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[Ala11,22,28]VIP

Potent, highly selective VPAC1 agonist CAS# 291524-04-4

[Ala11,22,28]VIP

2D Structure

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[Ala11,22,28]VIP

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Chemical Properties of [Ala11,22,28]VIP

Cas No. 291524-04-4 SDF Download SDF
PubChem ID 118856036 Appearance Powder
Formula C139H231N43O39S M.Wt 3160.68
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Sequence HSDAVFTDNYARLRKQMAVKKALNSILA-NH2
Chemical Name 4-[[1-[[1-[[1-[[1-[[1-[[4-amino-1-[[1-[[1-[[1-[[1-[[1-[[6-amino-1-[[5-amino-1-[[1-[[1-[[1-[[6-amino-1-[[6-amino-1-[[1-[[1-[[4-amino-1-[[1-[[1-[[1-[(1-amino-1-oxopropan-2-yl)amino]-4-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-1-oxohexan-2-yl]amino]-1-oxohexan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-1-oxohexan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-[[2-[[2-amino-3-(1H-imidazol-4-yl)propanoyl]amino]-3-hydroxypropanoyl]amino]-4-oxobutanoic acid
SMILES CCC(C)C(C(=O)NC(CC(C)C)C(=O)NC(C)C(=O)N)NC(=O)C(CO)NC(=O)C(CC(=O)N)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCCCN)NC(=O)C(CCCCN)NC(=O)C(C(C)C)NC(=O)C(C)NC(=O)C(CCSC)NC(=O)C(CCC(=O)N)NC(=O)C(CCCCN)NC(=O)C(CCCNC(=N)N)NC(=O)C(CC(C)C)NC(=O)C(CCCNC(=N)N)NC(=O)C(C)NC(=O)C(CC1=CC=C(C=C1)O)NC(=O)C(CC(=O)N)NC(=O)C(CC(=O)O)NC(=O)C(C(C)O)NC(=O)C(CC2=CC=CC=C2)NC(=O)C(C(C)C)NC(=O)C(C)NC(=O)C(CC(=O)O)NC(=O)C(CO)NC(=O)C(CC3=CNC=N3)N
Standard InChIKey VRCDGUGECIERMY-UHFFFAOYSA-N
Standard InChI InChI=1S/C139H231N43O39S/c1-20-71(12)108(136(220)174-90(52-66(2)3)123(207)156-72(13)110(147)194)181-133(217)100(64-184)178-129(213)96(59-103(146)189)171-127(211)91(53-67(4)5)168-112(196)74(15)157-116(200)83(34-24-27-46-140)162-119(203)85(36-26-29-48-142)167-134(218)106(69(8)9)179-113(197)75(16)158-117(201)89(45-51-222-19)166-122(206)88(43-44-101(144)187)165-118(202)84(35-25-28-47-141)163-120(204)87(38-31-50-154-139(150)151)164-126(210)92(54-68(6)7)169-121(205)86(37-30-49-153-138(148)149)161-111(195)73(14)159-124(208)93(56-79-39-41-81(186)42-40-79)170-128(212)95(58-102(145)188)172-130(214)98(61-105(192)193)176-137(221)109(77(18)185)182-131(215)94(55-78-32-22-21-23-33-78)175-135(219)107(70(10)11)180-114(198)76(17)160-125(209)97(60-104(190)191)173-132(216)99(63-183)177-115(199)82(143)57-80-62-152-65-155-80/h21-23,32-33,39-42,62,65-77,82-100,106-109,183-186H,20,24-31,34-38,43-61,63-64,140-143H2,1-19H3,(H2,144,187)(H2,145,188)(H2,146,189)(H2,147,194)(H,152,155)(H,156,207)(H,157,200)(H,158,201)(H,159,208)(H,160,209)(H,161,195)(H,162,203)(H,163,204)(H,164,210)(H,165,202)(H,166,206)(H,167,218)(H,168,196)(H,169,205)(H,170,212)(H,171,211)(H,172,214)(H,173,216)(H,174,220)(H,175,219)(H,176,221)(H,177,199)(H,178,213)(H,179,197)(H,180,198)(H,181,217)(H,182,215)(H,190,191)(H,192,193)(H4,148,149,153)(H4,150,151,154)
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 [Ala11,22,28]VIP

DescriptionPotent and highly selective agonist for the human VPAC1 receptor (Ki values are 7.4 and 2352 nM for binding to human recombinant VPAC1 and VPAC2 receptors respectively).

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References on [Ala11,22,28]VIP

Identification of key residues for interaction of vasoactive intestinal peptide with human VPAC1 and VPAC2 receptors and development of a highly selective VPAC1 receptor agonist. Alanine scanning and molecular modeling of the peptide.[Pubmed:10801840]

J Biol Chem. 2000 Aug 4;275(31):24003-12.

The widespread neuropeptide vasoactive intestinal peptide (VIP) has two receptors VPAC(1) and VPAC(2). Solid-phase syntheses of VIP analogs in which each amino acid has been changed to alanine (Ala scan) or glycine was achieved and each analog was tested for: (i) three-dimensional structure by ab initio molecular modeling; (ii) ability to inhibit (125)I-VIP binding (K(i)) and to stimulate adenylyl cyclase activity (EC(50)) in membranes from cell clones stably expressing human recombinant VPAC(1) or VPAC(2) receptor. The data show that substituting residues at 14 positions out of 28 in VIP resulted in a >10-fold increase of K(i) or EC(50) at the VPAC(1) receptor. Modeling of the three-dimensional structure of native VIP (central alpha-helice from Val(5) to Asn(24) with random coiled N and C terminus) and analogs shows that substitutions of His(1), Val(5), Arg(14), Lys(15), Lys(21), Leu(23), and Ile(26) decreased biological activity without altering the predicted structure, supporting that those residues directly interact with VPAC(1) receptor. The interaction of the analogs with human VPAC(2) receptor is similar to that observed with VPAC(1) receptor, with three remarkable exceptions: substitution of Thr(11) and Asn(28) by alanine increased K(i) for binding to VPAC(2) receptor; substitution of Tyr(22) by alanine increased EC(50) for stimulating adenylyl cyclase activity through interaction with the VPAC(2) receptor. By combining 3 mutations at positions 11, 22, and 28, we developed the [Ala(11,22,28)]VIP analog which constitutes the first highly selective (>1,000-fold) human VPAC(1) receptor agonist derived from VIP ever described.

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