241820-93-9

Upstream product

• 6553-96-4 2,4,6-triisopropylphenylsulfonyl chloride 
• 241820-92-8 hexa-N-Boc neomycin B 
• 119-04-0 neomycin B 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 241820-94-0 C₅₇H₁₀₂N₆O₂₅S₂ 
• 261518-54-1 C₅₅H₉₉N₇O₂₄S 
• 849676-07-9 5″-azide-1,3,2′,6′,2′″,6′″-hexa-N-(tert-butoxycarbonyl)-5″-deoxy-neomycin B 

Relevant academic research and scientific papers

Use of neomycin as a structured amino-containing side chain motif for phenanthroline-based G-quadruplex ligands and telomerase inhibitors

In this paper, we report the synthesis of a phenanthroline and neomycin conjugate (7). Compound 7 binds to a human telomeric G-quadruplex (G1) with a higher affinity compared with its parent compounds (phenanthroline and neomycin), which is determined by

Synthesis of nucleobase-neomycin conjugates and evaluation of their DNA binding, cytotoxicities, and antibacterial properties

Neomycin is known to preferentially bind to A-form nucleic acid structures including triplex DNA, DNA and RNA hybrid, and duplex RNA. Tethering a DNA intercalator moiety to the C5” position of the ring III of neomycin is a practical approach to develop po

Assisted enzyme replacement therapy

Reagents and methods useful for the synthesis of conjugates comprising guanidinylated cyclic acetals are provided. Also provided are methods for increasing the cellular uptake of various therapeutic compounds and treatment modalities using these conjugates.

Regulating miRNA-21 Biogenesis by Bifunctional Small Molecules

We report a new strategy to regulate microRNAs (miRNAs) biogenesis by using bifunctional small molecules that consist of a pre-miRNA binding unit connected by a linker to a Dicer inhibiting unit. In this effort, fluorescence polarization-based screening was used to identify neomycin as a pre-miR-21 binding ligand. Although neomycin cannot inhibit miR-21 maturation, linking it to the RNase inhibitor 1 forms the bifunctional conjugate 7A, which inhibits the production of miR-21. We expect that this strategy will be applicable to design other molecules for miRNA regulation.

Utilization of chromic polydiacetylene assemblies as a platform to probe specific binding between drug and RNA

Recognition of nucleic acids remains an important endeavor in biology. Nucleic acids adopt shapes ranging from A-form (RNA and GC rich DNA) to B-form (AT rich DNA). We show, in this contribution, shape-specific recognition of A-U rich RNA duplex by a neomycin (Neo)-polydiacetylene (PDA) complex. PDA assemblies are fabricated by using a well-known diacetylene (DA) monomer, 10,12-pentacosadiynoic acid (PCDA). The response of poly(PCDA) assemblies is generated by mixing with a modified neomycin-PCDA monomer (Neo-PCDA). The functionalization by neomycin moiety provides specific binding with homopolyribonucleotide poly(rA)-poly(rU) stimulus. Various types of alcohols are utilized as additives to enhance the sensitivity of poly(PCDA)/Neo-PCDA assemblies. A change of absorption spectra is clearly observed when a relatively low concentration of poly(rA)-poly(rU) is added into the system. Furthermore, poly(PCDA)/Neo-PCDA shows a clear specificity for poly(rA)-poly(rU) over the corresponding DNA duplex. The variation of linker between neomycin moiety and conjugated PDA backbone is found to significantly affect its sensitivity. We also investigate other parameters including the concentration of Neo-PCDA and the DA monomer structure. Our results provide here preliminary data for an alternative approach to improve the sensitivity of PDA utilized in biosensing and diagnostic applications.

Arginine-linked neomycin B dimers: Synthesis, rRNA binding, and resistance enzyme activity

The nucleotides comprising the ribosomal decoding center are highly conserved, as they are important for maintaining translational fidelity. The bacterial A-site has a small base variation as compared with the human analogue, allowing aminoglycoside (AG) antibiotics to selectively bind within this region of the ribosome and negatively affect microbial protein synthesis. Here, by using a fluorescence displacement screening assay, we demonstrate that neomycin B (NEO) dimers connected by l-arginine-containing linkers of varying length and composition bind with higher affinity to model A-site RNAs compared to NEO, with IC50 values ranging from ~40-70 nM, and that a certain range of linker lengths demonstrates a clear preference for the bacterial A-site RNA over the human analogue. Furthermore, AG-modifying enzymes (AMEs), such as AG O-phosphotransferases, which are responsible for conferring antibiotic resistance in many types of infectious bacteria, demonstrate markedly reduced activity against several of the l-arginine-linked NEO dimers in vitro. The antimicrobial activity of these dimers against several bacterial strains is weaker than that of the parent NEO.

Methods and compositions related to viral inhibition

Disclosed herein are compounds, compositions and methods related to viral inhibition. In some forms, the compounds, compositions and methods are related to binding RNA.

Rapid synthesis, RNA binding, and antibacterial screening of a peptidic-aminosugar (PA) library

A 215-member mono- and diamino acid peptidic-aminosugar (PA) library, with neomycin as the model aminosugar, was systematically and rapidly synthesized via solid phase synthesis. Antibacterial activities of the PA library, on 13 bacterial strains (seven G

Click dimers to target HIV TAR RNA conformation

A series of neomycin dimers have been synthesized using "click chemistry" with varying functionality and length in the linker region to target the human immunodeficiency virus type 1 (HIV-1) TAR RNA region of the HIV virus. The TAR (Trans-Activation Respo

Neomycin-neomycin dimer: An all-carbohydrate scaffold with high affinity for AT-rich DNA duplexes

A dimeric neomycin-neomycin conjugate 3 with a flexible linker, 2,2′-(ethylenedioxy)bis(ethylamine), has been synthesized and characterized. Dimer 3 can selectively bind to AT-rich DNA duplexes with high affinity. Biophysical studies have been performed b