A peptide with diverse biological activities
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VIP (human, porcine, rat, ovine) (trifluoroacetate salt)

Item No. 24996

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Synonyms
  • Vasoactive Intestinal Peptide
Molecular Formula
C147H238N44O42S • XCF3COOH
Formula Weight
3325.8
Purity
≥95%
Formulation (Request formulation change)
A lyophilized powder
Solubility(Learn about Variance in Solubility)
Formic Acid: 1 mg/mlWater: 1mg/mL
SMILES
NC([C@H](CC(N)=O)NC([C@H](CC(C)C)NC([C@@]([C@H](CC)C)([H])NC([C@H](CO)NC([C@H](CC(N)=O)NC([C@H](CC(C)C)NC([C@@H](NC([C@H](CCCCN)NC([C@H](CCCCN)NC([C@H](C(C)C)NC([C@@H](NC([C@@H](NC([C@H](CCC(N)=O)NC([C@H](CCCCN)NC([C@H](CCCNC(N)=N)NC([C@H](CC(C)C)NC([C@H](CCCNC(N)=N)NC([C@@]([C@@H](C)O)([H])NC([C@@H](NC([C@H](CC(N)=O)NC([C@@H](NC([C@@]([C@@H](C)O)([H])NC([C@@H](NC([C@H](C(C)C)NC([C@@H](NC([C@@H](NC([C@H](CO)NC([C@@H](N[H])CC1=CN=CN1)=O)=O)CC(O)=O)=O)C)=O)=O)CC2=CC=CC=C2)=O)=O)CC(O)=O)=O)=O)CC3=CC=C(O)C=C3)=O)=O)=O)=O)=O)=O)=O)CCSC)=O)C)=O)=O)=O)=O)CC4=CC=C(O)C=C4)=O)=O)=O)=O)=O)=O)=O.FC(F)(C(O)=O)F
InChi Code
InChI=1S/C147H238N44O42S.C2HF3O2/c1-18-75(12)115(143(231)182-97(56-72(6)7)131(219)174-94(118(156)206)61-108(153)199)189-140(228)106(68-193)186-135(223)102(63-110(155)201)179-132(220)96(55-71(4)5)176-133(221)98(58-81-37-41-84(196)42-38-81)177-126(214)88(33-23-26-49-149)168-124(212)89(34-24-27-50-150)172-141(229)113(73(8)9)187-119(207)76(13)165-122(210)93(47-53-234-17)171-128(216)92(45-46-107(152)198)170-123(211)87(32-22-25-48-148)167-125(213)90(35-28-51-162-146(157)158)169-130(218)95(54-70(2)3)175-127(215)91(36-29-52-163-147(159)160)173-144(232)116(78(15)194)190-137(225)99(59-82-39-43-85(197)44-40-82)178-134(222)101(62-109(154)200)180-136(224)104(65-112(204)205)184-145(233)117(79(16)195)191-138(226)100(57-80-30-20-19-21-31-80)183-142(230)114(74(10)11)188-120(208)77(14)166-129(217)103(64-111(202)203)181-139(227)105(67-192)185-121(209)86(151)60-83-66-161-69-164-83;3-2(4,5)1(6)7/h19-21,30-31,37-44,66,69-79,86-106,113-117,192-197H,18,22-29,32-36,45-65,67-68,148-151H2,1-17H3,(H2,152,198)(H2,153,199)(H2,154,200)(H2,155,201)(H2,156,206)(H,161,164)(H,165,210)(H,166,217)(H,167,213)(H,168,212)(H,169,218)(H,170,211)(H,171,216)(H,172,229)(H,173,232)(H,174,219)(H,175,215)(H,176,221)(H,177,214)(H,178,222)(H,179,220)(H,180,224)(H,181,227)(H,182,231)(H,183,230)(H,184,233)(H,185,209)(H,186,223)(H,187,207)(H,188,208)(H,189,228)(H,190,225)(H,191,226)(H,202,203)(H,204,205)(H4,157,158,162)(H4,159,160,163);(H,6,7)/t75-,76-,77-,78+,79+,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,113-,114-,115-,116-,117-;/m0./s1
InChi Key
LXPSGCIBCPYDQE-JEBDDVQLSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Vasoactive intestinal peptide (VIP) is a 28-amino acid peptide that has roles as a hormone and neurotransmitter and has diverse biological activities, including roles in vasodilation, inflammation, and metabolism, as well as regulation of the circadian rhythm.1 It is an agonist of vasoactive intestinal polypeptide receptor 1 (VPAC1) and VPAC2, inducing adenylate cyclase activity with EC50 values of 3 and 8 nM, respectively, in CHO cell membranes expressing the recombinant human receptors, and is selective for these receptors over proteasome assembly chaperone 1 (PAC1; Ki = 500-1,000 nM in radioligand binding assays).2,3 VIP (10-300 nM) induces relaxation of isolated human fundus or antrum circular smooth muscle strips precontracted with carbachol (carbamoylcholine; Item No. 14486).4 It reduces increases in gastric acid secretion and mucosal blood flow induced by the CCK2 receptor agonist pentagastrin (Item No. 28546) in conscious dogs when administered intravenously at a dose of 8 µg/kg.5 VIP (5-10 nmol/animal, i.p.) decreases serum and peritoneal lavage levels of TNF-α and IL-6 and reduces mortality in a mouse model of LPS-induced endotoxemia.6 It inhibits replication of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) in Calu-3 human lung epithelial cells and isolated human peripheral blood monocytes.7 It also inhibits production of IL-6, IL-8, and TNF-α in SARS-CoV-2-infected Calcu-3 cells.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Iwasaki, M., Akiba, Y., and Kaunitz, J.D. Recent advances in vasoactive intestinal peptide physiology and pathophysiology: Focus on the gastrointestinal system. F1000Res. 8, 1629 (2019).

    2. Van Rampelbergh, J., Juarranz, M.-G., Perret, J., et al. Characterization of a novel VPAC1 selective agonist and identification of the receptor domains implicated in the carboxyl-terminal peptide recognition. Br. J. Pharmacol. 130(4), 819-826 (2000).

    3. Harmar, A.J., Fahrenkrug, J., Gozes, I., et al. Pharmacology and functions of receptors for vasoactive intestinal peptide and pituitary adenylate cyclase-activating polypeptide: IUPHAR review 1. Br. J. Pharmacol. 166(1), 4-17 (2012).

    4. Severi, C., Tattoli, I., Corleto, V.D., et al. Vasoactive intestinal peptide receptor subtypes and signalling pathways involved in relaxation of human stomach. Neurogastroenterol. Motil. 18(11), 1009-1018 (2006).

    5. Konturek, S.J., Dembiński, A., Thor, P., et al. Comparison of vasoactive intestinal peptide (VIP) and secretin in gastric secretion and mucosal blood flow. Pflügers Arch. 361(2), 175-181 (1976).

    6. Delgado, M., Gomariz, R.P., Martinez, C., et al. Anti-inflammatory properties of the type 1 and type 2 vasoactive intestinal peptide receptors: role in lethal endotoxic shock. Eur. J. Immunol. 30(11), 3236-3246 (2000).

    7. Temerozo, J.R., Sacramento, C.Q., Fintelman-Rodrigues, N., et al. The neuropeptides VIP and PACAP inhibit SARS-CoV-2 replication in monocytes and lung epithelial cells, decrease the production of proinflammatory cytokines, and VIP levels are associated with survival in severe Covid-19 patients. bioRxiv Preprint, (2020).