19853-95-3

Usage

Family

Anthracenedione

Type

Synthetic molecule

Usage

Fluorescent dye and staining reagent

DNA Interaction

Intercalates with DNA

Applications

DNA-binding studies, visualization of DNA within cells

Potential Use

Cancer therapy (cytotoxic effects on cancer cells)

Additional Studies

Development of new materials and sensors

Molecular Structure

Unique molecular structure and properties

Upstream product

• 28736-42-7 1,4-difluoroanthracene-9,10-dione 
• 107-15-3 ethylenediamine 
• 17648-03-2 9,10-Dihydroxy-2,3-dihydro-anthracene-1,4-dione 
• 26786-15-2 1,4,9,9,10,10-hexachloroanthracene 
• 19853-94-2 C₁₈H₂₂N₄O₂ 
• 182931-36-8 {2-[4-(2-tert-Butoxycarbonylamino-ethylamino)-9,10-dioxo-9,10-dihydro-anthracen-1-ylamino]-ethyl}-carbamic acid tert-butyl ester 
• 40498-13-3 2,3-dihydro-1,4-dihydroxyanthraquinone 
• 602-25-5 1,4-dichloroanthraquinone 
• 70477-05-3 1,4-Bis-(2-aminoethyl-amino)-2,3-dihydro-anthrachinon 

Downstream Products

• 1327302-79-3 C₃₈H₃₈N₁₀O₈S₂ 

Relevant academic research and scientific papers

Development of colorimetric receptors for selective discrimination between isomeric dicarboxylate anions

Three new chromogenic receptors (1, 2, and 3) containing p-nitrophenyl or p-nitronaphthyl group appended to the thiourea units or containing p-nitrophenyl group appended to the urea moiety were synthesized and characterized. Upon addition of a series of i

Synthesis of colorimetric receptors for dicarboxylate anions: A unique color change for malonate

Three new chromogenic receptors (1, 2, and 3) containing p-nitrophenyl or p-nitronaphthyl or methyl groups appended to the thiourea groups were synthesized and characterized. Upon addition of a series of dicarboxylate anions to receptor 1 in DMSO, only th

Near-IR region absorbing 1,4-diaminoanthracene-9,10-dione motif?based?ratiometric chemosensors for Cu2+

1,4-Bis[2-aminoethylamino]anthracene-9,10-diones selectively bind with Cu2+ to form complexes with unusual selectivity under basic conditions. The deprotonation of the aryl amine NH in the case of these chemosensors causes a bathochromic shift in the absorption band from 585 nm and 635 nm to 725 nm and enables ratiometric estimation of Cu2+ between pH 8 and 12.

Synthesis of alanine-based colorimetric sensors and enantioselective recognition of aspartate and malate anions

Two chiral colorimetric sensors (1,2) were synthesized and characterized by spectroscopic techniques and their enantioselective recognition of chiral dicarboxylic anions (d/l-aspartate and d/l-malate) was examined by UV-vis and 1H NMR spectrosc

Synthesis, DNA binding, and cytotoxicity of 1,4-bis(2-amino-ethylamino)anthraquinone-amino acid conjugates

Two series of 1,4-bis(2-amino-ethylamino)anthraquinone-amino acid conjugates (BACs), ametantrone (AT)-amino acid conjugates (AACs) and mitoxantrone (MX)-amino acid conjugates (MACs), were designed and synthesized. The DNA binding of BACs was evaluated by

Synthesis of colorimetric sensors for isomeric dicarboxylate anions: Selective discrimination between maleate and fumarate

Four new colorimetric receptors (1-4) were synthesized and characterized. Upon addition of maleate to receptor 1 in DMSO, the appearance of the solution of receptor 1 showed a color change from dark-blue to dark-red, which can be detected by the naked eye at parts per million. Similar experiments were repeated using receptors 2-4; the solution showed a distinct color change from blue to violet for receptor 2 and from blue-green to purple for both receptors 3 and 4, when they are formed as complexes with maleate. The striking color changes are thought to be due to the deprotonation of the thiourea moiety of the 4-nitronaphthyl chromophore. Whereas, in the addition of fumarate to receptors 1-4, the color of the solution changed from dark-blue to bright yellow for receptor 1 and did not induce any color change for receptors 2-4. Thus, for a distinct color change, receptors 1-4 can act as optical chemosensors for recognition of maleate versus fumarate. Especially, only receptor 1 has a unique color change for the recognition of fumarate, accordingly it can be used for detection of the fumarate anion. In this research it was also found that the performance of the receptor is highly dependent on the substituent group on the phenyl ring; a stronger electron-withdrawing group resulted in a receptor with a higher binding constant with the maleate anion. The Royal Society of Chemistry.

Synthesis and Antitumor Evaluations of Symmetrically and Unsymmetrically Substituted 1,4-Bisanthracene-9,10-diones and 1,4-Bis-5,8-dihydroxyanthracene-9,10-diones

The ipso bis displacements of fluoride from 1,4-difluoroanthracene-9,10-dione (3) and 1,4-difluoro-5,8-dihydroxyanthracene-9,10-dione (4) by excess of a diamine (or a monoamine) in pyridine at room temperature lead to the symmetrically substituted 1,4-bis-substituted analogues 5 and 6, respectively.The ipso monodisplacements of fluoride from 3 and 4 can be accomplished by treatment with less than 1 molar equiv of a diamine (or a monoamine) to yield 7 and 8, respectively.Treatment of 7 or 8 with a different diamine leads to the unsymmetrically substituted1,4-bisanthracene-9,10-diones 9 and 10, respectively.Many of the synthetic unsymmetrical analogues have been evaluated for their antitumor activity against L1210 in vitro and in vivo.Cross resistance of analogue 10a with mitoxantrone (2) and doxorubicin was evaluated against MDR lines in vitro against human colon carcinoma LOVO and its subline resistant to DOXO (LOVO/DOXO).Potential mechanisms for the observed cytotoxicity are presented and discussed.

CONVENIENT SYNTHESIS ROUTES TO 1,4-DIFLUOROANTHRACENE-9,10-DIONE

Two convenient synthetic routes to 1,4-difluoroanthracene-9,10-dione are described.