Dansylcadaverine - ≥97% , CAS No.10121-91-2

CAS: 10121-91-2 Cat. No.: D131032 Molecular Weight: 335.46 Beilstein Registry Number: 2951070 EC Number: 233-326-9

GRADE & PURITY ≥97%

Synonyms

Monodansyl cadaverine | n-(5-aminopentyl)-5-(dimethylamino)naphthalene-1-sulfonamide | Dansylcadaverine, BioReagent, suitable for fluorescence, >=99.0% (HPLC) | EINECS 233-326-9 | SCHEMBL107806 | AKOS015915995 | N-(5-Aminopentyl)-5-(dimethylamino)naphthal

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

Dansylcadaverine, also called as monodansylcadaverine (MDC), is a lysosomotropic agent. It is present in acidic and lipid rich regions. Dansylcadaverine also acts as a solvent polarity probe. It inhibits vesicular transport and decreases the rotavirus sequestering in L cells, when pre-treated.

Dansylcadaverine in methanol has a reported λex of 335 nm and λem of 512 nm. It has been used:

as an endocytosis inhibitor in human proximal tubular HK-2 cells,(62) mouse J774A.1 macrophages and human A549 epithelial cells(63)

to label autophagic vacuoles in cardiomyocytes for fluorescence microscopy studies(64)

in monodansylcadaverine (MDC) staining of fibroblasts in Ankylosing spondylitis (AS) samples(65)

The autofluorescent dye dansylcadaverine, or monodansylcadaverine (MDC), is commonly used to monitor autophagy. MDC preferentially accumulates in autophagic vacuoles due to a combination of ion trapping and specific interactions with membrane lipids.

Specifications

Synonyms

Monodansyl cadaverine | n-(5-aminopentyl)-5-(dimethylamino)naphthalene-1-sulfonamide | Dansylcadaverine, BioReagent, suitable for fluorescence, >=99.0% (HPLC) | EINECS 233-326-9 | SCHEMBL107806 | AKOS015915995 | N-(5-Aminopentyl)-5-(dimethylamino)naphthal

Specifications & Purity

≥97%

Biochemical and Physiological Mechanisms

The autofluorescent dye dansylcadaverine, or monodansylcadaverine (MDC), is commonly used to monitor autophagy. MDC preferentially accumulates in autophagic vacuoles due to a combination of ion trapping and specific interactions with membrane lipids.

Storage

Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥97%

Names and Identifiers

• Pubchem Sid: 504750763
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504750763
• Canonical Smiles: CN(C)C1=CC=CC2=C1C=CC=C2S(=O)(=O)NCCCCCN
• IUPAC Name: N-(5-aminopentyl)-5-(dimethylamino)naphthalene-1-sulfonamide
• InChIKey: MLEBFEHOJICQQS-UHFFFAOYSA-N
• 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
• Isomeric SMILES: CN(C)C1=CC=CC2=C1C=CC=C2S(=O)(=O)NCCCCCN
• WGK Germany: 3
• Molecular Weight: 335.46
• Beilstein: 2951070
• Reaxy-Rn: 2951070
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2951070&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Naphthalenes
      • Subclass Naphthalene sulfonic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Naphthalenes
• Subclass: Naphthalene sulfonic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: 1-naphthalene sulfonic acids and derivatives
• Alternative Parents: 1-naphthalene sulfonamides Dialkylarylamines Organosulfonamides Aminosulfonyl compounds Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: 1-naphthalene sulfonic acid or derivatives - Naphthalene sulfonamide - 1-naphthalene sulfonamide - Tertiary aliphatic/aromatic amine - Dialkylarylamine - Organosulfonic acid amide - Organic sulfonic acid or derivatives - Organosulfonic acid or derivatives - Sulfonyl - Aminosulfonyl compound - Tertiary amine - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Primary amine - Organosulfur compound - Organonitrogen compound - Primary aliphatic amine - Amine - Aromatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as 1-naphthalene sulfonic acids and derivatives. These are organic aromatic compounds that contain a naphthalene moiety that carries a sulfonic acid group (or a derivative thereof) at the 1-position. Naphthalene is a bicyclic compound that is made up of two fused benzene ring.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: 10 mg/mL Methanol
• Sensitivity: air sensitive
• Molecular Weight: 335.500 g/mol
• XLogP3: 2.500
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 335.167 Da
• Monoisotopic Mass: 335.167 Da
• Topological Polar Surface Area: 83.800 Ų
• Heavy Atom Count: 23
• Formal Charge: 0
• Complexity: 447.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Hongbin Wang, Yuanfu Zhang, Zhaoting Yuan, Xiaotong Zou, Yuan Ji, Jiayi Hou, Jinfang Zhang, Fuping Lu, Yihan Liu.  (2022)  Crosslinking Mechanism on a Novel Bacillus cereus Transglutaminase-Mediated Conjugation of Food Proteins.  Foods,  11  (22): (3722).  [PMID:36429314] [10.3390/foods11223722]

2. Hongbin Wang, Yuan Ji, Zhaoting Yuan, Jishen Tian, Yuanfu Zhang, Fuping Lu, Yihan Liu.  (2022)  Insights into the mechanism on the high-temperature activity of transglutaminase from Bacillus clausii and its crosslinked mode at protein level.  BIOCHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.bej.2022.108544]

3. Dongdong Li, Jing Zhao, Jun Ma, Huiquan Yang, Xiaodong Zhang, Yuyu Cao, Peidang Liu.  (2022)  GMT8 aptamer conjugated PEGylated Ag@Au core-shell nanoparticles as a novel radiosensitizer for targeted radiotherapy of glioma.  COLLOIDS AND SURFACES B-BIOINTERFACES,      [PMID:35032851] [10.1016/j.colsurfb.2022.112330]

4. Xizhe Li, Fan Yang, Haojie Li, Zhi Hu, Weiting Yu, Yuchen Zhang, Jie Gao.  (2024)  Array-based specific classification of bacterial species via ligands with dimethylamino/amino groups.  Analytical Methods,  16  (34): (5812-5819).  [PMID:39140766] [10.1039/D4AY00903G]