Decapaptide-12

Decapaptide-12

Identifiers
IUPAC name (2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-3-hydroxypropanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]hexanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-hydroxypropanoyl]amino]-3-hydroxypropanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-3-(4-hydroxyphenyl)propanoic acid
CAS Number	137665-91-9
PubChem CID	25077748
Chemical and physical data
Formula	C65H90N18O17
Molar mass	1395.544 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1=CC=C2C(=C1)C(=CN2)C[C@@H](C(=O)N[C@@H](CC3=CC=C(C=C3)O)C(=O)O)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H](CC4=CC=C(C=C4)O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CO)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC5=CC=C(C=C5)O)N
InChI InChI=1S/C65H90N18O17/c66-24-4-3-9-45(76-55(91)47(11-6-26-73-65(70)71)77-60(96)51(32-84)81-57(93)46(10-5-25-72-64(68)69)75-54(90)43(67)27-35-12-18-39(87)19-13-35)56(92)78-48(28-36-14-20-40(88)21-15-36)58(94)82-53(34-86)62(98)83-52(33-85)61(97)79-49(30-38-31-74-44-8-2-1-7-42(38)44)59(95)80-50(63(99)100)29-37-16-22-41(89)23-17-37/h1-2,7-8,12-23,31,43,45-53,74,84-89H,3-6,9-11,24-30,32-34,66-67H2,(H,75,90)(H,76,91)(H,77,96)(H,78,92)(H,79,97)(H,80,95)(H,81,93)(H,82,94)(H,83,98)(H,99,100)(H4,68,69,72)(H4,70,71,73)/t43-,45-,46-,47-,48-,49-,50-,51-,52-,53-/m0/s1 Key:OYVFAMLECFSFEI-XJHNTGDTSA-N

Decapaptide-12 (Lumixyl) is a synthetic 10-amino acid peptide with the sequence YRSRKYSSWY or Tyr-Arg-Ser-Arg-Lys-Tyr-Ser-Ser-Trp-Tyr, which acts to inhibit the synthesis of melanin by blocking the enzyme tyrosinase. It has been investigated for medical uses in treatment of hyperpigmentation disorders such as melasma, and has also been sold off-label as a skin-lightening product. ^{[1] [2] [3] [4] [5] [6] [7]}

See also

• Hydroquinone
• Melanotan II

References

1. Abu Ubeid A, Zhao L, Wang Y, Hantash BM (September 2009). "Short-sequence oligopeptides with inhibitory activity against mushroom and human tyrosinase". The Journal of Investigative Dermatology. 129 (9): 2242–2249. doi:10.1038/jid.2009.124. PMID   19440221.
2. Kassim AT, Hussain M, Goldberg DJ (April 2012). "Open-label evaluation of the skin-brightening efficacy of a skin-brightening system using decapeptide-12". Journal of Cosmetic and Laser Therapy. 14 (2): 117–121. doi:10.3109/14764172.2012.672745. PMID   22401652.
3. Ramírez SP, Carvajal AC, Salazar JC, Arroyave G, Flórez AM, Echeverry HF (June 2013). "Open-label evaluation of a novel skin brightening system containing 0.01% decapeptide-12 in combination with 20% buffered glycolic acid for the treatment of mild to moderate facial melasma". Journal of Drugs in Dermatology. 12 (6): e106 –e110. PMID   23839199.
4. Bhatia A, Hsu JT, Hantash BM (January 2014). "Combined topical delivery and dermalinfusion of decapeptide-12 accelerates resolution of post-inflammatory hyperpigmentation in skin of color". Journal of Drugs in Dermatology. 13 (1): 84–85. PMID   24385124.
5. "Tyrosinase inhibitors with potent anti-senescence activity in human neonatal keratinocyte progenitors". Journal of Dermatologic Surgery, Research and Therapy: 30–39. 2019. doi:10.29199/derm.101018.
6. Chen J, Bian J, Hantash BM, Albakr L, Hibbs DE, Xiang X, et al. (September 2021). "Enhanced skin retention and permeation of a novel peptide via structural modification, chemical enhancement, and microneedles". International Journal of Pharmaceutics. 606 120868. doi:10.1016/j.ijpharm.2021.120868. PMID   34242628.
7. Hariri R, Saeedi M, Akbarzadeh T (July 2021). "Naturally occurring and synthetic peptides: Efficient tyrosinase inhibitors". Journal of Peptide Science. 27 (7) e3329. doi:10.1002/psc.3329. PMID   33860571.