A ferrochelatase inhibitor and turn-on biosensor for DNA
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N-methyl Mesoporphyrin IX

Item No. 27210

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
8,13-diethyl-3,7,12,17,23-pentamethyl-21H,23H-porphine-2,18-dipropanoic acid
CAS Number
142234-85-3
Molecular Formula
C35H40N4O4
Formula Weight
580.7
Purity
≥95% (mixture of isomers)
Emission
610 nm
Excitation
399 nm
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMF:PBS (pH 7.2) (1:5): 0.17 mg/mlDMSO: 15 mg/ml
λmax
299, 395, 564 nm
SMILES
CC1=C2[NH]C(/C=C(C(CCC(O)=O)=C3C)\[N]=C3/C=C4[N](C)/C(C(C)=C\4CC)=C\C5=[N]/C(C(C)=C5CC)=C\2)=C1CCC(O)=O
InChi Code
InChI=1S/C35H40N4O4/c1-8-22-18(3)26-14-27-19(4)24(10-12-34(40)41)29(36-27)15-30-25(11-13-35(42)43)20(5)28(38-30)16-33-23(9-2)21(6)32(39(33)7)17-31(22)37-26/h14-17,36H,8-13H2,1-7H3,(H,40,41)(H,42,43)/b26-14-,27-14-,28-16-,29-15-,30-15-,31-17-,32-17-,33-16-
InChi Key
XASXJWXLPCEQJN-UQOLDQHFSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $103

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    5 mg

    $229

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    Product Description

    N-methyl Mesoporphyrin IX is a transition state analog of porphyrin and an inhibitor of ferrochelatase.1 It inhibits ferrochelatase in mouse liver mitochondria in vitro and in vivo, leading to an accumulation of porphyrin in isolated liver mitochondria following administration of an intravenous dose of 80 nmol. N-methyl Mesoporphyrin IX has been used as a turn-on biosensor for target DNA sequences when used in complex with a G-quadruplex-forming sequence fused to a DNA sequence complementary to the target sequence.2 It has also been used to detect amyloid-β (1-40) (Aβ40) fibrils in vitro and in live PC12 cells overexpressing Aβ.3 N-methyl Mesoporphyrin displays excitation/emission maxima of 399/610 nm, respectively.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. de Matteis, F., Gibbs, A.H., and Smith, A.G. Inhibition of protohaem ferro-lyase by N-substituted porphyrins. Structural requirements for the inhibitory effect. Biochem. J. 189(3), 645-648 (1980).

    2. Ren, J., Qin, H., Wang, J., et al. Label-free detection of nucleic acids by turn-on and turn-off G-quadruplex-mediated fluorescence. Anal. Bioanal. Chem. 399(8), 2763-2770 (2011).

    3. Li, M., Zhao, A., Ren, J., et al. N‑Methyl mesoporphyrin IX as an effective probe for monitoring Alzheimer’s disease β‑amyloid aggregation in living cells. ACS Chem. Neurosci. 8(6), 1299-1304 (2017).

    4. Paramasivan, S., and Bolton, P.H. Mix and measure fluorescence screening for selective quadruplex binders. Nucleic Acids Res. 36(17), e106 (2008).