Novel diamino imidazole and pyrrole-containing polyamides: Synthesis and DNA binding studies of mono- and diamino-phenyl-ImPy*Im polyamides designed to target 5′-ACGCGT-3′ was written by Satam, Vijay;Babu, Balaji;Chavda, Sameer;Savagian, Mia;Sjoholm, Robert;Tzou, Samuel;Ramos, Joseph;Liu, Yang;Kiakos, Konstantinos;Lin, Shicai;Wilson, W. David;Hartley, John A.;Lee, Moses. And the article was included in Bioorganic & Medicinal Chemistry in 2012.Recommanded Product: Ethyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate This article mentions the following:
Pyrrole- and imidazole-containing polyamides are widely investigated as DNA sequence selective binding agents that have potential use as gene control agents. The key challenges that must be overcome to realize this goal is the development of polyamides with low molar mass so the mols. can readily diffuse into cells and concentrate in the nucleus. In addition, the mols. must have appreciable water solubility, bind DNA sequence specifically, and with high affinity. It is on this basis that the orthogonally positioned diamino/dicationic polyamide Ph-ImPy*Im (I) was designed to target the sequence 5′-ACGCGT-3′. Py* denotes the pyrrole unit that contains a N-substituted aminopropyl pendant group. The DNA binding properties of diamino polyamide I were determined using a number of techniques including CD, ΔT M, DNase I footprinting, SPR and ITC studies. The effects of the second amino moiety in Py* on DNA binding affinity over its monoamino counterpart Ph-ImPyIm II were assessed by conducting DNA binding studies of II in parallel with I. The results confirmed the minor groove binding and selectivity of both polyamides for the cognate sequence 5′-ACGCGT-3′. The diamino/dicationic polyamide 5 showed enhanced binding affinity and higher solubility in aqueous media over its monoamino/monocationic counterpart Ph-ImPyIm 3. The binding constant of I, determined from SPR studies, was 1.5×107 M-1, which is ∼3 times higher than that for its monoamino analog 3 (4.8×106 M-1). The affinity of I is now approaching that of the parent compound f-ImPyIm and its diamino equivalent The advantages of the design of diamino polyamide I over f-ImPyIm and its diamino equivalent are its sequence specificity and the ease of synthesis compared to the N-terminus pyrrole analog. In the experiment, the researchers used many compounds, for example, Ethyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate (cas: 109012-23-9Recommanded Product: Ethyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate).
Ethyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate (cas: 109012-23-9) belongs to imidazole derivatives. 1H-imidazole is an imidazole tautomer which has the migrating hydrogen at position 1. It is a conjugate base of an imidazolium cation. It is a conjugate acid of an imidazolide. It is a tautomer of a 4H-imidazole. Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam.Recommanded Product: Ethyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate
Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem