified oligo synthesis.

The palmitoyl group (derived from palmitic acid) is used in oligonucleotide chemistry primarily for enhancing the properties of oligonucleotides. When used in antisense oligonucleotides (ASOs) palmitic acid conjugation increases the plasma concentration of the ASO in mouse models thereby improving their potency. Palmitate can be added to the 3’- and the 5’-end of oligonucleotides. Fatty acid derivatization can reduce the rate by which drugs are absorbed from the subcutis.

Here are some key features of palmitate conjugates:

• Activity: Palmitoylated ASOs exhibit increased in vitro inhabitation effects.
• Increased Stability: The palmitoyl improves the thermal stability of oligonucleotides, helping them to maintain their structure under varying conditions.
• Cellular Uptake: The hydrophobic nature of the palmitoyl group can enhance the cellular uptake of oligonucleotides, making them more effective in therapeutic applications.
• Cell Delivery and Binding Affinity: Adding a palmityl group can increase the binding affinity of oligonucleotides to proteins and target molecules, such as RNA or DNA, enhancing their effectiveness in tissue and cell delivery, gene regulation or silencing.
• Lipidation: Palmitoylation can facilitate the incorporation of oligonucleotides into lipid nanoparticles, which are commonly used for drug delivery.
• Protection Against Nucleases: The palmitoyl modification can help protect oligonucleotides from degradation by nucleases, increasing their half-life in biological systems.

Product Information

 

Product Name:

Palmitoyl C16 Modification

Alternate Name:

Palmitate

Category:

Oligonucleotide Modification

Modification Code:

Palmitoyl C16

Structure:

Purification:

HPLC or PAGE

Delivery Format:

Lyophilized

Shipping Conditions:

Room Temperature

Storage Conditions:

-20°C To -70°C
Oligonucleotides are stable in solution at 4°C for up to 2 weeks. Properly reconstituted material stored at -20°C should be stable for at least 6 months. Dried DNA (when kept at 20°C) in a nuclease-free environment should be stable for years.

References/Citations:

References

Benizri S, Gissot A, Martin A, Vialet B, Grinstaff MW, Barthélémy P. Bioconjugated Oligonucleotides: Recent Developments and Therapeutic Applications. Bioconjug Chem. 2019 Feb 20;30(2):366-383. [PMC]

Biscans A, Caiazzi J, McHugh N, Hariharan V, Muhuri M, Khvorova A. Docosanoic acid conjugation to siRNA enables functional and safe delivery to skeletal and cardiac muscles. Mol Ther. 2021 Apr 7;29(4):1382-1394. Docosanoic acid conjugation to siRNA. [PMC]

Prakash TP, Mullick AE, Lee RG, Yu J, Yeh ST, Low A, Chappell AE, Østergaard ME, Murray S, Gaus HJ, Swayze EE, Seth PP. Fatty acid conjugation enhances potency of antisense oligonucleotides in muscle. Nucleic Acids Res. 2019 Jul 9;47(12):6029-6044. ASOs delivered to muscle. [PMC] 

Relizani K, Echevarría L, Zarrouki F, Gastaldi C, Dambrune C, Aupy P, Haeberli A, Komisarski M, Tensorer T, Larcher T, Svinartchouk F, Vaillend C, Garcia L, Goyenvalle A. Palmitic acid conjugation enhances potency of tricyclo-DNA splice switching oligonucleotides. Nucleic Acids Res. 2022 Jan 11;50(1):17-34.  Splice switching ASOs. [PMC] 

Tran P, Weldemichael T, Liu Z, Li HY. Delivery of Oligonucleotides: Efficiency with Lipid Conjugation and Clinical Outcome. Pharmaceutics. 2022 Feb 1;14(2):342. [PMC]

Wolfrum C, Shi S, Jayaprakash KN, Jayaraman M, Wang G, Pandey RK, Rajeev KG, Nakayama T, Charrise K, Ndungo EM, Zimmermann T, Koteliansky V, Manoharan M, Stoffel M. Mechanisms and optimization of in vivo delivery of lipophilic siRNAs. Nat Biotechnol. 2007 Oct;25(10):1149-57. Delivery of siRNA. [PubMed] 

Technical & Educational

Frequently Asked Questions

Scientific Literature

Scientific Apps and Calculators

No Product Found