Title

Synthesis of nucleobase-neomycin conjugates and evaluation of their biophysical and biochemical properties

Poster Number

13B

Lead Author Major

Chemistry

Lead Author Status

Junior

Second Author Major

Biochemistry

Second Author Status

Junior

Format

Poster Presentation

Faculty Mentor Name

Liang Xue

Faculty Mentor Email

lxue@pacific.edu

Faculty Mentor Department

Chemistry

Additional Faculty Mentor Name

Joan Lin-Cereghino

Additional Faculty Mentor Email

jlincere@pacific.edu

Additional Faculty Mentor Department

Biological Sciences

Additional Faculty Mentor Name

Geoff Lin-Cereghino

Additional Faculty Mentor Email

glincere@pacific.edu

Additional Faculty Mentor Department

Biological Sciences

Abstract/Artist Statement

Neomycin, an aminoglycoside, is known to bind to the A site of 16S ribosomal RNA and A-type DNA such as DNA triplex. It has been used as an antibiotic and a DNA triplex specific binding ligand. Conjugation of neomycin with other DNA binding moieties can further enhance its recognition to various nucleic acids. In the present work, we report the synthesis of four conjugates by coupling nucleobases (A, G, T, and C) with neomycin via click chemistry. The products were characterized using NMR and ESI mass spectrometry. All four conjugates thermally stabilized a DNA oligonucleotide triplex, and the guanine-neomycin conjugate showed a better triplex stabilization effect than neomycin. In addition, the effects of the conjugates on cancer cell viability and the growth of several Gram-negative and Gram-positive bacteria were investigated.

Location

DeRosa University Center, Ballroom

Start Date

29-4-2017 1:00 PM

End Date

29-4-2017 3:00 PM

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Apr 29th, 1:00 PM Apr 29th, 3:00 PM

Synthesis of nucleobase-neomycin conjugates and evaluation of their biophysical and biochemical properties

DeRosa University Center, Ballroom

Neomycin, an aminoglycoside, is known to bind to the A site of 16S ribosomal RNA and A-type DNA such as DNA triplex. It has been used as an antibiotic and a DNA triplex specific binding ligand. Conjugation of neomycin with other DNA binding moieties can further enhance its recognition to various nucleic acids. In the present work, we report the synthesis of four conjugates by coupling nucleobases (A, G, T, and C) with neomycin via click chemistry. The products were characterized using NMR and ESI mass spectrometry. All four conjugates thermally stabilized a DNA oligonucleotide triplex, and the guanine-neomycin conjugate showed a better triplex stabilization effect than neomycin. In addition, the effects of the conjugates on cancer cell viability and the growth of several Gram-negative and Gram-positive bacteria were investigated.