Ewha, Where Change Begins 유기소재및분자인식연구실 Lab.4 책임교수 성명 윤주영 1983-1987 서울대학교학사 주요학력 소속화학 나노과학과 1990-1994 Ohio State Univ. 박사 구성원 직책인원성명 ( 담당분야 ) 박사후연구원 2 명 Xin Zhang (CO2 형광센싱및포집연구 ), Jun Yin (NIR 형광프로브연구 ) 박사 2 명 Liu Yifan (NIR 형광프로브, 형광화학센서연구 ), 이송이 ( 바이오이미징, 형광화학센서연구 ) Hu Ying ( 형광화학센서연구 ), 김다빈 ( 형광화학센서연구 ), 김재미 ( 바이오이미징, 형광화학센서연구 ) 석사 8 명 박선희 ( 광열치료, 광역학치료시스템연구 ), 이다영 ( 광열치료, 광역학치료시스템연구 ) 이민지 (PDA 고분자센서연구 ), 이혜연 (PDA 고분자센서연구 ), 조선정 (NIR 형광프로브연구 ) 산학협력희망분야 개발된형광프로브들의기술이전혹은프로브판매 대표연구분야 CO2 형광센싱및포집에대한연구 다차원의약전달및광열치료, 광역학치료시스템연구 Cysteine, GSH, H2O2를이용한 NIR 형광프로브연구 금속이온및음이온에선택적인형광화학센서개발 활성산소종에선택적인형광화학센서를이용한바이오이미징연구 PDA 고분자를이용한분자인식센서연구 본연구실에서개발된 Zn(II) 이온에선택적인 CTMPA 프로브를이용하여 zebra fish에존재하는 Zn(II) 을이미징한사진 EWHA TECH in NANO 2013 35
EWHA TECH in NANO 2013 연구실적 ( 최근 3 년간 ) 논문게제 73 건, 기술이전 3 건 논문 연도제목학술지명 Sensors for the optical detection of cyanide ion A selective Off-On fluorescent sensor for Zn 2+ based on hydrazone-pyrene derivative and its Bioorg. Med. Chem. Lett. application for imaging of intracellular Zn 2+ Zn 2+ -Triggered Amide Tautomerization Produces a Highly Zn 2+ -Selective, Cell-Permeable, and Ratiometric Fluorescent Sensor Chiral binaphthyl receptors bearing imidazolium or urea groups for the recognition of anions Ratiometric fluorescent and colorimetric sensors for Cu 2+ based on 4,5-disubstituted-1,8-naphthalimide and sensing cyanide via Cu2+ displacement approach Thin-Film Formation of Imidazolium-Based Conjugated Polydiacetylenes and Their Application for Sensing Anionic Surfactants Fluorescein-Functionalized Silica Nanoparticles as a Selective Fluorogenic Chemosensor for Cu 2+ in Living Cells A Rationally Designed Fluorescence Turn-On Probe for the Gold(III) Ion Development of of-on fluorescent probes for heavy and transition metal ions J. Am. Chem. Soc. J. Incl. Phenom. Macrocycl. Chem. Tetrahedron Angew. Chem. Int. Ed. Eur. J. Inorg. Chem. Superior Anion-Binding Properties of a Cryptand-like Oligopyrrolic Macrocycle Chem. Asian J. 2010 Novel Bi-Nuclear Boron Complex with Pyrene Ligand: Red-Light Emitting as well as Electron Transporting Material in Organic Light-Emitting Diodes A selective and ratiometric Cu 2+ fluorescent probe based on naphthalimide excimer-monomer switching A thiol-specific fluorescent probe and its application for bioimaging Revisit to imidazolium receptors for the recognition of anions: highlighted research during 2006-2009 Fluorescent and colorimetric probes for detection of thiols A selenolactone-based fluorescent chemodosimeter to monitor mecury/methylmercury species in vitro and in vivo Fluorescent chemosensors for Zn 2+ New fluorescent and colorimetric chemosensors based on the rhodamine and boronic acid groups for the detection of Hg 2+ Colorimetric and fluorescent sensing of pyrophosphate in 100% aqueous solution by a system comprised of rhodamine B compound and Al 3+ complex Naphthalimide Modified Rhodamine Derivative: Ratiometric and Selective Fluorescent Sensor for Cu 2+ Based on Two Different Approaches Novel binaphthyl-containing bi-nuclear boron complex with low concentration quenching effect for efficient organic light-emitting diodes Discovery of a highly selective turn-on fluorescent probe for Ag + A near-infrared fluorescent sensor for detection of cyanide in aqueous solution and its application for bioimaging New 7-Hydroxycoumarin-Based Fluorescent Chemosensors for Zn(II) and Cd(II) Tetrahedron Tetrahedron Lett. Analyst Analyst 36 이화여자대학교화학 / 나노분야우수기술설명회및기술이전상담회
Ewha, Where Change Begins A thermally reversible temperature sensor based on polydiacetylene: Synthesis and thermochromic properties Dyes and Pigments Recent progress on polymer-based fluorescent and colorimetric chemosensors Spectrofluorimetric Determination of Bisphosphonates with a Fluorescent Chemosensor, Zinpyr-1-2Zn 2+ Induction-Driven Stabilization of the Anion-π Interaction in Electron-Rich Aromatics as the Key to Fluoride Inclusion in Imidazolium-Cage Receptors Chem. Eur. J. Studies leading to the development of a highly selective colorimetric and fluorescent chemosensor for lysine A Dual Colorimetric and Fluorometric Sensor for Lead Ion Based on Conjugated Polydiacetylenes Macromol. Rapid Commun. Ratiometric Fluorescent Chemosensor for Silver Ion at Physiological ph Inorg. Chem. Unique X-ray Sheet Structure of 1,8-Bis(imidazolium) Anthracene and Its Application as a Fluorescent Probe for DNA and DNase Rhodamine hydrazone derivatives as Hg 2+ selective fluorescent and colorimetric chemosensors and their applications to bioimaging and microfluidic system A specific and sensitive method for detection of hypochlorous acid for the imaging of microbe-induced HOCl production Analyst Study on various fluorescein derivatives as ph sensors Tetrahedron Lett. Fluorescence Sensing of Dihydrogen Phosphate and Pyrophosphate using Imidazolium Anthracene Derivatives 2011 Zebrafish as a good vertebrate model for molecular imaging using fluorescent probes Fluorescent and colorimetric chemosensors for detection of nucleotides, FAD and NADH: highlighted research during 2004-2010 A Novel Supermolecular Tetrameric Vanadate-Selective Colorimetric and Off-On Sensor with Pyrene Ligand Fluorescent Sensing of Triphosphate Nucleotides via Anthracene Derivatives J. Org. Chem. Synthesis of large ring 3,4-alkylenedioxythiophenes (ADOT) derivatives via Mitsunobu reaction Tetrahedron Lett. Recent progress in fluorescent and colorimetric chemosensors for detection of precious metal ions (silver, gold and platinum ions) In Vivo Fluorescence Imaging of Bacteriogenic Cyanide in the Lungs of Live Mice Infected with Cystic Fibrosis Pathogens Novel Bi-Nuclear Boron Complexes with Pyrene Ligand: Synthesis, Photoluminescence, and Electrochemistry Properties A Dual-Polymer Electrochromic Device with High Coloration Efficiency and Fast Response Time: Poly(3,4- (1,4-butylene-(2-ene)dioxy)thiophene)-Polyaniline ECD Fluorescent Sensing and Discrimination of ATP and ADP Based on a Unique Sandwich Assembly of Pyrene-Adenine-Pyrene Plos One Chem. Asian J. Chem. Asian J. Fluorescent and luminescent probes for detection of reactive oxygen and nitrogen species Visual detection of copper ions based on azide- and alkyne-functionalized polydiacetylene vesicles J. Mater. Chem. Base pair opening kinetics study of the aegpna:dna hydrid duplex containing a site-specific GNA-like chiral PNA monomer Nucleic Acids Res. A Polydiacetylenes-Based Sensor for Discriminating Oleic Acid from Stearic Acid and Elaidic Acid EWHA TECH in NANO 2013 37
EWHA TECH in NANO 2013 2011 Diverse colorimetric changes of polydiacetylenes with cationic surfactants and their mechanistic studies Visual detection of dopamine and monitoring tyrosinase activity using a pyrocatechol violet-sn4+ complex Bis- and tris-naphthoimidazolium derivatives for the fluorescent recognition of ATP and GTP in 100% aqueous solution Recent progress in fluorescent and colorimetric chemosensors for detection of amino acids J. Mater. Chem. Org. Biomol. Chem. A pyrene-imidazolium derivative that selectively Recognizes G-Quadruplex DNA Biomaterials A new rhodamine derivative bearing benzothiazole and thiocarbonyl moieties as a highly selective Sensors and Actuators B fluorescent and colorimetric chemodosimeter for Hg 2+ Recent progress on fluorescent chemosensors for metal ions Conjugated polydiacetylenes bearing quaternary ammonium groups as a dual colorimetric and fluorescent sensor for ATP Fluorescent Chemosensors Based on Spiroring-Opening of Xanthenes and Related Derivatives Inorg. Chim. Acta J. Mater. Chem. Chem. Rev. 2012 Fluorescent and colorimetric sensors for detection of lead, cadmium, and mercury ions Polydiacetylene-Based Electrospun Fibers for Detection of HCl Gas Recognition and sensing of various species using boronic acid derivatives Macromol. Rapid Commun. Biosensors and chemosensors based on the optical responses of polydiacetylenes Rhodamine Based Fluorescent Chemosensors for Hg 2+ and its Biological Application Recognition of myo-inositol 1,4,5-trisphosphate using a fluorescent imidazolium receptor New thiazolothiazole derivatives as fluorescent chemosensors for Cr3+ and Al3+ A highly selective ratiometric near-infrared fluorescent cyanine sensor for cysteine with remarkable shift and its application in bioimaging A cyanine-based fluorescent sensor for detecting endogenous zinc ions in live cells and organisms Dyes and Pigments Chem. Sci. Biomaterials Thermally reversible polydiacetylenes derived from ethylene oxide-containing bisdiacetylenes Sensors and Actuators B A Benzobisimidazolium-Based Fluorescent and Colorimetric Chemosensor for CO 2 J. Am. Chem. Soc. A highly selective turn-on fluorescent chemosensor based on hydroxy pyrene-hydrazone derivative for Zn 2+ Dyes and Pigments 2013 New fluorescent receptor composed of two imidazoliums, two pyrenes and a boronic acid for the Sensors and Actuators B recognition of DOPAC A thiazolothiazole based Cu 2+ selective colorimetric and fluorescent sensor via unique radical formation 보유장비 Sepctrofluorophotometer 2 대 UV-Visible Spectrophotometer 2 대 38 이화여자대학교화학 / 나노분야우수기술설명회및기술이전상담회
Ewha, Where Change Begins 소량에도민감하게반응하고대량생산에적합한생체센서기술 기술.1 개요 본기술의시아닌유도체는맹독성, 무색무취의신경작용계화학물질을소량에도민감하게반응한다. 산성의 ph에서활성화가능한비율측정근적외선프로브로활용할수있다. 본기술의또다른시아닌유도체는생체세포및조직에서아연에대한높은선택성과감도를보이며, 아연이온검출용형광프로브에이용될수있다. 기술의우수성 ( 종래기술과의차별성 ) 기존에는신경작용계화학물질을검출할수있는방법이거의없었으나, 본기술의시아닌유도체는합성방법이매우간단하여대량생산에적합하고, 종래의신경작용제검출용시약이두단계의반응과정을거쳐야하는반면에본발명의시아닌유도체는한단계의반응과정만을거치므로반응속도가매우빠르고민감도또한매우우수하며, 산성의 ph에서도활성화가능하고수성환경에서도사용가능하다. 제조공정이단순하여낮은비용으로생산할수있다. 기존의형광아연이온센서는, 자가형광 (autofluorescence), 높은광산란, 및상대적으로낮은결합친화성에의해일어나는고유의시그널오염 (signal contamination) 이발생하는문제가있으나, 본기술의아연센서는큰스펙트럼이동, 낮은형광백그라운드및 Zn2+ 에대한높은감도를가진다. 시장 한국과학기술정보연구원이국내나노와이어바이오센서를이용한질병치료기시장규모를전망한결과조기진단및예방의료패러다임의변화, 노령인구의증가등이시장의유리한기회요인과더불어연평균성장률 41% 로성장해 2015년에는 5602억원의시장규모로성장할것으로예측된다. EP&C 에따르면국내바이오센서시장은 2013년 1000억원에이를것으로예측되며, 세계바이오센서시장은 2011년약 54억달러규모에서 2012년약 61억달러, 2013년약 69억달러, 2014년에약 76억달러, 2015년에는약 86억달러로크게증가할것으로전망되고있다. 지식재산권 10-2012-0006796 ( 출원 ), PCT/KR2013/000089 ( 출원 ) / 폴리메틴체인에메조-반응작용기를갖는신규한시아닌유도체및이의제조방법 10-2012-0076859 ( 출원 ) / 아연이온검출용시아닌유도체, 이의제조방법, 및이를포함하는형광프로브 10-2012-0139682 ( 출원 ) / 시아닌계형광프로브, 이를이용한아연이온검출방법, 및이의제조방법 관련사진 신경작용게화학물질을검출할수있는 시아닌유도체의제조과정을나타낸반응식 시아닌유도체가신경독가스유사체 DCP 와반응하여 생성되는화합물의구조및이에따른색상변화 EWHA TECH in NANO 2013 39
EWHA TECH in NANO 2013 경독가스유사체 DCP 검출전후의색상변화 형광 Zn2+ 프로브 CTMPA 의합성 Zn2+ 를이용하여적정한 CTMPA 의흡광및발광스펙트럼 1 Zn2+ 를이용하여적정한 CTMPA 의흡광및발광스펙트럼 2 관련기술 다양한유도체를이용하여중금속이온, 인산염, 구리, ATP, 수은, 카드뮴, 시안화이온, 아연이온, 수은, 금등을검출하는생체센서기술을보 유하고있다. 10-2006-0123588 ( 등록 ) / 형광화학센서를포함하는미세유체소자및이를이용한중금속이온의광학적측정방법 10-2007-0000498 ( 등록 ) / 인산염선택성을갖는아크리딘 - 아연 (II) 복합체, 이의제조방법및이를이용한인산염검출방법 10-2007-0037701 ( 등록 ) / 피로인산염선택성을갖는나프탈렌디이미드 - 아연 (II) 복합체, 이의제조방법및이를이용한피로인산염검출방법 10-2007-0126526 ( 등록 ) / 플루오레세인유도체, 이의제조방법및이를이용한음이온검출방법 10-2007-0139008 ( 등록 ) / 아크리딘유도체, 이의제조방법및이를이용한수은이온및 / 또는카드뮴이온의선택적검출방법 10-2008-0036188 ( 등록 ) / 플루오레세인알데하이드를이용한시안화이온의검출방법 10-2008-0044447 ( 등록 ) / 플루오레세인다이알데하이드를이용한시안화이온의검출방법 10-2008-0054640 ( 등록 ) / NBD 계유도체, 이의제조방법및이를이용한아연이온의검출방법 10-2008-0055204 ( 등록 ) / 구리이온검출용로다민유도체및플루오레세인유도체, 및이를이용한프로브 10-2008-0084637 ( 등록 ) / 바이나프틸기를갖는로다민유도체, 이의제조방법및이를이용한구리이온의검출방법 10-2009-0010254 ( 등록 ) / 신규로다민유도체및이를포함하는수은이온검출용센서 10-2009-0031942 ( 등록 ) / 시안화이온선택성을갖는플루오레세인-구리 (Ⅱ) 복합체, 이의제조방법및이를이용한시안화이온검출방법 10-2009-0085481 ( 등록 ) / 금이온선택성을갖는로다민유도체를포함하는형광센서및이를이용한금이온검출방법 좌 : [ 수은이온검출화합물의결정구조 ] 중 : [ 수은이온과화합물의결합 ] 우 : [Au3+ 첨가시비색변화 ] 기술개발단계 기술개발완료및시제품생산 활용분야 실험실, 병원등물질센서필요처 40 이화여자대학교화학 / 나노분야우수기술설명회및기술이전상담회
Ewha, Where Change Begins 계면활성제의종류까지검출할수있는고분자센서기술 기술.2 개요 본기술의양이온성계면활성제검출용조성물은본래의파란색에서변하는색의종류를측정하여시료에존재하는양이온성계면활성제의종류를알아내고, 변화된색의정도에따른 UV/VIS 흡광도또는형광강도의변화를측정하여존재하는양이온성계면활성제의농도를측정할수있으므로, 양이온성계면활성제의종류및농도를용이하게검출할수있다. 기술의우수성 ( 종래기술과의차별성 ) 기존의계면활성제검출방법들은단색변화만을나타내므로시료에서계면활성제의유무를검출할수는있으나, 그종류까지는알수없는단점이있다. 본기술은폴리디아세틸렌에벤조산기를도입한화합물을단량체로하여중합한초분자체가검출되는양이온성계면활성제의종류에따라파란색 붉은색, 파란색 보라색, 파란색 노란색, 파란색 주황색으로선택적인비색및형광변화를나타낼수있다. 시장 기존에효과적인계면활성제센서가존재하지않아아직시장이형성되지않았으나, 앞으로여러분야에사용될것으로판단된다. 지식재산권 10-2011-0072119 ( 등록 ) / 양이온성계면활성제검출용조성물및이를이용한양이온성계면활성제검출방법 관련사진 초분자체에검출시료를첨가하였을경우색의변화 초분자체와검출시료를첨가한초분자체 를투사전자현미경으로촬영한이미지 초분자체에검출시료를첨가하였을경우흡수파장의 이동을나타내는 UV/VIS 흡광도그래프 1 초분자체에검출시료를첨가하였을경우흡수파장의 이동을나타내는 UV/VIS 흡광도그래프 2 EWHA TECH in NANO 2013 41
EWHA TECH in NANO 2013 관련기술 폴리아세틸렌초분자체를이용하여납및계면활성제를검출하는고분자센서를제공하는기술을보유하고있다. 10-2009-0031526 / 양이온계면활성제선택성을갖는폴리아세틸렌초분자체, 이의제조방법및이를이용한양이온계면활성제검출방법 ( 등록 ) 10-2009-0042835 / 음이온계면활성제선택성을갖는폴리아세틸렌초분자체, 이의제조방법및이를이용한음이온계면활성제검출방법 ( 등록 ) 10-2011-0017229 / 납이온선택성을갖는폴리아세틸렌초분자체, 이의제조방법및이를이용한납이온검출방법 ( 출원 ) PCDA-IM 1 단량체의제조공정 초분자체에검출시료농도를달리하여첨가시색변화 폴리아세틸렌초분자체의 TEM 사진 기술개발단계 기술개발완료및시제품생산 활용분야 실험실, 병원등물질센서필요처 42 이화여자대학교화학 / 나노분야우수기술설명회및기술이전상담회