Design and efficient synthesis of novel ascorbyl conjugated peptide with high collagen biosynthesis stimulating effects

Choi, Hee Cheul; Kim, Heung-Jae; Park, Jong-Il; Shin, Eun-Ho; Kim, Dong-Won; Kim, Soung-Soo

doi:10.1016/j.bmcl.2008.10.112

Cited by 21 publications

(11 citation statements)

References 9 publications

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“…[45,46] Flash column chromatography purifications were performed with silica gel 60 (230-400 mesh). (R)-3,4-Bis(benzyloxy)-5-[(S)-1,2-dihydroxyethyl]furan-2(5H)-one was prepared according to ap rocedure reported in the literature (see the Supporting Information).…”

Section: Synthesis and Sample Preparationmentioning

confidence: 99%

Organogels from Double‐Chained Vitamin C Amphiphilic Derivatives

et al. 2017

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The syntheses and physicochemical characterization of double-chained amphiphilic compounds obtained from vitamin C are reported: dialkanoyl-5,6-O-ascorbic acid esters (Di-ASCn, n=8, 10, and 12). The acetyl-5-dodecanoyl-6-ascorbic acid ester is synthesized and investigated for comparison. These products are quite insoluble in water and in polar solvents, although they form homogeneous dispersions in cyclohexane. Upon cooling, these dispersions turn into a gel-like phase. Differential scanning calorimetry, FTIR spectroscopy, and small- and wide-angle X-ray scattering experiments are performed to investigate the properties of pure solids and their liquid dispersions. Di-ASCn retain the same redox properties of the parent molecule and represent a valid candidate for the production of nanosized protective carriers for valuable guests that are sensitive to oxidative radical attack. Moreover, the contribution of the vitamin C hydroxyl group in position 5 to the overall hydration properties of single- and double-chained amphiphilic derivatives is discussed.

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Section: Synthesis and Sample Preparationmentioning

confidence: 99%

Organogels from Double‐Chained Vitamin C Amphiphilic Derivatives

et al. 2017

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“…These characteristics suggest that the SAP may be a useful cosmeceutical material (15). Here, we describe the activity of a novel compound, which is not only physically stable, but which also displays anti-aging, wound-healing, and skin-whitening activities.…”

Section: Discussionmentioning

confidence: 99%

“…SAP was synthesized by modifying the strategy (16) described in our previous report (15). The linear peptide KTTKS was synthesized on a 2-chlorotrityl resin preloaded with Fmoc-serine using standard Fmoc chemistry employing HBTU/HOBt as a coupling reagent.…”

Section: Synthesis Of the Sap Compound And The In Vitro Stability Testmentioning

confidence: 99%

A novel L-ascorbic acid and peptide conjugate with increased stability and collagen biosynthesis

Choi¹,

Park²,

Kim³

et al. 2009

BMB Reports

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L-ascorbic acid (Vitamin C) and peptide are both useful compounds for collagen biosynthesis in cosmeceuticals (cosmetic and pharmaceutical fields). The instability of these compounds, however, limit their application in these industries. In this report, we describe the development of a novel compound, Stabilized Ascorbyl Pentapeptide (SAP), which physically is much more stable than L-ascorbic acid in water. The inhibitory effects of this SAP compound on tyrosinase and melanin synthesis is comparable to that of L-ascorbic acid. Importantly, the SAP compound displays no cytotoxicity at a high concentration (5 mM). The ability of SAP to promote collagen biosynthesis is greater than that of L-ascorbic acid or the KTTKS peptide alone. Considering the in vitro stability and functional effects, our data strongly suggest that the SAP compound is a good candidate not only as a cosmetic ingredient, but also as a wound healing agent. [BMB reports 2009; 42(11): 743-746]

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“…Recently, Choi et al . reported the enhanced stability of an ascorbyl conjugate of KTTKS, known as stabilized ascorbyl pentapeptide (SAP), in the rat skin homogenate (Choi et al ., 2009). In this study, pal-KTTKS was found to be more stable than KTTKS in skin extracts and homogenate (Fig.…”

Section: Discussionmentioning

confidence: 99%

Dermal Stability and In Vitro Skin Permeation of Collagen Pentapeptides (KTTKS and palmitoyl-KTTKS)

Choi

Park

Kim

et al. 2014

Biomolecules & Therapeutics

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Collagen pentapeptide (Lys-Thr-Thr-Lys-Ser, KTTKS) and its palmitoylated derivative (pal-KTTKS) have received a great deal of attention as cosmeceutical ingredients for their anti-wrinkle effects. The objective of this study was to evaluate stability and permeability of KTTKS and pal-KTTKS in hairless mouse skin. In this study, a liquid chromatography-tandem mass spectrometric method was developed for the quantification of pal-KTTKS, and used for stability and permeability studies. Stability studies were performed using skin extracts and homogenates. Both KTTKS and pal-KTTKS were rapidly degraded, but pal-KTTKS was more stable than KTTKS. When protease inhibitors were added, the stability of both compounds (KTTKS and pal-KTTKS) improved significantly. In the skin permeation study, neither KTTKS nor pal-KTTKS was detected in the receptor solution, which indicates that neither compound could permeate through the full-thickness hairless mouse skin in the experimental conditions of this study. While KTTKS was not detected in any of the skin layers (the stratum corneum, epidermis, and dermis), pal-KTTKS was observed in all skin layers: 4.2 ± 0.7 μg/cm2 in the stratum corneum, 2.8 ± 0.5 μg/cm2 in the epidermis, and 0.3 ± 0.1 μg/cm2 in the dermis. In conclusion, this study indicated that pal-KTTKS had greater stability and permeability than that of un-modified KTTKS, and may be a useful anti-wrinkle and anti-aging cosmeceutical agent.

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Design and efficient synthesis of novel ascorbyl conjugated peptide with high collagen biosynthesis stimulating effects

Cited by 21 publications

References 9 publications

Organogels from Double‐Chained Vitamin C Amphiphilic Derivatives

Organogels from Double‐Chained Vitamin C Amphiphilic Derivatives

A novel L-ascorbic acid and peptide conjugate with increased stability and collagen biosynthesis

Dermal Stability and In Vitro Skin Permeation of Collagen Pentapeptides (KTTKS and palmitoyl-KTTKS)

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