Neuropeptide Y (13-36), amide, human
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Neuropeptide Y (13-36), amide, human

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Neuropeptide Y (13-36), amide, human is a selective neuropeptide Y2 receptor agonist.

Category
Peptide Inhibitors
Catalog number
BAT-010561
CAS number
122341-40-6
Molecular Formula
C134H207N41O36S
Molecular Weight
3000.39
Neuropeptide Y (13-36), amide, human
IUPAC Name
(4S)-5-[[(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-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-amino-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1,5-dioxopentan-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-methylsulfanyl-1-oxobutan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-5-oxo-4-[[(2S)-2-[[(2S)-pyrrolidine-2-carbonyl]amino]propanoyl]amino]pentanoic acid
Synonyms
Neuropeptide Y (13-36), human; Pro-Ala-Glu-Asp-Met-Ala-Arg-Tyr-Tyr-Ser-Ala-Leu-Arg-His-Tyr-Ile-Asn-Leu-Ile-Thr-Arg-Gln-Arg-Tyr-NH2; Neuropeptide Y (13-36) (human, rat); L-prolyl-L-alanyl-L-alpha-glutamyl-L-alpha-aspartyl-L-methionyl-L-alanyl-L-arginyl-L-tyrosyl-L-tyrosyl-L-seryl-L-alanyl-L-leucyl-L-arginyl-L-histidyl-L-tyrosyl-L-isoleucyl-L-asparagyl-L-leucyl-L-isoleucyl-L-threonyl-L-arginyl-L-glutaminyl-L-arginyl-L-tyrosinamide
Appearance
White or Off-white Lyophilized Powder
Purity
95%
Density
1.49±0.1 g/cm3 (Predicted)
Sequence
PAEDMARYYSALRHYINLITRQRY-NH2
Storage
Store at -20°C
Solubility
Soluble in DMSO
InChI
InChI=1S/C134H207N41O36S/c1-14-67(7)104(128(209)171-97(60-101(136)183)123(204)165-92(54-66(5)6)125(206)174-105(68(8)15-2)129(210)175-106(72(12)177)130(211)162-86(25-20-51-151-134(144)145)113(194)160-87(42-44-100(135)182)117(198)158-84(23-18-49-149-132(140)141)114(195)163-90(107(137)188)55-73-26-34-78(178)35-27-73)173-126(207)95(58-76-32-40-81(181)41-33-76)168-122(203)96(59-77-62-146-64-152-77)169-116(197)85(24-19-50-150-133(142)143)159-119(200)91(53-65(3)4)164-110(191)71(11)155-127(208)99(63-176)172-121(202)94(57-75-30-38-80(180)39-31-75)167-120(201)93(56-74-28-36-79(179)37-29-74)166-115(196)83(22-17-48-148-131(138)139)156-108(189)70(10)154-112(193)89(46-52-212-13)161-124(205)98(61-103(186)187)170-118(199)88(43-45-102(184)185)157-109(190)69(9)153-111(192)82-21-16-47-147-82/h26-41,62,64-72,82-99,104-106,147,176-181H,14-25,42-61,63H2,1-13H3,(H2,135,182)(H2,136,183)(H2,137,188)(H,146,152)(H,153,192)(H,154,193)(H,155,208)(H,156,189)(H,157,190)(H,158,198)(H,159,200)(H,160,194)(H,161,205)(H,162,211)(H,163,195)(H,164,191)(H,165,204)(H,166,196)(H,167,201)(H,168,203)(H,169,197)(H,170,199)(H,171,209)(H,172,202)(H,173,207)(H,174,206)(H,175,210)(H,184,185)(H,186,187)(H4,138,139,148)(H4,140,141,149)(H4,142,143,150)(H4,144,145,151)/t67-,68-,69-,70-,71-,72+,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,104-,105-,106-/m0/s1
InChI Key
WPVRWBQWAYQJSX-YGPTWXQHSA-N
Canonical 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(CCC(=O)N)C(=O)NC(CCCNC(=N)N)C(=O)NC(CC1=CC=C(C=C1)O)C(=O)N)NC(=O)C(CC2=CC=C(C=C2)O)NC(=O)C(CC3=CNC=N3)NC(=O)C(CCCNC(=N)N)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CO)NC(=O)C(CC4=CC=C(C=C4)O)NC(=O)C(CC5=CC=C(C=C5)O)NC(=O)C(CCCNC(=N)N)NC(=O)C(C)NC(=O)C(CCSC)NC(=O)C(CC(=O)O)NC(=O)C(CCC(=O)O)NC(=O)C(C)NC(=O)C6CCCN6
1. Structure of prejunctional receptor binding analog of human neuropeptide Y dimer ANA-NPY
J A Barden Biochem Biophys Res Commun . 1995 Oct 4;215(1):264-71. doi: 10.1006/bbrc.1995.2461.
Human neuropeptide Y (NPY) analog ANA-NPY or [L17, Q19, A20, A23, L28, L31]NPY (13-36)-amide binds weakly to postjunctional receptors to raise blood pressure but binds tightly to prejunctional receptors to inhibit neurotransmitter release. ANA-NPY forms a well-conserved anti-parallel helical structure overlapping E23-Y36 with strong amphipathic character. The C-terminal portions of the monomers are better defined than the N-terminal ends. The N-terminal helices extend only from D16-E23/L24. The prejunctional receptor-specific binding site is confined within the C-terminal helices while the residues responsible for partial binding to the postjunctional receptors are located in the more disordered N-terminal segments.
2. Conformational analysis of neuropeptide Y segments by CD, NMR spectroscopy and restrained molecular dynamics
S Mammi, K Bottazzo, C W Chung, M Gurrath, A Bisello, E Peggion J Pept Sci . 1996 May-Jun;2(3):176-93. doi: 10.1002/psc.62.
Neuropeptide Y (NPY), a peptide amide comprising 36 residue has been shown to act as a potent vasoconstrictor. In order to shed light on the structural requirements for the biological activities with respect to the different prerequisites for affinity to the NPY receptor subtypes Y1 and Y2, in the present study the syntheses and conformational analyses of two C-terminal segments, NPY(18-36) and NPY(13-36), are described. The results obtained by CD measurements, two-dimensional NMR spectroscopy and a conformational refinement of the NMR-derived structure by molecular mechanics stimulations support the findings of previously published structure-activity relationship studies for biologically active and selective compounds. In particular, the alpha-helical conformation as well as an appropriate exposure of the side chains of the critical C-terminal dipeptide within NPY(18-36) are in agreement with the prerequisites proposed for Y2 receptor binding of that segment.
3. Treatment strategies targeting excess hippocampal activity benefit aged rats with cognitive impairment
Michela Gallagher, Stacey Foti, Ming Teng Koh, Rebecca P Haberman, Thomas J McCown Neuropsychopharmacology . 2010 Mar;35(4):1016-25. doi: 10.1038/npp.2009.207.
Excess neural activity in the CA3 region of the hippocampus has been linked to memory impairment in aged rats. We tested whether interventions aimed at reducing this excess activity would improve memory performance. Aged (24 to 28 months old) male Long-Evans rats were characterized in a spatial memory task known to depend on the functional integrity of the hippocampus, such that aged rats with identified memory impairment were used in a series of experiments. Overexpression of the inhibitory neuropeptide Y 13-36 in the CA3 via adeno-associated viral transduction was found to improve hippocampal-dependent long-term memory in aged rats, which had been characterized with impairment. Subsequent experiments with two commonly used antiepileptic agents, sodium valproate and levetiracetam, similarly produced dose-dependent memory improvement in such aged rats. Improved spatial memory with low doses of these agents was observed in both appetitve and aversive spatial tasks. The benefits of these different modalities of treatment are consistent with the concept that excess activity in the CA3 region of the hippocampus is a dysfunctional condition that may have a key role underlying age-related impairment in hippocampal-dependent memory processes. Because increased hippocampal activation occurs in age-related memory impairment in humans as observed in functional neuroimaging, the current findings also suggest that low doses of certain antiepileptic drugs in cognitively impaired elderly humans may have therapeutic potential and point to novel targets for this indication.
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