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| Targets |
N-Acetyloxytocin targets the oxytocin receptor (OXTR), a class A G protein-coupled receptor (GPCR). The compound's structural similarity to endogenous oxytocin allows it to interact with oxytocin receptors while the acetylation may influence its metabolic profile and alter receptor affinity. Upon receptor binding, it activates downstream G protein-coupled signaling pathways, regulating intracellular second messenger levels such as cAMP, influencing cellular physiological activities. It does not bind appreciably to vasopressin receptors due to the N-acetyl modification altering selectivity.
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| ln Vitro |
A post-translational alteration of oxytocin (OT) and vasopressin (VP) is called N-acetyloxytocin. The acetylated versions are found in different systems that produce OT and VP in addition to the pineal gland, the tissue in which N-acetyloxytocin is first identified[1].
In vitro, N-Acetyloxytocin is used in receptor binding assays to evaluate how structural modifications affect receptor affinity, signal transduction, and peptide degradation. Competition binding assays using radiolabeled oxytocin (e.g., [3H]oxytocin) measure the compound's ability to displace the native ligand, with IC50 values typically in the low nanomolar range for the oxytocin receptor, although the N-acetyl group reduces binding affinity compared to unmodified oxytocin. The peptide also serves as a negative control in cellular assays to study oxytocin-specific effects. |
| ln Vivo |
In vivo, N-Acetyloxytocin has been studied in animal models of social behavior, anxiety, and reproductive physiology. In rodent models, N-acetylated oxytocin analogs show altered pharmacokinetic profiles with extended half-life due to reduced proteolytic degradation. The compound modulates social behavior, anxiety-like behavior, maternal behavior, and uterine contraction frequency in animal models, with the acetylation potentially improving stability and duration of action compared to native oxytocin while reducing non-specific effects.
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| Enzyme Assay |
For in vitro receptor binding assays, N-Acetyloxytocin is dissolved in an appropriate buffer (e.g., 50 mM Tris-HCl, pH 7.4, containing 5 mM MgCl2 and 0.1% BSA). The compound is prepared at concentrations ranging from 10-¹¹ to 10-⁵ M. Membrane preparations from cells expressing the human oxytocin receptor (e.g., CHO-OXTR cells) are incubated with radiolabeled oxytocin (e.g., 0.5 nM [3H]oxytocin) and increasing concentrations of N-Acetyloxytocin. After incubation at room temperature for 60-90 minutes, bound and free radioligands are separated by rapid filtration through GF/B filters. Filters are washed with ice-cold buffer and radioactivity is counted. IC50 values are calculated by nonlinear regression analysis.
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| Cell Assay |
For cell-based studies, cells expressing oxytocin receptors (e.g., HEK293-OXTR, CHO-OXTR, or primary uterine smooth muscle cells) are cultured in standard medium (DMEM with 10% FBS, 1% penicillin-streptomycin) at 37degC with 5% CO2. Cells are seeded in 96-well plates at 2-5 × 10⁴ cells/well and grown to 80-90% confluence. For calcium mobilization assays, cells are loaded with a calcium-sensitive dye (e.g., Fluo-4 AM) and treated with N-Acetyloxytocin (0.1 nM-10 uM). Fluorescence is measured in a microplate reader to monitor intracellular calcium release. For cAMP assays, cells are treated with N-Acetyloxytocin in the presence of a phosphodiesterase inhibitor (e.g., IBMX). cAMP levels are quantified by ELISA or HTRF.
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| Animal Protocol |
For in vivo studies, N-Acetyloxytocin is typically dissolved in sterile saline or PBS and administered to rodents via intracerebroventricular (ICV) injection (1-10 ug per mouse), intraperitoneal injection (0.1-5 mg/kg), or intranasal administration (for behavioral studies). For social behavior assays (e.g., three-chamber social approach test), animals are treated 30-60 minutes before testing. For uterine contraction studies in pregnant animals, N-Acetyloxytocin is administered intravenously and uterine contractile activity is monitored via indwelling catheters or external tocodynamometry. Blood and brain tissue samples are collected at various time points for pharmacokinetic analysis.
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| ADME/Pharmacokinetics |
N-Acetyloxytocin exhibits altered pharmacokinetics compared to native oxytocin due to the N-terminal acetyl group blocking aminopeptidase recognition, thereby conferring resistance to enzymatic degradation. The modification reduces first-pass metabolism and extends plasma half-life (estimated 15-30 minutes vs. 3-5 minutes for oxytocin). The peptide is distributed in plasma and crosses the blood-brain barrier to a limited extent. It is cleared primarily by the kidneys and metabolized by endopeptidases and deacetylases in the liver and other tissues. Detailed PK parameters are not fully characterized for this specific analog.
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| Toxicity/Toxicokinetics |
N-Acetyloxytocin is considered a research-use peptide with low acute toxicity at typical experimental doses (ug-mg/kg range in rodents). The unmodified oxytocin has a wide safety margin with LD50 >15 mg/kg (IV in rodents). The acetylation does not introduce additional toxicophores. No significant adverse effects have been reported in published studies at research doses. Standard laboratory precautions for handling peptides (gloves, safety glasses, fume hood) are recommended. Not intended for human consumption.
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| References |
[1]. Liu B, et al. N-acetyl-vasopressin- and N-acetyl-oxytocin-like substances: isolation and characterization in the rat neurointermediate pituitary and presence in the brain. J Neuroendocrinol. 1989;1(1):47-52.
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| Additional Infomation |
Found in bovine pineal gland
N-Acetyloxytocin is not a drug but a research-use peptide analog. It has no approved therapeutic status, no active clinical trials as a standalone agent, and is not intended for human consumption. This compound is used exclusively for research applications including receptor-ligand interaction studies to evaluate modified folding and conformational transitions, neuroendocrine signaling research to dissect oxytocin-mediated signaling pathways, and high-resolution biophysical assays. It serves as a valuable probe for neuropeptide function, synthetic peptide design, and mapping neuropeptide communication networks. |
| Molecular Formula |
C45H68N12O13S2
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|---|---|
| Molecular Weight |
1049.22
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| Exact Mass |
1048.447
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| CAS # |
10551-48-1
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| PubChem CID |
118136951
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| Appearance |
White to off-white solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
1593.2±65.0 °C at 760 mmHg
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| Flash Point |
917.3±34.3 °C
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| Vapour Pressure |
0.0±0.3 mmHg at 25°C
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| Index of Refraction |
1.628
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| LogP |
-3.89
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| Hydrogen Bond Donor Count |
12
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| Hydrogen Bond Acceptor Count |
15
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| Rotatable Bond Count |
18
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| Heavy Atom Count |
72
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| Complexity |
1990
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| Defined Atom Stereocenter Count |
9
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| SMILES |
S1C[C@@H](C(N2CCC[C@H]2C(N[C@H](C(NCC(N)=O)=O)CC(C)C)=O)=O)NC([C@H](CC(N)=O)NC([C@H](CCC(N)=O)NC([C@H]([C@@H](C)CC)NC([C@H](CC2C=CC(=CC=2)O)NC([C@H](CS1)NC(C)=O)=O)=O)=O)=O)=O
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| InChi Key |
RROMYFJBCBPTNU-RANNHORISA-N
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| InChi Code |
InChI=1S/C45H68N12O13S2/c1-6-23(4)37-44(69)51-27(13-14-34(46)60)39(64)53-30(18-35(47)61)40(65)55-32(45(70)57-15-7-8-33(57)43(68)54-28(16-22(2)3)38(63)49-19-36(48)62)21-72-71-20-31(50-24(5)58)42(67)52-29(41(66)56-37)17-25-9-11-26(59)12-10-25/h9-12,22-23,27-33,37,59H,6-8,13-21H2,1-5H3,(H2,46,60)(H2,47,61)(H2,48,62)(H,49,63)(H,50,58)(H,51,69)(H,52,67)(H,53,64)(H,54,68)(H,55,65)(H,56,66)/t23-,27-,28-,29-,30-,31-,32-,33-,37-/m0/s1
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| Chemical Name |
(2S)-1-[(4R,7S,10S,13S,16S,19R)-19-acetamido-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-[(2S)-butan-2-yl]-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]-N-[(2S)-1-[(2-amino-2-oxoethyl)amino]-4-methyl-1-oxopentan-2-yl]pyrrolidine-2-carboxamide
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO: ≥ 50 mg/mL (47.65 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (1.98 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (1.98 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.08 mg/mL (1.98 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 0.9531 mL | 4.7654 mL | 9.5309 mL | |
| 5 mM | 0.1906 mL | 0.9531 mL | 1.9062 mL | |
| 10 mM | 0.0953 mL | 0.4765 mL | 0.9531 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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