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PKC β pseudosubstrate

Selective cell-permeable PKC inhibitor peptide (attached to vector) CAS# 172308-76-8

PKC β pseudosubstrate

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Chemical structure

PKC β pseudosubstrate

3D structure

Chemical Properties of PKC β pseudosubstrate

Cas No. 172308-76-8 SDF Download SDF
PubChem ID 90488712 Appearance Powder
Formula C177H294N62O38S3 M.Wt 3994.84
Type of Compound N/A Storage Desiccate at -20°C
Synonyms Protein kinase C beta pseudosubstrate
Solubility Soluble to 1 mg/ml in water
Sequence CRQIKIWFQNRRMKWKK CRFARKGALRQKNV*

(Modifications: Disulfide bridge between 17 -1*)

SMILES CCC(C)C(C(=O)NC(CCCCN)C(=O)NC(C(C)CC)C(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)NC(CC3=CC=CC=C3)C(=O)NC(CCC(=O)N)C(=O)NC(CC(=O)N)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCSC)C(=O)NC(CCCCN)C(=O)NC(CC4=CNC5=CC=CC=C54)C(=O)NC(CCCCN)C(=O)NC(CCCCN)C(=O)O)NC(=O)C(CCC(=O)N)NC(=O)C(CCCNC(=N)N)NC(=O)C(CSSCC(C(=O)NC(CCCNC(=N)N)C(=O)NC(CC6=CC=CC=C6)C(=O)NC(C)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCCCN)C(=O)NCC(=O)NC(C)C(=O)NC(CC(C)C)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCC(=O)N)C(=O)NC(CCCCN)C(=O)NC(CC(=O)N)C(=O)NC(C(C)C)C(=O)O)N)N
Standard InChIKey KIWJPYSSLFMLBZ-OSCDWKIESA-N
Standard InChI InChI=1S/C177H294N62O38S3/c1-12-96(7)140(168(272)228-114(54-28-34-73-182)159(263)238-141(97(8)13-2)169(273)236-130(86-103-90-210-109-49-23-21-47-105(103)109)165(269)232-128(84-101-44-18-15-19-45-101)163(267)226-122(63-66-134(187)241)157(261)234-131(87-136(189)243)166(270)223-119(60-40-79-207-176(199)200)149(253)220-118(59-39-78-206-175(197)198)151(255)227-124(68-81-278-11)158(262)219-112(52-26-32-71-180)153(257)233-129(85-102-89-209-108-48-22-20-46-104(102)108)164(268)221-111(51-25-31-70-179)152(256)229-125(170(274)275)55-29-35-74-183)239-160(264)123(64-67-135(188)242)225-148(252)116(57-37-76-204-173(193)194)215-144(248)106(184)92-279-280-93-107(185)145(249)216-117(58-38-77-205-174(195)196)155(259)231-127(83-100-42-16-14-17-43-100)161(265)213-99(10)143(247)214-115(56-36-75-203-172(191)192)147(251)217-110(50-24-30-69-178)146(250)211-91-138(245)212-98(9)142(246)230-126(82-94(3)4)162(266)222-120(61-41-80-208-177(201)202)150(254)224-121(62-65-133(186)240)156(260)218-113(53-27-33-72-181)154(258)235-132(88-137(190)244)167(271)237-139(95(5)6)171(276)277/h14-23,42-49,89-90,94-99,106-107,110-132,139-141,209-210H,12-13,24-41,50-88,91-93,178-185H2,1-11H3,(H2,186,240)(H2,187,241)(H2,188,242)(H2,189,243)(H2,190,244)(H,211,250)(H,212,245)(H,213,265)(H,214,247)(H,215,248)(H,216,249)(H,217,251)(H,218,260)(H,219,262)(H,220,253)(H,221,268)(H,222,266)(H,223,270)(H,224,254)(H,225,252)(H,226,267)(H,227,255)(H,228,272)(H,229,256)(H,230,246)(H,231,259)(H,232,269)(H,233,257)(H,234,261)(H,235,258)(H,236,273)(H,237,271)(H,238,263)(H,239,264)(H,274,275)(H,276,277)(H4,191,192,203)(H4,193,194,204)(H4,195,196,205)(H4,197,198,206)(H4,199,200,207)(H4,201,202,208)/t96-,97-,98-,99-,106-,107-,110-,111-,112-,113-,114-,115-,116-,117-,118-,119-,120-,121-,122-,123-,124-,125-,126-,127-,128-,129-,130-,131-,132-,139-,140-,141-/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 PKC β pseudosubstrate

DescriptionSelective cell-permeable peptide inhibitor of protein kinase C (IC50 ~ 0.5 μM). Consists of amino acids 19 - 31 of PKC pseudosubstrate domain linked by a disulphide bridge to a cell permeabilisation Antennapedia domain vector peptide. The Antennapedia peptide is actively taken up by intact cells, at 4 or 37°C, ensuring rapid and effective uptake of the inhibitor peptide. Once inside the cell, the disulphide bonds are subjected to reduction in the cytoplasm leading to release of the inhibitor peptide.

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References on PKC β pseudosubstrate

Intraneuronal delivery of protein kinase C pseudosubstrate leads to growth cone collapse.[Pubmed:7472470]

J Neurosci. 1995 Nov;15(11):7158-67.

Axonal navigation during development requires that cues present in the extracellular environment be capable of modifying the structure of the cone in a dynamic way. Protein kinase C (PKC) has long been suspected to be one of the multiple molecular relays present in the terminal structure of the developing axon and involved in the transduction of extracellular signals. The latter proposal is, however, based on the use of drugs or of protocols leading to pleiotropic and often nonspecific effects. In the present study, we have taken advantage of the discovery of a peptide capable of translocating across biological membranes and to accumulate in the cytoplasm and nucleus of cells in culture, to internalize a highly specific peptidic inhibitor of PKC. We demonstrate that linking the two peptides (vector and PKC inhibitor) allows the internalization of the latter in live cells, specifically inhibits PKC and provokes a rapid modification of growth cone morphology. This set of data thus establishes that a peptidic inhibitor of PKC activity, once internalized, provokes a change in growth cone morphology, reminiscent of the collapse phenotype. In addition, the present study describes a new efficient and harmless way to introduce pharmacologically active substances in neural cells in culture.

The third helix of the Antennapedia homeodomain translocates through biological membranes.[Pubmed:8144628]

J Biol Chem. 1994 Apr 8;269(14):10444-50.

The 60-amino acid long homeodomain of Antennapedia crosses biological membranes by an energy-independent mechanism, a phenomenon abolished by directed mutagenesis within the polypeptide C-terminal region. This finding led us to study the internalization of several chemically synthesized peptides derived from the third helix of the homeodomain. We report here that a polypeptide of 16 amino acids in length corresponding to the third helix of the homeodomain deleted of its N-terminal glutamate is still capable of translocating through the membrane. A longer peptide of 20 amino acids also translocates, whereas shorter peptides (15 amino acids) are not internalized by the cells. As is also the case for the entire homeodomain, the 20- and 16-amino acid long peptides are internalized at 4 degrees C, suggesting an energy-independent mechanism of translocation not involving classical endocytosis. The two translocated peptides can be recovered, intact, within the cells, strongly suggesting that they are not targeted to the lysosomal compartment. Finally, substitution of two tryptophans by two phenylalanines strongly diminishes translocation, raising the possibility that the internalization of the third helix is not solely based on its general hydrophobicity.

Protein kinase C contains a pseudosubstrate prototope in its regulatory domain.[Pubmed:3686012]

Science. 1987 Dec 18;238(4834):1726-8.

The regulatory domain of protein kinase C contains an amino acid sequence between residues 19 and 36 that resembles a substrate phosphorylation site in its distribution of basic residue recognition determinants. The corresponding synthetic peptide (Arg19-Phe-Ala-Arg-Lys-Gly-Ala25-Leu-Arg-Gln-Lys-Asn-Val-His -Glu-Val-Lys-Asn36) acts as a potent substrate antagonist with an inhibitory constant of 147 +/- 9 nM. It is a specific inhibitor of protein kinase C and inhibits both autophosphorylation and protein substrate phosphorylation. Substitution of Ala25 with serine transforms the pseudosubstrate into a potent substrate. These results demonstrate that the conserved region of the regulatory domain (residues 19 to 36) of protein kinase C has the secondary structural features of a pseudosubstrate and may be responsible for maintaining the enzyme in the inactive form in the absence of allosteric activators such as phospholipids.

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