[Ala92]-p16 (84-103)

Cyclin-dependent kinase inhibitor CAS# 189064-08-2

[Ala92]-p16 (84-103)

2D Structure

Catalog No. BCC5837----Order now to get a substantial discount!

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[Ala92]-p16 (84-103)

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Chemical Properties of [Ala92]-p16 (84-103)

Cas No. 189064-08-2 SDF Download SDF
PubChem ID 71308539 Appearance Powder
Formula C93H155N31O26 M.Wt 2123.44
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble to 2 mg/ml in water
Sequence DAAREGFLATLVVLHRAGAR
Chemical Name (4S)-4-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-3-carboxypropanoyl]amino]propanoyl]amino]propanoyl]amino]-5-carbamimidamidopentanoyl]amino]-5-[[2-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S,3R)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-5-carbamimidamido-1-[[(2S)-1-[[2-[[(2S)-1-[[(1S)-4-carbamimidamido-1-carboxybutyl]amino]-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-1-oxopropan-2-yl]amino]-1-oxopentan-2-yl]amino]-3-(1H-imidazol-4-yl)-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-2-oxoethyl]amino]-5-oxopentanoic acid
SMILES CC(C)CC(C(=O)NC(C)C(=O)NC(C(C)O)C(=O)NC(CC(C)C)C(=O)NC(C(C)C)C(=O)NC(C(C)C)C(=O)NC(CC(C)C)C(=O)NC(CC1=CNC=N1)C(=O)NC(CCCNC(=N)N)C(=O)NC(C)C(=O)NCC(=O)NC(C)C(=O)NC(CCCNC(=N)N)C(=O)O)NC(=O)C(CC2=CC=CC=C2)NC(=O)CNC(=O)C(CCC(=O)O)NC(=O)C(CCCNC(=N)N)NC(=O)C(C)NC(=O)C(C)NC(=O)C(CC(=O)O)N
Standard InChIKey SRSWQMWUNOIPDH-QCDQIEFZSA-N
Standard InChI InChI=1S/C93H155N31O26/c1-43(2)33-61(118-84(143)64(36-54-23-18-17-19-24-54)113-67(127)41-106-79(138)59(28-29-68(128)129)116-81(140)58(26-21-31-103-92(97)98)114-76(135)51(14)109-74(133)50(13)110-78(137)56(94)38-69(130)131)82(141)112-52(15)77(136)124-72(53(16)125)89(148)121-63(35-45(5)6)86(145)122-71(47(9)10)88(147)123-70(46(7)8)87(146)120-62(34-44(3)4)83(142)119-65(37-55-39-101-42-107-55)85(144)115-57(25-20-30-102-91(95)96)80(139)111-48(11)73(132)105-40-66(126)108-49(12)75(134)117-60(90(149)150)27-22-32-104-93(99)100/h17-19,23-24,39,42-53,56-65,70-72,125H,20-22,25-38,40-41,94H2,1-16H3,(H,101,107)(H,105,132)(H,106,138)(H,108,126)(H,109,133)(H,110,137)(H,111,139)(H,112,141)(H,113,127)(H,114,135)(H,115,144)(H,116,140)(H,117,134)(H,118,143)(H,119,142)(H,120,146)(H,121,148)(H,122,145)(H,123,147)(H,124,136)(H,128,129)(H,130,131)(H,149,150)(H4,95,96,102)(H4,97,98,103)(H4,99,100,104)/t48-,49-,50-,51-,52-,53+,56-,57-,58-,59-,60-,61-,62-,63-,64-,65-,70-,71-,72-/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of [Ala92]-p16 (84-103)

DescriptionPeptide derived from the tumor suppressor protein p16; inhibits cyclin-dependent kinase-4 (cdk4)/cyclin D1 (IC50 ~ 1.5 μM) and binds to cdk6.

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References on [Ala92]-p16 (84-103)

Characterization of the cyclin-dependent kinase inhibitory domain of the INK4 family as a model for a synthetic tumour suppressor molecule.[Pubmed:9482104]

Oncogene. 1998 Feb 5;16(5):587-96.

We have previously shown that a 20 amino acid peptide derived from the third ankyrin-like repeat of the p16CDKN2/INK4a (p16) tumour suppressor protein (residues 84-103 of the human p16 protein) can bind to cdk4 and cdk6 and inhibit cdk4-cyclin D1 kinase activity in vitro as well as block cell cycle progression through G1. Substitution of two valine residues corresponding to amino acids 95 and 96 (V95A and V96A) of the p16 peptide reduces the binding to cdk4 and cdk6 and increases its IC0.5 for kinase inhibition approximately threefold when linked to the Antennapedia homeodomain carrier sequence. The same mutations increase the IC0.5 approximately fivefold in the p16 protein. Substitution of aspartic acid 92 by alanine instead increases the binding of the peptide to cdk4 and cdk6 and the kinase inhibitory activity. The p16 peptide blocks S-phase entry in non-synchronized human HaCaT cells by approximately 90% at a 24 microM concentration. The V95A and V96A double substitution minimizes the cell cycle inhibitory capacity of the peptide whereas the D92A substitution increases its capacity to block cell cycle progression. A deletion series of the p16 derived peptide shows that a 10 residue peptide still retains cdk4-cyclin D1 kinase and cell cycle inhibitory activity. The p16 peptide inhibited S-phase entry in five cell lines tested, varying between 47-75%, but had only a limited (11%) inhibitory effect in the pRb negative Saos-2 cells at a concentration of 24 microM. Like the full length p16 protein, the p16 peptide does not inhibit cyclin E dependent cdk2 kinase activity in vitro. These data suggest that acute inhibition of CDK-cyclin D activity by a peptide derived from the INK4 family will stop cells in late G1 in a pRb dependent fashion.

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