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05-23-2101

Sigma-Aldrich

Vasoactive Intestinal Peptide, Human, Porcine, and Rat

Acts as a mitogenic factor for embryonic neurons in the sympathetic nervous system.

Synonym(s):

Vasoactive Intestinal Peptide, Human, Porcine, and Rat, VIP

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About This Item

Empirical Formula (Hill Notation):
C147H238N44O42S
CAS Number:
40077-57-4
Molecular Weight:
3325.80
MDL number:
MFCD00167535
UNSPSC Code:
12352202
NACRES:
NA.77

Quality Level

100

Assay

≥95% (HPLC)

form

lyophilized solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
desiccated (hygroscopic)

color

white to off-white

solubility

5% acetic acid: 1 mg/mL

shipped in

ambient

storage temp.

−20°C

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

InChI key

VBUWHHLIZKOSMS-RIWXPGAOSA-N

General description

Acts as a mitogenic factor for embryonic neurons in the sympathetic nervous system. Has powerful hypotensive and vasodilatory effects. Behaves either as a circulating hormone or as a neurotransmitter. Stimulates cAMP production in rat peritoneal macrophages. Inhibits the growth of human small-cell lung carcinoma (SCLC) both in vitro and in vivo, suggesting that it may be useful as a less toxic alternative to conventional chemotherapeutic agents in the treatment of SCLC. Nitric oxide stimulates the release of this peptide.
Acts as a mitogenic factor for embryonic neurons in the sympathetic nervous system. Has powerful hypotensive and vasodilatory effects. Behaves either as a circulating hormone or as a neurotransmitter. Stimulates cAMP production in rat peritoneal macrophages. Nitric oxide stimulates the release of this peptide. Inhibits human small-cell lung carcinoma (SCLC) in nude mice both in vitro and in vivo, suggesting that it may be useful as a less toxic alternative to conventional chemotherapeutic agents in the treatment of SCLC.

Biochem/physiol Actions

Cell permeable: no
Primary Target
Mitogenic factor for embryonic neurons
Product does not compete with ATP.
Reversible: no

Packaging

Yes

Warning

Toxicity: Harmful (C)

Sequence

H-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

Physical form

Supplied as a trifluoroacetate salt.

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Maruno, K., et al. 1998. Proc. Natl. Acad. Sci. USA 95, 14373.
Bakker, R., et al. 1993. Am. J. Physiol.264, R362.
Grider, J.R. 1993. Am. J. Physiol.264, G334.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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J R Grider
The American journal of physiology, 264(2 Pt 1), G334-G340 (1993-02-01)
Involvement of vasoactive intestinal peptide (VIP) and nitric oxide (NO) in neurally induced relaxation was examined in smooth muscle from rat colon. Relaxation induced by field stimulation or radial stretch (i.e., descending relaxation phase of the peristaltic reflex) was accompanied
K Maruno et al.
Proceedings of the National Academy of Sciences of the United States of America, 95(24), 14373-14378 (1998-11-25)
Small-cell lung carcinoma (SCLC) is an aggressive, rapidly growing and metastasizing, and highly fatal neoplasm. We report that vasoactive intestinal peptide inhibits the proliferation of SCLC cells in culture and dramatically suppresses the growth of SCLC tumor-cell implants in athymic
R Bakker et al.
The American journal of physiology, 264(2 Pt 2), R362-R368 (1993-02-01)
Bidirectional fluxes of Cl- across isolated and stripped goldfish intestinal epithelium mounted in Ussing-type chambers increased after addition of 8-bromoadenosine 3',5'-cyclic monophosphate (8-Br-cAMP), suggesting an increase of the paracellular permeability for Cl-. Confirming this, the addition of 8-Br-cAMP to the

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