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[D-Arg1,D-Phe5,D-Trp7,9,Leu11]-Substance P

[D-Arg1,D-Phe5,D-Trp7,9,Leu11]-Substance P

Catalog No. BCC7211
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1mg $153.00 Ship Within 7 Days
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Quality Control of [D-Arg1,D-Phe5,D-Trp7,9,Leu11]-Substance P

Chemical structure

[D-Arg1,D-Phe5,D-Trp7,9,Leu11]-Substance P

[D-Arg1,D-Phe5,D-Trp7,9,Leu11]-Substance P Dilution Calculator

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[D-Arg1,D-Phe5,D-Trp7,9,Leu11]-Substance P Molarity Calculator

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Chemical Properties of [D-Arg1,D-Phe5,D-Trp7,9,Leu11]-Substance P

Cas No. 96736-12-8 SDF Download SDF
Sequence RPKPFQWFWLL

(Modifications: Arg-1 = D-Arg, Phe-5 = D-Phe, Trp-7 = Trp-9 = D-Trp, Leu-11 = C-terminal amide)

Chemical Name (2S)-2-[[(2R)-2-[[(2S)-1-[(2S)-6-amino-2-[[(2S)-1-[(2R)-2-amino-5-(diaminomethylideneamino)pentanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-3-phenylpropanoyl]amino]-N-[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]pentanediamide
SMILES CC(C)CC(C(=O)N)NC(=O)C(CC(C)C)NC(=O)C(CC1=CNC2=CC=CC=C21)NC(=O)C(CC3=CC=CC=C3)NC(=O)C(CC4=CNC5=CC=CC=C54)NC(=O)C(CCC(=O)N)NC(=O)C(CC6=CC=CC=C6)NC(=O)C7CCCN7C(=O)C(CCCCN)NC(=O)C8CCCN8C(=O)C(CCCN=C(N)N)N
Standard InChIKey XVOCEQLNJQGCQG-UNAVROQCSA-N
Standard InChI InChI=1S/C79H109N19O12/c1-46(2)38-59(68(83)100)91-70(102)60(39-47(3)4)92-73(105)64(43-51-45-88-56-28-14-12-25-53(51)56)95-72(104)61(40-48-20-7-5-8-21-48)93-74(106)63(42-50-44-87-55-27-13-11-24-52(50)55)94-69(101)57(32-33-67(82)99)89-71(103)62(41-49-22-9-6-10-23-49)96-76(108)66-31-19-37-98(66)78(110)58(29-15-16-34-80)90-75(107)65-30-18-36-97(65)77(109)54(81)26-17-35-86-79(84)85/h5-14,20-25,27-28,44-47,54,57-66,87-88H,15-19,26,29-43,80-81H2,1-4H3,(H2,82,99)(H2,83,100)(H,89,103)(H,90,107)(H,91,102)(H,92,105)(H,93,106)(H,94,101)(H,95,104)(H,96,108)(H4,84,85,86)/t54-,57-,58-,59-,60-,61-,62-,63-,64-,65-,66-/m0/s1
Formula C79H109N19O12 M.Wt 1516.85
Solubility Soluble to 1 mg/ml in water
Storage Desiccate at -20°C
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.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other courier with RT , or blue ice upon request.

Preparing Stock Solutions of [D-Arg1,D-Phe5,D-Trp7,9,Leu11]-Substance P

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 0.6593 mL 3.2963 mL 6.5926 mL 13.1852 mL 16.4815 mL
5 mM 0.1319 mL 0.6593 mL 1.3185 mL 2.637 mL 3.2963 mL
10 mM 0.0659 mL 0.3296 mL 0.6593 mL 1.3185 mL 1.6482 mL
50 mM 0.0132 mL 0.0659 mL 0.1319 mL 0.2637 mL 0.3296 mL
100 mM 0.0066 mL 0.033 mL 0.0659 mL 0.1319 mL 0.1648 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

References on [D-Arg1,D-Phe5,D-Trp7,9,Leu11]-Substance P

Agonist function of the neurokinin receptor antagonist, [D-Arg1,D-Phe5,D-Trp7,9,Leu11]substance P, in monocytes.[Pubmed: 12972327]


G-protein-coupled bombesin receptors are capable of signaling through the G(i) protein even when receptor-coupling to G(q) is blocked by [D-Arg1,D-Phe5,D-Trp7,9,Leu11]substance P (SpD), a neurokinin-1 receptor antagonist and "biased" agonist to bombesin receptors. As bombesin is a monocyte and tumor cell attractant, we were interested in the effects of SpD on cell migration. Chemotaxis of monocytes was tested in micropore filter assays. SpD was a dose-dependent agonist in monocyte migration and was not inhibited by antagonists to neurokinin-1 or -2 receptors. SpD failed to inhibit chemotaxis toward bombesin, suggesting that inhibition of bombesin receptor coupling to G(q) with SpD does not impair migratory responses elicited by bombesin. As pertussis toxin inhibited migration, coupling of receptors to G(i) may signal migration. Chemotaxis toward SpD was inhibited by bombesin receptor antagonists as well as by blocking signaling enzymes downstream of G(q) (phospholipase-3 and protein kinase C with wortmannin and bisindolylmaleimide, respectively), suggesting transactivation of G(q)-mediated chemotaxis signaling by SpD via bombesin receptors. Protein kinase C that induces sphingosine kinase activation and production of sphingosine-1-phosphate, which may lead to G(q)-dependent chemoattraction, was involved in SpD-dependent migration. Inhibition of sphingosine-1-phosphate production with dimethylsphingosine inhibited monocyte migration toward SpD. Data suggest that SpD induces migration in monocytes and signaling events involving activation of sphingosine kinase in a G(i) protein- and protein kinase C-dependent fashion. "Biased" agonism of SpD at bombesin receptors may affect normal and tumor cell migration.

[D-Arg1,D-Phe5,D-Trp7,9,Leu11]Substance P acts as a biased agonist toward neuropeptide and chemokine receptors.[Pubmed: 9446627]


Substance P derivatives are potential therapeutic compounds for the treatment of small cell lung cancer and can cause apoptosis in small cell lung cancer cells in culture. These peptides act as broad spectrum neuropeptide antagonists, blocking calcium mobilization induced by gastrin-releasing peptide, bradykinin, cholecystokinin, and other neuropeptides. We show that [D-Arg1,D-Phe5,D-Trp7,9, Leu11]substance P has unique agonist activities in addition to this described antagonist function. At doses that block calcium mobilization by neuropeptides, this peptide causes activation of c-Jun N-terminal kinase and cytoskeletal changes in Swiss 3T3 fibroblasts and stimulates migration and calcium flux in human neutrophils. Activation of c-Jun N-terminal kinase is dependent on the expression of the gastrin-releasing peptide receptor in rat 1A fibroblasts, demonstrating that the responses to the peptide are receptor-mediated. We hypothesize that [D-Arg1,D-Phe5,D-Trp7,9, Leu11]substance P acts as a biased agonist on neuropeptide and related receptors, activating certain guanine nucleotide-binding proteins through the receptor, but not others.

Processing of [D-Arg1,D-Phe5,D-Trp7,9,Leu11]substance P in xenograft bearing Nu/Nu mice.[Pubmed: 9357069]


[D-Arg1,D-Phe5,D-Trp7,9,Leu11]Substance P is a broad-spectrum neuropeptide growth factor antagonist that has exhibited in vitro activity against a range of human cancer cell lines. The fate of this compound in vivo following i.p. administration at 12 micrograms/g to nu/nu mice bearing the H69 small-cell lung cancer xenograft has been studied. Metabolism was confined to the C-terminus producing [D-Arg1,D-Phe5,D-Trp7,9,Leu11]substance P acid and [D-Arg1,D-Phe5,D-Trp7,9]substance P(1-10). The peptide had a long half-life in plasma (45.9 min) and became widely distributed among the tissues studied with the highest accumulation observed in the liver (AUC 1102 micrograms/g x min) and the lowest in the brain (5 micrograms/g x min). Uptake into the tumor xenograft was poor (AUC 189 micrograms/g x min); however, uptake into the lungs was much greater (AUC 507 micrograms/g x min), offering encouragement that therapeutic concentrations may be targeted to primary lung tumors.

Metabolism of the broad-spectrum neuropeptide growth factor antagonist: [D-Arg1, D-Phe5, D-Trp7,9, Leu11]-substance P.[Pubmed: 8611370]


Broad-spectrum neuropeptide growth factor antagonists, such as [D-Arg1, D-Phe5, D-Trp7,9, Leu11]substance P (antagonist D) and [Arg6, D-Trp7,9, NmePhe8]substance P(6-11) (antagonist G), are currently being investigated as possible anti-tumour agents. These compounds are hoped to be effective against neuropeptide-driven cancers such as small-cell lung cancer. Antagonist D possesses a broader antagonistic spectrum than antagonist G and hence may be of greater therapeutic use. The in vitro metabolism of antagonist D has been characterised and the structures of two major metabolites have been elucidated by amino acid analysis and mass spectrometry. Metabolism was confined to the C-terminus where serine carboxypeptidase action produced [deamidated]-antagonist D (metabolite 1) and [des-Leu11]-antagonist D (metabolite 2) as the major metabolites. Biological characterisation of the metabolites demonstrated that these relatively minor changes in structure resulted in a loss of antagonist activity. These results provide some of the first structure-activity information on the factors that determine which neuropeptides these compounds inhibit and on the relative potency of that inhibition.

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[D-Arg1,D-Phe5,D-Trp7,9,Leu11]-Substance P,96736-12-8,GPCR/G protein,Ghrelin Receptors, supplier, inhibitor,Antagonist,Blocker,Modulator,Agonist, activators, activates, potent, BioCrick

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