Membrane-destabilizing activity of pH-responsive cationic lysine-based surfactants: role of charge position and alkyl chain length

Nogueira, Daniele Rubert; Mitjans, Montserrat; Morán, Carmen; Pérez, Lourdes; Vinardell, M. Pilar

doi:10.1007/s00726-011-1176-8

Cited by 24 publications

(61 citation statements)

References 53 publications

(72 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Interestingly, commercial AgSD cream at the same AgSD concentration showed higher cytotoxicity than AgSD bulk powders. Maybe the solubilization effect and cytomembrane permeability prompting effect of surfactants existing in the cream aggravated the cytotoxicity of AgSD [38].…”

Section: Discussionmentioning

confidence: 99%

Evaluation of genipin-crosslinked chitosan hydrogels as a potential carrier for silver sulfadiazine nanocrystals

Gao

Gan²,

Meng³

et al. 2016

Colloids and Surfaces B: Biointerfaces

View full text Add to dashboard Cite

Section: Discussionmentioning

confidence: 99%

Evaluation of genipin-crosslinked chitosan hydrogels as a potential carrier for silver sulfadiazine nanocrystals

Gao

Gan²,

Meng³

et al. 2016

Colloids and Surfaces B: Biointerfaces

View full text Add to dashboard Cite

“…16 For these surfactants, the variation of pH promotes a variation in the protonation state that would lead to changes in their amphiphilicity and aggregation shape, 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 13 (having specific phospholipid composition and mechanical properties of the cytoskeleton 32,33 ) also had varied hemolytic behavior in the presence of surfactants 34,35 and of other different substances.…”

Section: Surfactants Induced Hemolysis and Antihemolysismentioning

confidence: 99%

“…Therefore, to gain better mechanistic understanding of surfactant-induced biomembrane destabilization and to complete our previous study, 16 here we assessed the phospholipid bilayerperturbing properties of three novel cationic lysine-based surfactants derived from the salts, N ε and N α -acyl lysine methyl ester. We chose rat and human erythrocytes and their membranes as in vitro models to study the hemolytic activity of surfactants and their effects on osmotic resistance and morphology of cells, as well as on membrane fluidity and the membrane protein profile with varying pH.…”

Section: Introductionmentioning

confidence: 99%

“…4,7 Previous studies by our group showed that one novel class of cationic surfactants derived from the amino acid lysine (hydrochloride salts of N ε -acyl lysine methyl ester) has pH-sensitive membrane-lytic activity, which is dependent on the fine-tuning of the cationic charge position, and thus is promising as a bioactive excipient in intracellular drug delivery systems. 16 This knowledge, together with a deeper study of the interaction properties of these compounds with the phospholipid bilayer, is key to the design of efficient intracellular drug carriers with specific endosome-destabilizing activity.…”

Section: Introductionmentioning

confidence: 99%

“…8,11,43 In our previous study, we found no significant correlation between the HC 50 and the CMC of the surfactants. 16 Here, we have studied the potential correlation between antihemolytic activity and the CMC. We found that the cAH max values were lower than the CMC (Table 1), but no significant correlations were obtained.…”

mentioning

confidence: 99%

See 2 more Smart Citations

Phospholipid Bilayer-Perturbing Properties Underlying Lysis Induced by pH-Sensitive Cationic Lysine-Based Surfactants in Biomembranes

Nogueira¹,

Mitjans

Busquets³

et al. 2012

Langmuir

Self Cite

View full text Add to dashboard Cite

Amino acid-based surfactants constitute an important class of natural surface-active biomolecules with unpredictable number of industrial applications. To gain better mechanistic understanding of surfactant-induced membrane destabilization, we assessed the phospholipid bilayer-perturbing properties of new cationic lysine-based surfactants. We used erythrocytes as biomembrane models to study the hemolytic activity of surfactants and their effects on cells' osmotic resistance and morphology, as well as on membrane fluidity and membrane protein profile with varying pH. The antihemolytic capacity of amphiphiles correlated negatively with the length of the alkyl chain.Anisotropy measurements showed that the pH-sensitive surfactants, with the positive charge on the α-amino group of lysine, significantly increased membrane fluidity at acidic conditions. SDS-PAGE analysis revealed that surfactants induced significant degradation of membrane proteins in hypo-osmotic medium and at pH 5.4. By scanning electron microscopy examinations, we corroborated the interaction of surfactants with lipid bilayer. We found that varying the surfactant chemical structure is a way to modulate the positioning of the molecule inside bilayer and, thus, the overall effect on the membrane. Our work showed that pH-sensitive lysine-based surfactants significantly disturb the lipid bilayer of biomembranes especially at acidic conditions, which suggests that these compounds are promissing as a new class of multifunctional bioactive excipients for active intracellular drug delivery.

show abstract

A study of the anti‐plasmodium activity of angiotensin II analogs

Chamlian

Bastos

Maciel

et al. 2013

Journal of Peptide Science

View full text Add to dashboard Cite

Controlling the dissemination of malaria requires the development of new drugs against its etiological agent, a protozoan of the Plasmodium genus. Angiotensin II and its analog peptides exhibit activity against the development of immature and mature sporozoites of Plasmodium gallinaceum. In this study, we report the synthesis and characterization of angiotensin II linear and cyclic analogs with anti-plasmodium activity. The peptides were synthesized by a conventional solid-phase method on Merrifield's resin using the t-Boc strategy, purified by RP-HPLC and characterized by liquid chromatography/ESI (+) MS (LC-ESI(+)/MS), amino acid analysis, and capillary electrophoresis. Anti-plasmodium activity was measured in vitro by fluorescence microscopy using propidium iodine uptake as an indicator of cellular damage. The activities of the linear and cyclic peptides are not significantly different (p < 0.05). Kinetics studies indicate that the effects of these peptides on plasmodium viability overtime exhibit a sigmoidal profile and that the system stabilizes after a period of 1 h for all peptides examined. The results were rationalized by partial least-square analysis, assessing the position-wise contribution of each amino acid. The highest contribution of polar amino acids and a Lys residue proximal to the C-terminus, as well as that of hydrophobic amino acids in the N-terminus, suggests that the mechanism underlying the anti-malarial activity of these peptides is attributed to its amphiphilic character.

show abstract

Membrane-destabilizing activity of pH-responsive cationic lysine-based surfactants: role of charge position and alkyl chain length

Cited by 24 publications

References 53 publications

Evaluation of genipin-crosslinked chitosan hydrogels as a potential carrier for silver sulfadiazine nanocrystals

Evaluation of genipin-crosslinked chitosan hydrogels as a potential carrier for silver sulfadiazine nanocrystals

Phospholipid Bilayer-Perturbing Properties Underlying Lysis Induced by pH-Sensitive Cationic Lysine-Based Surfactants in Biomembranes

A study of the anti‐plasmodium activity of angiotensin II analogs

Contact Info

Product

Resources

About