Cholesterol-linked fluorescent molecular beacons with enhanced cell permeability.
We appended pyrene units covalently onto adenosine (forming A(P) units) and then incorporated them into oligonucleotides such that they were positioned in complementary locations in opposite strands in the middle positions of hairpin stems. System 1 (A(P)A(P)) behaves as an effective molecular beacon (MB) that changes color from green to blue upon duplex formation. In addition, we attached a cholesterol unit to a free terminus of one of these hairpins; this approach enhanced the cellular delivery of the modified MB relative to those encountered when using conventional transfection methods. These structurally simple cholesterol-based MB systems, which can be synthesized very efficiently, have good potential for opening up new and exciting opportunities in the field of in vivo biosensors.
Seo
Young Jun
YJ
National Research Laboratory, Department of Chemistry, Pohang University of Science and Technology, San 31 Hyoja Dong, Pohang 790-784, Korea.
Jeong
Hyun Seok
HS
Bang
Eun-Kyoung
EK
Hwang
Gil Tae
GT
Jung
Jong Ha
JH
Jang
Sung Key
SK
Kim
Byeang Hyean
BH
D000241:Adenosine / Q000737:chemistry* / Q000378:metabolism; D015374:Biosensing Techniques; D002460:Cell Line; D002784:Cholesterol / Q000737:chemistry* / Q000378:metabolism; D005456:Fluorescent Dyes / Q000737:chemistry* / Q000378:metabolism; D018014:Gene Transfer Techniques; D006801:Humans; D015394:Molecular Structure; D009690:Nucleic Acid Conformation; D009841:Oligonucleotides / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D010539:Permeability; D011721:Pyrenes / Q000737:chemistry*
D005456:Fluorescent Dyes; D009841:Oligonucleotides; D011721:Pyrenes; D002784:Cholesterol; D000241:Adenosine