Argireline

• CAT Number: I004327
• CAS Number: 616204-22-9
• Molecular Formula: C34H60N14O12S
• Molecular Weight: 888.99
• Purity: ≥95%
• Solubility: H2O: ≥ 8.8 mg/mL
• Storage: Store at -20°C
• IUPAC Name: (4S)-4-acetamido-5-[[(2S)-1-[[(2S)-1-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-amino-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-5-oxopentanoic acid
• InChI: InChI=1S/C34H60N14O12S/c1-17(49)43-20(8-11-25(51)52)29(57)47-22(9-12-26(53)54)31(59)48-23(13-16-61-2)32(60)46-21(7-10-24(35)50)30(58)45-19(6-4-15-42-34(39)40)28(56)44-18(27(36)55)5-3-14-41-33(37)38/h18-23H,3-16H2,1-2H3,(H2,35,50)(H2,36,55)(H,43,49)(H,44,56)(H,45,58)(H,46,60)(H,47,57)(H,48,59)(H,51,52)(H,53,54)(H4,37,38,41)(H4,39,40,42)/t18-,19-,20-,21-,22-,23-/m0/s1
• InChIKey: RJZNPROJTJSYLC-LLINQDLYSA-N
• SMILES: CC(=O)NC(CCC(=O)O)C(=O)NC(CCC(=O)O)C(=O)NC(CCSC)C(=O)NC(CCC(=O)N)C(=O)NC(CCCN=C(N)N)C(=O)NC(CCCN=C(N)N)C(=O)N

Argireline (CAT: I004327) is a synthetic peptide that is used in skincare and cosmetic products. It is known for its anti-wrinkle properties and is often referred to as a “Botox alternative” due to its ability to mimic the effects of botulinum toxin (BoNTs). Argireline works by inhibiting the release of neurotransmitters involved in muscle contractions, which can help relax facial muscles and reduce the appearance of wrinkles and fine lines. It is considered non-toxic and is widely used in various anti-aging formulations to target specific areas of the face and promote a more youthful appearance.

Reference

[1]. J Cosmet Laser Ther. 2013 Aug;15(4):237-41. doi: 10.3109/14764172.2013.769273. Epub 2013 Mar 6.
The anti-wrinkle efficacy of Argireline.
Wang Y(1), Wang M, Xiao XS, Huo J, Zhang WD.
Author information: (1)The second hospital of Xi'an Jiaotong University, Xi'an, PR China.
BACKGROUND: Argireline, a synthetic peptide, which is patterned from the N-terminal end of the protein SNAP-25, can both reduce the degree of existing facial wrinkles and demonstrate effectively against their development. In our past studies, we found out that Argireline had a significant anti-wrinkle effect in Chinese subjects and that it was safe and well tolerated. OBJECTIVE: To observe the effect of Argireline on histological changes in the skin in the aged mice induced by D-galactose. METHODS: Argireline was applied to the aged mice twice daily for 6 weeks. The histological changes in skin tissue were evaluated using hematoxylin-eosin (HE) and picrosirius-polarization (PSP) stains. The amount of type I and of type III collagen fibers were also semi-quantitatively compared using software Image-ProPlus. RESULTS: There was an improvement in the histological structure of skin tissue in the aged mice; the amount of type I collagen fibers increased (P < 0.01), while that of type III collagen fibers decreased (P < 0.05). CONCLUSIONS: This study revealed that Argireline could improve the histological structure of skin tissue and rejuvenate the aging skin.
DOI: 10.3109/14764172.2013.769273 PMID: 23464592 [Indexed for MEDLINE]

[2]. Chem Biodivers. 2021 Mar;18(3):e2000992. doi: 10.1002/cbdv.202000992. Epub 2021 Feb 8.
Argireline: Needle-Free Botox as Analytical Challenge.
Kluczyk A(1), Ludwiczak J(1), Modzel M(1), Kuczer M(1), Cebrat M(1), Biernat M(1), Bąchor R(1).
Author information: (1)Faculty of Chemistry, University of Wroclaw, F. Joliot-Curie 14, PL-50-383, Wroclaw, Poland.
Argireline-containing cosmetics attract public interest due to their confirmed reduction of facial wrinkles. Argireline is a peptide that works by inhibiting the release of neurotransmitters in the neuromuscular junction, producing a botox-like effect. Therefore, it is used as a safe needle-free alternative to botox treatment. In this work we investigated the presence of Argireline in cosmetic creams and sera by application of reversed phase liquid chromatography and tandem mass spectrometry (RP-HPLC/MS and MS/MS). The analysis revealed the presence of argireline and its oxidized form in several different cosmetics. The methionine residue in Argireline sequence was indicated as oxidation point according to neutral loss MS studies. The developed sample preparation strategy minimizes and monitors methionine oxidation, bringing to our attention the question of impact of ingredients on the stability of cosmetic product.
DOI: 10.1002/cbdv.202000992 PMID: 33482052 [Indexed for MEDLINE]

[3]. Acta Biochim Pol. 2014;61(1):29-32. Epub 2014 Mar 17.
The study of cellular cytotoxicity of argireline – an anti-aging peptide.
Grosicki M(1), Latacz G(1), Szopa A(1), Cukier A(1), Kieć-Kononowicz K(1).
Author information: (1)Department of Technology and Biotechnology of Drugs, Jagiellonian University Medical College, Kraków, Poland.
Argireline is well know, innovative anti-aging product used in the cosmetic market. This short chain peptide is used as active ingredient in dermal ointment and creams. Argireline prevents formation of skin lines and wrinkles in a very similar way to the botulinum toxin (Botox), inhibiting neurotransmitter release at the neuromuscular junction. Argireline does not require under skin muscle injections and it is believed to be relatively safe. However, despite the fact that some toxicity data has been provided by the product manufacturer, there is an evident lack of reliable information about cytotoxicity of argireline in the literature. The aim of the presented study was to estimate the antiproliferation effect of argireline solution in several concentrations. The influence of argireline on cellular proliferation was examined against: human embryonic kidney HEK-293 cell line, human neuroblastoma IMR-32 cell line, and human primary skin fibroblasts. Tests were performed using formazan-based cell proliferation assay: EZ4U, which allows to measure the efficiency of mitochondrial oxidative activity in living cells. The argireline inhibitory concentration, IC50 values were calculated and the results were compared to the IC50 value of the reference compound: doxorubicin. In conclusion, the considered method resulted in dose-dependent argireline anti-proliferation effects. However, the significant cytotoxicity of argireline solution was observed under 18 to 10 000 fold higher concentrations (depending on cells that were examined) in comparison to doxorubicin.
PMID: 24644551 [Indexed for MEDLINE]

[4]. Am J Clin Dermatol. 2013 Apr;14(2):147-53. doi: 10.1007/s40257-013-0009-9.
The anti-wrinkle efficacy of argireline, a synthetic hexapeptide, in Chinese subjects: a randomized, placebo-controlled study.
Wang Y(1), Wang M, Xiao S, Pan P, Li P, Huo J.
Author information: (1)The Second Hospital of Xi'an Jiaotong University, No. 157 of Xi Wu Road, Xi'an, China.
BACKGROUND: Argireline is a synthetic peptide that is patterned from the N-terminal end of the protein SNAP-25 and has been shown to reduce the degree of facial wrinkles. It is reported to inhibit vesicle docking by preventing formation of the ternary SNARE complex and by interfering in catecholamine release. The anti-wrinkle efficacy of argireline has not been studied in Chinese subjects. OBJECTIVE: The objective of the study was to evaluate the safety and efficacy of argireline in the treatment of peri-orbital wrinkles in Chinese subjects. METHODS: A total of 60 subjects received a randomized treatment of argireline or placebo in a ratio of 3:1. Argireline or placebo was applied to their peri-orbital wrinkles twice daily for 4 weeks, and then evaluations were made for the improvements in wrinkles. In the subjective evaluation, Daniell's classification and Seeman's standard were applied to make a global assessment of changes in the appearance of peri-orbital lines. In the objective evaluation, silicone replicas of the skin at the application area were made before and after the treatment, which were analyzed by a wrinkle-analysis apparatus. RESULTS: In the subjective evaluation, the total anti-wrinkle efficacy in the argireline group was 48.9 %, compared with 0 % in the placebo group. In the objective evaluation, the parameters of roughness were all decreased in the argireline group (p < 0.01), while no decrease was obvious in the placebo group (p > 0.05). CONCLUSIONS: This study showed that argireline had a significant anti-wrinkle effect in Chinese subjects.
DOI: 10.1007/s40257-013-0009-9 PMID: 23417317 [Indexed for MEDLINE]

[5]. J Cosmet Laser Ther. 2013 Apr 22. doi: 10.3109/14764172.2012.759234. Online ahead of print.
The anti wrinkle efficacy of synthetic hexapeptide (Argireline) in Chinese Subjects.
Wang Y, Wang M, Xiao XS, Pan P, Li P, Huo J.
Abstract Background: This is the first multicenter clinical and experimental study of the anti wrinkle efficacy of Argireline in Chinese subjects. Objective: To evaluate the safety and efficacy of Argireline in the treatment of periorbital lines in Chinese subjects, and to observe the effect of Argireline on microstructural changes of the skin in the aged mice induced by D-galactose. Methods: The study was comprised of two parts: i) Clinical study: A total of 60 subjects received a single treatment in a 3:1 randomization ratio of Argireline: placebo. Argireline or placebo was applied to their periorbital wrinkles twice daily for 4 weeks, evaluations were made for the improvements in wrinkles. ii) Animal study: Argireline was applied to the aged mice twice daily for 6 weeks and the histopathological changes of skin tissue were evaluated. Results: In humans, the total anti wrinkle efficiency in the Argireline group was 48.9%, the depth of the wrinkles was notably reduced(P<0.01). In the aged mice, there was improvements in the morphology of skin tissue, the amount of typeⅠcollagen fibers increased(P<0.01) while type Ⅲ collagen fibers decreased (P<0.05). Conclusions: The studies revealed that Argireline had significant anti wrinkle effects in Chinese subjects.
DOI: 10.3109/14764172.2012.759234 PMID: 23607739