A zonulin antagonist
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Larazotide (acetate)

Item No. 43008

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
glycylglycyl-L-valyl-L-leucyl-L-valyl-L-glutaminyl-L-prolyl-glycine, monoacetate salt
CAS Number
881851-50-9
Synonyms
  • AT-1001
  • Gly-Gly-Val-Leu-Val-Gln-Pro-Gly
Molecular Formula
C32H55N9O10 • C2H4O2
Formula Weight
785.9
Purity
≥98%
Formulation (Request formulation change)
A solid
Peptide Sequence
GGVLVQPG-OH
Solubility(Learn about Variance in Solubility)
DMSO: Sparingly Soluble: 1-10 mg/mlPBS pH 7.2: Sparingly Soluble: 1-10 mg/ml
SMILES
CC(O)=O.NCC(NCC(N[C@@H](C(C)C)C(N[C@@H](CC(C)C)C(N[C@@H](C(C)C)C(N[C@@H](CCC(N)=O)C(N1[C@@H](CCC1)C(NCC(O)=O)=O)=O)=O)=O)=O)=O)=O
InChi Code
InChI=1S/C32H55N9O10.C2H4O2/c1-16(2)12-20(38-30(49)26(17(3)4)39-24(44)14-35-23(43)13-33)28(47)40-27(18(5)6)31(50)37-19(9-10-22(34)42)32(51)41-11-7-8-21(41)29(48)36-15-25(45)46;1-2(3)4/h16-21,26-27H,7-15,33H2,1-6H3,(H2,34,42)(H,35,43)(H,36,48)(H,37,50)(H,38,49)(H,39,44)(H,40,47)(H,45,46);1H3,(H,3,4)/t19-,20-,21-,26-,27-;/m0./s1
InChi Key
NYGCNONRVCGHAT-UFIKZEAMSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $28

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    5 mg

    $110

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    10 mg

    $180

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    50 mg

    $413

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    Product Description

    Larazotide is a peptide zonulin antagonist.1 It inhibits human zonulin- or V. cholerae zonula occludens toxin-induced decreases in intestinal permeability in rhesus monkey ileal sheets at 1 µg/ml. Larazotide decreases inflammatory cytokine-induced tight junction dysfunction in isolated rat intestinal epithelial cells and inhibits the apical-to-basolateral translocation of a fragment of gliadin, a protein implicated in celiac disease, in Caco-2 intestinal epithelial cells.2,3 It increases intestinal epithelial cell bridging and decreases intestinal damage but does not reduce liver damage in a rat model of acute liver failure.4 Larazotide is also an antagonist of α3β4 nicotinic acetylcholine receptors (nAChRs; IC50 = 91 nM) and is selective for α3β4 nAChRs over α4β2 nAChRs (IC50 = 276 nM).5 It inhibits nicotine self-administration and varenicline-induced reinstatement of nicotine-seeking behavior in rats at 0.3, 3, and 30 µg/kg.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wang, W., Uzzau, S., Goldblum, S.E., et al. Human zonulin, a potential modulator of intestinal tight junctions. J. Cell Sci. 113(Pt 24), 4435-4440 (2000).

    2. Khaleghi, S., Ju, J.M., Lamba, A., et al. The potential utility of tight junction regulation in celiac disease: focus on larazotide acetate. Therap. Adv. Gastroenterol. 9(1), 37-49 (2016).

    3. Gopalakrishnan, S., Durai, M., Kitchens, K., et al. Larazotide acetate regulates epithelial tight junctions in vitro and in vivo. Peptides 35(1), 86-94 (2012).

    4. Caliskan, A.R., Gul, M., Yilmaz, I., et al. Effects of larazotide acetate, a tight junction regulator, on the liver and intestinal damage in acute liver failure in rats. Hum. Exp. Toxicol. 40 (12 suppl), S693-S701 (2021).

    5. Cippitelli, A., Wu, J., Gaiolini, K.A., et al. AT-1001: A high-affinity α3β4 nAChR ligand with novel nicotine-suppressive pharmacology. Br. J. Pharmacol. 172(7), 1834-1845 (2015).