304448-55-3

Basic information

• Product Name: Dynasore
• Synonyms: 3-Hydroxy-naphthalene-2-carboxylic acid (3,4-dihydroxy-benzylidene)-hydrazide monohydrate;Dynasore monohydrate;Dynasore;3-Hydroxynaphthalene-2-carboxylicacid(3,4-dihydroxybenzylidene)hydrazide;3-Hydroxy-2-naphthalenecarboxylic acid [(3,4-dihydroxyphenyl)Methylene]hydrazide;2-Naphthalenecarboxylic acid, 3-hydroxy-, 2-[(3,4-dihydroxyphenyl)methylene]hydrazide;3-Hydroxy-2-naphthalenecarboxylic acid [(3,4-dihydroxyphenyl)methylene]hydrazide Dynasore;Dynasore, >=98%
• CAS NO: 304448-55-3
• Molecular Formula: C₁₈H₁₄N₂O₄
• Molecular Weight: 322.31
• EINECS: 200-256-5
• Product Categories: Signalling;Cell Cycle Regulation;Inhibitors
• Mol File: 304448-55-3.mol
• Article Data: 1

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.36g/cm³
• Storage Temp.: −20°C
• Solubility: Soluble in DMSO (up to 30 mg/ml), or in Ethanol (up to 1 mg/ml).
• PKA: 8.49±0.35(Predicted)
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 1 month.
• CAS DataBase Reference: Dynasore(CAS DataBase Reference)
• NIST Chemistry Reference: Dynasore(304448-55-3)
• EPA Substance Registry System: Dynasore(304448-55-3)

Safety Data

• Hazard Codes: N
• Statements: 50
• Safety Statements: 22-24/25-61
• RIDADR: UN 3077 9/PG 3
• Hazardous Substances Data: 304448-55-3(Hazardous Substances Data)

Usage

Description

Dynasore (304448-55-3) is a noncompetitive inhibitor of dynamin GTPase activity and blocks dynamin-dependent endocytosis in cells, including neurons. It inhibits the GTPase activity of dynamin1, dynamin2, and Drp1 (mitochondrial dynamin). It is cell permeable, fast acting (seconds) and reversible.1,2 Dynasore is a extremely useful tool for studying endocytosis and other cellular events which are dependent on dynamin.3-5

Uses

Different sources of media describe the Uses of 304448-55-3 differently. You can refer to the following data:
1. Dynasore is a cell-permeable, reversible inhibitor of dynamin 1, dynamin 2, and mitochondrial dynamin, Drp1 GTPase activity (IC50 = 15 μM). Through this action, dynasore inhibits clathrin-dependent vesicle formation and endocytosis, which is necessary for internalization of certain parasites and viruses, as well as particles and receptor ligands. In some cases, dynasore can also augment the release of neurotransmitters and secreted cytokines.[Cayman Chemical]
2. Dynamin Inhibitor I, Dynasore is an inhibitor of Dynamin I and Dynamin II.

Definition

ChEBI: A carbohydrazide resulting from the formal condensation of the hydrazone moiety of 3,4-dihydroxybenzaldehyde hydrazone with the carboxy group of 3-hydroxy-2-naphthoic acid. It is a cell-permeable, reversible noncompetitive inhibitor of the GTPase activity f dynamin 1 and 2 and Drp1 (mitochondrial), while exhibiting no significant effect against two other small GTPases, MxA and Cdc42.

Biological Activity

Non-competitive inhibitor of dynamin 1, dynamin 2 and mitochondrial dynamin (Drp1) GTPase activity. Does not inhibit other small GTPases. Blocks endocytic pathways dependent on dynamin and inhibits cell spreading and migration of BSC1 cells.

References

1) Macia et al. (2006), Dynasore, a cell-permeable inhibitor of dynamin; Dev. Cell, 10 839 2) Kirschhausen et al. (2008), Use of dynasore, the small molecule inhibitor of dynamin, in the regulation of endocytosis; Methods Enzymol., 438 77 3) Lu et al. (2009), Dynamin and activity regulate synaptic vesicle recycling in sympathetic neurons; J. Biol. Chem., 284 1930 4) Chung et al. (2010), Acute dynamin inhibition dissects synaptic vesicle recycling pathways that drive spontaneous and evoked neurotransmission; J. Neurosci., 30 1363 5) Poirer et al. (2009), Dissection of the endogenous cellular pathways of PCSK9-induced low density lipoprotein receptor degradation: evidence for an intracellular route; J. Biol. Chem., 284 28856

Upstream product

• 5341-58-2 3-hydroxy-2-naphthohydrazide 
• 139-85-5 3,4-dihydroxybenzaldehyde 

Relevant articles and documents

Synthesis of potent chemical inhibitors of dynamin GTPase

Dynamin is a key regulatory protein in clathrin mediated endocytosis. Compared to genetic or immunological tools, small chemical dynamin inhibitors such as dynasore have the potential to study the dynamic nature of endocytic events in cells. Dynasore inhibits dynamin GTPase activity and transferrin uptake at IC50 ～15 μM but use in some biological applications requires more potent inhibitor than dynasore. Here, we chemically modified the side chains of dynasore and found that two derivatives, DD-6 and DD-11 more potently inhibited transferrin uptake (IC50: 4.00 μM for DD-6, 2.63 μM for DD-11) and dynamin GTPase activity (IC50: 5.1 μM for DD-6, 3.6 μM for DD-11) than dynasore. The effect was reversible and they were washed more rapidly out than dynasore. TIRF microscopy showed that they stabilize the clathrin coats on the membrane. Our results indicated that new dynasore derivatives are more potent inhibitor of dynamin, displaying promise as leads for the development of more effective analogues for broader biological applications.