VIP

Product Name:VIP

Cas No:37221-79-7

Purity:95%

Chemical Formula:C147H237N43O43S

Molar Mass:3326.8

Synonyms:VASOACTIVE INTESTINAL PEPTIDE; 37221-79-7; UNII-6J2WVD66KR

IUPAC Name:(2S)-4-amino-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-3-(1H-imidazol-4-yl)propanoyl]amino]-3-hydroxypropanoyl]amino]-3-carboxypropanoyl]amino]propanoyl]amino]-3-methylbutanoyl]amino]-3-phenylpropanoyl]amino]-3-hydroxybutanoyl]amino]-3-carboxypropanoyl]amino]-4-oxobutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-hydroxybutanoyl]amino]-5-carbamimidamidopentanoyl]amino]-4-methylpentanoyl]amino]-5-carbamimidamidopentanoyl]amino]hexanoyl]amino]-5-oxopentanoyl]amino]-4-methylsulfanylbutanoyl]amino]propanoyl]amino]-3-methylbutanoyl]amino]hexanoyl]amino]hexanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-methylpentanoyl]amino]-4-oxobutanoyl]amino]-3-hydroxypropanoyl]amino]-3-methylpentanoyl]amino]-4-methylpentanoyl]amino]-4-oxobutanoic acid

SMILES:CC[C@H](C)[C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(=O)N)C(=O)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC1=CC=C(C=C1)O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(=O)N)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]([C@@H](C)O)NC(=O)[C@H](CC2=CC=C(C=C2)O)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC3=CC=CC=C3)NC(=O)[C@H](C(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC4=CNC=N4)N

InChIKey:VBUWHHLIZKOSMS-RIWXPGAOSA-N

InChI:InChI=1S/C147H237N43O43S/c1-18-75(12)115(142(229)180-96(56-72(6)7)131(218)183-104(145(232)233)63-110(155)200)188-139(226)106(68-192)185-134(221)101(62-109(154)199)177-130(217)95(55-71(4)5)174-132(219)97(58-81-37-41-84(195)42-38-81)175-125(212)88(33-23-26-49-149)167-123(210)89(34-24-27-50-150)171-140(227)113(73(8)9)186-118(205)76(13)164-121(208)93(47-53-234-17)170-127(214)92(45-46-107(152)197)169-122(209)87(32-22-25-48-148)166-124(211)90(35-28-51-161-146(156)157)168-129(216)94(54-70(2)3)173-126(213)91(36-29-52-162-147(158)159)172-143(230)116(78(15)193)189-136(223)98(59-82-39-43-85(196)44-40-82)176-133(220)100(61-108(153)198)178-135(222)103(65-112(203)204)182-144(231)117(79(16)194)190-137(224)99(57-80-30-20-19-21-31-80)181-141(228)114(74(10)11)187-119(206)77(14)165-128(215)102(64-111(201)202)179-138(225)105(67-191)184-120(207)86(151)60-83-66-160-69-163-83/h19-21,30-31,37-44,66,69-79,86-106,113-117,191-196H,18,22-29,32-36,45-65,67-68,148-151H2,1-17H3,(H2,152,197)(H2,153,198)(H2,154,199)(H2,155,200)(H,160,163)(H,164,208)(H,165,215)(H,166,211)(H,167,210)(H,168,216)(H,169,209)(H,170,214)(H,171,227)(H,172,230)(H,173,213)(H,174,219)(H,175,212)(H,176,220)(H,177,217)(H,178,222)(H,179,225)(H,180,229)(H,181,228)(H,182,231)(H,183,218)(H,184,207)(H,185,221)(H,186,205)(H,187,206)(H,188,226)(H,189,223)(H,190,224)(H,201,202)(H,203,204)(H,232,233)(H4,156,157,161)(H4,158,159,162)/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

Storage:-20 degree Celsius

Sequence:HSDAVFTDNYTRLRKQMAVKKYLNSILN

Application:Vasoactive Intestinal Peptide (VIP) is a 28-amino acid neuropeptide and hormone widely expressed in the central and peripheral nervous systems, as well as in the gastrointestinal tract, lungs, and immune tissues. VIP plays crucial roles in vasodilation, smooth muscle relaxation, circadian rhythm regulation, and anti-inflammatory immune signaling. It acts through VPAC1 and VPAC2 receptors to modulate cytokine production, T-cell responses, and neuroendocrine balance. VIP is a key molecule in studies of autoimmune disorders, asthma, neurodegeneration, IBD, and cardiopulmonary function, offering a broad-spectrum, endogenous regulatory mechanism for immune homeostasis and tissue protection.

Current Research:Introduction: What Is VIP?
Vasoactive Intestinal Peptide (VIP) is a highly conserved neuropeptide composed of 28 amino acids, first identified in the gut but now known to be distributed widely in the nervous, immune, endocrine, and cardiovascular systems. VIP functions both as a neurotransmitter and neurohormone, playing pivotal roles in smooth muscle regulation, vasodilation, immunomodulation, and neuronal signaling.

It is primarily synthesized by parasympathetic neurons, including those in the enteric nervous system, and exerts its effects via VPAC1 and VPAC2 receptors, which are G protein-coupled receptors expressed in a wide array of tissues.

Mechanism of Action: Receptor Signaling and Gene Modulation
VIP acts through VPAC1 and VPAC2 receptors to initiate cyclic AMP (cAMP)-dependent signaling pathways, which regulate numerous physiological processes. VIP binding activates:

Adenylyl cyclase, increasing intracellular cAMP

Protein kinase A (PKA) activation

Downstream transcription factors like CREB, influencing gene expression

Through these signaling cascades, VIP modulates:

Cytokine secretion

Smooth muscle tone

Neurotransmitter release

Cell survival and apoptosis

Its pleiotropic nature allows it to influence diverse physiological domains, including immune balance, vascular tone, and neuroendocrine regulation.

Immunomodulatory Effects
VIP is a potent anti-inflammatory and immunoregulatory peptide, known to:

Inhibit pro-inflammatory cytokines such as TNF-α, IL-1β, IL-6

Promote anti-inflammatory cytokines like IL-10

Induce differentiation of regulatory T cells (Tregs)

Suppress Th1 and Th17 responses, which are implicated in autoimmunity

These actions have positioned VIP as a therapeutic target in autoimmune diseases such as:

Rheumatoid arthritis

Multiple sclerosis

Inflammatory bowel disease (IBD)

Type 1 diabetes

Its ability to rebalance immune tone without broad immunosuppression is a major advantage in peptide immunotherapy.

Neuroprotective and Neurological Roles
In the central nervous system, VIP contributes to:

Neuronal survival and plasticity

Regulation of circadian rhythms via the suprachiasmatic nucleus (SCN)

Modulation of cognition, learning, and behavior

Reduction of oxidative stress and excitotoxicity

It has shown promise in models of:

Alzheimer’s disease

Parkinson’s disease

Amyotrophic lateral sclerosis (ALS)

Epilepsy and stroke recovery

VIP protects neurons through anti-apoptotic signaling, modulation of glial cell activation, and enhancement of cerebral blood flow.

Pulmonary and Cardiovascular Applications
VIP is also a potent vasodilator and bronchodilator, acting on vascular and airway smooth muscle. In pulmonary research, it has shown value in:

Asthma and COPD, by relaxing bronchial smooth muscle and reducing airway inflammation

Pulmonary arterial hypertension (PAH), by decreasing vascular resistance and improving perfusion

Enhancing microcirculation and cardiovascular resilience under hypoxic stress

Its role in systemic vascular tone regulation makes it a candidate for managing vascular inflammation, hypertension, and ischemic events.

Gastrointestinal and Endocrine Functions
Originally isolated from the gut, VIP regulates:

Gastrointestinal motility

Secretion of digestive enzymes and bicarbonate

Inhibition of gastric acid secretion

Pancreatic endocrine balance, including stimulation of insulin release

VIP contributes to maintaining gut epithelial integrity, modulating enteric inflammation, and supporting gut-brain communication.

Conclusion
Vasoactive Intestinal Peptide (VIP) is a multifunctional regulatory peptide with far-reaching effects across the immune, nervous, cardiovascular, and gastrointestinal systems. Its ability to promote anti-inflammatory signaling, protect neurons, and regulate smooth muscle and endocrine function makes it a key target in regenerative medicine, immunotherapy, and neuroendocrinology. As a natural, endogenous peptide, VIP offers broad therapeutic potential for restoring homeostasis and resilience in complex disease states.

Reference:

Gomariz, R. P., Martinez, C., Abad, C., Leceta, J., & Delgado, M. (2001). Immunology of VIP: a review and therapeutical perspectives. Current pharmaceutical design, 7(2), 89-111.