PeptideDB

Decapeptide-12 137665-91-9

Decapeptide-12 137665-91-9

CAS No.: 137665-91-9

Decapeptide-12, a small oligopeptide, is a tyrosinase inhibitor that interacts with the C-terminal residue of tyrosinase
Data collection:peptidedb@qq.com

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Decapeptide-12, a small oligopeptide, is a tyrosinase inhibitor that interacts with the C-terminal residue of tyrosinase (Kd: 61.1 μM). Decapeptide-12 is a competitive inhibitor of mushroom tyrosinase (IC50= 40 µM). Decapeptide-12 upregulates the transcription level of SIRT. Decapeptide-12 reduces melanin content in melanocytes and may be utilized to study melanogenesis, aging, and inflammation.

Physicochemical Properties


Molecular Formula C65H90N18O17
Molecular Weight 1395.52051401138
Exact Mass 1394.673
CAS # 137665-91-9
PubChem CID 25087629
Appearance Typically exists as solid at room temperature
LogP -6.5
Hydrogen Bond Donor Count 23
Hydrogen Bond Acceptor Count 21
Rotatable Bond Count 42
Heavy Atom Count 100
Complexity 2690
Defined Atom Stereocenter Count 0
InChi Key OYVFAMLECFSFEI-UHFFFAOYSA-N
InChi Code

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)
Chemical Name

2-[[2-[[2-[[2-[[2-[[6-amino-2-[[2-[[2-[[2-[[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
HS Tariff Code 2934.99.9001
Storage

Powder-20°C 3 years

4°C 2 years

In solvent -80°C 6 months

-20°C 1 month

Shipping Condition Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity


ln Vitro Decapeptide-12 (P4, 0.01-10 mM) inhibits human tyrosinase by 25-35% at 100 µM and inhibits mushroom tyrosinase with an IC50 value of 40 µM in a dose-dependent manner [1]. Melanocytes' melanin content is reduced by 43% by decapeptide-12 (100 μM, 7 days), while cell proliferation is unaffected [1]. With an IC50 value of 123 μM, decapeptide-12 (peptide P4, 0-400 μM) inhibits the monophenolase process [2]. Tyrosinase and decapeptide-12 interact with a Kd value of 61.1 μM[2]. Decapeptide-12 (100 μM, 72 hours) decreases the cytotoxicity of human newborn keratinocyte progenitor cells while increasing the transcription of SIRT1, SIRT3, SIRT6, and SIRT7 [3]. The proliferation of PBMC cells triggered by phytohemagglutinin (PHA) is inhibited by decapeptide-12 (0–1 mM, 72 hours) [3].
Cell Assay Cell proliferation assay[3]
Cell Types: Phytohemagglutinin (PHA) stimulated PBMC Cell
Tested Concentrations: 0, 0.025, 0.05, 0.1, 0.3, 1 mM
Incubation Duration: 72 hrs (hours)
Experimental Results: diminished cell proliferation at 0.05 mM and 54% 28% 0.1mm.

RT-PCR[3]
Cell Types: Human Neonatal Keratinocyte Progenitor Cells
Tested Concentrations: 3, 10, 30, 50, 100, 300, 500, 1000 μM
Incubation Duration: 72 hrs (hours)
Experimental Results: SIRT1 relative to untreated cells Transcription increased by 141%, and SIRT3, SIRT6, and SIRT7 increased by 121%, 147%, and 95%, respectively.
References

[1]. Short-sequence oligopeptides with inhibitory activity against mushroom and human tyrosinase. J Invest Dermatol. 2009 Sep;129(9):2242-9.

[2]. New tyrosinase inhibitory decapeptide: Molecular insights into the role of tyrosine residues. J Biosci Bioeng. 2016 Jun;121(6):607-613.

[3]. Tyrosinase inhibitors with potent anti-senescence activity in human neonatal keratinocyte progenitors. J Dermatol Surg Res Ther, 2019, 2019: 30-39.


Solubility Data


Solubility (In Vitro) May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
Solubility (In Vivo) Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300 :Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300:Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)

Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders

Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 0.7166 mL 3.5829 mL 7.1658 mL
5 mM 0.1433 mL 0.7166 mL 1.4332 mL
10 mM 0.0717 mL 0.3583 mL 0.7166 mL
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.