A fluorescent probe for DNA and pH gradients
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9-Amino-6-chloro-2-methoxyacridine

Item No. 22439

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
6-chloro-2-methoxy-9-acridinamine
CAS Number
3548-09-2
Synonyms
  • ACMA
  • NSC 15300
Molecular Formula
C14H11ClN2O
Formula Weight
258.7
Purity
≥98%
Emission
475 nm
Excitation
411 nm
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Methanol: 1 mg/mlWater: miscible
λmax
218, 277, 340, 412, 435 nm
SMILES
ClC1=CC=C2C(N=C(C=CC(OC)=C3)C3=C2N)=C1
InChi Code
InChI=1S/C14H11ClN2O/c1-18-9-3-5-12-11(7-9)14(16)10-4-2-8(15)6-13(10)17-12/h2-7H,1H3,(H2,16,17)
InChi Key
IHHSSHCBRVYGJX-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $81

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    10 mg

    $135

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    25 mg

    $279

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    Product Description

    9-Amino-6-chloro-2-methoxyacridine (ACMA) is a cell-permeable fluorescent probe that intercalates into DNA.1 It selectively binds to poly(dA-dT) sequences with the fluorescence lifetime decreasing with incorporation of guanosine. It is used for labeling DNA and displays excitation/emission spectra of 411/475 nm, respectively.2 ACMA fluorescence is pH-dependent and is quenched when a pH gradient is established, a property that has been utilized in animal- and plant-based studies.3,4,5 It also inhibits acetylcholinesterase with a Ki value of 49 nM.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. 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).

    2. Härd, T., Fan, P., Magde, D., et al. On the flexibility of DNA: Time-resolved fluorescence polarization of intercalated quinacrine and 9-amino-6-chloro-2-methoxyacridine. J. Phys. Chem. 93(10), 4338-43458 (1989).

    3. Baracca, A., Bucchi, L., Ghelli, A., et al. Protonophoric activity of NADH coenzyme Q reductase and ATP synthase in coupled submitochondrial particles from horse platelets. Biochem. Biophys. Res. Commun. 235(3), 469-473 (1997).

    4. Uzdavinys, P., Coinçon, M., Nji, E., et al. Dissecting the proton transport pathway in electrogenic Na+/H+ antiporters. Proc. Natl. Acad. Sci. USA 114(7), E1101-E1110 (2017).

    5. Carqueijeiro, I., Martins, V., Noronha, H., et al. Analytical and fluorimetric methods for the characterization of the transmembrane transport of specialized metabolites in plants. Methods Mol. Biol. 1405, 121-135 (2016).

    6. Bencharit, S., Morton, C.L., Hyatt, J.L., et al. Crystal structure of human carboxylesterase 1 complexed with the Alzheimer’s drug tacrine: From binding promiscuity to selective inhibition. Chem. Biol. 10(4), 341-349 (2003).