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Acridine Orange

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Identification
Molecular formula
C23H28Cl3N3
CAS number
65-61-2
IUPAC name
9,9-dimethyl-10-[3-[4-(4-methylpiperazine-1,4-diium-1-yl)piperidin-1-ium-1-yl]propyl]acridine;trichloride
State
State

At room temperature, acridine orange is typically in a solid state in the form of a powder. When used in experiments, it is dissolved in solvents to form a liquid solution for use as a dye.

Melting point (Celsius)
268.00
Melting point (Kelvin)
541.15
Boiling point (Celsius)
300.00
Boiling point (Kelvin)
573.15
General information
Molecular weight
463.87g/mol
Molar mass
463.8650g/mol
Density
1.4900g/cm3
Appearence

Acridine orange appears as a reddish-orange powder. It can form a fluorescent green solution in ethyl alcohol, and when diluted, it gives off a characteristic bright green fluorescence under blue light or ultraviolet light. It is commonly used as a nucleic acid-selective fluorescent cationic dye useful for cell cycle determination.

Comment on solubility

Solubility of 9,9-Dimethyl-10-[3-[4-(4-methylpiperazine-1,4-diium-1-yl)piperidin-1-ium-1-yl]propyl]acridine; Trichloride

The solubility of 9,9-dimethyl-10-[3-[4-(4-methylpiperazine-1,4-diium-1-yl)piperidin-1-ium-1-yl]propyl]acridine; trichloride can be influenced by various factors. As a quaternary ammonium compound, this compound is likely to exhibit good solubility in polar solvents. Here are some aspects to consider:

  • Polar Solvents: Compounds with quaternary ammonium groups often dissolve well in water and other polar solvents due to strong ion-dipole interactions.
  • Non-Polar Solvents: Conversely, solubility in non-polar solvents is limited, as the ionic nature of the compound is not conducive to interaction with non-polar molecules.
  • Temperature Influence: Increasing temperature may enhance solubility, particularly in cases where dissolution is endothermic.
  • pH Conditions: The solubility may also be affected by the pH of the solution, as the protonation state of the nitrogen atoms can influence solvation.

In summary, the highly polar nature of 9,9-dimethyl-10-[3-[4-(4-methylpiperazine-1,4-diium-1-yl)piperidin-1-ium-1-yl]propyl]acridine; trichloride suggests favorable solubility in aqueous environments, while limited solubility can be expected in organic non-polar solvents. As always, experimental data is essential for precise solubility assessments.

Interesting facts

Facts About 9,9-Dimethyl-10-[3-[4-(4-Methylpiperazine-1,4-Diium-1-Yl)piperidin-1-Ium-1-Yl]Propyl]Acridine; Trichloride

This compound is an intriguing member of the acridine family, known for its unique structure and potential applications in various fields.

Structural Features

  • Acridine Moiety: The acridine structure is notable for its planar and rigid conformation, which contributes to its ability to intercalate into nucleic acids.
  • Methyl Groups: The presence of dimethyl substitutions alters the compound's solubility and binding properties, potentially enhancing its biological activity.
  • Piperazine and Piperidine: The inclusion of piperazine and piperidine rings introduces basic nitrogen atoms, which may facilitate interactions with cellular targets.

Biological Significance

This compound has garnered attention due to its potential applications in:

  • Anticancer Research: Compounds with acridine structures have been studied for their ability to inhibit DNA replication in rapidly dividing cancer cells.
  • Aromaticity: The planar nature of acridine allows for efficient stacking interactions with nucleic acids, explaining its use in various biological studies.
  • Pharmaceutical Development: The unique combination of piperazine and piperidine derivatives offers opportunities for designing new therapeutics.

Research Insights

As researchers delve deeper into the properties and applications of this compound, several points of interest have emerged:

  • Potential for Fluorescent Applications: Due to its structural characteristics, this compound could potentially be used in fluorescent probes for biological imaging.
  • Targeting Mechanisms: Understanding how this compound interacts with biological macromolecules can reveal insights into molecular targeting strategies.
  • Outlook on Modification: The synthesis of derivatives with varied functional groups may lead to compounds with enhanced selectivity and potency.

In summary, 9,9-dimethyl-10-[3-[4-(4-methylpiperazine-1,4-diium-1-yl)piperidin-1-ium-1-yl]propyl]acridine; trichloride illustrates how complex molecular design can pave the way for innovative approaches in medicinal chemistry and biophysics.

Synonyms
28028-11-7
Acridan, 9,9-dimethyl-10-(3-(4-(4-methyl-1-piperazinyl)piperidino)propyl)-, hydrochloride, hydrate (2:6:1)
RefChem:317041