[12]aneN ₃ -based multifunctional compounds as fluorescent probes and nucleic acids delivering agents

Abstract

A series of multifunctional compounds (MFCs) 1a-1e based on 1,8-naphthalimide and [12]aneN 3 building blocks were designed and synthesized. They were used as not only fluorescent probes for recognition of Cu 2þ ions but also as non-viral gene vectors for DNA and RNA delivery. Furthermore, their complexes with Cu 2þ (1-Cu) could also selectively stain lysosome in HeLa cells. In order to achieve high performance multifunctional materials, structure-performance relationship of MFCs 1a-1e was studied. It was found that MFCs 1a-1e exhibited highly selective fluorescence turn-off for Cu 2þ , without interference by other metal ions in aqueous solution. The fluorescence emission of 1a-1e was quenched by a factor of 10-fold, 47-fold, 6-fold, 64-fold, and 15-fold respectively in the presence of Cu 2þ ions. Due to high sensitivity, good water solubility, and low cytotoxicity, MFCs 1a-1d were successfully applied in the recognition of Cu 2þ and selectively staining lysosome in HeLa cells. Most importantly, MFCs 1a and 1b had excellent HeLa cell selectivity in RNA delivery, and their performances were far better than lipofectamine 2000 and 25 kDa PEI.

Iron-Catalyzed Trimerization of Terminal Alkynes Enabled by Pyrimidinediimine Ligands: A Regioselective Method for the Synthesis of 1,3,5-Substituted Arenes

“…Remarkably, the adamantyl-substituted analogue ( Ad P Pym DI)­FeCl 2 29 reached full conversion within 30 min, to form 4a in >95% selectivity. A challenge in first-row transition-metal-catalyzed alkyne trimerization is suppressing competitive alkyne polymerization pathways, , which lead to apparently high NMR conversions but modest isolated yields of the target products. However, as evident from the mass balance data for 2 (Figure , right), 29 and 35 (see the Supporting Information), no competing alkyne polymerization could be noted.…”

“…The excellent tolerance of a variety of functional groups gives products suitable for downstream elaboration, for example, by nucleophilic displacement ( 8a and 9a ), deprotection and further functionalization ( 10a , 11a , 13a , and 15a – 17a ), or cross-coupling reactivity ( 8a , 9a , 12a , and 18a ). These products therefore function as useful synthons for targets containing a C 3 -symmetrical arene center. − Apart from being atom economical, our Fe-catalyzed methodology provides an advantage over potential one-step routes to access the same substrates (for example, via cross-coupling from 1,3,5-tribromobenzene), where functionalities incorporated in 8 , 9 , 12 , or 18 would be challenging to preserve. The substitution pattern in the immediate vicinity of the CC triple bond plays an important role in selectivity.…”

“…Examples of such cases include bimetallic complexes based on a Mo–Mo multiple bond core or N-heterocyclic carbene (NHC) supported iron amides. , Arylacetylenes can undergo trimerization in the presence of InCl 3 to yield the 1,3,5-substituted arene products, albeit with limited functional group tolerance. , The paucity of a straightforward and functional-group-tolerant method for the synthesis of 1,3,5-substituted arenes contrasts with their prevalence in complex structural motifs. Applications of such motifs include inter alia drug precursors, solar energy conversion materials, ionic liquids, labeling for RNA delivery, or supramolecular receptors …”

Recent Advance of Liposome Nanoparticles for Nucleic Acid Therapy

“…The study of transport mechanisms showed that the liposome/DNA complex mainly entered cells in an energy-independent manner. Further research found that [12]aneN 3 compounds modified with naphthalimide can not only be used as gene carriers to deliver nucleic acids, but can also be used as fluorescent probes to identify copper ions and small biological molecules [ 123 , 124 ].…”

Naphthalimide‐modified dendrimers as efficient and low cytotoxic nucleic acid delivery vectors

“…In recent years, we have developed a series of rigid‐naphthalimide‐modified lipids 30–33 . We found that the transfection efficiency was improved due to the introduction of rigid naphthalimide.…”