Photocontrol of polypeptide membrane permeabilities by cis–trans isomerism in side chain azobenzene groups

Triggered cellular uptake of a synthetic graft copolymer carrying an anticancer drug is achieved through self-immolation of the side-chain azobenzene groups.

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Synthesis and Characterization of a Novel Liquid Crystalline Polymer Bearing Azobenzene

Solid State Phenomena ◽

10.4028/www.scientific.net/ssp.181-182.47 ◽

2011 ◽

Vol 181-182 ◽

pp. 47-50

Author(s):

Xin De Tang ◽

Ye Chen ◽

Xin Wang ◽

Fa Qi Yu ◽

Mei Shan Pei

Keyword(s):

Liquid Crystalline Polymer ◽

Liquid Crystalline ◽

Gel Permeation Chromatography ◽

Crystalline Polymer ◽

Side Chain ◽

Scanning Calorimetry ◽

Polymer Bearing ◽

Mesomorphic Properties ◽

Azobenzene Groups

A novel liquid crystalline polymer bearing azobenzene groups in both main chain and side chain has been successfully synthesized by atom transfer radical polymerization (ATRP). Dual bromide-terminated azobenzene was used as the initiator for the ATRP of azobenzene-containing monomer (M6C). The structure of the resulting polymer was confirmed by nuclear magnetic resonance (NMR), and the molecular weight and its dispersity was characterized by gel permeation chromatography (GPC). The mesomorphic properties of this novel polymer were characterized by means of polarized optical microscopy (POM) and differential scanning calorimetry (DSC). The results demonstrated that this polymer can form mesophases.

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Photocontrol of polypeptide membrane functions by cis-trans isomerization in side-chain azobenzene groups

Macromolecules ◽

10.1021/ma00155a010 ◽

1986 ◽

Vol 19 (1) ◽

pp. 51-55 ◽

Cited By ~ 20

Author(s):

Takatoshi Kinoshita ◽

Morimasa Sato ◽

Akira Takizawa ◽

Yoshiharu Tsujita

Keyword(s):

Side Chain ◽

Trans Isomerization ◽

Azobenzene Groups

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Photomodulation of the hydrophilic properties of acrylic polymers containing side-chain azobenzene chromophores

Canadian Journal of Chemistry ◽

10.1139/v95-228 ◽

1995 ◽

Vol 73 (11) ◽

pp. 1849-1854 ◽

Cited By ~ 3

Author(s):

Nicola Tirelli ◽

Angelina Altomare ◽

Roberto Solaro ◽

Francesco Ciardelli

Keyword(s):

Structural Parameters ◽

Radical Copolymerization ◽

Side Chain ◽

Suspension Stability ◽

Trans Form ◽

Free Radical Copolymerization ◽

Acrylic Polymers ◽

Turbidimetric Method ◽

Polymer Properties ◽

Azobenzene Groups

Partially hydrophilic polymers have been prepared by free-radical copolymerization of trans-4-acryloyloxyazobenzene with N-tert-butylacrylamide and N-isopropylacrylamide. A turbidimetric method has been adapted to investigate the dependence of the polymer hydrophilic–hydrophobic balance on chemical composition and extent of photoisomerization of side-chain azobenzene chromophores. Irradiation at 366 nm of polymer suspension in THF–water induces the isomerization of azobenzene groups from the planar apolar trans form to the nonplanar polar cis form. Correspondingly, the solution turbidity is appreciably modified. Experimental results are discussed in terms of polymer structural parameters. Suspension stability and the possibility of carrying out photochemical cycles have been also investigated. Keywords: photochromic polymers, photoresponsive polymer, photomodulation of polymer properties, azobenzene-containing polymers, acryloyloxyazobenzene, N-tert-butylacrylamide.

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Combined Main-Chain/Side-Chain Liquid Crystalline Polymer with Main-Chain On the basis of “Jacketing” Effect and Side-Chain Containing Azobenzene Groups

Macromolecules ◽

10.1021/ma200851v ◽

2011 ◽

Vol 44 (19) ◽

pp. 7600-7609 ◽

Cited By ~ 36

Author(s):

He-Lou Xie ◽

Shao-Jie Wang ◽

Guan-Qun Zhong ◽

Yi-Xin Liu ◽

Hai-Liang Zhang ◽

...

Keyword(s):

Liquid Crystalline Polymer ◽

Liquid Crystalline ◽

Main Chain ◽

Crystalline Polymer ◽

Side Chain ◽

Azobenzene Groups

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PHOTO-INDUCED POLYPEPTIDE MEMBRANE POTENTIAL CHANGES BY cis–trans ISOMERISM IN SIDE-CHAIN AZOBENZENE GROUPS

Chemistry Letters ◽

10.1246/cl.1984.1963 ◽

1984 ◽

Vol 13 (11) ◽

pp. 1963-1966 ◽

Cited By ~ 5

Author(s):

Akira Takizawa ◽

Morimasa Sato ◽

Takatoshi Kinoshita ◽

Yoshiharu Tsujita

Keyword(s):

Membrane Potential ◽

Side Chain ◽

Azobenzene Groups

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Azo polymers for reversible optical storage. 8. The effect of polarity of the azobenzene groups

Canadian Journal of Chemistry ◽

10.1139/v95-218 ◽

1995 ◽

Vol 73 (11) ◽

pp. 1773-1778 ◽

Cited By ~ 69

Author(s):

Mei-Sing Ho ◽

A. Natansohn ◽

C. Barrett ◽

P. Rochon

Keyword(s):

Optical Storage ◽

Side Chain ◽

Relaxation Rates ◽

No Donor ◽

Azo Polymers ◽

Azobenzene Moiety ◽

Donor Acceptor ◽

Storage Properties ◽

Effect Of Polarity ◽

Azobenzene Groups

Poly[4′-[[(2-methacryloyloxy)ethyl]ethylamino]azobenzene] (pMAEA) was prepared. Its reversible optical storage properties were studied and compared with the properties of previously reported poly[4-(2-methacryloyloxy)ethylazobenzene] (pMEA) and poly[4-nitrophenyl-4′-[[2-(methacryloyloxy)ethyl]ethyl-amino]phenyldiazene] (pDR1M). The effect of the dipole moment of the azobenzene moiety on the optical storage properties was studied by comparing the photochemically induced birefringence "writing" and "relaxation" behaviors. The writing and relaxation rates are both in the order pDR1M > pMAEA > pMEA. In addition, pDR1M, which contains donor/acceptor substituents in the azobenzene side chain, exhibits the highest saturation level of optically induced birefringence. The fraction of birefringence conserved after relaxation is lowest for pMEA, which has no donor/acceptor substituents in the azobenzene side chain, and highest for pDR1M. Keywords: polymers, azobenzene type, birefringence, photochemically induced orientation, reversible optical storage.

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