Caulerpin
Caulerpin is an orally active natural product with anti-tumor, anti-viral, anti-oxidant, anti-fungal, anti-bacteria and analgesic activities. Caulerpin acts as an inhibitor of mitochondrial ETC complex I and acetylcholinesterase. Caulerpin blocks hypoxia-induced activation of HIF-1α protein, inhibits VEGF secretion and tumor angiogenesis under hypoxic conditions, reduces the expression of NLRP3 and the production of pro-inflammatory cytokines, and suppresses the load of Mycobacterium tuberculosis. Caulerpin can be used in studies related to breast cancer, prostate cancer, tuberculosis and viral infections.
For research use only. We do not sell to patients.
- CAS No.: 26612-48-6
- Formula: C24H18N2O4
- Molecular Weight:398.42
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Storage:Powder -20°C, 3 years ; In solvent -80°C, 6 months , -20°C, 1 month
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Tel: 609-228-6898 E-mail: [email protected] [email protected]
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Biological Activity
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Chemical Information
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Solvent & Solubility
- Protocols
- Purity & Documentation
- References
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Help & FAQs
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Biological Activity
Description
IC50 & Target
[1]|
NLRP3 |
HIF-1α |
Cellular Effect
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Cell Line
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Type | Value | Description | References |
|---|---|---|---|---|
| HepG2 | IC50 |
24.6 μg/mL
Compound: 55
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Antiproliferative activity against human HepG2 cells assessed as inhibition of cell growth incubated for 24 hrs by colorimetric method
Antiproliferative activity against human HepG2 cells assessed as inhibition of cell growth incubated for 24 hrs by colorimetric method
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[PMID: 36170798] |
In Vitro
Caulerpin (compound 1) (1-30 μM; 16 h) inhibits hypoxia- and chemical hypoxia-induced HIF-1 activation in T47D human breast tumor cells[1].
Caulerpin (15 μM; 24 h post-infection) reduces intracellular Mycobacterium smegmatis mc2155 loads in RAW 264.7 murine macrophages by 0.230 log10 CFU after 24 h of post-infection treatment[2].
Caulerpin (15 μM; 24 h post-infection) reduces intracellular Mycobacterium tuberculosis H37Ra loads in RAW 264.7 murine macrophages by 0.250 log10 CFU after 24 h of post-infection treatment[2].
Caulerpin (15 μM; 8 h pre-incubation) reduces intracellular Mycobacterium smegmatis mc2155 loads in RAW 264.7 murine macrophages by 0.360 log10 CFU when used as an 8 h pre-incubation treatment, and (15 μM; 12 h post-infection re-treatment) by an additional 0.287 log10 CFU when used as a re-treatment at 12 h post-infection[2].
Caulerpin (1.25-5 μM) dose-dependently inactivates CHIKV particles[4].
Caulerpin (10-50 μM) inhibits the alpha (0-3 h p.i.) and beta (3-6 h p.i.) phases of the HSV-1 replicative cycle in Vero cells, with no cell-free virucidal activity[3].
Caulerpin (20 h) inhibits HSV-1 replication in Vero cells with an EC50 of 1.29 μM and a selectivity index of 904[3].
Caulerpin (5 μM; 72 hours total incubation) completely inhibits CHIKV replication in Vero cells when added up to 3 hours post-infection, with activity declining at later time points including 4, 6, 9, 12, and 16 hours post-infection[4].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:T47D human breast tumor cells
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Concentration:30 μM
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Incubation Time:16 h
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Result:Suppressed hypoxia-induced VEGF and GLUT-1 mRNA expression.
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Cell Line:MDA-MB-231 human breast tumor cells
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Concentration:10, 30 μM
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Incubation Time:22 h (under normoxia or hypoxia)
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Result:Suppressed MDA-MB-231 cell migration in a concentration-dependent manner over 22 h.
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Cell Line:T47D, MCF-7, MDA-MB-231, DU145, PC-3 human tumor cell lines; primary human mammary epithelial cells (HMEC)
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Concentration:1, 3, 10, 30 μM
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Incubation Time:48 h (under normoxia)
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Result:Exhibited cell line-dependent growth inhibitory effects after 48 h of incubation.
Achieved the highest inhibition of 52% in PC-3 prostate tumor cells at 30 μM.
Caused less than 25% inhibition in HMEC cells at concentrations up to 30 μM.
DU145 prostate tumor cells were the least sensitive.
Extended incubation (48 h vs 22 h) increased growth inhibition in MDA-MB-231 cells.
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Cell Line:T47D human breast tumor cell
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Concentration:10 μM
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Incubation Time:30 min pre-incubation, followed by 4 h exposure
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Result:Blocked hypoxia-induced HIF-1α protein accumulation in T47D human breast tumor cell nuclear extracts.
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Cell Line:RAW 264.7 murine macrophage cells
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Concentration:3.75, 7.5, 15, 30 μM (24 h incubation); 3.75, 7.5, 15 μM (48 h incubation)
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Incubation Time:24 h; 48 h
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Result:Reduced RAW 264.7 cell viability only at the 30 μM concentration after 24 h incubation.
Reduced cell viability at the 15 and 30 μM concentrations after 48 h incubation.
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Cell Line:Vero (African green monkey kidney) cells
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Concentration:50 μM, 250 μM, 500 μM, 1000 μM
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Incubation Time:72 h caulerpin
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Result:Showed low cytotoxicity in Vero cells, with a CC50 of 1167 μM.
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Cell Line:Vero cells
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Concentration:100, 200, 400, 800, 1000 μg/mL
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Incubation Time:3 days prior to MTT addition
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Result:Exhibited low cytotoxicity relative to antiviral activity; no specific numerical values provided.
In Vivo
Caulerpin (100 µmol/kg; p.o.) exhibits anti-inflammatory activity in capsaicin (HY-10448)-induced ear edema, reducing edema by 55.8%[5].
Caulerpin (100 µmol/kg; p.o.) exhibits anti-inflammatory activity in carrageenan-induced peritonitis, reducing total leukocyte recruitment by 48.3% and suppressing neutrophil migration to the inflammatory site[5].
Caulerpin (100 µmol/kg; p.o.) exhibits both centrally and peripherally mediated antinociceptive activity in formalin-induced pain, inhibiting the neurogenic phase by 28.5% and the inflammatory phase by 55.7%[5].
Caulerpin (100 µmol/kg; p.o.) exhibits centrally mediated antinociceptive activity in hot plate-induced thermal nociception, significantly increasing reaction latency at 90, 120, and 150 minutes post-treatment without motor impairment[5].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:Swiss albino mice (adult male and female, 20-35 g)[5]
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Dosage:0.01 µmol/kg; 0.1 µmol/kg; 1 µmol/kg; 10 µmol/kg; 100 µmol/kg
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Administration:p.o.
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Result:Inhibited acetic acid-induced nociception with an IC50 of 0.0945 μmol.
Produced approximate percent inhibitions of 80%, 60%, 60%, 30%, and 0% at doses of 100, 10, 1, 0.1, and 0.01 µmol/kg, respectively.
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Animal Model:Swiss albino mice (adult male and female, 20-35 g)[5]
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Dosage:100 µmol/kg
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Administration:p.o.
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Result:Significantly increased reaction latency at 90 minutes (4.6 sec), 120 minutes (3.8 sec), and 150 minutes (4.0 sec) relative to control group latencies (3.2 sec, 2.8 sec, 2.6 sec, respectively).\nInhibited the neurogenic phase of formalin-induced licking by 28.5%.
Inhibited the inflammatory phase of formalin-induced licking by 55.7%.
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Animal Model:Swiss albino mice (adult male and female, 20-35 g)[5]
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Dosage:100 µmol/kg
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Administration:p.o.
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Result:Inhibited capsaicin-induced ear edema by 55.8% relative to the control group.\nReduced total recruited leukocytes in peritoneal exudate by 48.3% relative to the carrageenan-only control group.
Decreased polymorphonuclear neutrophil counts to 6.0% and increased lymphocyte counts to 63.0% and monocyte counts to 31.0% relative to the carrageenan-only group (34.5% polymorphonuclear, 44.0% lymphocytes, 20.5% monocytes).
- RNA extraction experimental
- Human pluripotent stem cell endothelial-cell differentiation
- Vascular/Branching Fractal Analysis
- LPS-Induced Endotoxemia/Systemic Inflammation
- Endothelial Tube Formation Assay
- Research Protocol for Inflammation-related Diseases
- Breast Cancer Modeling
- Endothelial Cell Migration/Angiogenic Sprouting Assay
Chemical Information
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CAS No. 26612-48-6
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Appearance Solid
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Molecular Weight 398.42
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Formula C24H18N2O4
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Color Orange to reddish brown
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SMILES
O=C(OC)C1=CC=2C=3C=CC=CC3NC2C(=CC=4C=5C=CC=CC5NC14)C(=O)OC
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Structure Classification
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Initial Source
Caulerpa racemosa (Forssk?l) J.Agardh
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Powder -20°C 3 years In solvent -80°C 6 months -20°C 1 month
Solvent & Solubility
In Vitro:
DMSO : 25 mg/mL (62.75 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
In Vivo:
Select the appropriate dissolution method based on your experimental animal and administration route.
- For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
- To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
- The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.
Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline
Solubility: ≥ 2.5 mg/mL (6.27 mM); Clear solution
This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.
Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
In Vivo Dissolution Calculator
Please enter the basic information of animal experiments:
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Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Please enter your animal formula composition:
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%DMSO +
Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
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%+
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+%Tween-80 + +
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%Saline +
The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).
Working solution concentration: 0.22 mg/mL
Method for preparing stock solution: mg drug dissolved in μL DMSO. Stock solution concentration: mg/mL.
1. Take μL DMSO stock solution;
2. Add μL .
μL , mix evenly;
3. Then add μL Tween 80, mix evenly;
4. Then add μL
Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.
Purity & Documentation
References
[1]. Liu Y, et al. The Caulerpa pigment caulerpin inhibits HIF-1 activation and mitochondrial respiration. Journal of natural products. 2009 Dec;72(12):2104-9. [Content Brief]
[2]. Sidrônio MGS, et al. Host-Mediated Antimicrobial Effects and NLRP3 Inflammasome Modulation by Caulerpin and Its Derivatives in Macrophage Models of Mycobacterial Infections. Microorganisms. 2025 Mar 01;13(3):561. [Content Brief]
[5]. de Souza ET, et al. The antinociceptive and anti-inflammatory activities of caulerpin, a bisindole alkaloid isolated from seaweeds of the genus Caulerpa. Marine drugs. 2009 Nov 26;7(4):689-704. [Content Brief]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| DMSO | 1 mM | 2.5099 mL | 12.5496 mL | 25.0991 mL | 62.7479 mL |
| 5 mM | 0.5020 mL | 2.5099 mL | 5.0198 mL | 12.5496 mL | |
| 10 mM | 0.2510 mL | 1.2550 mL | 2.5099 mL | 6.2748 mL | |
| 15 mM | 0.1673 mL | 0.8366 mL | 1.6733 mL | 4.1832 mL | |
| 20 mM | 0.1255 mL | 0.6275 mL | 1.2550 mL | 3.1374 mL | |
| 25 mM | 0.1004 mL | 0.5020 mL | 1.0040 mL | 2.5099 mL | |
| 30 mM | 0.0837 mL | 0.4183 mL | 0.8366 mL | 2.0916 mL | |
| 40 mM | 0.0627 mL | 0.3137 mL | 0.6275 mL | 1.5687 mL | |
| 50 mM | 0.0502 mL | 0.2510 mL | 0.5020 mL | 1.2550 mL | |
| 60 mM | 0.0418 mL | 0.2092 mL | 0.4183 mL | 1.0458 mL |
Caulerpin Related Classifications
HY-N10650 Related Classifications
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Keywords
- Caulerpin
- 26612-48-6
- Fungal
- Bacterial
- HIF/HIF Prolyl-Hydroxylase
- VEGFR
- NOD-like Receptor (NLR)
- CHIKV
- Hypoxia-inducible factors
- HIFs
- HIF-PH
- Vascular endothelial growth factor receptor
- Chikungunya virus
- herpes simplex virus type 1
- chikungunya virus
- acetylcholinesterase
- RAW 264.7 murine macrophage cells
- mitochondrial ETC complex I
- Mycobacterium tuberculosis H37Ra
- T47D human breast tumor cells
- NLRP3 inflammasome
- MDA-MB-231 human breast tumor cells
- HIF-1
- Inhibitor
- inhibitor
- inhibit