28728-55-4

Usage

Uses

Used in Molecular Biology:
Hexadimethrine bromide is used as a transfection agent for mammalian cells with DNA, enhancing the efficiency of lipofection transfections. It is also utilized in the context of viral infections, specifically for lentivirus and retrovirus, to facilitate the infection process in cells.
Used in Antiheparin Applications:
Hexadimethrine bromide serves as an antiheparin agent, where a 3mg quantity has been found to enhance peptide degradation in automated sequential analysis.
Used in Protein Sequencing:
In the field of protein sequencing, hexadimethrine bromide is employed as a protein/peptide carrier, aiding in the analysis and sequencing of proteins and peptides.

Purification Methods

Purify it by chromatography on Dowex 50 and/or by filtration through alumina before use [Frank Hoppe-Seyler's Z Physiol Chemie 360 997 1979]. It is hygroscopic, and its solubility in H2O is 10%.

InChI:InChI=1/C10H24N2.C3H6Br2/c1-11(2)9-7-5-6-8-10-12(3)4;4-2-1-3-5/h5-10H2,1-4H3;1-3H2

Upstream product

• 110-95-2 N,N,N'N'-tetramethyl-1,3-propanediamine 
• 143-15-7 1-dodecylbromide 
• 112-18-5 N,N-dimethylaminododecane 
• 109-64-8 1,3-dibromo-propane 
• 112-69-6 N,N-dimethylhexadecylamine 
• 7378-99-6 N,N-dimethyloctanamide 
• 3779-42-8 3-bromo-N,N,N-trimethyl-1-propanaminium bromide 
• 438492-52-5 6-(1-pyrenyl)-1-bromohexane 
• 438492-51-4 6-bromo-1-(pyren-1-yl)hexan-1-one 
• 22809-37-6 6-bromohexanoyl chloride 
• 129-00-0 pyrene 
• 124-28-7 N,N-dimethyl-n-octadecylamine 
• 143-28-2 oleoyl alcohol 
• 13044-38-7 (Z)-1-bromo-9-octadecene 

Relevant academic research and scientific papers

Synthesis and characterization of asymmetrical gemini surfactants

The effect of variation in the length of surfactant hydrocarbon tail groups was tested in a series of dissymmetric gemini surfactants (N1-alkyl N1,N1,N3,N3-tetramethyl-N3-(6-pyren-6yl)-hexyl)propane-1,3-diammonium dibromide designated as CmC3CnBr, with m = hexyl pyrene, and n = 8, 12, 14, 16, and 18. The aggregation properties of these surfactants have been investigated by means of 1H NMR, fluorescence spectroscopy, surface tension and electrical conductivity measurements. The critical micelle concentration (CMC) was determined using surface tension and confirmed using the specific conductance method. Krafft temperatures and the degree of micelle ionization (α) were obtained from specific conductance measurements. With an increase of the dissymmetry (m/n) ratio, the CMC decreased linearly and an increase in the Krafft temperatures was observed for all of the gemini surfactants. α values for the dissymmetric GS were higher than those of the m-3-m counterparts, which may be attributed to enhanced micelle-micelle interactions that arise from increased hydrophobicity of the hydrocarbon chains. The introduction of the bulky pyrenyl tail group resulted in much lower CMC values compared to their symmetrical counterparts affecting the packing of these surfactants at the air/water interface, which resulted in high-ordered structures (lamellar and inverted micelles). This in turn affected the thermodynamic parameters of the micellization.

A general strategy for the rational design of size-selective mesoporous catalysts

A series of functionalized mesoporous silicas with cagelike pore topology has been synthesized and screened for size-selective catalytic transformations. The aluminum-catalyzed Meerwein-Ponndorf-Verley (MPV) reduction of differently sized aromatic aldehydes (benzaldehyde and 1-pyrenecarbox-aldehyde) has been investigated as a test reaction. The catalysts were synthesized in a two-step grafting sequence comprising pore-size engineering of mesoporous silicas (SBA-1, SBA-2, SBA-16) with longchain alkyl dimethylaminosilanes and surface organoaluminum chemistry with triethylaluminum [{Al-(CH2CH 3)3)2]. Size-selective reaction behavior was found for small pore SBA-1 materials, and the selectivity could be efficiently tuned by selecting a silylating reagent of appropriate size. The results are compared with the catalytic performance of a large-pore periodic mesoporous organosilica PMO-[SBA-1] and the nonporous high-surface-area silicas Aerosil 300/380.

Micellization behavior of cationic gemini surfactants in aqueous-ethylene glycol solution

The micellization behavior of gemini surfactants i.e. alkanediyl-α, ω-bis(cetyldimethylammonium bromide) (C16-s-C 16,2Br- where s = 3, 4, 10) in 10% (v/v) ethylene glycol solution was investigated by surface tension and conductometric measurements at 300 K. The critical micelle concentration, degree of micellar ionization, surface excess concentration, minimum surface area per molecule of surfactant, surface pressure at the CMC and Gibbs energy of adsorption of the dimeric surfactants have also been determined in the presence of different salts (NaCl, NaBr and NaI). The critical micelle concentration and degree of micellar ionization values decrease significantly in the presence of sodium halides and follows the sequence NaCl NaBr NaI. The free energy, enthalpy and entropy of micellization of dimeric surfactants in 10% (v/v) ethylene glycol solution were determined using the temperature dependence of the critical micelle concentration. The standard free energy of micellization was found to be negative in all the cases. AOCS 2011.

Synthesis of carboxylic group functionalized mesoporous silicas (CFMSs) with various structures

Carboxylic group functionalized mesoporous silicas (CFMSs) were successfully synthesized by using cationic surfactants as templates and carboxyethylsilanetriol sodium salt (CES) as a co-structure directing agent (CSDA). Well ordered two-dimensional (2D) p6mm, cubic Fm3m, intergrowth of Fm3m and P63/mmc, and cubic Fd3m with uniform carboxyl group distributions have been synthesized with increasing charge density of carboxylate of CES on the surface of the mesopore, which will provide new families of mesoporous materials with different functionalities and structures. The Royal Society of Chemistry 2007.

Determination of the Aggregation Number of Pyrene-Labeled Gemini Surfactant Micelles by Pyrene Fluorescence Quenching Measurements

A cationic gemini surfactant referred to as Py-3-12 and composed of two alkylated diammonium bromide head groups, a propyl spacer, and dodecyl and 1-pyrenehexyl hydrophobic tails was synthesized. Its critical micellar concentration (CMC) was determined to equal 0.15 (±0.02) mM by surface tension and time-resolved fluorescence measurements. The state of the pyrene molecules, whether they were incorporated inside the Py-3-12 micelles or unassociated in the aqueous solution, was determined by applying the global model-free analysis (MFA) to the fluorescence decays acquired with Py-3-12 aqueous solutions. The unassociated Py-3-12 surfactants emitted as pyrene monomers and showed a long fluorescence lifetime. The excited pyrenyl groups located inside Py-3-12 micelles formed an excimer by a rapid encounter with a ground-state pyrene with an average rate constant equal to 0.69 (±0.06) ns-1. After having the photophysical properties of Py-3-12 in aqueous solution characterized, the number (Nagg) of surfactants per micelle was determined by conducting quenching experiments with dinitrotoluene (DNT). Although DNT is fairly hydrophobic, it was found to partition itself between the Py-3-12 micelles and the aqueous phase. Fluorescence quenching experiments performed on the pyrene monomer and excimer generated by the Py-3-12 aqueous solutions yielded the concentration ([Q]b) of DNT bound to the Py-3-12 micelles and the average number ?n?d of DNT quenching an excimer by diffusive encounters. A combination of steady-state and time-resolved fluorescence quenching experiments on the excimer yielded the number (?n?s) of DNT molecules that were bound to the micelles and quenched the excimer in a static manner. A plot of the sum ?n?d + ?n?s as a function of [Q]b yielded an Nagg value of 14.0 (±0.2) Py-3-12 units per micelle. This study represents the first example in the literature where Nagg is determined for a micelle, where each surfactant molecule is labeled with pyrene.

Conformational analysis of (Phenylenedimethylene)bis(n-octylammonium)dibromides in aqueous solution. Conformational change upon micellization

Three gemini surfactants, in which two quaternary ammonium species (CH3(CH2)7N+(CH3) 2) are linked at the polar headgroups by ο-, m-, or p-phenylenedimethylene spacers, have been synthesized. The critical micelle concentration (cmc) of these surfactants in aqueous solutions was determind by electrical conductivity. Selective-decoupling 13C NMR and 1H NMR spectra were measured at various concentrations below and above the cmc. The selective-decoupling 13C NMR results revealed that the specific rotational isomers about the CH2-aromatic carbon single bonds for the gemini surfactant having a m-phenylenedimethylene spacer are preferentially stabilized upon micellization, while for the gemini surfactant having an ο-phenylenedimethylene spacer, the presence of only the conformation in which the aromatic ring is sandwiched between two n-octyl chains was confirmed. Furthermore, it was found that variation in the stacking pattern of the aromatic rings after micellization of the surfactants is reflected in the 1H spectral features of the aromatic protons. Comparison is made with the conformations of bis(quaternaryammonium) bromides with flexible spacer chains ((CH2)x) and of the corresponding n-alkylammonium bromide monomeric surfactants.

Influence of Amine-Based Cationic Gemini Surfactants on Catalytic Activity of α-Chymotrypsin

The α-chymotrypsin activity was tested in aqueous media with the presence of novel cationic amine–based gemini surfactant, with different spacer chain lengths and head group size, and also compared with the cationic cetyltrimethylammonium bromide (CTAB) a

Retarding action of poly(amidoamine) dendrimers and cationic gemini surfactants in acrylic dyeing

Two cationic gemini surfactants and two generations of poly(amidoamine) (PAMAM) dendrimers (G = -0.5 and G = 0.5) were studied as retarders in acrylic dyeing with a cationic dye. Effects of retarder concentrations, dyeing time, and temperature were investigated by means of UV-Vis spectrophotometry. The results indicated that the dye adsorption decreased in the presence of the species and more uniform dyeing was achieved. The PAMAM dendrimers had lower retarding action than the cationic gemini surfactants which was attributed to their non-permanent and lower cationic charge density. Kinetics of the dyeing systems were also evaluated by four different empirical models. The modified Cegarra-Puente model fitted the dyeing kinetic data somewhat better than the other empirical kinetic models. Moreover, the activation energy of the dyeing systems was calculated and reported.

Gemini surfactants foam formation ability and foam stability depends on spacer length

A series of cationic gemini surfactants containing different spacer length were synthesized and analyzed structurally. It was shown that the surface tension (σ) and critical micelle concentration (CMC), which had a maximum for the n-C4H8 spacer depended on the spacer length. The foaming ability and foam stability are high for the gemini surfactants with short spacers (C2H4 to n-C4H8), while longer spacers lead to a distinct decrease of these foam parameters. Foaming properties are discussed in terms of configuration and conformation of a surfactant molecule and in relation to micellization state kinetic.

Designing pH-sensitive gemini nanoparticles for non-viral gene delivery into keratinocytes

This study aimed to develop a more effective non-viral gene delivery system for keratinocyte transfection. To this end, gemini nanoparticles were formulated from plasmid DNA, the lipid DOPE (dioleoylphosphatidylethanolamine) and surfactants, where the sur