Synthesis and Gene Transfer Activities of Novel Serum Compatible Reducible Tocopherol-Based Cationic Lipids

Kedika, Bhavani; Patri, Srilakshmi V.

doi:10.1021/mp200435y

Cited by 38 publications

(46 citation statements)

References 59 publications

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“…From a structure-function relationship perspective, it was observed that the presence of unsaturation and functional unit on carbon chain proved important to exhibit the antifungal activity. This observation also corroborates the observations made in the earlier reports that compounds containing alkyl chain with unsaturation and functional group conjugated to cholesterol as a core moiety which exhibited promising antibacterial and antifungal activities 21,22 .…”

Section: Scheme: Synthesis Of Cholesteryl Lactate-fatty Acid Conjugatsupporting

confidence: 92%

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2016

IJPSR

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A series of novel cholesteryl lactate-fatty acid conjugates (4a-i) were prepared by esterification of cholesterol with lactic acid, followed by coupling hydroxyl group of cholesteryl lactate with -COOH group of fatty acids including, saturated fatty acids of varying carbon chain of C 10 -C 18 , unsaturated fatty acids like 10-undecenoic, oleic ((9Z)-octadec-9-enoic), ricinoleic ((9Z,12R)-12-hydroxyoctadec-9-enoic) and 11-bromoundecanoic acid. Cholesteryl lactate-fatty acid conjugates were characterized by spectroscopic techniques like FT-IR, 1H-NMR, 13C-NMR, ESI-MS and HRMS. All the synthesized compounds were tested for their antimicrobial activity against a panel of seven bacterial strains like Staphylococcus aureus MTCC 96, Bacillus subtilis MTCC 121, Micrococcus luteus MTCC 2470, Klebsiella planticola MTCC 530, Escherichia coli MTCC 739, Pseudomonas aeruginosa MTCC 2453 and fungal strain like Candida albicans. Among them, the compounds with unsaturation (4f and 4h), and functional groups like bromine and hydroxyl group (4g and 4i) showed good antibacterial activity. But, promising activity was observed against Staphylococcus aureus MTCC 96 strain ranging from 7.8-15.6 µg/ml. These compounds (4f-i) are also exhibited good to moderate antifungal activity against different Candida strains ranging between 7.8-31.2 µg/ml.

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Section: Scheme: Synthesis Of Cholesteryl Lactate-fatty Acid Conjugatsupporting

confidence: 92%

“…Isolated yield obtained was 95%. 21 . The N, N-dicyclohexylurea was filtered off and the filtrate was washed with water (3 times), 5% acetic acid (3 times) and again with water (3 times) followed by drying over anhydrous sodium sulphate.…”

Section: Synthesis: Synthesis Of Cholesteryl Lactate (Or) Cholesterylmentioning

confidence: 99%

Untitled

2016

IJPSR

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“…We speculate that the relatively higher DNA‐binding ability and lower cytotoxicity of 5c may benefit its transfection behavior. It is also reported recently that α‐tocopherol‐containing lipids showed high gene delivery efficiency and low cytotoxicity . Although the transfection efficiency was still lower than commercially available lipofectamine 2000, these results further revealed the superiority of α‐tocopherol as hydrophobic moiety in cationic lipid structure for non‐viral transfection.…”

Section: Resultsmentioning

confidence: 57%

Biotinylated Cyclen‐Contained Cationic Lipids as Non‐Viral Gene Delivery Vectors

Liu

Zhang

et al. 2013

Chem Biol Drug Des

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A series of 1, 4, 7, 10-tetraazacyclododecane (cyclen)-based cationic lipids, namely 5a-c bearing a biotin moiety and a variety of end groups (cholesterol, diosgenin, and α-tocopherol) via biodegradable carbamate bond linkage were prepared and applied as non-viral gene delivery vectors. The liposomes formed from 5 and dioleoylphosphatidylethanolamine could bind and condense plasmid DNA into nanoparticles with appropriate size and zeta potentials. All biotinylated cyclen cationic lipids showed higher cell viability than commercially available lipofectamine 2000 even at high N/P ratios, while their transfection efficiency was relatively lower. Further, results indicate that among the three lipids, α-tocopherol-containing compound 5c has higher DNA-binding ability, lower cytotoxicity, and higher transfection efficiency. Transfection in two different cell lines revealed that these lipoplexes have higher gene delivery efficiency toward tumor cells.

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“…These approaches oen showed good biocompatibility and serum-tolerance ability. [22][23][24] However, these reported lipids either showed low TE or poor serum-tolerance ability. Many reports have noted that modifying hydroxy groups on the gene transfection vectors might help reduce their cytotoxicity as well as improve gene delivery efficiency and serum-tolerance ability.…”

Section: Introductionmentioning

confidence: 99%

Hydroxyl-containing non-viral lipidic gene vectors with macrocyclic polyamine headgroups

Wang

Zhang

et al. 2015

RSC Adv.

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Cationic lipids are the most widely used non-viral gene vectors, and it is important to develop novel lipids that have high transfection efficiency (TE) and good biocompatibility. A series of macrocyclic polyamine (cyclen and TACN)-based cationic lipids bearing different hydrophobic tails were synthesized with the ring-opening reaction. Several assays were used to study their interactions with plasmid DNA, and these lipoplexes could efficiently condense DNA into nanoparticles with proper sizes and zeta potentials.CCK-8-based cell viability assays showed relatively lower cytotoxicity of the lipoplexes compared with the commercially available Lipofectamine 2000. With transfection in vitro, lipid 6a had comparable or better TE than Lipofectamine 2000 in both 7402 and A549 cells. Interestingly, the TE of 6a was significantly increased in the presence of serum. The results not only demonstrate that lipid 6a can be a promising non-viral gene vector, they also provide clues for developing cationic gene vectors for future in vivo applications.

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Synthesis and Gene Transfer Activities of Novel Serum Compatible Reducible Tocopherol-Based Cationic Lipids

Cited by 38 publications

References 59 publications

Untitled

Untitled

Biotinylated Cyclen‐Contained Cationic Lipids as Non‐Viral Gene Delivery Vectors

Hydroxyl-containing non-viral lipidic gene vectors with macrocyclic polyamine headgroups

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