Art. -Nr.: HY-N2150

Psammaplin A

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Psammaplin A is a marine metabolite. Psammaplin A is a selective HDAC1 (IC₅₀: 45 nM), DNA methyltransferases (IC₅₀: 18.6 nM) and aminopeptidase N (APN) (IC₅₀: 18 μM) inhibitor. Psammaplin A also inhibits DNA topoisomerase and farnesyl protein transferase. Psammaplin A is a PPARγ activator and induces apoptosis. Psammaplin A has antitumor and anti-inflammatory activities. Psammaplin A has antibacterial activity against Gram-positive bacteria and inhibits DNA synthesis and DNA gyrase activity. Psammaplin A inhibits angiogenesis.

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Reinheit: 96.0%
CAS. Nr.: 110659-91-1
Formel: C₂₂H₂₄Br₂N₄O₆S₂
Molecular Weight:664.39

Speicherung:

4°C, stored under nitrogen

* In solvent : -80°C, 6 months; -20°C, 1 month (stored under nitrogen)

Psammaplin A Chemical Structure

CAS. Nr.: 110659-91-1

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Biologische Aktivität
- Beschreibung
- IC₅₀ & Target
- Cellular Effect
- In Vitro
- In Vivo
Chemical Information
Lösungsmittel & Löslichkeit
- In Vitro
Reinheit & Dokumentation
Verweise
Help & FAQs
Classifications
Bioz

Biologische Aktivität

Beschreibung

IC₅₀ & Target^[1]^[3]^[5]^[8]

HDAC1

45 nM (IC₅₀)

DNA Methyltransferase

18.6 nM (IC₅₀)

PPARγ

APN

18 μM (IC₅₀)

Alle HDAC Isoform-spezifische Produkte anzeigen :

Alle DNA Methyltransferase Isoform-spezifische Produkte anzeigen :

Alle DNA/RNA Synthesis Isoform-spezifische Produkte anzeigen :

Alle Aminopeptidase Isoform-spezifische Produkte anzeigen :

CD13
LTA4H

Alle PPAR Isoform-spezifische Produkte anzeigen :

Cellular Effect

Cell Line	Type	Value	Description	References
A549	ED₅₀	0.57 μg/mL Compound: 1	Cytotoxicity against human A549 cells Cytotoxicity against human A549 cells	[PMID: 14640526]
A549	GI₅₀	4.5 μM Compound: Psammaplin A	Cytotoxicity against human A549 cells assessed as reduction in cell growth inhibition after 96 hrs by MTT assay Cytotoxicity against human A549 cells assessed as reduction in cell growth inhibition after 96 hrs by MTT assay	[PMID: 27460171]
A549	GI₅₀	7.5 μM Compound: 11c	Growth inhibition of human A549 cells after 96 hrs by sulphorhodamine B assay Growth inhibition of human A549 cells after 96 hrs by sulphorhodamine B assay	[PMID: 22280363]
A549	IC₅₀	1.18 μM Compound: 1, PsA	Cytotoxicity against human A549 cells by SRB assay Cytotoxicity against human A549 cells by SRB assay	[PMID: 25884112]
A549	IC₅₀	1.76 μM Compound: PsA	Cytotoxicity against human A549 cells assessed as reduction in cell viability by SRB assay Cytotoxicity against human A549 cells assessed as reduction in cell viability by SRB assay	[PMID: 33636429]
CHO-K1	EC₅₀	0.9 μM Compound: 4	Cytotoxicity against CHO-K1 cells by Alamar blue assay Cytotoxicity against CHO-K1 cells by Alamar blue assay	[PMID: 16962325]
HCT-116	IC₅₀	0.61 μM Compound: PsA	Cytotoxicity against human HCT-116 cells assessed as reduction in cell viability by SRB assay Cytotoxicity against human HCT-116 cells assessed as reduction in cell viability by SRB assay	[PMID: 33636429]
HCT-116	IC₅₀	1.62 μM Compound: 1, PsA	Cytotoxicity against human HCT116 cells by SRB assay Cytotoxicity against human HCT116 cells by SRB assay	[PMID: 25884112]
HCT-116	IC₅₀	3.05 μM Compound: PsA	Antiproliferative activity against human HCT-116 cells incubated for 48 hrs by MTT assay Antiproliferative activity against human HCT-116 cells incubated for 48 hrs by MTT assay	[PMID: 38851056]
HCT-15	ED₅₀	0.68 μg/mL Compound: 1	Cytotoxicity against human HCT15 cells Cytotoxicity against human HCT15 cells	[PMID: 14640526]
HeLa	IC₅₀	0.05 μM Compound: Psammaplin A	Inhibition of HDAC in human HeLa cells using Fluor deLys as substrate assessed as deacetylation of substrate by fluorescence assay Inhibition of HDAC in human HeLa cells using Fluor deLys as substrate assessed as deacetylation of substrate by fluorescence assay	[PMID: 27460171]
HL-60	GI₅₀	0.29 μM Compound: Psammaplin A	Cytotoxicity against human HL60 cells assessed as reduction in cell growth inhibition after 72 hrs by trypan blue-staining based hemocytometric analysis Cytotoxicity against human HL60 cells assessed as reduction in cell growth inhibition after 72 hrs by trypan blue-staining based hemocytometric analysis	[PMID: 27460171]
HL-60	GI₅₀	0.37 μM Compound: 1; PsA	Growth inhibition of human HL-60 cells after 72 hrs by trypan blue dye based assay Growth inhibition of human HL-60 cells after 72 hrs by trypan blue dye based assay	[PMID: 33488962]
MCF7	EC₅₀	5.7 μM Compound: 1	Activation of PPARgamma transfected in human MCF7 cells by luciferase reporter gene assay Activation of PPARgamma transfected in human MCF7 cells by luciferase reporter gene assay	[PMID: 16643023]
MCF7	GI₅₀	1.27 μM Compound: 11c	Growth inhibition of human MCF7 cells after 96 hrs by sulphorhodamine B assay Growth inhibition of human MCF7 cells after 96 hrs by sulphorhodamine B assay	[PMID: 22280363]
MCF7	GI₅₀	2.26 μM Compound: Psammaplin A	Cytotoxicity against human MCF7 cells assessed as reduction in cell growth inhibition after 96 hrs by MTT assay Cytotoxicity against human MCF7 cells assessed as reduction in cell growth inhibition after 96 hrs by MTT assay	[PMID: 27460171]
MCF7	IC₅₀	5 μM Compound: 1	Antiproliferative activity against human MCF7 cells by neutral red method Antiproliferative activity against human MCF7 cells by neutral red method	[PMID: 16643023]
MDA-MB-231	IC₅₀	1.31 μM Compound: PsA	Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viability by SRB assay Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viability by SRB assay	[PMID: 33636429]
P388	IC₅₀	0.3 μg/mL Compound: 9	Cytotoxicity against mouse P388 cells assessed as cell growth inhibition Cytotoxicity against mouse P388 cells assessed as cell growth inhibition	[PMID: 34826681]
PC-3	GI₅₀	3.52 μM Compound: Psammaplin A	Cytotoxicity against human PC3 cells assessed as reduction in cell growth inhibition after 96 hrs by MTT assay Cytotoxicity against human PC3 cells assessed as reduction in cell growth inhibition after 96 hrs by MTT assay	[PMID: 27460171]
SK-HEP1	IC₅₀	1.29 μM Compound: PsA	Cytotoxicity against human SK-HEP1 cells assessed as reduction in cell viability by SRB assay Cytotoxicity against human SK-HEP1 cells assessed as reduction in cell viability by SRB assay	[PMID: 33636429]
SK-MEL-2	ED₅₀	0.13 μg/mL Compound: 1	Cytotoxicity against human SK-MEL-2 cells Cytotoxicity against human SK-MEL-2 cells	[PMID: 14640526]
SK-OV-3	ED₅₀	0.14 μg/mL Compound: 1	Cytotoxicity against human SKOV3 cells Cytotoxicity against human SKOV3 cells	[PMID: 14640526]
SNU-638	IC₅₀	0.56 μM Compound: PsA	Cytotoxicity against human SNU-638 cells assessed as reduction in cell viability by SRB assay Cytotoxicity against human SNU-638 cells assessed as reduction in cell viability by SRB assay	[PMID: 33636429]
T-cell	EC₅₀	0.2 μM Compound: Psammaplin A	Reactivation of latent HIV1 NL4-3-Luc expression in human naive CD4+ T cells treated 7 days post-infection measured after 48 hrs by luminescence plate reader analysis Reactivation of latent HIV1 NL4-3-Luc expression in human naive CD4+ T cells treated 7 days post-infection measured after 48 hrs by luminescence plate reader analysis	[PMID: 24495105]
WI-38	GI₅₀	3.44 μM Compound: 11c	Growth inhibition of human WI38 cells after 96 hrs by sulphorhodamine B assay Growth inhibition of human WI38 cells after 96 hrs by sulphorhodamine B assay	[PMID: 22280363]
XF498	ED₅₀	0.57 μg/mL Compound: 1	Cytotoxicity against human XF498 cells Cytotoxicity against human XF498 cells	[PMID: 14640526]

In Vitro

Psammaplin A inhibits the viability of A549 (GI₅₀: 7.5 μM), MCF7 (GI₅₀: 1.27 μM), and WI38 (GI₅₀: 3.44 μM) cells^[1].
Psammaplin A (72 h) inhibits the viability of A549 (IC₅₀: 1.18 μM) and HCT116 (IC₅₀: 1.62 μM) cells^[2].
Psammaplin A (0.5-5 μM) inhibits bFGF-induced angiogenesis in bovine aortic endothelial cells (BAEC) in a dose-dependent manner^[3].
Psammaplin A (0-100 μg/mL, 1-4 h) inhibits the toxicity of INT-407 cells induced by V. vulnificus in a concentration- and time-dependent manner^[4].
Psammaplin A (0-100 μg/mL, 0-13 h) inhibits the growth of V. vulnificus in a concentration-dependent manner^[4].
Psammaplin A (0-40 μM, 12 h) inhibits the viability of the macrophage cell line RAW264.7 in a concentration-dependent manner^[6].
Psammaplin A (0-500 μM, 2 h) inhibits SV40 DNA replication in HeLa cells in a concentration-dependent manner. Psammaplin A (125-500 μM, 30 min) inhibits the catalytic activity of topoisomerase I^[6].
Psammaplin A (125-500 μM, 15 min) inhibits the binding activity of RPA to single-stranded DNA^[6].
Psammaplin A (1-40 μM, 30 min) inhibits the activity of polymerase α-primase in a concentration-dependent manner^[6].
Psammaplin A (3-30 μM, 4-16 h) induces apoptosis in T47D and MCF-7 cells^[8].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Western Blot Analysis^[1]

Cell Line:

MCF7 cells
Concentration:

5 μM
Incubation Time:

24 h
Result:

Up-regulated the expression of Ac-H3 protein.

Cell Cytotoxicity Assay^[4]

Cell Line:

INT-407 cells
Concentration:

0, 12.5, 25, 50, 100 μg/mL
Incubation Time:

1, 2, 3, 4 h
Result:

Reduced cytotoxicity.
Reduced cell damage.

Cell Viability Assay^[6]

Cell Line:

Macrophage cell line RAW 264.7
Concentration:

0, 1, 5, 10, 20, 40 μM
Incubation Time:

12 h
Result:

Reduced the number of viable cells.

Apoptosis Analysis^[8]

Cell Line:

MCF-7 and T47D cells
Concentration:

3, 10, 30 μM
Incubation Time:

4, 8, 16 h
Result:

Increased cells apoptosis.

In Vivo

Psammaplin A (30 mg/kg, i.p., three times a week for 35 d) has antitumor activity in mice in the A549 xenograft model^[2].
Psammaplin A (5-50 μg, i.p., once) improves the survival rate of mice in the V. vulnificus-infected model^[4].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:

A549 cell-implanted xenograft model (male athymic BALB/c mice, 6 weeks old, 18-20 g)^[2]
Dosage:

30 mg/kg
Administration:

Intraperitoneal injection (i.p.), three times a week for 35 d
Result:

Inhibited the tumor growth.
Inhibited the expression of the proliferation biomarker Ki-67 in both central and edge region of tumor tissues.

Animal Model:

V. vulnificus-infected model (35 female ICR mice, 8 weeks old, 20-22 g)^[4]
Dosage:

5, 10, 25 and 50 μg
Administration:

Intraperitoneal injection (i.p.), once
Result:

Prolonged survival time of mice.
Inhibited damage to the intestines, liver and spleen of mice.

Chemical Information

CAS. Nr. 110659-91-1
Appearance Solid
Molecular Weight 664.39
Formel C₂₂H₂₄Br₂N₄O₆S₂
Color Off-white to yellow
SMILES

O=C(NCCSSCCNC(/C(CC1=CC(Br)=C(O)C=C1)=N/O)=O)/C(CC2=CC(Br)=C(O)C=C2)=N/O
Structure Classification
- Phenols
- Polyphenols
- Antibiotics
- Other Antibiotics
Initial Source
- Marine natural products
- Sponge
- Animals
- Microorganisms
marine sponge
Versand

Room temperature in continental US; may vary elsewhere.
Speicherung

4°C, stored under nitrogen

* In solvent : -80°C, 6 months; -20°C, 1 month (stored under nitrogen)

Lösungsmittel & Löslichkeit

In Vitro:

DMSO : 33.3 mg/mL (50.12 mM; Need ultrasonic and warming; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

View the Complete Stock Solution Preparation Table

Preparing Stock Solutions

View the Complete Stock Solution Preparation Table

Concentration Solvent Mass

1 mg

5 mg

10 mg

Concentration

Solvent

Mass

1 mM

1.5051 mL

7.5257 mL

15.0514 mL

5 mM

0.3010 mL

1.5051 mL

3.0103 mL

10 mM

0.1505 mL

0.7526 mL

1.5051 mL

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 (stored under nitrogen). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Molaritätsrechner

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass Mass

Konzentration Konzentration

Volumen Volumen

Molecular Weight Molecular Weight

Verdünnungsrechner

Konzentration _{(Stammlösung)} × Volumen _{(Stammlösung)} = Konzentration _{(Ziellösung)} × Volumen _{(Ziellösung)}

Konzentration _{(Stammlösung)} Konzentration _{(Stammlösung)}

Volumen _{(Stammlösung)} Volumen _{(Stammlösung)}

Konzentration _{(Ziellösung)} Konzentration _{(Ziellösung)}

Volumen _{(Ziellösung)} Volumen _{(Ziellösung)}

Reinheit & Dokumentation

Select Batch:

Reinheit: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (277 KB)
SDS (393 KB)
- English - EN (393 KB)
- Français - FR (393 KB)
- Deutsch - DE (393 KB)
- Norwegian - NO (393 KB)
- Español - ES (393 KB)
- Swedish - SV (393 KB)
- Italian - IT (393 KB)
- Korean - KR (393 KB)
- Portuguese - PT (393 KB)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

Verweise

[1]. Baud MG, et al. Defining the mechanism of action and enzymatic selectivity of psammaplin A against its epigenetic targets. J Med Chem. 2012 Feb 23;55(4):1731-50. [Content Brief]

[2]. Hong S, et al. Efficient synthesis and biological activity of Psammaplin A and its analogues as antitumor agents. Eur J Med Chem. 2015;96:218-30. [Content Brief]

[3]. Shim JS, et al. Psammaplin A, a marine natural product, inhibits aminopeptidase N and suppresses angiogenesis in vitro. Cancer Lett. 2004 Jan 20;203(2):163-9. [Content Brief]

[4]. Lee BC, et al. In vitro and in vivo anti-Vibrio vulnificus activity of psammaplin A, a natural marine compound. Mol Med Rep. 2016 Sep;14(3):2691-6. [Content Brief]

[5]. Piña IC, et al. Psammaplins from the sponge Pseudoceratina purpurea: inhibition of both histone deacetylase and DNA methyltransferase. J Org Chem. 2003 May 16;68(10):3866-73. [Content Brief]

[6]. Jiang Y, et al. Cytotoxicity of psammaplin A from a two-sponge association may correlate with the inhibition of DNA replication. BMC Cancer. 2004 Sep 30;4:70. [Content Brief]

[7]. Jongheon S, et al, New Bromotyrosine Metabolites from the Sponge Aplysinella rhax, Tetrahedron, Volume 56, Issue 46, 2000, Pages 9071-9077, ISSN 0040-4020

[8]. Mora FD, et al. Bioassay for the identification of natural product-based activators of peroxisome proliferator-activated receptor-gamma (PPARgamma): the marine sponge metabolite psammaplin A activates PPARgamma and induces apoptosis in human breast tumor cells. J Nat Prod. 2006 Apr;69(4):547-52. [Content Brief]

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

Complete Stock Solution Preparation Table

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg
DMSO	1 mM	1.5051 mL	7.5257 mL	15.0514 mL	37.6285 mL
	5 mM	0.3010 mL	1.5051 mL	3.0103 mL	7.5257 mL
	10 mM	0.1505 mL	0.7526 mL	1.5051 mL	3.7629 mL
	15 mM	0.1003 mL	0.5017 mL	1.0034 mL	2.5086 mL
	20 mM	0.0753 mL	0.3763 mL	0.7526 mL	1.8814 mL
	25 mM	0.0602 mL	0.3010 mL	0.6021 mL	1.5051 mL
	30 mM	0.0502 mL	0.2509 mL	0.5017 mL	1.2543 mL
	40 mM	0.0376 mL	0.1881 mL	0.3763 mL	0.9407 mL
	50 mM	0.0301 mL	0.1505 mL	0.3010 mL	0.7526 mL

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Psammaplin A

Alle HDAC Isoform-spezifische Produkte anzeigen

Alle DNA Methyltransferase Isoform-spezifische Produkte anzeigen

Alle DNA/RNA Synthesis Isoform-spezifische Produkte anzeigen

Alle Aminopeptidase Isoform-spezifische Produkte anzeigen

Alle PPAR Isoform-spezifische Produkte anzeigen

Biologische Aktivität

Chemical Information

Lösungsmittel & Löslichkeit

Reinheit & Dokumentation

Verweise

Help & FAQs

Complete Stock Solution Preparation Table

Psammaplin A Related Classifications

Art. -Nr.: HY-N2150