Hemolysis and antihemolysis induced by amino acid-based surfactants

Sánchez, Lourdes; Martı́nez, Verónica; Infante, M. R.; Mitjans, Montserrat; Vinardell, M. Pilar

doi:10.1016/j.toxlet.2007.01.003

Cited by 43 publications

(39 citation statements)

References 35 publications

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“…In an attempt to find a correlation between antihemolytic potency and the volume changes induced by the surfactants to the cell, 2 we calculated the cell volume expansion (Table 1) using the equation (1) and the data from the concentration-response curves at different osmolarities ( Figure 3). We found no significant correlations between antihemolytic potency and cell volume expansion (r = 0.9459 and r = 0.7196, p > 0.05, for human and rat erythrocytes, respectively).…”

Section: Surfactants Induced Hemolysis and Antihemolysismentioning

confidence: 99%

“…[2][3][4][5][6] Surfactants derived from amino acids constitute an important class of natural surface-active biomolecules that usually have biocompatible properties and multifunctional capabilities, which make them extremely relevant for pharmaceutical applications, especially in the field of novel non-viral drug delivery devices. 4,7,8 Our group has considerable experience in the synthesis of surfactants derived from amino acids.…”

Section: Introductionmentioning

confidence: 99%

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

Nogueira¹,

Mitjans

Busquets³

et al. 2012

Langmuir

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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.

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Section: Surfactants Induced Hemolysis and Antihemolysismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

Nogueira¹,

Mitjans

Busquets³

et al. 2012

Langmuir

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“…The cationic amino acid-derived surfactants show higher hemolytic activity than DTAB, but lower than HTAB. The anionic 12Lys12 shows higher hemolytic activity than the reference surfactant SDS due to its higher hydrophobicity (two alkyl chains) and significantly higher than 8Lys8 [51,52], indicating that for these Lys-based surfactants the biological activity is highly dependent on chain length. This can be understood if one considers that upon contact the surfactant molecules immediately insert themselves into the erythrocyte lipid bilayer [53,54], likely increasing its permeability or even its lateral expansion ability, and hence initially conferring hypotonic protection.…”

Section: Hemolytic Activitymentioning

confidence: 99%

“…This can be understood if one considers that upon contact the surfactant molecules immediately insert themselves into the erythrocyte lipid bilayer [53,54], likely increasing its permeability or even its lateral expansion ability, and hence initially conferring hypotonic protection. Ultimately, however, they induce hemolysis due to bilayer solubilisation [17,51,[55][56][57] and formation of mixed micelles. Bilayer solubilisation seems to be more efficient if the added surfactants and the bilayer lipids have similar hydrocarbon chain lengths [22].…”

Section: Hemolytic Activitymentioning

confidence: 99%

“…At cationic/anionic molar ratios where vesicles occur here (2.5:1 for 12Lys12/DTAB and 2:1 for 12Lys12/12Ser), close to equimolarity, the surfactant monomer concentration in equilibrium with the aggregates, is presumed to be rather low. This implies also that less monomeric surfactant is available in the medium to interact with the membrane and cause its disruption [51,57]. These two effects (catanionic bilayer formation and low monomer concentration) in combination could lie behind the observed decrease in toxicity of the vesicles compared to that of the neat surfactants (in micellar form).…”

Section: Hemolytic Activitymentioning

confidence: 99%

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Physicochemical and toxicological properties of novel amino acid-based amphiphiles and their spontaneously formed catanionic vesicles

Brito

Marques

Silva

et al. 2009

Colloids and Surfaces B: Biointerfaces

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a b s t r a c tThe design of efficient liposomal systems for drug delivery is of considerable biomedical interest. In this context, vesicles prepared from cationic/anionic surfactants may offer several advantages, mainly due to their spontaneity in formation and long-term stability. There is also an impending need to produce less toxic, more biocompatible amphiphiles, while maintaining the desirable aggregation properties. In this work, we present data for acute toxicity to Daphnia magna (IC 50 ), and potential ocular irritation (HC 50 ) for some newly prepared ionic surfactants with dodecyl chains, derived from the amino acids tyrosine (Tyr), serine (Ser), hydroxyproline (Hyp) and lysine (Lys). The micellization behavior of the compounds, evaluated from surface tension measurements, is presented and compared to more conventional ionic amphiphiles. Two types of spontaneouly formed catanionic vesicles, composed either by a dodecyltrimethylammonium bromide (DTAB)/Lys-derivative and or Ser-/Lys-derivative mixture, have also been tested for their ecotoxicity and hemolytic potential. All the micelle-forming surfactants as well as the vesicle-containing mixtures are found to have lower ecotoxicity than the reference surfactant DTAB. Moreover, the results from hemolysis and hemoglobin denaturation tests show that the Tyr-and Lys-derivatives are moderately irritant, whereas the Hyp-and Ser-ones are just slightly irritant. Even more significantly, the vesicle-containing mixtures exhibit lower hemolytic activity than the neat surfactants, a positive result for their potential use in liposomal formulations.

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pH‐Sensitive Vesicles Containing a Lipidic β‐Amino Acid with Two Hydrophobic Chains

Capone

Walde

Seebàch

et al. 2008

Chemistry & Biodiversity

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The lipidic beta-amino acid 2-(aminomethyl)-2-pentadecylheptadecanoic acid (1) was synthesized via the alkylation of the C(alpha)-atom of fully protected beta-alanine. Mixed large unilamellar vesicles with a diameter between 100 and 200 nm containing POPC (1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine) and 1 at a molar ratio of 9 : 1 were prepared and found to have a surface charge which is dependent on pH. At slightly acidic pH, the vesicles were positively charged, and at alkaline pH negatively charged. Dynamic light scattering, zeta potential, and cryo-transmission electron-microscopy measurements indicated that the mixed vesicles fused at pH 4-5 with negatively charged mixed vesicles composed of POPC and POPG (9.8 : 1, molar ratio), POPG being 1-palmitoyl-2-oleoyl-sn-glycero-3-[phospho-rac-(1-glycerol)].

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Hemolysis and antihemolysis induced by amino acid-based surfactants

Cited by 43 publications

References 35 publications

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

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

Physicochemical and toxicological properties of novel amino acid-based amphiphiles and their spontaneously formed catanionic vesicles

pH‐Sensitive Vesicles Containing a Lipidic β‐Amino Acid with Two Hydrophobic Chains

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