2-Naphthalenecarboxylic acid, 3-hydroxy-, 2-[(2,4,5-trihydroxyphenyl)Methylene]hydrazide

Modify Date: 2024-01-02 16:06:58

2-Naphthalenecarboxylic acid, 3-hydroxy-, 2-[(2,4,5-trihydroxyphenyl)Methylene]hydrazide Structure
2-Naphthalenecarboxylic acid, 3-hydroxy-, 2-[(2,4,5-trihydroxyphenyl)Methylene]hydrazide structure
Common Name 2-Naphthalenecarboxylic acid, 3-hydroxy-, 2-[(2,4,5-trihydroxyphenyl)Methylene]hydrazide
CAS Number 1256493-34-1 Molecular Weight 338.314
Density 1.5±0.1 g/cm3 Boiling Point N/A
Molecular Formula C18H14N2O5 Melting Point N/A
MSDS Chinese USA Flash Point N/A
Symbol GHS09
GHS09
Signal Word Warning

 Use of 2-Naphthalenecarboxylic acid, 3-hydroxy-, 2-[(2,4,5-trihydroxyphenyl)Methylene]hydrazide


Hydroxy Dynasore (Dyngo-4a), a structural analog of Dynasore (HY-15304), is an potency improved, low cytotoxicity and non‐specific binding dynamin inhibitor with IC50 values of 0.38 μM and 2.3 μM for brain dynamin I and recombinant rat dynamin II, respectively. Hydroxy Dynasore inhibits dynamin‐dependent endocytosis of transferrin with an IC50 of 5.7 μM in vitro.

 Names

Name Hydroxy-Dynasore
Synonym More Synonyms

  Biological Activity

Description Hydroxy Dynasore (Dyngo-4a), a structural analog of Dynasore (HY-15304), is an potency improved, low cytotoxicity and non‐specific binding dynamin inhibitor with IC50 values of 0.38 μM and 2.3 μM for brain dynamin I and recombinant rat dynamin II, respectively. Hydroxy Dynasore inhibits dynamin‐dependent endocytosis of transferrin with an IC50 of 5.7 μM in vitro.
Related Catalog
In Vitro Dynamin is a large GTPase enzyme that severs membrane‐bound clathrin‐coated vesicles.Endocytosis internalizes portions of cells’ plasma membrane along with extracellular material, is fundamentally important in cell physiology. Hydroxy Dynasore inhibits Dynamin I (Dyn I) activity with IC50 values of 2.7 μM and 0.38 μM with or without 0.06% Tween‐80 in the GTPase assay[1]. Hydroxy Dynasore shows an IC50 of 5.7 μM in clathrin‐mediated endocytosis (CME) assay for inhibition of Tfn‐A594 uptake in U2OS cells[1]. Hydroxy Dynasore shows IC50 values of 0.38 μM and 1.1 μM in absence of Tween-80, and exhibits IC50 values of 4.9 μM and 30.0 μM in presence of Tween-80, respectively. Hydroxy Dynasore is 2.1‐fold selective for DynI versus DynII from Sf21 cells] and DynII (recombinant protein from Sf21 cells) in this GTPase assay[1]. Hydroxy Dynasore prevents the uptake of BoNT/A-Hc in cultured hippocampal neurons and in motor nerve terminals[2]. Hydroxy Dynasore (1-100μM; 20 min prior to the addition of Alexa Fluor 488-BoNT/A-Hc) results in depolarization of Hippocampal neurons, it dose-dependently inhibits internalization of Alexa Fluor 488-BoNT/A-Hc with an IC50 of 16.0 ± 1.2 μM[2].
In Vivo Hydroxy Dynasore (intraperitoneal injection; 30 mg/kg; 1.5-2 h before BoNT/A injection) provides protection again BoNT/A-induced paralysis in the phrenic nerve-hemidiaphragm twitch model in CD-1 mice[2]. Animal Model: CD-1 mice[2]. Dosage: 30 mg/kg Administration: Intraperitoneal injection; 1.5–2 h before BoNT/A injection Result: Protected BoNT/A-induced paralysis in vivo.
References

[1]. Adam McCluskey, et al. Building a Better Dynasore: The Dyngo Compounds Potently Inhibit Dynamin and Endocytosis. Traffic. 2013 Dec;14(12):1272-89.

[2]. Callista B Harper, et al.Dynamin Inhibition Blocks Botulinum Neurotoxin Type A Endocytosis in Neurons and Delays Botulism.J Biol Chem. 2011 Oct 14;286(41):35966-76.

 Chemical & Physical Properties

Density 1.5±0.1 g/cm3
Molecular Formula C18H14N2O5
Molecular Weight 338.314
Exact Mass 338.090271
PSA 122.38000
LogP 5.12
Index of Refraction 1.683
Storage condition -20℃

 Safety Information

Symbol GHS09
GHS09
Signal Word Warning
Hazard Statements H400
Precautionary Statements P273
RIDADR UN 3077 9 / PGIII

 Synonyms

3-Hydroxynaphthalene-2-carboxylic acid-(2,4,5-trihydroxybenzylidene)-hydrazide
3-Hydroxy-N'-[(E)-(2,4,5-trihydroxyphenyl)methylene]-2-naphthohydrazide
Dynamin Inhibitor IV
2-Naphthalenecarboxylic acid, 3-hydroxy-, 2-[(1E)-(2,4,5-trihydroxyphenyl)methylene]hydrazide
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