N-methyl Mesoporphyrin IX

N-methyl Mesoporphyrin IX (NMM) is a transition state analog of porphyrin and an effective inhibitor of ferrochelatase with a K_d value of 7nM^[1]. N-methyl Mesoporphyrin IX is a specific stain for G-quadruplexes, with excitation/emission maxima at 399/610 nm^{[2, 3]}. G-quadruplexes (G4s) are higher-order structures formed by DNA or RNA sequences rich in tandem guanine repeats, and are stabilized by G-quartets through π-π stacking^[4]. N-methyl Mesoporphyrin IX can serve as an effective probe for monitoring Aβ-amyloid aggregation in live cells related to Alzheimer's disease^[5]. N-methyl Mesoporphyrin IX can stabilize human telomeric DNA dAG₃ (TTAG₃)₃ (Tel22) and selectively bind to its parallel conformation with a 1:1 stoichiometry and a binding constant of approximately 1.0 × 10⁵ M^−1[6].

References:
[1] Xu L, Qi Q, Zhu J, et al. N-Methyl Protoporphyrin IX: An Understudied Porphyrin[J]. Chemical research in toxicology, 2022, 35(12): 2186-2193.
[2] Paramasivan S, Bolton P H. Mix and measure fluorescence screening for selective quadruplex binders[J]. Nucleic acids research, 2008, 36(17): e106-e106.
[3] Koralewska N, Szczepanska A, Ciechanowska K, et al. RNA and DNA G-quadruplexes bind to human dicer and inhibit its activity[J]. Cellular and Molecular Life Sciences, 2021, 78(7): 3709-3724.
[4] Kolesnikova S, Curtis E A. Structure and function of multimeric G-quadruplexes[J]. Molecules, 2019, 24(17): 3074.
[5] 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[J]. ACS Chemical Neuroscience, 2017, 8(6): 1299-1304.
[6] Nicoludis J M, Barrett S P, Mergny J L, et al. Interaction of human telomeric DNA with N-methyl mesoporphyrin IX[J]. Nucleic acids research, 2012, 40(12): 5432-5447.

N-methyl Mesoporphyrin IX（NMM）是卟啉的过渡态类似物，是亚铁螯合酶的有效抑制剂，K_d值为7 nM^[1]。N-methyl Mesoporphyrin IX是G-四链体的特异性染色剂，激发/发射最大值分别为399/610 nm^{[2, 3]}。G-四链体（G-quadruplex）是由富含串联重复鸟嘌呤的DNA或 RNA折叠形成的高级结构，由G-四分体（G-quartet）通过π-π堆积形成^[4]。N-methyl Mesoporphyrin IX可以作为监测阿尔茨海默病活细胞中Aβ-淀粉样蛋白聚集的有效探针^[5]。N-methyl Mesoporphyrin IX可以稳定人端粒DNA dAG₃ (TTAG₃)₃ （Tel22），并且对其平行构象具有选择性，以 1:1 化学计量比结合，结合常数约为1.0 × 10⁵ M^−1[6]。