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[D-Trp34]-Neuropeptide Y

Potent NPY Y5 agonist; orexigenic CAS# 153549-84-9

[D-Trp34]-Neuropeptide Y

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Chemical structure

[D-Trp34]-Neuropeptide Y

3D structure

Chemical Properties of [D-Trp34]-Neuropeptide Y

Cas No. 153549-84-9 SDF Download SDF
PubChem ID 90488847 Appearance Powder
Formula C196H289N55O56 M.Wt 4311.77
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble to 0.20 mg/ml in 20% acetonitrile
Sequence YPSKPDNPGEDAPAEDLARYYSALRHYINLITRWRY

(Modifications: Trp-34 = D-Trp, Tyr-36 = C-terminal amide)

Chemical Name (4S)-4-[[2-[[(2S)-1-[(2S)-4-amino-2-[[(2S)-2-[[(2S)-1-[(2S)-6-amino-2-[[(2S)-2-[[(2S)-1-[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]pyrrolidine-2-carbonyl]amino]-3-hydroxypropanoyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-3-carboxypropanoyl]amino]-4-oxobutanoyl]pyrrolidine-2-carbonyl]amino]acetyl]amino]-5-[[(2S)-1-[[(2S)-1-[(2S)-2-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S,3S)-1-[[(2S)-4-amino-1-[[(2S)-1-[[(2S,3S)-1-[[(2S,3R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-amino-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-(1H-imidazol-4-yl)-1-oxopropan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]carbamoyl]pyrrolidin-1-yl]-1-oxopropan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
SMILES CCC(C)C(C(=O)NC(CC(=O)N)C(=O)NC(CC(C)C)C(=O)NC(C(C)CC)C(=O)NC(C(C)O)C(=O)NC(CCCNC(=N)N)C(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)NC(CCCNC(=N)N)C(=O)NC(CC3=CC=C(C=C3)O)C(=O)N)NC(=O)C(CC4=CC=C(C=C4)O)NC(=O)C(CC5=CNC=N5)NC(=O)C(CCCNC(=N)N)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CO)NC(=O)C(CC6=CC=C(C=C6)O)NC(=O)C(CC7=CC=C(C=C7)O)NC(=O)C(CCCNC(=N)N)NC(=O)C(C)NC(=O)C(CC(C)C)NC(=O)C(CC(=O)O)NC(=O)C(CCC(=O)O)NC(=O)C(C)NC(=O)C8CCCN8C(=O)C(C)NC(=O)C(CC(=O)O)NC(=O)C(CCC(=O)O)NC(=O)CNC(=O)C9CCCN9C(=O)C(CC(=O)N)NC(=O)C(CC(=O)O)NC(=O)C1CCCN1C(=O)C(CCCCN)NC(=O)C(CO)NC(=O)C1CCCN1C(=O)C(CC1=CC=C(C=C1)O)N
Standard InChIKey YZSPVSFRBZGLIZ-QIJQHHJSSA-N
Standard InChI InChI=1S/C196H289N55O56/c1-16-98(9)155(186(301)241-136(84-147(199)260)175(290)232-130(76-97(7)8)178(293)246-156(99(10)17-2)187(302)247-157(104(15)254)188(303)227-123(36-25-69-214-196(208)209)165(280)236-134(82-110-89-215-119-31-19-18-30-117(110)119)173(288)226-121(34-23-67-212-194(204)205)162(277)229-127(158(201)273)78-106-43-53-113(256)54-44-106)245-179(294)133(81-109-49-59-116(259)60-50-109)235-174(289)135(83-111-90-210-94-217-111)237-164(279)122(35-24-68-213-195(206)207)225-170(285)129(75-96(5)6)230-161(276)101(12)219-180(295)141(92-252)243-172(287)132(80-108-47-57-115(258)58-48-108)234-171(286)131(79-107-45-55-114(257)56-46-107)233-163(278)120(33-22-66-211-193(202)203)223-159(274)100(11)218-168(283)128(74-95(3)4)231-176(291)138(87-153(269)270)239-167(282)125(62-64-151(265)266)224-160(275)102(13)220-183(298)144-38-27-70-248(144)189(304)103(14)221-169(284)137(86-152(267)268)238-166(281)124(61-63-150(263)264)222-149(262)91-216-182(297)143-37-26-72-250(143)192(307)140(85-148(200)261)242-177(292)139(88-154(271)272)240-184(299)146-40-29-73-251(146)191(306)126(32-20-21-65-197)228-181(296)142(93-253)244-185(300)145-39-28-71-249(145)190(305)118(198)77-105-41-51-112(255)52-42-105/h18-19,30-31,41-60,89-90,94-104,118,120-146,155-157,215,252-259H,16-17,20-29,32-40,61-88,91-93,197-198H2,1-15H3,(H2,199,260)(H2,200,261)(H2,201,273)(H,210,217)(H,216,297)(H,218,283)(H,219,295)(H,220,298)(H,221,284)(H,222,262)(H,223,274)(H,224,275)(H,225,285)(H,226,288)(H,227,303)(H,228,296)(H,229,277)(H,230,276)(H,231,291)(H,232,290)(H,233,278)(H,234,286)(H,235,289)(H,236,280)(H,237,279)(H,238,281)(H,239,282)(H,240,299)(H,241,301)(H,242,292)(H,243,287)(H,244,300)(H,245,294)(H,246,293)(H,247,302)(H,263,264)(H,265,266)(H,267,268)(H,269,270)(H,271,272)(H4,202,203,211)(H4,204,205,212)(H4,206,207,213)(H4,208,209,214)/t98-,99-,100-,101-,102-,103-,104+,118-,120-,121-,122-,123-,124-,125-,126-,127-,128-,129-,130-,131-,132-,133-,134+,135-,136-,137-,138-,139-,140-,141-,142-,143-,144-,145-,146-,155-,156-,157-/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 [D-Trp34]-Neuropeptide Y

DescriptionPotent neuropeptide Y (NPY) Y5 receptor agonist (pEC50 values are 7.82, 6.28, 6.44 and > 6 at rat Y5, Y4, Y1 and Y2 receptors respectively) that displays > 26-fold, > 1000-fold and > 1000-fold selectivity over Y1, Y2 and Y4 receptors respectively. Induces hyperphagia, body weight gain, adiposity, hypercholesterolemia, hyperinsulinemia and hyperleptinemia in vivo. Orally active.

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References on [D-Trp34]-Neuropeptide Y

Responsiveness of obese Zucker rats to [D-Trp34]-NPY supports the targeting of Y5 receptor for obesity treatment.[Pubmed:18284029]

Nutr Neurosci. 2007 Oct-Dec;10(5-6):211-4.

The increased synthesis and release of neuropeptide Y (NPY) in the hypothalamus participate in the development of overeating and obesity in the Zucker fa/fa rat. The orexigenic effects of NPY are mediated through the Y1 and Y5 receptors. The substitution of [D-Trp34] in the NPY amino-acid sequence increases selectivity without lowering potency at the Y5 receptor. In the present study, to address the role of the NPY Y5 receptor in obesity, we investigated the acute effect of [D-Trp 34]-NPY in lean and obese Zucker rats. Obese rats were markedly hyperphagic (27.1 +/- 0.6 vs. 18.7 +/- 0.4 (lean) g/day; p < 0.01). Injection of [D-Trp34]-NPY in the lateral brain ventricle at a dose of 16 microg stimulated food intake to the same extent in both lean (p < 0.01) and obese (p < 0.01) rats 1 h after injection. This effect was still observed after 6 h (p < 0.01). These results indicate, therefore, that the obese rats are responsive to [D-Trp34]-NPY. They support the role of the neuropeptide Y5 receptor in the regulation of food intake and suggest that NPY Y5 antagonism might be useful for treating obesity.

Characterization of neuropeptide Y (NPY) Y5 receptor-mediated obesity in mice: chronic intracerebroventricular infusion of D-Trp(34)NPY.[Pubmed:12697685]

Endocrinology. 2003 May;144(5):1793-801.

To clarify the role of the neuropeptide Y (NPY) Y5 receptor subtype in energy homeostasis, the effect of the intracerebroventricular infusion of a selective Y5 agonist, D-Trp(34)NPY, was investigated in C57BL/6J mice. Intracerebroventricular infusion of D-Trp(34)NPY (5 and 10 microg/d) produced hyperphagia and body weight gain, accompanied by increased adipose tissue weight, hypercholesterolemia, hyperinsulinemia, and hyperleptinemia. Oral administration of a selective Y5 antagonist at a dose of 100 mg/kg twice a day completely suppressed all of these D-Trp(34)NPY-induced changes, indicating that chronic activation of the Y5 receptor produces hyperphagia and obesity. In addition, D-Trp(34)NPY still resulted in an increase in adipose tissue weight accompanied by hyperleptinemia and hypercholesterolemia, although D-Trp(34)NPY-induced food intake was restricted by pair-feeding. Under the pair-fed condition, D-Trp(34)NPY decreased hormone-sensitive lipase activity in white adipose tissue and uncoupling protein-1 mRNA expression in brown adipose tissue. These findings indicate that Y5-mediated obesity may involve metabolic changes, such as decreased lipolysis and thermogenesis, as well as hyperphagia. Therefore, the Y5 receptor can play a key role in regulating energy homeostasis.

[D-Trp(34)] neuropeptide Y is a potent and selective neuropeptide Y Y(5) receptor agonist with dramatic effects on food intake.[Pubmed:10793222]

Peptides. 2000 Mar;21(3):393-9.

The neuropeptide Y (NPY) Y(5) receptor has been proposed to mediate several physiological effects of NPY, including the potent orexigenic activity of the peptide. However, the lack of selective NPY Y(5) receptor ligands limits the characterization of the physiological roles of this receptor. Screening of several analogs of NPY revealed that [D-Trp(34)]NPY is a potent and selective NPY Y(5) receptor agonist. Unlike the prototype selective NPY Y(5) receptor agonist [D-Trp(32)]NPY, [D-Trp(34)]NPY markedly increases food intake in rats, an effect that is blocked by the selective NPY Y(5) receptor antagonist CGP 71683A. These data demonstrate that [D-Trp(34)]NPY is a useful tool for studies aimed at determining the physiological roles of the NPY Y(5) receptor.

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