Visible-Light Photocontrol of (E)/(Z) Isomerization of the 4-(Dimethylamino)azobenzene Pseudo-Nucleotide Unit Incorporated into an Oligonucleotide and DNA Hybridization in Aqueous Media

被引：12

作者：

Kamei, Takashi ^{[1
,2
,3
]}

Akiyama, Haruhisa ^{[3
]}

Morii, Hisayuki ^{[4
]}

Tamaoki, Nobuyuki ^{[1
,3
]}

Uyeda, Taro Q. P. ^{[2
]}

机构：

[1] Hokkaido Univ, Res Inst Elect Sci, Sapporo, Hokkaido 0010021, Japan

[2] Natl Inst Adv Ind Sci & Technol, Res Inst Cell Engn, Tsukuba, Japan

[3] Natl Inst Adv Ind Sci & Technol, Nanotechnol Res Inst, Tsukuba, Japan

[4] Natl Inst Adv Ind Sci & Technol, Inst Biol Resources & Funct, Tsukuba, Japan

来源：

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS | 2009年 / 28卷 / 01期

关键词：

Photoregulating DNA hybridization; photoresponsive oligonucleotides; visible light; (E); (Z) isomerization; 4-(dimethylamino)azobenzene; aqueous media; CIS-TRANS ISOMERIZATION; H-AGGREGATION; AZOBENZENE; MOLECULES; STACKING; LINKER; PROBES; DYES; ION;

D O I：

10.1080/15257770802581641

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

We demonstrate significant photoresponsivity in aqueous media to visible light of pseudo-oligonucleotides possessing 4-(dimethylamino)azobenzene (4-DMAzo) side chains. The spectrum of the 4-DMAzo moiety during 436 nm light irradiation at pH 9 was clearly different from that of the all (E)-form, indicating the presence of the (Z)-form. Thermal (Z)-to-(E) recovery isomerization was faster at pH 9 (kZ-E = 101 s-1) than at pH 11; however, addition of 50% ethanol significantly slowed the thermal recovery isomerization at pH 9 (kZ-E = 2 s-1) and increased the magnitude of the spectral changes. Significant photoregulation of DNA hybridization by visible light was demonstrated under this condition.

引用

页码：12 / 28

页数：17

共 34 条

[1] Polymers derived from N-isopropylacrylamide and azobenzene-containing acrylamides:: Photoresponsive affinity to water [J].

Akiyama, H ;

Tamaoki, N .

JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2004, 42 (20) :5200-5214

[2] Synthesis and photoinduced phase transitions of poly(N-isopropylacrylamide) derivative functionalized with terminal azobenzene units [J].

Akiyama, Haruhisa ;

Tamaoki, Nobuyuki .

MACROMOLECULES, 2007, 40 (14) :5129-5132

[3] DNA-dye conjugates for controllable H* aggregation [J].

Asanuma, H ;

Shirasuka, K ;

Takarada, T ;

Kashida, H ;

Komiyama, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (08) :2217-2223

[4] H-aggregation of methyl reds by the hybridization of DNA-dye conjugates [J].

Asanuma, H ;

Shirasuka, K ;

Komiyama, M .

CHEMISTRY LETTERS, 2002, (04) :490-491

[5] Spiropyran as a regulator of DNA hybridization with reversed switching mode to that of azobenzene [J].

Asanuma, H ;

Shirasuka, K ;

Yoshida, T ;

Takarada, T ;

Liang, XG ;

Komiyama, M .

CHEMISTRY LETTERS, 2001, (02) :108-109

[6] Photo-responsive oligonucleotides carrying azobenzene in the side-chains [J].

Asanuma, H ;

Ito, T ;

Komiyama, M .

TETRAHEDRON LETTERS, 1998, 39 (49) :9015-9018

[7]

Asanuma H, 1999, ANGEW CHEM INT EDIT, V38, P2393, DOI 10.1002/(SICI)1521-3773(19990816)38:16<2393::AID-ANIE2393>3.0.CO

[8]

2-7

[9] Light-activated ion channels for remote control of neuronal firing [J].

Banghart, M ;

Borges, K ;

Isacoff, E ;

Trauner, D ;

Kramer, RH .

NATURE NEUROSCIENCE, 2004, 7 (12) :1381-1386

[10] Cis-trans isomerization of organic molecules and biomolecules: Implications and applications [J].

Dugave, C ;

Demange, L .

CHEMICAL REVIEWS, 2003, 103 (07) :2475-2532

← 1 2 3 4 →