Synthesis of a pyridyl disulfide end-functionalized glycopolymer for conjugation to biomolecules and patterning on gold surfaces.
A pyridyl disulfide end-functionalized polymer with N-acetyl-d-glucosamine pendant side-chains was synthesized by atom transfer radical polymerization (ATRP). The glycopolymer was prepared from a pyridyl disulfide initiator catalyzed by a Cu(I)/Cu(II)/2,2'-bipyridine system in a mixture of methanol and water at 30 degrees C. The final polymer had a number-average molecular weight (M(n)) of 13.0 kDa determined by (1)H NMR spectroscopy and a narrow polydispersity index (1.12) determined by gel permeation chromatography (GPC). The pyridyl disulfide end-group was then utilized to conjugate the glycopolymer to a double-stranded short interfering RNA (siRNA). Characterization of the glycopolymer-siRNA by polyacrylamide gel electrophoresis (PAGE) showed 97% conjugation. The activated disulfide polymer was also patterned on gold via microcontact printing. The pyridyl disulfide allowed for ready immobilization of the glycopolymer into 200 microm sized features on the surface.
Vázquez-Dorbatt
Vimary
V
Department of Chemistry and Biochemistry and California Nanosystems Institute, University of California-Los Angeles, Los Angeles, California 90095-1569.
Tolstyka
Zachary P
ZP
Chang
Chien-Wen
CW
Maynard
Heather D
HD
D015082:2,2'-Dipyridyl / Q000737:chemistry*; D001672:Biocompatible Materials / Q000138:chemical synthesis* / Q000737:chemistry; D002850:Chromatography, Gel; D004220:Disulfides / Q000737:chemistry*; D006046:Gold / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry; D011134:Polysaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D034741:RNA, Small Interfering / Q000378:metabolism*; D013499:Surface Properties
D001672:Biocompatible Materials; D004220:Disulfides; D011108:Polymers; D011134:Polysaccharides; D034741:RNA, Small Interfering; D015082:2,2'-Dipyridyl; D006046:Gold