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ACS Omega
2026 Mar 07;1113:20691-20702. doi: 10.1021/acsomega.5c12526.
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Novel Palmitoyl Pentapeptides: Self-Assembly, Collagen Stimulation, Antioxidant Activity, and Influence of Skin Microbiota Health.
Pelin JNBD, de Mello LR, Siqueira RAGB, de Souza Alves M, Castelletto V, Almeida JF, Seitsonen J, Lopes PS, Leite-Silva V, Andreo-Filho N, Hamley IW.
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New lipopeptide analogues of C16-KTTKS, containing tyrosine (C16-KTTKY) and glutamic acid (C16-KTTKE) residues, were characterized by physicochemical and biological assays to understand their collagen stimulation and ability to control skin commensal microorganism growth. The presence of nanotapes based on stacked lipopeptide lamellae was confirmed by cryogenic transmission electron microscopy and small-angle X-ray scattering. Variations in zeta potential as a function of lipopeptide concentration indicated the electrostatic stability of C16-KTTKE, while C16-KTTKY was stable at a lower concentration, with a similar aggregation state. Circular dichroism spectra revealed a transition from random coil to β-sheet for both peptides with increasing temperature (up to 50 °C). Significant statistical reductions in cell viability below 70% were observed at concentrations above 0.00625 wt % for C16-KTTKE and 0.00156 wt % for C16-KTTKY, respectively. At higher lipopeptide concentrations, C16-KTTKE promotes a decrease in total collagen production by human dermal fibroblasts; however, it has antioxidant properties. In contrast, C16-KTTKY stimulates a considerable increase in the level of total collagen production. The lipopeptides were found to stimulate S. epidermidis growth, a microorganism very important for skin microbiota health. Therefore, both lipopeptides have interesting characteristics as active ingredients in antiaging cosmetic products.
1. Molecular structures
of C16–KTTKY and C16–KTTKE lipopeptides.
2. Emission spectra for solutions containing
2.2 × 10–5 wt % pyrene and solutions with different
concentrations (2.5 ×
10–4 to 0.1 wt %) of (a) C16–KTTKE
and (c) C16–KTTKY with λexcitation = 339 nm and slits of 2.5/5. Intensity of pyrene fluorescence as
a function of concentration for (b) C16–KTTKE and
(d) C16–KTTKY.
3. CD spectra
for 0.5 wt % aqueous solutions of (a) C16–KTTKE
and (b) C16–KTTKY, at the temperatures
indicated.
4. Cryo-TEM images from 1 wt % solutions of (a) C16–KKTKE
and (b) C16–KTTKY.
5. SAXS data for 1 wt % solutions of C16–KTTKE and
C16–KTTKY, as indicated. The data for C16–KTTKE have been fitted with a bilayer form factor model,
as described in the text. For ease of visualization, only every 5th
data point is shown.
6. Cell viability (relative
to control, media only) from MTT assays
for (a) C16–KTTKE and (b) C16–KTTKY.
The statistical test used was ANOVA, n = 3 with Bonferroni
correction multiple comparisons with ** p < 0.01.
7. Total collagen deposited
was quantified with the help of the picrosirius
for (a) C16–KTTKE, (b) C16–KTTKY.
The production of collagen per cell is shown in (c) and (d) for C16–KTTKE and C16–KTTKY, respectively.
The statistical test used for data treatment was ANOVA, n = 3 with Bonferroni correction multiple comparisons, with ** p < 0.01.
8. Inhibition of growth
of S. epidermidis: (a) film paper before
TTC staining (1 and 2: C16–KTTKE;
3 and 4: C16–KTTKY; (b) inhibition by film paper,
after TTC staining (1 and 2: C16–KTTKE; 3 and 4:
C16–KTTKY); (c) inhibition by well, before TTC staining
(1 and 2: C16–KTTKE; 3 and 4: C16–KTTKY)
and (d) after TTC staining (1 and 2: C16–KTTKE;
3 and 4: C16–KTTKY). Microdilution tests: (e) C16–KTTKE and (f) C16–KTTKY. PC: positive
control (medium + microorganisms) and CC: cell control (medium). ANOVA
test ***p < 0.001.
9. Antioxidant activity using two different concentrations
of lipopeptides
C16–KTTKY (a) and C16–KTTKE (b)
lipopeptides. Fluorescence obtained with the ROS test in comparison
to resveratrol 250 μM. Resveratrol was used as a positive control,
H2O2 as a negative control, and CC as cell control.
ANOVA test ***p < 0.001.
