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[Ala11,D-Leu15]-Orexin B

Potent, selective OX2 receptor agonist CAS# 532932-99-3

[Ala11,D-Leu15]-Orexin B

2D Structure

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[Ala11,D-Leu15]-Orexin B

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Chemical Properties of [Ala11,D-Leu15]-Orexin B

Cas No. 532932-99-3 SDF Download SDF
PubChem ID 90473850 Appearance Powder
Formula C120H206N44O35S M.Wt 2857.28
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble to 0.30 mg/ml in water
Sequence RSGPPGLQGRAQRLLQASGNHAAGILTM

(Modifications: Met-28 = C-terminal amide)

Chemical Name (2S)-N-[(2S)-1-[[(2S)-1-[[(2R)-1-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-[[2-[[(2S)-4-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[2-[[(2S,3S)-1-[[(2S)-1-[[(2S,3R)-1-[[(2S)-1-amino-4-methylsulfanyl-1-oxobutan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-2-oxoethyl]amino]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-(1H-imidazol-4-yl)-1-oxopropan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-2-oxoethyl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-5-amino-2-[[(2S)-2-[[2-[[(2S)-1-[(2S)-1-[2-[[(2S)-2-[[(2S)-2-amino-5-carbamimidamidopentanoyl]amino]-3-hydroxypropanoyl]amino]acetyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]amino]acetyl]amino]-4-methylpentanoyl]amino]-5-oxopentanoyl]amino]acetyl]amino]-5-carbamimidamidopentanoyl]amino]propanoyl]amino]pentanediamide
SMILES CCC(C)C(C(=O)NC(CC(C)C)C(=O)NC(C(C)O)C(=O)NC(CCSC)C(=O)N)NC(=O)CNC(=O)C(C)NC(=O)C(C)NC(=O)C(CC1=CNC=N1)NC(=O)C(CC(=O)N)NC(=O)CNC(=O)C(CO)NC(=O)C(C)NC(=O)C(CCC(=O)N)NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=O)C(CCCNC(=N)N)NC(=O)C(CCC(=O)N)NC(=O)C(C)NC(=O)C(CCCNC(=N)N)NC(=O)CNC(=O)C(CCC(=O)N)NC(=O)C(CC(C)C)NC(=O)CNC(=O)C2CCCN2C(=O)C3CCCN3C(=O)CNC(=O)C(CO)NC(=O)C(CCCNC(=N)N)N
Standard InChIKey SURUUKNICBOUOQ-UBNRXWOCSA-N
Standard InChI InChI=1S/C120H206N44O35S/c1-17-60(10)93(115(197)158-77(44-59(8)9)113(195)162-94(65(15)167)116(198)150-68(95(126)177)34-40-200-16)161-91(175)51-137-96(178)61(11)143-97(179)62(12)146-108(190)78(45-66-47-133-55-142-66)157-112(194)79(46-87(125)171)149-89(173)49-139-102(184)80(53-165)159-99(181)64(14)145-105(187)72(29-32-85(123)169)154-110(192)75(42-57(4)5)156-111(193)76(43-58(6)7)155-106(188)70(25-20-37-136-120(131)132)152-107(189)73(30-33-86(124)170)151-98(180)63(13)144-104(186)69(24-19-36-135-119(129)130)147-88(172)48-138-101(183)71(28-31-84(122)168)153-109(191)74(41-56(2)3)148-90(174)50-140-114(196)82-26-21-39-164(82)117(199)83-27-22-38-163(83)92(176)52-141-103(185)81(54-166)160-100(182)67(121)23-18-35-134-118(127)128/h47,55-65,67-83,93-94,165-167H,17-46,48-54,121H2,1-16H3,(H2,122,168)(H2,123,169)(H2,124,170)(H2,125,171)(H2,126,177)(H,133,142)(H,137,178)(H,138,183)(H,139,184)(H,140,196)(H,141,185)(H,143,179)(H,144,186)(H,145,187)(H,146,190)(H,147,172)(H,148,174)(H,149,173)(H,150,198)(H,151,180)(H,152,189)(H,153,191)(H,154,192)(H,155,188)(H,156,193)(H,157,194)(H,158,197)(H,159,181)(H,160,182)(H,161,175)(H,162,195)(H4,127,128,134)(H4,129,130,135)(H4,131,132,136)/t60-,61-,62-,63-,64-,65+,67-,68-,69-,70-,71-,72-,73-,74-,75+,76-,77-,78-,79-,80-,81-,82-,83-,93-,94-/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 [Ala11,D-Leu15]-Orexin B

DescriptionHighly potent and selective OX2 receptor agonist; displays 400-fold selectivity over OX1 receptors. EC50 values are 0.13 and 52 nM for human OX2 and OX1 receptors respectively.

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References on [Ala11,D-Leu15]-Orexin B

Orexin-2 receptors inhibit primary afferent fiber-evoked responses of ventral roots in the neonatal rat isolated spinal cord.[Pubmed:18511021]

Brain Res. 2008 Jul 7;1218:97-102.

Orexin-A and orexin-B are hypothalamic peptides. Orexin-A binds equally to both orexin-1 and orexin-2 receptors but orexin-B has a preferential affinity for orexin-2 receptor. In the spinal dorsal horn, orexins have been shown to be concentrated in the superficial laminae. In the present study, the authors examined the effect of spinally applied orexin-A and orexin-B on the primary afferent fiber-evoked nociceptive reflex in the isolated spinal cord of the neonatal rat. In the isolated spinal cord preparation from 0-3day old rats, single-shock stimulation of a dorsal root (L3-L5) at a strength which can activate C-fibers induced a slow depolarizing response lasting about 30s (slow ventral root potential: slow VRP) in the ipsilateral ventral root of the same segment. Bath application of orexin-A and orexin-B inhibited the slow VRP in a concentration-dependent manner. Bath application of SB-334867, a selective orexin-1 receptor antagonist, had no effect on the depressant effect of orexin-A on slow VRP. Bath application of [Ala11,D-Leu15]-Orexin B, a selective orexin-2 receptor agonist, depressed the slow VRP. Both orexin-A and orexin-B depressed the level of temporal summation of synaptic activity evoked by 20 repetitive stimulations of the dorsal root. These data suggest that orexin-2 receptor, but not orexin-1 receptor, may play an inhibitory role in nociceptive transmission in the neonatal rat spinal cord.

Development of an orexin-2 receptor selective agonist, [Ala(11), D-Leu(15)]orexin-B.[Pubmed:12467628]

Bioorg Med Chem Lett. 2003 Jan 6;13(1):111-3.

Investigation of L-alanine and D-amino acid replacement of orexin-B revealed that three L-leucine residues at the positions of 11, 14, and 15 in orexin-B were important to show selectivity for the orexin-2 receptor (OX(2)) over the orexin-1 receptor (OX(1)). L-Alanine substitution at position 11 and D-leucine substitution at positions 14 and 15 maintained the potency of orexin-B to mobilize [Ca(2+)](i) in CHO cells expressing the OX(2), while their potency for the OX(1) was significantly reduced. In combined substitutions, we identified that [Ala(11), D-Leu(15)]orexin-B showed a 400-fold selectivity for the OX(2) (EC(50)=0.13nM) over OX(1) (EC(50)=52nM). [Ala(11), D-Leu(15)]orexin-B is a beneficial tool for addressing the functional roles of the OX(2).

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