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
Molecular Weight
463.87g/mol
Melting Point
(Celsius)
Boiling Point
(Celsius)
Density
1.4900g/cm3
Synonyms
28028-11-7
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.

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