Biologically active bisquaternary ammonium chlorides: physico?chemical properties of long chain amphiphiles and their evaluation as non-viral vectors for gene delivery

Fisicaro, E.; Compari, Carlotta; Duce, Elenia; Donofrío, Gaetano; Różycka‐Roszak, Bożenna; Woźniak, Edyta

doi:10.1016/j.bbagen.2004.12.013

Cited by 41 publications

(68 citation statements)

References 45 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[1][2][3]. The scientific and applicative interest in cationic surfactants has greatly increased, partly because of the urge for cationic amphiphiles to be used as vectors in gene delivery [4][5][6][7][8]. Quite recently, the use of gemini surfactants-i.e.…”

Section: Introductionmentioning

confidence: 99%

Thermodynamics of aqueous solutions of dodecyldimethylethylammonium bromide

Fisicaro¹,

Biemmi²,

Compari³

et al. 2007

Journal of Colloid and Interface Science

View full text Add to dashboard Cite

Section: Introductionmentioning

confidence: 99%

Thermodynamics of aqueous solutions of dodecyldimethylethylammonium bromide

Fisicaro¹,

Biemmi²,

Compari³

et al. 2007

Journal of Colloid and Interface Science

View full text Add to dashboard Cite

“…In fact, they have been proposed as noncovalent functionalization agents for carbon nanotubes-based formulations for drug delivery [5] and as non viral vectors in gene therapy [6][7][8][9], owing their multiple positive charges, suitable for binding and compacting DNA, and their superior surface activity. We are for some time collecting chemico physical, particularly thermodynamic, and biological data about homologous series of cationic gemini surfactants with the idea of correlating in a quantitative way their structure with their biological activity, particularly gene delivery ability [9][10][11][12][13][14]. In this perspective, synthetic vectors present the advantage that their constituent parts can be quite easily modified, thereby facilitating the elucidation of structure-activity relationships.…”

Section: Introductionmentioning

confidence: 99%

Is the counterion responsible for the unusual thermodynamic behaviour of the aqueous solutions of gemini bispyridinium surfactants?

Fisicaro

Compari

Bacciottini

et al. 2014

Colloids and Surfaces A: Physicochemical and Engineering Aspect

View full text Add to dashboard Cite

Apparent and partial molar enthalpies at 298 K of the aqueous solutions of cationic gemini surfactants 1,1′-didodecyl-2,2′-trimethylenebispyridinium dichloride (12-Py(2)-3-(2)Py-12 Cl); 1,1′-didodecyl-2,2′-tetramethylenebispyridinium dichloride (12-Py(2)-4-(2)Py-12 Cl); 1,1′-didodecyl-2,2′-octamethylenebispyridinium dichloride (12-Py(2)-8-(2)Py-12 Cl); 1,1′-didodecyl-2,2′-dodecamethylenebispyridinium dichloride (12-Py(2)-12-(2)Py-12 Cl) were measured as a function of concentration and are here reported for the first time. The curve of the compound with the four carbon atoms spacer lies between those of the compound with spacer of 2 and 3 carbon atoms, not below the latter, as expected. This behaviour, we have already found for the same compounds here studied, but having methanesulfonate as counterion, is interpreted as an evidence of a conformation change of the molecule determined by stacking interactions between the two pyridinium rings, appearing at an optimum length of the spacer. The curves of apparent and molar enthalpies vs. concentration and surface tension measurements, here reported, show that this behaviour is independent on the counterion. On the contrary, the group contribution additivity for the counterion is respected, independently on the spacer length.Keywords. Apparent and partial molar enthalpies; cationic gemini surfactants; 1,1′-didodecyl-2,2′-trimethylenebispyridinium dichloride; 1,1′-didodecyl-2,2′-tetramethylenebispyridinium dichloride; 1,1′-didodecyl-2,2′-octamethylenebispyridinium dichloride; 1,1′-didodecyl-2,2′-dodecamethylenebispyridinium dichloride; micellization enthalpy, group contribution.Briefs. Apparent and partial molar enthalpies at 298 K of the aqueous solutions of cationic gemini surfactants 1,1′-didodecyl-2,2′-trimethylenebispyridinium dichloride (12-Py(2)-3-(2)Py-12 Cl);1,1′-didodecyl-2,2′-tetramethylenebispyridinium dichloride (12-Py(2)-4-(2)Py-12 Cl); 1,1′-didodecyl-2,2′-octamethylenebispyridinium dichloride (12-Py(2)-8-(2)Py-12 Cl); 1,1′-didodecyl-2,2′-dodecamethylenebispyridinium dichloride (12-Py(2)-12-(2)Py-12 Cl) have been measured as a function of concentration, in order to confirm the lack of methylene group additivity with respect to the enthalpic properties of the solutions, when it is added in the spacer, already found in the case of methansulfonates. The data obtained support the hypothesis of a conformation change dependent on the spacer length, but independent on the counterion.

show abstract

“…[17,[44][45][46][47] Encouraging results in gene delivery have been obtained by some of us by using ammonium geminis urfactants as derivatives of N,N-bisdimethyl-1,2-ethanediamine with the general formula C n H 2n+ +1 OOCCH 2 (CH 3 ) 2 N + CH 2 CH 2 N + (CH 2 ) 2 CH 2 COOC n H 2n+ +1 /2 Cl À (bis-C n BEC), in which the subscript n stands for the number of Pyridinium geminis urfactants with hexadecyl chains linked to nitrogen atoms and at uned aliphatic spacer that bridges the two pyridinium polar heads in 2,2'-positions have been synthesized and characterized. Am ultitechnique approachallowed us to study the aggregation behavior,u sing conductivity,s urface tension,a nd fluorescence.…”

Section: Introductionmentioning

confidence: 97%

“…[17] We then synthesized cationic gemini surfactants that contained two pyridinium groups with dodecyl [10] and fluoroalkyl chains. [48] Thep yridinium group should account for better interaction with the DNA phosphate group owing to higherc harge dispersion with respect to ammonium head groups;c hloride counterion is normally used since it is nontoxic.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Physicochemical Characterization, and Interaction with DNA of Long‐Alkyl‐Chain Gemini Pyridinium Surfactants

et al. 2015

View full text Add to dashboard Cite

Pyridinium gemini surfactants with hexadecyl chains linked to nitrogen atoms and a tuned aliphatic spacer that bridges the two pyridinium polar heads in 2,2′‐positions have been synthesized and characterized. A multitechnique approach allowed us to study the aggregation behavior, using conductivity, surface tension, and fluorescence. Graphs of the specific conductivity (κ) versus the surfactant molar concentration (C), and graphs of the molar conductivity (Λ) versus C0.5 suggest pre‐aggregation phenomena of these amphiphiles at very low concentration. The trends of Amin as a function of the spacer length confirm the hypothesis of a conformational change of the molecule with four methylene groups as spacer owing to stacking interactions between the two pyridinium rings mediated by the counterion. Moreover, the trends of Amin and counterion binding (β) suggest that the spacer must be longer than eight carbon atoms to fold efficiently toward the micellar core. The opportunity to tune the surfactant structure and aggregation properties make those surfactants—particularly the long‐chain ones for which the DNA complexing ability was shown by means of atomic force microscopy (AFM) imaging—desirable candidates for gene‐delivery experiments.

show abstract

Biologically active bisquaternary ammonium chlorides: physico?chemical properties of long chain amphiphiles and their evaluation as non-viral vectors for gene delivery

Cited by 41 publications

References 45 publications

Thermodynamics of aqueous solutions of dodecyldimethylethylammonium bromide

Thermodynamics of aqueous solutions of dodecyldimethylethylammonium bromide

Is the counterion responsible for the unusual thermodynamic behaviour of the aqueous solutions of gemini bispyridinium surfactants?

Synthesis, Physicochemical Characterization, and Interaction with DNA of Long‐Alkyl‐Chain Gemini Pyridinium Surfactants

Contact Info

Product

Resources

About