[Ac-Tyr1,D-Phe2]GRF 1-29, amide (human)VIP receptor antagonist CAS# 93965-89-0 |
![[Ac-Tyr1,D-Phe2]GRF 1-29, amide (human)](/media/images/struct/BCC5719.png "[Ac-Tyr1,D-Phe2]GRF 1-29, amide (human)")
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Quality Control & MSDS
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Chemical structure
3D structure
| Cas No. | 93965-89-0 | SDF | Download SDF |
| PubChem ID | 56841984 | Appearance | Powder |
| Formula | C157H252N44O43S | M.Wt | 3476.0 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Solubility | Soluble to 2 mg/ml in water | ||
| Sequence | YFDAIFTNSYRKVLGQLSARKLLQDIMSR (Modifications: Tyr-1 = N-terminal Ac, Phe-2 = D-Phe, Arg-29 = C-terminal amide) | ||
| Chemical Name | (3S)-3-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-acetamido-3-(4-hydroxyphenyl)propanoyl]amino]-3-phenylpropanoyl]amino]-3-carboxypropanoyl]amino]propanoyl]amino]-3-methylpentanoyl]amino]-3-phenylpropanoyl]amino]-3-hydroxybutanoyl]amino]-4-amino-4-oxobutanoyl]amino]-3-hydroxypropanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-5-carbamimidamidopentanoyl]amino]-6-aminohexanoyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]acetyl]amino]-5-amino-5-oxopentanoyl]amino]-4-methylpentanoyl]amino]-3-hydroxypropanoyl]amino]propanoyl]amino]-5-carbamimidamidopentanoyl]amino]-6-aminohexanoyl]amino]-4-methylpentanoyl]amino]-4-methylpentanoyl]amino]-5-amino-5-oxopentanoyl]amino]-4-[[(2S,3S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-amino-5-carbamimidamido-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-4-oxobutanoic acid | ||
| SMILES | CCC(C)C(C(=O)NC(CC1=CC=CC=C1)C(=O)NC(C(C)O)C(=O)NC(CC(=O)N)C(=O)NC(CO)C(=O)NC(CC2=CC=C(C=C2)O)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCCCN)C(=O)NC(C(C)C)C(=O)NC(CC(C)C)C(=O)NCC(=O)NC(CCC(=O)N)C(=O)NC(CC(C)C)C(=O)NC(CO)C(=O)NC(C)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCCCN)C(=O)NC(CC(C)C)C(=O)NC(CC(C)C)C(=O)NC(CCC(=O)N)C(=O)NC(CC(=O)O)C(=O)NC(C(C)CC)C(=O)NC(CCSC)C(=O)NC(CO)C(=O)NC(CCCNC(=N)N)C(=O)N)NC(=O)C(C)NC(=O)C(CC(=O)O)NC(=O)C(CC3=CC=CC=C3)NC(=O)C(CC4=CC=C(C=C4)O)NC(=O)C | ||
| Standard InChIKey | ZADZHIQNEPVWIV-QSAFYHFUSA-N | ||
| Standard InChI | InChI=1S/C157H252N44O43S/c1-20-83(13)124(199-129(219)86(16)174-138(228)112(72-121(213)214)191-144(234)108(67-89-35-24-22-25-36-89)188-142(232)107(176-88(18)206)69-91-44-48-93(207)49-45-91)153(243)193-110(68-90-37-26-23-27-38-90)146(236)201-126(87(17)205)154(244)194-111(71-119(162)211)145(235)197-116(77-204)150(240)189-109(70-92-46-50-94(208)51-47-92)143(233)182-99(43-34-61-172-157(168)169)132(222)181-97(40-29-31-58-159)137(227)198-123(82(11)12)151(241)192-103(63-78(3)4)130(220)173-74-120(212)177-100(52-54-117(160)209)134(224)186-106(66-81(9)10)141(231)196-114(75-202)148(238)175-85(15)128(218)179-98(42-33-60-171-156(166)167)131(221)180-96(39-28-30-57-158)133(223)185-105(65-80(7)8)140(230)187-104(64-79(5)6)139(229)183-101(53-55-118(161)210)135(225)190-113(73-122(215)216)147(237)200-125(84(14)21-2)152(242)184-102(56-62-245-19)136(226)195-115(76-203)149(239)178-95(127(163)217)41-32-59-170-155(164)165/h22-27,35-38,44-51,78-87,95-116,123-126,202-205,207-208H,20-21,28-34,39-43,52-77,158-159H2,1-19H3,(H2,160,209)(H2,161,210)(H2,162,211)(H2,163,217)(H,173,220)(H,174,228)(H,175,238)(H,176,206)(H,177,212)(H,178,239)(H,179,218)(H,180,221)(H,181,222)(H,182,233)(H,183,229)(H,184,242)(H,185,223)(H,186,224)(H,187,230)(H,188,232)(H,189,240)(H,190,225)(H,191,234)(H,192,241)(H,193,243)(H,194,244)(H,195,226)(H,196,231)(H,197,235)(H,198,227)(H,199,219)(H,200,237)(H,201,236)(H,213,214)(H,215,216)(H4,164,165,170)(H4,166,167,171)(H4,168,169,172)/t83-,84-,85-,86-,87+,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,111-,112-,113-,114-,115-,116-,123-,124-,125-,126-/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. |
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| 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. |
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| 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. | ||
| Description | VIP receptor antagonist; inhibits [125I]iodo-VIP binding and selectively inhibits VIP- and GRF-induced effects on adenylyl cyclase. |
[Ac-Tyr1,D-Phe2]GRF 1-29, amide (human) Dilution Calculator
[Ac-Tyr1,D-Phe2]GRF 1-29, amide (human) Molarity Calculator
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Evidence that endogenous vasoactive intestinal peptide (VIP) is involved in the regulation of rat pituitary-adrenocortical function: in vivo studies with a VIP antagonist.[Pubmed:7862261]
Neuropeptides. 1994 Nov;27(5):297-303.
The effect of a subcutaneous bolus injection of 2 micrograms magnitude of Ac,Tyr1,D-Phe2-GRF(1-29) amide, a specific VIP antagonist (VIP-A), on the hypothalamo-pituitary-adrenocortical (HPA) axis were investigated in both normal and ether- or cold-stressed rats. Blood concentrations of ACTH, aldosterone (ALDO) and corticosterone (B) were measured by specific RIA 1, 2 or 4 h after VIP-A injection. VIP-A administration to normal rats strikingly lowered the plasma concentration of ALDO, without significantly affecting those of ACTH and B. Ether and cold stresses notably raised the blood levels of ACTH, ALDO and B, and these rises lasted unchanged until 4 h. VIP-A did not affect the response of HPA axis to ether stress, but provoked a marked depression of that to cold stress. In light of these findings the following conclusions can be drawn: (i) endogenous VIP does not regulate HPA-axis function under basal conditions, but it plays a pivotal role in the mechanisms involved in the activation of HPA axis induced by cold exposure; and (ii) endogenous VIP exerts a tonic stimulatory action on ALDO secretion, probably by acting directly on the adrenal zona glomerulosa.
Interaction of growth hormone-releasing factor (GRF) and 14 GRF analogs with vasoactive intestinal peptide (VIP) receptors of rat pancreas. Discovery of (N-Ac-Tyr1,D-Phe2)-GRF(1-29)-NH2 as a VIP antagonist.[Pubmed:2859987]
Endocrinology. 1985 Jun;116(6):2643-9.
Adenylate cyclase stimulation by GH-releasing factor (GRF) and 14 GRF analogs (modified in the N-terminal part) was compared to the capacity of the same peptides to inhibit [125I]iodo-vasoactive intestinal peptide (VIP) binding in rat pancreatic plasma membranes. These peptides interfered with VIP receptors as they inhibited [125I]iodo-VIP binding, and probably acted through VIP-preferring receptors as one of these peptides [(N-Ac-Tyr1,D-Phe2)-GRF(1-29)-NH2] selectively inhibited both VIP- and GRF-stimulated adenylate cyclase activities. In general, alterations in positions 6 and 7 (but not in positions 1-4) markedly reduced the affinity of the resulting GRF analog [based on Kact (concentration exerting half-maximal stimulation) values]. The intrinsic activity exerted by GRF analogs on adenylate cyclase was reduced by acetylation of the free NH2 group and by the replacement of Asp3, Ala4, Phe6, and Thr7 by the corresponding D-isomer. The presence of pCl-Phe6 and Trp6 also depressed this parameter. Substitution in GRF (or its N-acetylated derivative) by D-Phe2, D-Arg2, and D-Ala4 again reduced the intrinsic activity, whereas substitution of the natural L-amino acid residue by D-Ala2 and Phe4 gave superagonists.
