Rotigaptide (ZP123) is a novel and specific modulator of connexin 43 (Cx43). Rotigaptide prevents the uncoupling of Cx43-mediated gap junction communication and normalizes cell-to-cell communication during acute metabolic stress. Rotigaptide is a potent antiarrhythmic peptide (AAP) with improved stability and has the potential for the investigation of cardiac arrhythmias-specifically atrial fibrillation.

Product information

CAS Number: 355151-12-1

Molecular Weight: 617.65

Formula: C28H39N7O9

Synonym:

ZP123

Chemical Name: (2R)-N-(carbamoylmethyl)-2-(2-{[(2R,4S)-1-[(2R)-1-[(2R)-2-acetamido-3-(4-hydroxyphenyl)propanoyl]pyrrolidine-2-carbonyl]-4-hydroxypyrrolidin-2-yl]formamido}acetamido)propanamide

Smiles: CC(=O)N[C@H](CC1=CC=C(O)C=C1)C(=O)N1CCC[C@@H]1C(=O)N1C[C@@H](O)C[C@@H]1C(=O)NCC(=O)N[C@H](C)C(=O)NCC(N)=O

InChiKey: GFJRASPBQLDRRY-TWTQBQJDSA-N

InChi: InChI=1S/C28H39N7O9/c1-15(25(41)30-12-23(29)39)32-24(40)13-31-26(42)22-11-19(38)14-35(22)28(44)21-4-3-9-34(21)27(43)20(33-16(2)36)10-17-5-7-18(37)8-6-17/h5-8,15,19-22,37-38H,3-4,9-14H2,1-2H3,(H2,29,39)(H,30,41)(H,31,42)(H,32,40)(H,33,36)/t15-,19+,20-,21-,22-/m1/s1

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: Soluble in DMSO

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Rotigaptide (100 nM; 24 hours) has a positive effect on cycloheximide-mediated decrease in Cx43 protein levels in cultured neonatal ventricular myocytes. Rotigaptide (100 nM; 24 hours) dose not affect INS-1 cell apoptosis itself. And it significantly reduces apoptosis in cytokine-exposed cells ~10% at IL-1b concentrations above 15 pg/ml in rat insulin-producing INS-1 cells.

In Vivo:

Rotigaptide (intravenous administration; 300 mg/kg; single dose) treatment in mice and rats does not result in toxicity in either species. In escalating dose studies, Rotigaptide (continuous intravenous infusion; 5-14 days) in rats (100 mg/kg) and dogs (10 mg/kg) are well tolerated and produces no compound-related effects or histological toxicological findings.

References:

1. Seyed Mojtaba Ghiasi, et al. The connexin 43 regulator Rotigaptide reduces cytokine-induced cell death in human islets
2. Stahlhut M, et al. The antiarrhythmic peptide rotigaptide (ZP123) increases connexin 43 protein expression in neonatal rat ventricular cardiomyocytes.Cell Commun Adhes. 2006 Jan-Apr;13(1-2):21-7.
3. Kjølbye AL, et al. Pharmacological modulation of gap junction function with the novel compound rotigaptide: a promising new principle for prevention of arrhythmias.Basic Clin Pharmacol Toxicol. 2007 Oct;101(4):215-30.

Products are for research use only. Not for human use.