An azaarene
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Acridine

Item No. 35607

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
CAS Number
260-94-6
Synonyms
  • 2,3,5,6-Dibenzopyridine
  • 10-Azaanthracene
  • Dibenzopyridine
  • NSC 3408
Molecular Formula
C13H9N
Formula Weight
179.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 2 mg/mlDMSO: 10 mg/mlEthanol: 10 mg/mlPBS (pH 7.2): insol
λmax
249 nm
SMILES
C1(N=C2C=CC=CC2=C3)=C3C=CC=C1
InChi Code
InChI=1S/C13H9N/c1-3-7-12-10(5-1)9-11-6-2-4-8-13(11)14-12/h1-9H
InChi Key
DZBUGLKDJFMEHC-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    5 g

    $49

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    10 g

    $93

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    25 g

    $194

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    50 g

    $363

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    Cayman Chemical
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    Product Description

    Acridine is an azaarene.1 It is a scaffold component of many pharmacologically active compounds, including topoisomerase inhibitors and DNA intercalators, as well as compounds with anticancer and antimalarial activities.2,3,4,5 Acridine is also the backbone of some fluorescent probes, such as acridine orange (Item No. 14338) and ICAAc (Item No. 28564).6,7 It is genotoxic to bacteria when used at a concentration of 50 µg/ml.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Skarek, M., Cupr, P., Réblova, K., et al. Assessment of toxic and genotoxic effects of N-heterocyclic polyaromatic hydrocarbons with miniaturized in vitro screening bioassays. 1-4.

    2. Nelson, E.M., Tewey, K.M., and Liu, L.F. Mechanism of antitumor drug action: Poisoning of mammalian DNA topoisomerase II on DNA by 4'-(9-acridinylamino)-methanesulfon-m-anisidide. Proc. Natl. Acad. Sci. USA 81(5), 1361-1365 (1984).

    3. Fukui, K., Tanaka, K., Fujitsuka, M., et al. Distance dpendence of electron transfer in acridine-intercalated DNA. J. Photochem. Photobiol. B Biol. 50(1), 18-27 (1999).

    4. Heald, R.A., Modi, C., Cookson, J.C., et al. Antitumor polycyclic acridines. 8.1 Synthesis and telomerase-inhibitory activity of methylated pentacyclic acridinium salts. J. Med. Chem. 45(3), 590-597 (2002).

    5. Kumar, R., Kaur, M., and Kumari, M. Acridine: A versatile heterocyclic nucleus. Acta Pol. Pharm. 69(1), 3-9 (2012).

    6. Han, J., and Burgess, K. Fluorescent indicators for intracellular pH. Chem. Revs. 110(5), 2709-2728 (2010).

    7. Nagy, M., Racz, D., Nagy, Z.L., et al. Amino-isocyanoacridines: Novel, tunable solvatochromic fluorophores as phystiological pH probes. Sci. Rep. 9, 8250 (2019).