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Related Concept Videos

EDTA: Chemistry and Properties01:22

EDTA: Chemistry and Properties

Polydentate ligands are most widely used in complexometric titrations because they form more stable complexes with the metal ions than mono- or bidentate ligands due to the chelate effect. Examples of polydentate ligands are ethylenediaminetetraacetic acid (EDTA), crown ethers, and cryptands. The most important feature of optimal polydentate ligands is the ability to form 1:1 complexes in a single-step process. Amino carboxylic acid derivatives are frequently used as complexing agents. EDTA is...
Metal-Ligand Bonds02:51

Metal-Ligand Bonds

The hemoglobin in the blood, the chlorophyll in green plants, vitamin B-12, and the catalyst used in the manufacture of polyethylene all contain coordination compounds. Ions of the metals, especially the transition metals, are likely to form complexes.
In these complexes, transition metals form coordinate covalent bonds, a kind of Lewis acid-base interaction in which both of the electrons in the bond are contributed by a donor (Lewis base) to an electron acceptor (Lewis acid). The Lewis acid in...
Formation of Complex Ions03:45

Formation of Complex Ions

A type of Lewis acid-base chemistry involves the formation of a complex ion (or a coordination complex) comprising a central atom, typically a transition metal cation, surrounded by ions or molecules called ligands. These ligands can be neutral molecules like H2O or NH3, or ions such as CN− or OH−. Often, the ligands act as Lewis bases, donating a pair of electrons to the central atom. These types of Lewis acid-base reactions are examples of a broad subdiscipline called coordination...
Complexation Equilibria: The Chelate Effect01:19

Complexation Equilibria: The Chelate Effect

In complexation reactions, metal atoms or cations interact with ligands to form donor-acceptor adducts called metal complexes. Ligands that bind through one donor site are monodentate, ligands with two donor sites are bidentate, and those with more than two donor sites are polydentate ligands. For example, ethylene diamine is a bidentate ligand that binds through two nitrogen donor atoms, forming a five-membered ring. EDTA is a polydentate ligand that binds through four oxygen and two nitrogen...
Nucleophiles02:30

Nucleophiles

The word “nucleophile” has a Greek root and translates to nucleus-loving. Nucleophiles are either negatively charged or neutral species with a pair of electrons in a high-energy occupied molecular orbital (HOMO). As these species tend to donate electron pairs, nucleophiles are considered Lewis bases as well. Negatively charged species, like OH−, Cl−, or HS−, with one or several pairs of electrons, are typically nucleophiles. Similarly, neutral species such as ammonia, amines, water, and alcohol...
Reactivity of Enolate Ions01:23

Reactivity of Enolate Ions

Enolate ions are formed by the acid–base reaction of a carbonyl compound with a base. This leads to deprotonation of the α hydrogen atom, leading to a resonance-stabilized enolate ion where one of the contributing structures is an oxyanion, which imparts additional stability. Therefore, the proton on the α carbon is more acidic in nature than that of other sp3-hybridized C–H bonds but less acidic than those in O–H bonds where the negative charge in the conjugate base is localized on the oxygen...

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Nucleoside Triphosphates - From Synthesis to Biochemical Characterization
15:22

Nucleoside Triphosphates - From Synthesis to Biochemical Characterization

Published on: April 3, 2014

Protonatable ionenes for nucleic acid complexation.

Sean M Ramirez1, John M Layman, Timothy E Long

  • 1Department of Chemistry, Macromolecules and Interfaces Institute, Virginia Tech, Blacksburg, VA 24061-0212, USA.

Macromolecular Bioscience
|July 29, 2009
PubMed
Summary
This summary is machine-generated.

Novel ionenes were synthesized and shown to be pH-sensitive, forming polyplexes that efficiently complex plasmid DNA for transfection into human microvascular endothelial cells (HBMECs). These polyplexes demonstrate potential for gene delivery applications.

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A Polyaniline-based Sensor of Nucleic Acids
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Last Updated: Jun 21, 2026

Nucleoside Triphosphates - From Synthesis to Biochemical Characterization
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Published on: April 3, 2014

Sequence-specific and Selective Recognition of Double-stranded RNAs over Single-stranded RNAs by Chemically Modified Peptide Nucleic Acids
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A Polyaniline-based Sensor of Nucleic Acids
07:58

A Polyaniline-based Sensor of Nucleic Acids

Published on: November 1, 2016

Area of Science:

  • Polymer Chemistry
  • Materials Science
  • Biotechnology

Background:

  • Ionenes are polymers containing positively charged atoms in the polymer backbone.
  • Developing efficient and safe non-viral gene delivery vectors remains a significant challenge in biotechnology.
  • pH-sensitive polymers offer potential for targeted drug and gene delivery due to environmental responsiveness.

Purpose of the Study:

  • To synthesize novel tert-butyloxycarbonyl (TBOC)-protected ionenes with high molecular weight.
  • To characterize the pH-sensitivity and protonation behavior of the synthesized ionenes.
  • To evaluate the ability of these ionenes to form polyplexes with plasmid DNA and assess their transfection efficiency and cytotoxicity in endothelial cells.

Main Methods:

  • Step-growth polymerization of tert-butyl bis[3-(dimethylamino)propyl]carbamate and 1,12-dibromododecane to synthesize TBOC-protected ionenes.
  • Characterization of ionene properties, including molecular weight (M(w)) and pK(a) determination.
  • Formation and characterization of ionene/plasmid DNA polyplexes.
  • Cytotoxicity assessment using the MTT assay and membrane destabilization analysis using the lactate dehydrogenase (LDH) assay.
  • In vitro transfection studies in human microvascular endothelial cells (HBMECs).

Main Results:

  • Novel TBOC-protected ionenes with M(w) > 30 kDa were successfully synthesized.
  • The ionenes exhibited pH-sensitivity with a pK(a) of approximately 6.6, indicating protonation of secondary amines.
  • Polyplexes formed efficiently between both protected and deprotected ionenes and plasmid DNA.
  • Polyplexes showed low cytotoxicity at effective transfection concentrations (< 10 µg/mL) in HBMECs, although membrane destabilization occurred at high concentrations.
  • Successful transfection of HBMECs was achieved at various polymer/DNA mass ratios (2-16).

Conclusions:

  • TBOC-protected ionenes are effective materials for creating pH-sensitive polyplexes with plasmid DNA.
  • These ionenes demonstrate potential as non-viral vectors for gene delivery, showing efficient complexation and successful transfection of endothelial cells with manageable cytotoxicity.
  • The pH-responsive nature of these ionenes may allow for controlled release of genetic material within cellular environments.