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V6130

Sigma-Aldrich

Vasoactive Intestinal Peptide human, porcine, rat

synthetic, ≥95% (HPLC), powder

Synonym(s):
VIP
Empirical Formula (Hill Notation):
C147H238N44O42S
CAS Number:
Molecular Weight:
3325.80
MDL number:
PubChem Substance ID:
NACRES:
NA.32

Quality Level

biological source

synthetic

assay

≥95% (HPLC)

form

powder

solubility

1% acetic acid: soluble, clear, colorless

UniProt accession no.

storage temp.

−20°C

SMILES string

CC[C@H](C)[C@H](NC(=O)[C@H](CO)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](Cc3ccccc3)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)Cc4c[nH]cn4)C(C)C)[C@@H](C)O)[C@@H](C)O)C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(N)=O

InChI

1S/C147H238N44O42S/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/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)/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

HEOYHMUESMJFDC-RIWXPGAOSA-N

Gene Information

human ... VIP(7432)

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Amino Acid Sequence

His-Ser-Asp-Ala-Val-Phe-Thr-Asp-Asn-Tyr-Thr-Arg-Leu-Arg-Lys-Gln-Met-Ala-Val-Lys-Lys-Tyr-Leu-Asn-Ser-Ile-Leu-Asn-NH2

General description

Vasoactive Intestinal Peptide (VIP) is expressed in airway epithelial cells, secretory glands, immune and inflammatory cells. It functions as a neuroendocrine hormone and putative neurotransmitter. It stimulates neuronal survival and modulates glycogen metabolism. VIP blocks mitogen-activated proliferation of T cells by preventing interleukin-2 production. It promotes electrolyte secretion and provides protection against oxidant injury.

Application

Vasoactive Intestinal Peptide human, porcine, rat was used to treat human donor corneoscleral explants to maintain corneal endothelial (CE) integrity during eye banking. The product was also used as a test compound for studying its impact on swimbladder blood flow by using saline- or blood-perfused swimbladder preparations of the freshwater European eel Anguilla Anguilla.
Vasoactive Intestinal Peptide human, porcine, rat has been used to study its ability to stimulate adenosine 3′,5′-cyclic monophosphate (cyclic AMP) formation in the hypothalamus and cerebral cortex of chick and rats.

Biochem/physiol Actions

Neuropeptide that is widely distributed in the central and peripheral nervous systems. It is a vasodilator, bronchodilator and smooth muscle relaxant. It modulates the activity of many immune system cell types. It is a mitogen for embryonic sympathetic neurons. Its neuroprotective actions are mediated by the release of activity-dependent neurotrophic factors from glial cells.
Vasoactive Intestinal Peptide human, porcine, rat (VIP) is a neuropeptide synthesized in the central nervous system that enhances the formation of adenosine 3′,5′-cyclic monophosphate in cerebral cortex and hypothalamus of chick and rat. VIP modulates the cholinergic as well as serotonergic neurotransmitter systems.

Preparation Note

Vasoactive Intestinal Peptide human, porcine, rat dissolves in distilled water and1% acetic acid to yield a clear, colorless solution.

Other Notes

Lyophilized from 0.1% TFA in H2O

Storage Class Code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Schwerte et al.
The Journal of experimental biology, 202 (Pt 8), 1005-1013 (1999-03-23)
The effects of &bgr;-adrenergic stimulation, vasoactive intestinal polypeptide (VIP), adenosine, the nitric oxide (NO)-releasing agent sodium nitroprusside and of metabolic end-products of gas gland cell metabolism on swimbladder blood flow were investigated using saline- or blood-perfused swimbladder preparations of the...
Andrzej Rychlik et al.
Animals : an open access journal from MDPI, 10(10) (2020-10-02)
Canine inflammatory bowel disease (IBD) is a group of enteropathies with nonspecific chronic symptoms and poorly understood etiology. Many aspects connected with IBD are not understood. One of them is the participation of the intestinal nervous system in the development...
International Union of Pharmacology. XVIII. Nomenclature of receptors for vasoactive intestinal peptide and pituitary adenylate cyclase-activating polypeptide
Harmar AJ, et al.
Pharmacological Reviews, 50(2), 265-270 (1998)
Vasoactive intestinal peptide
Said SI.
Handbook of Biologically Active Peptides, 1307-1311 (2006)
Nobuyuki Hinata et al.
The Journal of urology, 193(3), 1052-1059 (2014-09-23)
We identified the cavernous nerve mesh that exists caudal or posterior to the periprostatic region between the bilateral slings of the levator ani. We also assessed whether nonnerve sparing radical prostatectomy could be modified. Using histological sections from 24 elderly...

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