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[Leu31,Pro34]-Neuropeptide Y (porcine)

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[Leu31,Pro34]-Neuropeptide Y (porcine) is a high affinity neuropeptide Y Y1 receptor agonist (Ki = 0.54 nM).

Category

Peptide Inhibitors

Catalog number

BAT-015905

CAS number

125580-28-1

Molecular Formula

C190H286N54O56

Molecular Weight

4222.63

Specification
Reference Reading

IUPAC 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)-1-[[(2S,3R)-1-[[(2S)-1-[(2S)-2-[[(2S)-1-[[(2S)-1-amino-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]carbamoyl]pyrrolidin-1-yl]-5-carbamimidamido-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-4-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

Synonyms

(Leu(31),pro(34))npy; 31-Leu-34-pro-neuropeptide Y; Pancreatic polypeptide (chicken), 1-L-tyrosine-4-L-lysine-6-L-aspartic acid-7-L-asparagine-10-L-glutamic acid-14-L-alanine-18-L-alanine-20-L-tyrosine-22-L-serine-23-L-alanine-25-L-arginine-26-L-histidine-28-L-isoleucine-30-L-leucine-31-L-leucine-34-L-proline

Sequence

YPSKPDNPGEDAPAEDLARYYSALRHYINLLTRPRY

Storage

Store at -20°C

InChI

InChI=1S/C190H286N54O56/c1-16-96(10)150(180(294)234-130(82-142(193)253)168(282)225-124(74-94(6)7)164(278)226-125(75-95(8)9)171(285)239-151(101(15)247)181(295)221-120(32-22-66-208-190(202)203)185(299)243-70-26-36-140(243)177(291)219-116(31-21-65-207-189(200)201)156(270)222-121(152(195)266)77-103-40-50-109(249)51-41-103)238-172(286)128(80-106-46-56-112(252)57-47-106)229-167(281)129(81-107-87-204-91-210-107)230-158(272)115(30-20-64-206-188(198)199)218-163(277)123(73-93(4)5)223-155(269)98(12)212-173(287)135(89-245)236-166(280)127(79-105-44-54-111(251)55-45-105)228-165(279)126(78-104-42-52-110(250)53-43-104)227-157(271)114(29-19-63-205-187(196)197)216-153(267)97(11)211-161(275)122(72-92(2)3)224-169(283)132(85-148(262)263)232-160(274)118(59-61-146(258)259)217-154(268)99(13)213-176(290)138-34-24-67-240(138)182(296)100(14)214-162(276)131(84-147(260)261)231-159(273)117(58-60-145(256)257)215-144(255)88-209-175(289)137-33-23-69-242(137)186(300)134(83-143(194)254)235-170(284)133(86-149(264)265)233-178(292)141-37-27-71-244(141)184(298)119(28-17-18-62-191)220-174(288)136(90-246)237-179(293)139-35-25-68-241(139)183(297)113(192)76-102-38-48-108(248)49-39-102/h38-57,87,91-101,113-141,150-151,245-252H,16-37,58-86,88-90,191-192H2,1-15H3,(H2,193,253)(H2,194,254)(H2,195,266)(H,204,210)(H,209,289)(H,211,275)(H,212,287)(H,213,290)(H,214,276)(H,215,255)(H,216,267)(H,217,268)(H,218,277)(H,219,291)(H,220,288)(H,221,295)(H,222,270)(H,223,269)(H,224,283)(H,225,282)(H,226,278)(H,227,271)(H,228,279)(H,229,281)(H,230,272)(H,231,273)(H,232,274)(H,233,292)(H,234,294)(H,235,284)(H,236,280)(H,237,293)(H,238,286)(H,239,285)(H,256,257)(H,258,259)(H,260,261)(H,262,263)(H,264,265)(H4,196,197,205)(H4,198,199,206)(H4,200,201,207)(H4,202,203,208)/t96-,97-,98-,99-,100-,101+,113-,114-,115-,116-,117-,118-,119-,120-,121-,122-,123-,124-,125-,126-,127-,128-,129-,130-,131-,132-,133-,134-,135-,136-,137-,138-,139-,140-,141-,150-,151-/m0/s1

InChI Key

ZNBZLZXDILRJJT-CCPZSHQESA-N

Canonical SMILES

CCC(C)C(C(=O)NC(CC(=O)N)C(=O)NC(CC(C)C)C(=O)NC(CC(C)C)C(=O)NC(C(C)O)C(=O)NC(CCCNC(=N)N)C(=O)N1CCCC1C(=O)NC(CCCNC(=N)N)C(=O)NC(CC2=CC=C(C=C2)O)C(=O)N)NC(=O)C(CC3=CC=C(C=C3)O)NC(=O)C(CC4=CNC=N4)NC(=O)C(CCCNC(=N)N)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CO)NC(=O)C(CC5=CC=C(C=C5)O)NC(=O)C(CC6=CC=C(C=C6)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)C7CCCN7C(=O)C(C)NC(=O)C(CC(=O)O)NC(=O)C(CCC(=O)O)NC(=O)CNC(=O)C8CCCN8C(=O)C(CC(=O)N)NC(=O)C(CC(=O)O)NC(=O)C9CCCN9C(=O)C(CCCCN)NC(=O)C(CO)NC(=O)C1CCCN1C(=O)C(CC1=CC=C(C=C1)O)N

1. High-affinity binding of [3H]neuropeptide Y to a polypeptide from the venom of Conus anemone

G Vauquelin, P M Vanderheyden, J P De Backer, E Czerwiec Eur J Pharmacol . 1996 Nov 21;315(3):355-62. doi: 10.1016/s0014-2999(96)00647-4.

Venom preparation from Conus anemone contains a component that binds radiolabeled neuropeptide Y ([3H]neuropeptide Y) with high affinity (KD = 2.9 nM +/- 0.2 nM, Bmax = 15.2 +/- 0.5 pmol/mg protein). Binding of [3H]neuropeptide Y to the venom component is displaced with nanomolar affinity of unlabeled human and porcine neuropeptide Y, porcine [Leu31-Pro34]neuropeptide Y, peptide YY, avian and bovine pancreatic polypeptide, and the (18-36) and (25-36) C-terminal fragments from neuropeptide Y. No displacement is found with the (1-24) N-terminal neuropeptide Y fragment, human secretin, porcine dynorphin A and Boc-DAKLI (bolton Hunter coupled dynorphin A analog kappa ligand) nor with the non-peptide neuropeptide Y receptor antagonist BIBP3266. Gel filtration chromatography and denaturing (sodium dodecyl sulfate-polyacrylamide gel electrophoresis) show that the [3H]neuropeptide Y-binding component is very likely a single-chain polypeptide with a molecular mass of 18.5 kDa.

2. BIIE0246, a potent and highly selective non-peptide neuropeptide Y Y(2) receptor antagonist

E Hamel, R Quirion, Y Dumont, A Cadieux, D Jacques, L H Pheng, H Doods, R Abounader, D Regoli Br J Pharmacol . 2000 Mar;129(6):1075-88. doi: 10.1038/sj.bjp.0703162.

1. BIIE0246, a newly synthesized non-peptide neuropeptide Y (NPY) Y(2) receptor antagonist, was able to compete with high affinity (8 to 15 nM) for specific [(125)I]PYY(3 - 36) binding sites in HEK293 cells transfected with the rat Y(2) receptor cDNA, and in rat brain and human frontal cortex membrane homogenates. 2. Interestingly, in rat brain homogenates while NPY, C2-NPY and PYY(3 - 36) inhibited all specific [(125)I]PYY(3 - 36) labelling, BIIE0246 failed to compete for all specific binding suggesting that [(125)I]PYY(3 - 36) recognized, in addition to the Y(2) subtype, another population of specific NPY binding sites, most likely the Y(5) receptor. 3. Quantitative receptor autoradiographic data confirmed the presence of [(125)I]PYY(3 - 36)/BIIE0246-sensitive (Y(2)) and-insensitive (Y(5)) binding sites in the rat brain as well as in the marmoset monkey and human hippocampal formation. 4. In the rat vas deferens and dog saphenous vein (two prototypical Y(2) bioassays), BIIE0246 induced parallel shifts to the right of NPY concentration-response curves with pA(2) values of 8.1 and 8.6, respectively. In the rat colon (a Y(2)/Y(4) bioassay), BIIE0246 (1 microM) completely blocked the contraction induced by PYY(3 - 36), but not that of [Leu(31), Pro(34)]NPY (a Y(1), Y(4) and Y(5) agonist) and hPP (a Y(4) and Y(5) agonist). Additionally, BIIE0246 failed to alter the contractile effects of NPY in prototypical Y(1) in vitro bioassays. 5. Taken together, these results demonstrate that BIIE0246 is a highly potent, high affinity antagonist selective for the Y(2) receptor subtype. It should prove most useful to establish further the functional role of the Y(2) receptor in the organism.

3. Characterisation of the neuropeptide Y receptor that mediates feeding in the rat: a role for the Y5 receptor?

J R Arch, S McClue, S Wilson, R E Buckingham, A C Haynes Regul Pept . 1998 Sep 25;75-76:355-61. doi: 10.1016/s0167-0115(98)00088-3.

Food intake was measured in freely fed rats following intracerebroventricular administration of neuropeptide Y (NPY) and several of its analogues and antagonists to investigate the hypothesis that the NPY Y5 receptor mediates feeding. Rat NPY (rNPY), rNPY(2-36) and rNPY(3-36) produced similar feeding responses over the dose range 0.7-7.0 nmol. Rat peptide YY (rPYY) was more potent and at least as efficacious as rNPY. [Leu31 Pro34]-rNPY (agonist potency: Y1 > Y5 > Y4 = y6) and human pancreatic polypeptide (hPP) produced flatter dose-response curves, suggesting partial agonism at the receptor(s). rNPY(13-36) (agonist potency: Y2 > Y5) had little activity and rPP was inactive. [D-Trp32]-NPY was a weak orexigenic agent given alone and, consistent with partial agonism, it markedly antagonised the response to porcine NPY (pNPY). Similarly, the receptor antagonist (Y1 > Y4) 1229U91 stimulated feeding slightly, and markedly inhibited rNPY-induced feeding. In contrast to a previous report, BIBP 3226 (70 nmol), another Y1 receptor antagonist, failed to inhibit the response to rNPY. Our data in vivo are inconsistent with findings that hPP, [Leu31 Pro34]-rNPY and [D-Trp32]-rNPY are full agonists at the rat cloned Y5 receptor. Thus, whilst the Y5 receptor may be involved, its participation as the sole receptor mediating the orexigenic action of NPY in the rat remains unproven.