scholarly journals Synthesis and Evaluation of Tetramethylguanidinium-Polyethylenimine Polymers as Efficient Gene Delivery Vectors

2014 ◽  
Vol 2014 ◽  
pp. 1-11 ◽  
Author(s):  
Manohar Mahato ◽  
Santosh Yadav ◽  
Pradeep Kumar ◽  
Ashwani Kumar Sharma
Keyword(s):  
Cell Viability ◽  
Size Range ◽  
Transfection Efficiency ◽  
Single Step ◽  
Primary Amines ◽  
Gene Delivery Vectors ◽  
Efficient Gene ◽  
One Step ◽  
Efficient Uptake ◽  
Single Step Reaction

Previously, we demonstrated that 6-(N,N,N′,N′-tetramethylguanidinium chloride)-hexanoyl-polyethylenimine (THP) polymers exhibited significantly enhanced transfection efficiency and cell viability. Here, in the present study, we have synthesized a series of N,N,N′,N′-tetramethylguanidinium-polyethylenimine (TP1-TP5) polymers via a single-step reaction involving peripheral primary amines of bPEI and varying amounts of 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HBTU). These polymers were found to interact efficiently with negatively charged pDNA and formed stable complexes in the size range of ~240–450 nm. Acid-base titration profiles revealed improved buffering capacity of TP polymers as compared to bPEI. Transfection and cytotoxicity assays performed with TP/pDNA complexes on HEK293, CHO, and HeLa cells showed significantly higher transfection efficiency and cell viability with one of the complexes, TP2/pDNA complex, exhibited the highest transfection efficiency (~1.4–2.3-fold) outcompeting native bPEI and the commercially available transfection reagent, Lipofectamine 2000. Compared to previously reported THP polymers, the transfection efficiency of TP/pDNA complexes was found to be lower, as examined by flow cytometry. These results highlight the importance of the hydrophobic C-6 linker in THP polymers in forming compact nanostructures with pDNA, which might lead to efficient uptake and internalization of the complexes; however, the projected TP polymers offer an advantage of their rapid and economical one-step synthesis.

scholarly journals A Single-Step Synthesis of Azetidine-3-Amines

2020 ◽  
Author(s):  
Brian J Wang ◽  
Matthew Duncton
Keyword(s):  
Functional Groups ◽  
Late Stage ◽  
Single Step ◽  
Secondary Amines ◽  
High Yield ◽  
Primary Amines ◽  
Privileged Structure ◽  
One Step ◽  
Alternative Procedures ◽  
Approved Drugs

<div> <p>The azetidine group is frequently encountered within contemporary medicinal chemistry where it is viewed as a privileged structure. However, the introduction of an azetidine can be synthetically challenging. Herein, a straight-forward one step synthesis of azetidine-3-amines, starting from a bench stable, commercial material is presented. The reaction tolerates functional groups commonly encountered in biological-, medicinal- and agro-chemistry, and proceeds in moderate-to-high yield with secondary amines, and moderate-to-low yield with primary amines. The methodology compares favorably to recent alternative procedures and can be utilized in “any-stage” functionalization, including late-stage azetidinylation of approved drugs and other compounds with pharmacological activity.</p> </div>

Peptide amphiphiles with multifunctional fragments promoting cellular uptake and endosomal escape as efficient gene vectors

2015 ◽  
Vol 3 (6) ◽  
pp. 1068-1078 ◽  
Author(s):  
Liang Luan ◽  
Qingbin Meng ◽  
Liang Xu ◽  
Zhao Meng ◽  
Husheng Yan ◽  
...  
Keyword(s):  
Gene Delivery ◽  
Cellular Uptake ◽  
Transfection Efficiency ◽  
Endosomal Escape ◽  
Peptide Amphiphiles ◽  
Gene Delivery Vectors ◽  
Efficient Gene ◽  
Gene Vectors ◽  
Lipofectamine 2000

A series of peptides containing multiple functional fragments were designed as gene-delivery vectors with transfection efficiency comparable to Lipofectamine 2000.

Novel Poly(amidoamine)s with Pendant Primary Amines as Highly Efficient Gene Delivery Vectors

2010 ◽  
Vol 10 (4) ◽  
pp. 384-392 ◽  
Author(s):  
Min Liu ◽  
Jun Chen ◽  
Yan-Ping Cheng ◽  
Ya-Nan Xue ◽  
Ren-Xi Zhuo ◽  
...  
Keyword(s):  
Gene Delivery ◽  
Primary Amines ◽  
Highly Efficient ◽  
Gene Delivery Vectors ◽  
Efficient Gene

scholarly journals Aromatic Thioacetal-Bridged ROS-Responsive Nanoparticles as Novel Gene Delivery Vehicles

Molecules ◽  
2018 ◽  
Vol 23 (8) ◽  
pp. 2061 ◽  
Author(s):  
Guo-Qing Lin ◽  
Wen-Jing Yi ◽  
Qiang Liu ◽  
Xue-Jun Yang ◽  
Zhi-Gang Zhao
Keyword(s):  
Gene Delivery ◽  
Transfection Efficiency ◽  
Gene Transfection ◽  
Zeta Potentials ◽  
Sar Studies ◽  
Gene Delivery Vectors ◽  
Efficient Gene ◽  
Delivery Vehicles ◽  
Low Cytotoxicity

In this report, a series of polycations are designed and synthesized by conjugating reactive oxygen species (ROS)-responsive thioacetal-linkers to low molecular weight (LMW) polyethylenimine (PEI) via ring-opening polymerization. Their structure–activity relationships (SARs) as gene delivery vectors are systematically studied. Although the MWs of the target polymers are only ~9 KDa, they show good DNA binding ability. The formed polyplexes, which are stable toward serum but decomposed under ROS-conditions, have appropriate sizes (180~300 nm) and positive zeta-potentials (+35~50 mV). In vitro experiments reveal that these materials have low cytotoxicity, and higher transfection efficiency (TE) than controls. Furthermore, the title polymers exhibit excellent serum tolerance. With the present of 10% serum, the TE of the polymers even increases up to 10 times higher than 25 KDa PEI and 9 times higher than Lipofectamine 2000. The SAR studies also reveal that electron-withdrawing groups on the aromatic ring in 4a may benefit to balance between the DNA condensation and release for efficient gene transfection.

2,2′-Biphen[n]arenes (n = 4–8): one-step, high-yield synthesis, and host–guest properties

2017 ◽  
Vol 53 (89) ◽  
pp. 12096-12099 ◽  
Author(s):  
Lu Dai ◽  
Zhi-Jun Ding ◽  
Lei Cui ◽  
Jian Li ◽  
Xueshun Jia ◽  
...  
Keyword(s):  
Single Step ◽  
High Yield ◽  
New Family ◽  
One Step ◽  
Single Step Reaction

A new family of supramolecular macrocycles, 2,2′-biphen[n]arenes (n = 4–8), has been synthesized through a single-step reaction with a yield of 51%.

scholarly journals A Single-Step Synthesis of Azetidine-3-Amines

2020 ◽  
Author(s):  
Brian J Wang ◽  
Matthew Duncton
Keyword(s):  
Functional Groups ◽  
Late Stage ◽  
Single Step ◽  
Secondary Amines ◽  
High Yield ◽  
Primary Amines ◽  
Privileged Structure ◽  
One Step ◽  
Alternative Procedures ◽  
Approved Drugs

<div> <p>The azetidine group is frequently encountered within contemporary medicinal chemistry where it is viewed as a privileged structure. However, the introduction of an azetidine can be synthetically challenging. Herein, a straight-forward one step synthesis of azetidine-3-amines, starting from a bench stable, commercial material is presented. The reaction tolerates functional groups commonly encountered in biological-, medicinal- and agro-chemistry, and proceeds in moderate-to-high yield with secondary amines, and moderate-to-low yield with primary amines. The methodology compares favorably to recent alternative procedures and can be utilized in “any-stage” functionalization, including late-stage azetidinylation of approved drugs and other compounds with pharmacological activity.</p> </div>

Computational Study on the Kinetics and Mechanisms of Unimolecular Reactions of (Z)-(Z)-N-(λ5-phosphanylidene) Formohydrazonic Formic Anhydride: Intramolecular aza-Wittig Reaction in Competition with Mumm Rearrangement

2020 ◽  
Vol 17 (11) ◽  
pp. 884-889
Author(s):  
Somayeh Mirdoraghi ◽  
Hamed Douroudgari ◽  
Farideh Piri ◽  
Morteza Vahedpour
Keyword(s):  
Rate Constants ◽  
Density Functional ◽  
Wittig Reaction ◽  
Computational Study ◽  
Single Step ◽  
Low Energy ◽  
Coupled Cluster ◽  
Unimolecular Reaction ◽  
Single Step Reaction ◽  
Good Agreement

For (Z)-(Z)-N-(λ5-phosphanylidene) formohydrazonic formic anhydride, Aza-Wittig reaction and Mumm rearrangement are studied using both density functional and coupled cluster theories. For this purpose, two different products starting from one substrate are considered that are competing with each other. The obtained products, P1 and P2, are thermodynamically favorable. The product of the aza-Wittig reaction, P1, is more stable than the product of Mumm rearrangement (P2). For the mentioned products, just one reliable pathway is separately proposed based on unimolecular reaction. Therefore, the rate constants based on RRKM theory in 300-600 K temperature range are calculated. Results show that the P1 generation pathway is a suitable path due to low energy barriers than the path P2. The first path has three steps with three transition states, TS1, TS2, and TS3. The P2 production path is a single-step reaction. In CCSD level, the computed barrier energies are 14.55, 2.196, and 10.67 kcal/mol for Aza-Wittig reaction and 42.41 kcal/mol for Mumm rearrangement in comparison with the corresponding complexes or reactants. For final products, the results of the computational study are in a good agreement with experimental predictions.

Ruthenium-catalyzed synthesis of N-substituted lactams by acceptorless dehydrogenative coupling of diols with primary amines

2019 ◽  
Vol 55 (82) ◽  
pp. 12384-12387 ◽  
Author(s):  
Yanling Zheng ◽  
Xufeng Nie ◽  
Yang Long ◽  
Li Ji ◽  
Haiyan Fu ◽  
...  
Keyword(s):  
Phosphine Ligand ◽  
Primary Amines ◽  
Dehydrogenative Coupling ◽  
One Step

The first synthesis of N-substituted lactams via an acceptorless dehydrogenative coupling of diols with primary amines in one step was enabled by combining Ru3(CO)12 with a hybrid N-heterocyclic carbene–phosphine–phosphine ligand as the catalyst.

Synthesis of Polycycles and Oxacycles by Tandem Metathesis of endo–norbornene Derivatives

Synthesis ◽  
2021 ◽  
Author(s):  
Sambasivarao Kotha ◽  
Sunil Pulletikurti ◽  
Ambareen Fatma ◽  
gopal dhangar ◽  
gonna somu Naidu
Keyword(s):  
Natural Products ◽  
Metal Complex ◽  
Carbonyl Group ◽  
Single Step ◽  
Time Dependent ◽  
Computational Studies ◽  
Nmr Studies ◽  
Tricyclic Compounds ◽  
One Step ◽  
Norbornene Derivatives

Here, we have demonstrated that the presence of a carbonyl group at C7 position is preventing the olefin metathesis of endo-norbornene derivatives due to the complexation of the metal alkylidene. Time-dependent NMR studies showed the presence of new proton signals in the metal alkylidene region, which indicate the formation of metal complex with the carbonyl group of the substrate. These observations were further proved by ESI-MS analysis. Whereas, computational studies provided that the catalyst was interacting with the C7 carbonyl group and aligned perpendicular to that of norbornene olefin. Later, these endo-keto norbornene derivatives were reduced to hydroxyl derivatives diastereoselectively. Ring-rearrangement metathesis (RRM) of these hydroxyl derivatives, produced the [6/5/6], and [5/6/5] carbo-tricyclic cores of the natural products in one step. Whereas the RRM of O-allyl derivatives, delivered the oxa-tricyclic compounds in a single step with excellent yields.

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