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.
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- No. CAS: 26612-48-6
- Fòrmula: C24H18N2O4
- Peso molecular:398.42
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Almacenamiento:
Please store the product under the recommended conditions in the Certificate of Analysis.
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Actividad biológica
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Chemical Information
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Actividad biológica
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NLRP3 |
HIF-1α |
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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] |
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 (30 μM; 16 h) suppresses hypoxia-induced VEGF and GLUT-1 mRNA expression in T47D human breast tumor cells over 16 h[1].
Caulerpin (10 μM) suppresses hypoxia-induced secreted VEGF protein production in T47D human breast tumor cells[1].
Caulerpin (10-30 μM) suppresses the hypoxia-induced angiogenic activity of T47D human breast tumor cell-conditioned media in HUVEC tube formation assays[1].
Caulerpin (10 μM; 30 min pre-incubation, followed by 4 h exposure) blocks hypoxia-induced HIF-1α protein accumulation in T47D human breast tumor cell nuclear extracts[1].
Caulerpin (10-30 μM; 22 h) suppresses migration of MDA-MB-231 human breast tumor cells over 22 h, without significant cytotoxicity under the same conditions[1].
Caulerpin (1-30 μM; 48 h) induces cell line-dependent growth inhibition in human tumor cell lines (T47D, MCF-7, MDA-MB-231, DU145, PC-3) after 48 h of normoxic incubation, with maximum 52% inhibition in PC-3 cells, and less pronounced effects on primary HMEC cells[1].
Caulerpin (10-30 μM; 2 h pre-incubation for permeabilized cells) inhibits mitochondrial respiration at electron transport chain complex I in T47D human breast tumor cells,[1].
Caulerpin (compound CP) (3.25-30 μM; 24-48 h) reduces RAW 264.7 murine macrophage cell viability[2].
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; 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 (15 μM; 24 h post-infection) modulates the immune response in Mycobacterium smegmatis-infected RAW 264.7 murine macrophages by reducing TNF-α, IL-1β, and NLRP3 inflammasome levels after 24 h of treatment, without affecting IL-10 production[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; 12 h post-infection re-treatment) reduces intracellular Mycobacterium tuberculosis H37Ra loads in RAW 264.7 murine macrophages when used as a re-treatment at 12 h post-infection, but (15 μM; pre-incubation) not when used as a pre-incubation treatment prior to infection[2].
Caulerpin (50-1000 μM; 72 h) exhibits low cytotoxicity in Vero cells, with a CC50 of 1167 μM[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 (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 (0.65-20 μM; 3 days post-adsorption) potently inhibits CHIKV replication in Vero cells, with an EC50 of 0.8 μM[4].
Caulerpin (1.25-5 μM) dose-dependently inactivates CHIKV particles[4].
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].
Caulerpin (100-1000 μg/mL; 3 days prior to MTT addition) exhibits low cytotoxicity toward Vero cells at concentrations up to 1000 μg/mL over a 3-day incubation[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.
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].
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 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].
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).
Chemical Information
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No. CAS 26612-48-6
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Peso molecular 398.42
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Fòrmula C24H18N2O4
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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
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Envío
Room temperature in continental US; may vary elsewhere.
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Almacenamiento
Please store the product under the recommended conditions in the Certificate of Analysis.
Pureza y Documentación
Referencias
[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]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Caulerpin Related Classifications
HY-N10650 Related Classifications
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- Caulerpin
- 26612-48-6
- Fungal
- Bacterial
- HIF/HIF Prolyl-Hydroxylase
- VEGFR
- NOD-like Receptor (NLR)
- CHIKV
- 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