70402-14-1

Usage

Uses

Used in Research Applications:
6-Amino-1-phenalenone is used as a detection reagent for biological macromolecules, capitalizing on its fluorescent properties to aid in the observation and analysis of these complex molecules.
Used in Cellular Process Studies:
As a fluorescent probe, 6-Amino-1-phenalenone is instrumental in studying various cellular processes, providing insights into the dynamics and interactions within the cellular environment.
Used in Fluorescence Microscopy:
Leveraging its strong absorption and fluorescence, 6-Amino-1-phenalenone is utilized in fluorescence microscopy, enhancing the visualization of biological samples and facilitating detailed examination of cellular structures and functions.
Used in Flow Cytometry:
6-AMINO-1-PHENALENONE's fluorescent characteristics also make it suitable for use in flow cytometry, allowing for the rapid analysis and sorting of cells based on specific fluorescent markers.
Used in OLED Manufacturing:
6-Amino-1-phenalenone is employed in the production of organic light-emitting diodes (OLEDs), contributing to the development of advanced display and lighting technologies.
Used as a Chemical Intermediate:
In the realm of organic synthesis, 6-Amino-1-phenalenone serves as a valuable chemical intermediate, enabling the creation of a variety of other organic compounds for diverse applications.

InChI:InChI=1/C13H9NO/c14-11-6-4-8-5-7-12(15)10-3-1-2-9(11)13(8)10/h1-7H,14H2

Upstream product

• 3352-82-7 6-Hydroxyphenalenone 
• 548-39-0 Perinaphthenon 
• 91-20-3 naphthalene 

Downstream Products

• 1128246-95-6 C₂₄H₂₄NO₄P 
• 1128246-99-0 C₂₈H₃₃N₂O₄P 
• 1128247-03-9 6-triphenylphosphazo-1H-phenalen-1-one 
• 859175-12-5 C₂₀H₁₄BNO₄ 
• 859176-26-4 C₂₆H₂₄BNO₄ 

Relevant academic research and scientific papers

A Green-Absorbing, Red-Fluorescent Phenalenone-Based Photosensitizer as a Theranostic Agent for Photodynamic Therapy

Phenalenone is a synthetically accessible, highly efficient photosensitizer with a near-unity singlet oxygen quantum yield. Unfortunately, its UV absorption and lack of fluorescence has made it unsuitable for fluorescence-guided photodynamic therapy against cancer. In this work, we synthesized a series of phenalenone derivatives containing electron-donating groups to red-shift the absorption spectrum and bromine(s) to permit good singlet oxygen production via the heavy-atom effect. Of the derivatives synthesized, the phenalenone containing an amine at the 6-position with bromines at the 2- and 5-positions (OE19) exhibited the longest absorption wavelength (i.e., green) and produced both singlet oxygen and red fluorescence efficiently. OE19 induced photocytotoxicity with nanomolar potency in 2D cultured PANC-1 cancer cells as well as light-induced destruction of PANC-1 spheroids with minimal dark toxicity. Overall, OE19 opens up the possibility of employing phenalenone-based photosensitizers as theranostic agents for photodynamic cancer therapy.

Measuring human carboxylesterase 2 activity in pancreatic cancer patient-derived xenografts using a ratiometric fluorescent chemosensor

Irinotecan-based therapy is a common treatment for pancreatic cancer. To elicit its anticancer activity, the drug requires first the hydrolysis action of the enzyme human carboxylesterase 2 (hCES2). It has been established that pancreatic cancer patients have various levels of hCES2, whereby patients having low levels respond poorer to Irinotecan than patients with higher levels, suggesting that hCES2 can be used to predict response. However, current methods that measure hCES2 activity are inaccurate, complex or lengthy, thus being incompatible for use in a clinical setting. Here, we developed a small molecule ratiometric fluorescent chemosensor that accurately measures hCES2 activity in a single-step within complex mixtures. Our chemosensor is highly selective for hCES2 over hCES1, cell permeable and can measure hCES2 activity in pancreatic cancer patient-derived xenografts. Given the simplicity, accuracy and tissue compatibility of our assay, we anticipate our chemosensor can be used to predict patient response to Irinotecan-based therapy.

Design, synthesis and evaluation of amino-substituted 1H-phenalen-1-ones as anti-leishmanial agents

Screening of a designed collection of mono-substituted amino-1H-phenalen-1-ones against promastigote forms of L. donovani and L. amazonensis, identified seven compounds with anti-leishmanial activities comparable or better than the commonly prescribed anti-leishmanial drug, miltefosine. Structure-activity analysis revealed that appendages containing a basic tertiary nitrogen were favored, and that the position of the appendage also affected their potency. Like miltefosine, several of these active compounds significantly reduced the mitochondrial membrane potential in promastigotes. Further studies in amastigotes of L. amazonensis revealed that compounds 14, 15 and 33 were more active and more selective than miltefosine, with sub-micromolar potencies and selectivity indices >100.

TRANSFORMATIONS OF POLYCYCLIC KETONES. XIV. 6-AMINOPHENALENONE AND ITS N-SUBSTITUTED DERIVATIVES

6-Aminophenalenone and its N-alkyl and N-aryl derivatives are easily obtained by the action of ammonia and primary amines on 6-hydroxyphenalenone under mild conditions.