Azidophosphonate Chemistry as a Route for a Novel Class of Vesicle‐Forming Phosphonolipids. Issue 5 (15th December 2017)

• Record Type: Journal Article
• Authors: Saha, Abhishek; Panda, Subhankar; Pradhan, Nirmalya; Kalita, Kangkan; Trivedi, Vishal; Manna, Debasis
• Is Part Of: Chemistry. Volume 24:Issue 5(2018)
• Page Start: 1121
• Page End: 1127
• Publication Date: 2017-12-15
• Subjects: ampiphiles -- biomaterials -- lipids -- phosphonolipids -- physicochemical; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201704000
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: Membrane forming synthetic lipids constitutes a new class of biomaterials with impressive applications in the field of biological and pharmaceutical sciences. Interestingly, alteration(s) in the headgroup region of the lipids offer a wide chemical space to investigate their specific properties. In this regard, we have utilized β‐azidophosphonate chemistry to gain access to a novel class of triazole‐phosphonate (TP) amphiphiles with fascinating physicochemical properties of lipids. TP lipids form stable vesicles that exhibit negative surface potential across a broad pH range. These anionic lipids have high phase‐transition temperatures, phospholipase resistance, slow vesicle leakage profiles, and doxorubicin delivery efficacy. We hypothesize that these readily synthesizable phosphonolipids could find several applications as phospholipid substituents. Abstract : Alternative for phospholipids : The crucial choice of β‐azidophosphonate chemistry provided the access of a unique class of triazole‐phosphonate amphiphiles with fascinating physicochemical properties of lipids.