Systematic Construction of a Monotetrahydrofuran‐Ring Library in Annonaceous Acetogenins by Asymmetric Alkynylation and Stereodivergent Tetrahydrofuran‐Ring Formation

Abstract

An intrinsically fluorescent cationic polyfluorene (CCP) has been designed, synthesized, characterized, and examined as a plasmid DNA (pDNA) delivery vector. This material facilitates nucleic acid binding, encapsulation and efficient cellular uptake. CCP can effectively protect pDNA against nuclease degradation, which is necessary for gene carriers. Green fluorescent protein (GFP) expression experiments reveal that CCP can achieve efficient delivery and transfection of pDNA encoding GFP gene with 92% efficiency, which surpasses that of commercial transfection agents, lipofectamine 2000 (Lipo) and polyethylenimine (PEI). CCP is also highly fluorescent, with 43% quantum yield in water, and exhibits excellent photostability, which allows for real‐time tracking the location of gene delivery and transfection. These features and capabilities represent a major step toward designing and applying conjugated polymers that function in both imaging and therapeutic applications.

Structure–antitumor activity relationship of hybrid acetogenins focusing on connecting groups between heterocycles and the linker moiety

“…The synthesis of all analogs 7a–7k was initiated using a common α-tetrahydrofuranyl aldehyde 2 prepared by a method previously reported by us. 15 Scheme 1 illustrates the synthesis of analogs 7a–7h. Under Carreira's conditions, 16 the asymmetric alkynylation of 2 with 10-azido-1-decyne 3 resulted in a high yield of propargyl alcohol 4, which shows a high diastereoselectivity; this threo / trans / threo stereochemical configuration on 4 is the same as that of the stereoisomer, which is reported to show the most potent anti-tumor activity.…”