Basic information
- CAS
10121-91-2- Standard SMILES
CN(C)c1cccc2c(S(=O)(=O)NCCCCCN)cccc12- InChIKey
MLEBFEHOJICQQS-UHFFFAOYSA-N- Molecular formula
- C17H25N3O2S
- Average molar mass
- 335.5 g/mol
- Monoisotopic mass
- 335.16674822
Overview
Monodansylcadaverine is a sulfonamide obtained by formal condensation of the sulfo group of 5-(dimethylamino)naphthalene-1-sulfonic acid with one of the amino groups of cadaverine. It has a role as a protective agent, a fluorochrome and an EC 2.3.2.13 (protein-glutamine gamma-glutamyltransferase) inhibitor. It is a sulfonamide, an aminonaphthalene, a primary amino compound and a tertiary amino compound. It is functionally related to a cadaverine.
Names & identifiers
- Preferred name
- Monodansylcadaverine
- IUPAC
- N-(5-aminopentyl)-5-(dimethylamino)naphthalene-1-sulfonamide
- English name
- DANSYLCADAVERINE
- Molecular formula
- C17H25N3O2S
- Molecular weight
- 335.46
Names & synonyms
Dansylcadaverine10121-91-2monodansylcadaverine1-Naphthalenesulfonamide, N-(5-aminopentyl)-5-(dimethylamino)-I9N81SC5HDDTXSID40143788N-(5-Aminopentyl)-5-dimethylamino-1-naphthalenesulfonamideCHEBI:52007RefChem:159553DTXCID7066279233-326-9n-(5-aminopentyl)-5-(dimethylamino)naphthalene-1-sulfonamide
Show more names
5-<WBRDansylcadaverine, 10 mM in DMSOMONODANSYLCADAVERINE CRYSTALLINEDANSYLCADAVERINE, FOR FLUORESCENCEDANSYLCADAVERINE MONODANSYLCADAVERINEN-(DIMETHYL-AMINO-NAPHTHA-LENE-SULFONYL)-1
Monodansyl cadaverineMFCD00042704EINECS 233-326-9N-(5-Aminopentyl)-5-(dimethylamino)naphthalene-1-sulphonamideUNII-I9N81SC5HDMLEBFEHOJICQQS-UHFFFAOYSA-NN-(5-Aminopentyl)-5-(dimethylamino)-1-naphthalenesulfonamide; Dansylcadaverine; Monodansylcadaverine;N-monodansylcadaverine
Database identifiers
- CAS
10121-91-2
Properties
Computed structural properties
- XLogP
- 2.5
- Topological polar surface area
- 83.8 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 8
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 447
Physicochemical properties
- Melting point
- 137 · 137-140 °C
- Boiling point
- 505.5 · 505.5±60.0 °C(Predicted)
- Density
- 1.19 · 1.190±0.06 g/cm3(Predicted)
- storage temp.
- 20 °C · −20°C
- solubility
- 10 mg/ml · Methanol: 10 mg/ml
- form
- powder
- pka
- 11.96 · 11.96±0.50(Predicted)
- color
- Yellow to yellowish green
- Appearance
- Solid Powder
- λmax
- 335 nm · 335 nm
- BRN
- 2951070 · 2951070
- Stability
- 1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO or methanol may be stored at -20°C for up to 1 month.
- Biological Applications
- Measuring cardiac autophagic flux; treating cataract,fibrosis,Parkinson’s disease,peritoneal ovarian tumor dissemination,respiratory diseases,lung diseases,Huntington’s disease,spinobulbar atrophy,spinocerebellar ataxia,denta
- InChI
- 1S/C17H25N3O2S/c1-20(2)16-10-6-9-15-14(16)8-7-11-17(15)23(21,22)19-13-5-3-4-12-18/h6-11,19H,3-5,12-13,18H2,1-2H3
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information1-Naphthalenesulfonamide, N-(5-aminopentyl)-5-(dimethylamino)-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- F
- 10-23
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Chemicals that emit light after excitation by light. The wave length of the emitted light is usually longer than that of the incident light. Fluorochromes are substances that cause fluorescence in other substances, i.e., dyes used to mark or label other compounds with fluorescent tags.
Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging.
Applications
DescriptionMonodansylcadaverine (MDC) is a fluorescent marker for autophagic vacuoles. It is an autofluorescent substance incorporated into multilamellar bodies by both an ion trapping mechanism and interaction with membrane lipids, exhibiting a Stokes shift and increased relative fluorescence in hydrophobic environments. MDC selectively accumulates in PaTu 8902 subcellular fractions containing the lysosomal enzymes acid phosphatase and cathepsin D, but not those containing the rough and smooth endoplasmic reticulum markers TRAM and cytochrome P450, respectively.
UsesFluorescent substrate for the assay of transamidating enzymes.
UsesLysosomotropic fluorescent Probe
UsesDansylcadaverine is a fluorescent amine probe, which is believed to directly inhibit vesicular transport. Studies indicate that Dansylcadaverine can act as a marker used to study autophagy in the cytoplasm and vacuoles of plants and mammalian cells.
Suppliers66 total
Related reactions
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Compound notes
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