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BroadPharm技術講座-What is ALC-0315?

更新時間:2023-09-08   點擊次數:1082次

中文介紹:

脂質納米顆粒(LNP)在mRNA疫苗的創建和批準中發揮了重要作用。輝瑞公司的疫苗 BNT162b2 中使用的脂質之一是 ALC-0315。

ALC-0315是一種氨基脂質,其叔胺通過酯鍵與支鏈尾相連。叔胺允許脂質形成兩性離子脂質。ALC-0315是一種無色油性化合物,分子量為766.3,CAS號為2036272-55-4 IUPAC名稱為[(4-羥基丁基)氮雜二基]二(己烷-6,1-二基)雙(2-己基癸酸酯)。

ALC-0315因其快速清除率、耐受性、免疫原性和蛋白表達而成為理想的藥物載體。雖然ALC-0315可溶于有機溶劑,但懸浮在極性溶劑中時會形成膜。叔胺與mRNA形成離子鍵,允許mRNA有效載荷的理想封裝。ALC-0315在生理pH下保持中性,并在酸性環境中帶正電荷。這種在生理pH下保持中性的特性允許脂質與血細胞陰離子膜的相互作用更少。ALC-0315帶正電荷的能力在細胞攝取后起著重要作用。當ALC-0315與酸性內體相互作用時,叔胺變成質子化并形成錐形離子對,驅動從雙層到倒六邊形相的轉變。這個階段促進內體逃逸和mRNA釋放到細胞質中。一旦mRNA被釋放,ALC-0315通過兩個連續的酯水解反應代謝,首先產生單酯代謝物,然后產生雙重脫酯代謝物。兩種水解反應的產物是6-己基癸酸。剩余的脂肪族頭組通過膽道和腎臟清除消除。

隨著納米顆粒藥物遞送技術的最新進展,科學界正處于許多新療法的邊緣。為了進一步增強藥物輸送能力,BroadPharm(國內客戶聯系靶點科技)提供了廣泛的可電離脂質、陽離子脂質、PEG 脂質和磷脂選擇。BroadPharm(國內客戶聯系靶點科技)還提供定制的脂質合成,以進一步滿足您的研究需求。

英文介紹:

Lipid nanoparticles (LNP) have played an important role in the creation and approval of mRNA vaccines. One of the more notable lipids found in Pfizer’s vaccine BNT162b2 is ALC- 0315.

ALC-0315 is an amino lipid with a tertiary amine linked with a branched tail through ester bonds. The tertiary amine allows the lipid to form a zwitterionic lipid. ALC-0315 is a colorless oily compound with a molecular weight of 766.3 and a CAS number of 2036272-55-4 IUPAC name is [(4-Hydroxybutyl)azanediyl]di(hexane-6,1-diyl) bis(2-hexyldecanoate).

ALC-0315 can be synthesized through the route as shown in Figure 1.

alc-0315 image

Figure 1. Shows the synthesis route of ALC-0315.

ALC-0315 is an ideal drug carrier due to its fast clearance rate, tolerability, immunogenicity, and protein expression. While ALC-0315 is soluble in organic solvents, it forms a membrane when suspended in polar solvents. The tertiary amine forms an ionic bond to mRNA allowing for ideal encapsulation of the mRNA payload. ALC-0315 remains neutral at physiological pH and takes on a positive charge in an acidic environment. This property to stay neutral at physiological pH allows the lipid to have fewer interactions with the anionic membranes of blood cells. ALC- 0315’s ability to take on a positive charge plays an important role after cellular uptake. When ALC-0315 interacts with the acidic endosome, the tertiary amine becomes protonated and forms cone-shaped ion pairs that drive the transition from a bilayer to an inverted hexagon phase. This phase promotes endosomal escape and the release of the mRNA into the cytosol. Once the mRNA is released, ALC-0315 is metabolized through two sequential ester hydrolysis reactions first yielding the monoester metabolite followed by the doubly de-esterified metabolite. The product of both hydrolysis reactions is 6-hexyldecanoic acid. The remaining aliphatic head group is eliminated via biliary and renal clearance.

With the recent advances in nanoparticle drug delivery technology, the scientific community is on the edge of many new therapeutics being created. To further empower drug delivery, BroadPharm offers a broad selection of ionizable lipids, cationic lipids, PEG lipids, and Phospholipids. BroadPharm also offers custom lipid syntheses to further satisfy your research need.



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