Editing Acridine (section)

==Applications==
Several [[dye]]s and drugs feature the acridine skeleton.<ref>{{cite journal |doi=10.2174/0929867023369277|title=Acridine Derivatives as Chemotherapeutic Agents|year=2002|last1=Denny|journal=Current Medicinal Chemistry|volume=9|issue=18|pages=1655–65|pmid=12171548}}</ref>  Many acridines, such as [[proflavine]], also have [[antiseptic]] properties. Acridine and related derivatives (such as [[amsacrine]]) bind to [[DNA]] and [[RNA]] due to their abilities to [[Intercalation (biochemistry)|intercalate]].  [[Acridine orange]] (3,6-dimethylaminoacridine) is a [[nucleic acid]]-selective metachromatic [[Staining (biology)|stain]] useful for cell cycle determination.

===Dyes===
At one time acridine dyes were commercially significant, but they are now uncommon because they are not [[Lightfastness|lightfast]]. Acridine dyes are prepared by condensation of [[m-Phenylenediamine|1,3-diaminobenzene]] derivatives.  Illustrative is the reaction of [[2,4-Diaminotoluene|2,4-diaminotoluene]] with acetaldehyde:<ref>{{Ullmann|first1=Thomas|last1=Gessner|first2=Udo|last2=Mayer|title=Triarylmethane and Diarylmethane Dyes|doi=10.1002/14356007.a27_179}}</ref>

[[File:SynthesisBasicYellow9.png|thumb|left|420px|Synthesis of C.I. Basic Yellow 9, an acridine dye.]]

9-Phenylacridine is the parent base of '''chrysaniline''' or 3,6-diamino-9-phenylacridine, which is the chief constituent of the dyestuff phosphine (not to be confused with [[phosphine]] gas), a byproduct in the manufacture of [[rosaniline]]. Chrysaniline forms red-coloured salts, which dye [[silk]] and [[wool]] in a fine yellow; and the solutions of the salts are characterized by their fine yellowish-green fluorescence.  Chrysaniline was synthesized by O. Fischer and G. Koerner by condensing ''o''-nitrobenzaldehyde with aniline, the resulting ''o''-nitro-''p''-diaminotriphenylmethane being reduced to the corresponding ''o''-amino compound, which on oxidation yields chrysaniline.

'''Benzoflavin''', an isomer of chrysaniline, is also a dyestuff, and has been prepared by K. Oehler from ''m''-phenylenediamine and [[benzaldehyde]].  These substances condense to form tetraaminotriphenylmethane, which, on heating with acids, loses ammonia and yields 3,6-diamino-9,10-dihydrophenylacridine, from which benzoflavin is obtained by oxidation.  It is a yellow powder, soluble in hot water.<ref name="Chisholm"/>

=== Molecular biology ===
Acridine is known to induce small insertions or deletions in nucleotide sequences, resulting in [[Frameshift mutation|frameshift mutations]].<ref name=":0">{{cite book |last1=Krebs |first1=Jocelyn E. |url=https://books.google.com/books?id=pNdLDgAAQBAJ |title=Lewin's GENES XII |last2=Goldstein |first2=Elliott S. |last3=Kilpatrick |first3=Stephen T. |date=2017-03-02 |publisher=Jones & Bartlett Learning |isbn=978-1-284-10449-3 |pages=157, 2927 |language=en}}</ref> This compound was useful to identify the triplet nature of the [[Genetic code|genetic codes]].<ref name=":0" />