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Hirao Akira,Tsunoda Yuji,Matsuo Akira,Sugiyama Kenji,Watanabe Takumi The Polymer Society of Korea 2006 Macromolecular Research Vol.14 No.3
Dendritic hyperbranched poly(methyl methacrylate)s (PMMA)s, whose branched architectures resemble the 'dendron' part(s) of dendrimer, were synthesized by an iterative methodology consisting of two reactions in each iteration process: (a) a coupling reaction of u-functionalized, living, anionic PMMA having two tert-butyldimethylsilyloxymethylphenyl(SMP) groups with benzyl bromide(BnBr)-chain-end-functionalized PMMA, and (b) a transformation reaction of the introduced SMP groups into BnBr functionalities. These two reactions, (a) and (b), were repeated three times to afford a series of dendron-like, hyperbranched (PMMA)s up to third generation. Three dendron-like, hyperbranched (PMMA)s different in branched architecture were also synthesized by the same iterative methodology using a low molecular weight, functionalized 1,1-diphenylalkyl anion prepared from sec-BuLi and 1,1-bis(3-tert-butyldime-thylsilyloxymethylphenyl)ethylene in the reaction step (b) in each iterative process. Furthermore, structurally similar, dendron-like, hyperbranched block copolymers could be successfully synthesized by the iterative methodology using $\alpha$-functionalized, living, anionic poly(2-(perfluorobutyl) ethyl methacrylate) (PRfMA) in addition to $\alpha$-functionalized, living PMMA. Accordingly, the resulting block copolymers were comprised of both PMMA and PRfMA segments with different sequential orders. After the block copolymers were cast into films and annealed, their surface structures were characterized by angle-dependent XPS and contact angle measurements. All three samples showed significant segregation and enrichment of PRfMA segments at the surfaces.
Identification of glyco-biomarker candidates for lung cancer using novel glyco-technologies
Yoshitoshi Hirao,Hideki Matsuzaki,Jun Iwaki,Minako Abe,Akira Togayachi,Atsushi Kuno,Takashi Ohkura,Hiroyuki Kaji,Masaharu Nomura,Masayuki Noguchi,Yuzuru Ikehara,Hisashi Narimatsu 한국당과학회 2012 한국당과학회 학술대회 Vol.2012 No.1
Lung cancer is the leading cause of cancer death worldwide. Currently, lung cancer is classified into two major types, small-cell lung cancer carcinoma (SCLC) and non-small-cell lung carcinoma (NSCLC), based on the histological appearance. The histological classification has important implications in the clinical practice guideline and the prediction of the patient prognosis. However, conventional serum markers used in clinical tests are insufficient for clinical demands due to the low sensitivity and the low specificity to distinguish them. We have identified a number of glyco-biomarker candidate molecules from lung cancer cell lines using our developed glycoproteomics technologies such as lectin microarray and LC/MS-based protein analysis. On the validation studies, we found out that the selected molecules showed characteristic lectin biding profiles depending on either SCLC or NSCLC. Therefore, combination of these glyco-biomarkers could be expected to improve the diagnostic accuracy for histological classification in lung cancer compared to protein expression alone.
Lee, Sanghoon,Lee, Hyojoon,Chang, Taihyun,Hirao, Akira American Chemical Society 2017 Macromolecules Vol.50 No.7
<P>An exact polystyrene-graft-polyisoprene (PS-g-PI) synthesized by iterative anionic polymerization and graft reaction using diphenylethylene functional groups was characterized by liquid chromatography. As-prepared graft copolymer contains various byproducts other than the target PS-g-PI. After the fractionation by size exclusion chromatography (SEC), the PS-g-PI appears quite homogeneous by SEC analysis, but the temperature gradient interaction chromatography (TGIC) separation with respect to the PI branch number showed a significantly wide distribution in the number of PI grafts. The resolved TGIC peaks were fractionated, and the molecular weight of each block (backbone or branches) was estimated by liquid chromatography at critical condition (LCCC) analysis at the critical adsorption condition of the opposite block. The composition determined by LCCC analysis and H-1 NMR analysis yielded a reasonably self-consistent result. Through this study, we demonstrated that SEC analysis of this type of branched copolymers can lead to erroneous result and needs to be done with proper caution.</P>
Higashihara Tomoya,Inoue Kyoichi,Nagura Masato,Hirao Akira The Polymer Society of Korea 2006 Macromolecular Research Vol.14 No.3
To successively synthesize star-branched polymers, we developed a new iterative methodology which involves only two sets of the reactions in each iterative process: (a) an addition reaction of DPE or DPE-functionalized polymer to a living anionic polymer, and (b) an in-situ reaction of 1-(4-(4-bromobutyl)phenyl)-1-phenylethylene with the generated 1,1-diphenylalkyl anion to introduce one DPE functionality. With this methodology, 3-, 4-, and 5-arm, regular star-branched polystyrenes, as well as 3-arm ABC, 4-arm ABCD, and a new 5-arm ABCDE, asymmetric star-branched polymers, were successively synthesized. The A, B, C, D, and E arm segments were poly(4-trimethylsilylstyrene), poly(4-methoxystyrene), poly(4-methylstyrene), polystyrene, and poly(4-tert-butyldimethylsilyloxystyrene), respectively. All of the resulting star-branched polymers were well-defined in architecture and precisely controlled in chain length, as confirmed by SEC, $^1H$ NMR, VPO, and SLS analyses. Furthermore, we extended the iterative methodology by the use of a new functionalized DPE derivative, 1-(3-chloromethylphenyl)-1-((3-(1-phonyletheny1)phenyl) ethylene, capable of introducing two DPE functionalities via one DPE anion reaction site in the reaction (b). The number of arm segments of the star-branched polymer synthesized by the methodology could be dramatically increased to 2, 6, and up to 14 by repeating the iterative process.