公开(公告)号：US20160274123A1

公开(公告)日：2016-09-22

申请号：US15037168

申请日：2014-02-26

Applicant: POSTECH ACADEMY-INDUSTRY FOUNDATION

Inventor： Kyo Han Ahn ,  Dokyoung Kim ,  Subhankar Singha

IPC: G01N33/58

CPC classification number: G01N33/582 ,  C07C225/22 ,  G01N1/30 ,  G01N33/6815

Abstract: The present invention relates to a one-photon and/or two-photon fluorescent probe for selectively detecting hydrogen sulfide in the human body using a compound including an α,β-unsaturated carbonyl group and an acedan (2-acyl-6-dimethyl-amino-naphthalene) fluorescent material; to an imaging method of hydrogen sulfide in cells using the same; and to a manufacturing method of the fluorescent probe. More specifically, in the fluorescent probe of the present invention, the α,β-unsaturated carbonyl group of the compound selectively binds to hydrogen sulfide, inducing an increase in fluorescence of the acedan fluorescent material. The fluorescent probe according to the present invention can be conveniently synthesized, enables two-photon excitation, and corresponds to a small-molecule probe having stability and low toxicity in the body. In addition, the fluorescent probe according to the present invention can exhibit a fluorescent change by selectively reacting with hydrogen sulfide, thereby imaging the distribution of hydrogen sulfide in cells or tissues, and thus can be useful for a composition for imaging and an imaging method.

Abstract translation: 本发明涉及一种用于使用包含α，β-不饱和羰基和acedan（2-酰基-6-二甲基-2-吡咯烷酮）的化合物选择性地检测人体中的硫化氢的单光子和/或双光子荧光探针， 氨基萘）荧光材料; 涉及使用其的细胞中硫化氢的成像方法; 以及荧光探针的制造方法。 更具体地说，在本发明的荧光探针中，该化合物的α，β-不饱和羰基选择性地与硫化氢结合，诱导了白色荧光物质的荧光增加。 根据本发明的荧光探针可以方便地合成，实现双光子激发，并且对应于在体内具有稳定性和低毒性的小分子探针。 此外，根据本发明的荧光探针可以通过选择性地与硫化氢反应而显示荧光变化，从而对硫化氢在细胞或组织中的分布进行成像，因此可用于成像用组合物和成像方法。

公开(公告)号：US09658235B2

公开(公告)日：2017-05-23

申请号：US14745973

申请日：2015-06-22

Applicant: POSTECH ACADEMY-INDUSTRY FOUNDATION

Inventor： Kyo Han Ahn ,  Hyunsoo Moon ,  Dokyoung Kim ,  Ki Hean Kim ,  Hye Gun Ryu

IPC: G01N33/58 ,  G01N21/64 ,  C07D311/92 ,  G01N33/68 ,  C07D311/78 ,  C07D311/94 ,  A61K49/00

CPC classification number: G01N33/582 ,  A61K49/0021 ,  C07D311/78 ,  C07D311/92 ,  C07D311/94 ,  G01N21/6428 ,  G01N33/6896 ,  G01N2021/6439 ,  G01N2333/4709 ,  G01N2800/2821

Abstract: Provided are acedan derivatives having an extended π bond, a method for preparing the acedan derivatives, and a method for two-photon microscopy imaging of amyloid-beta plaque using the acedan derivatives; more particularly, to two-photon absorbing fluorescent compounds having a longer absorption wavelength and emission wavelength than acedan and acedan derivatives which are conventional two-photon absorbing fluorophores. The compounds provided may be usefully used for in vivo imaging studies by imaging cells or tissue using the compounds, and may also be usefully used for diagnosing Alzheimer's disease by imaging amyloid-beta plaque using the compounds.

公开(公告)号：US09958434B2

公开(公告)日：2018-05-01

申请号：US14888883

申请日：2014-03-10

Applicant: POSTECH ACADEMY-INDUSTRY FOUNDATION

Inventor： Kyo Han Ahn ,  Dokyoung Kim ,  Sungjee Kim ,  Ki Hean Kim

IPC: C12Q1/48 ,  G01N33/50 ,  C07C223/06 ,  G01N33/574 ,  G01N33/58 ,  C09K11/06

CPC classification number: G01N33/5023 ,  C07C223/06 ,  C09K11/06 ,  C12Q1/485 ,  G01N33/574 ,  G01N33/582 ,  G01N2333/91205 ,  G01N2333/9121 ,  G01N2500/10

Abstract: A fluorescent probe for detecting a tyrosine kinase using a compound having an ortho-hydroxy-benzaldehyde structure, and use thereof are provided. The fluorescent probe can show a change in fluorescence when the compound binds with a tyrosine kinase. The compound can be readily synthesized and has high stability and low cytotoxicity in vivo. The fluorescent probe can be used to image cells or tissues overexpressing the tyrosine kinase, the fluorescent probe can be effectively used in a composition for imaging the tissues and a method of imaging the tissues. Also, the fluorescent probe can be used to image cancer cells or tissues since the fluorescent probe can exhibit fluorescence when the fluorescent probe binds to the cancer cells or tissues overexpressing the tyrosine kinase.

公开(公告)号：US20180371256A1

公开(公告)日：2018-12-27

申请号：US15955877

申请日：2018-04-18

Applicant: POSTECH ACADEMY-INDUSTRY FOUNDATION

Inventor： Kyo Han Ahn ,  Yong Woong Jun ,  Hyerim Kim ,  Subhankar Singha ,  Ye Jin Reo

IPC: C09B57/02 ,  G01N33/58 ,  C09K11/06

Abstract: Provided is a method for preparing a novel benzocoumarin-based two-photon absorbing fluorescent dye, such as a pyridinium-benzocoumarin (Py+BC) derivative compound and its precursor compound (pyridyl-benzocoumarin, PyBC), an aryl-benzocoumarin (ArBC) derivative compound, a benzothiazolyl-benzocoumarin (BtBC) derivative compound or a keto-benzocoumarin (KetoBC) derivative compound. The Py+BC derivative compound of the present invention is a two-photon absorbing near-infrared fluorescent dye, which may minimize interference of autofluorescence compared to conventional two-photon absorbing fluorescent dyes such as acedan and naphthalimide, thereby obtaining a high-definition image, and therefore is expected to be effectively used in imaging studies. In addition, when the two-photon absorbing near-infrared fluorescent dye of the present invention is used, it is expected to be suitable for high resolution imaging of deep tissue.

公开(公告)号：US20140377791A1

公开(公告)日：2014-12-25

申请号：US14345137

申请日：2013-03-21

Applicant: POSTECH ACADEMY - INDUSTRY FOUNDATION

Inventor： Kyo Han Ahn ,  Dokyoung Kim

IPC: C12Q1/26 ,  C07C221/00 ,  C07C255/43 ,  C07F7/18 ,  C07D311/58 ,  C07C223/06

CPC classification number: C12Q1/26 ,  C07C221/00 ,  C07C223/06 ,  C07C253/30 ,  C07C255/42 ,  C07C255/43 ,  C07D311/58 ,  C07D311/92 ,  C07F7/1804 ,  C12Q1/42 ,  G01N2333/90638 ,  G01N2800/2835 ,  G01N2800/304

Abstract: The present invention relates to a compound which is a novel two-photon absorbing fluorescent substance, a production method for the compound, a fluorescence sensor and molecular probe able to sense various substrates or enzyme activity or the like using the same, and a method of sensing enzyme activity or the like using the same. More specifically, the present invention relates to a novel two-photon absorbing fluorescent substance which has the high photo-stability and large two-photon absorption cross-section value of acedan which is a two-photon absorbing fluorescent substance, and has the high fluorescence efficiency of coumarin which is a one-photon absorbing fluorescent substance, while exhibiting absorption and emission characteristics at a longer wavelength than existing acedan and coumarin and so being advantageous in in-vivo imaging. The compound according to the present invention can be used as a fluorescence sensor which is highly sensitive and selective for various substrates, and more particularly, can be used in the study and treatment of diseases in which MAO enzymes are involved such as mood disorders using MAO enzyme activity and inhibitor screening.

Abstract translation: 本发明涉及一种新型双光子吸收荧光物质的化合物，该化合物的制备方法，荧光传感器和能够感测各种底物或酶活性等的分子探针，以及使用其的方法 感测酶活性等。 更具体地说，本发明涉及一种新颖的双光子吸收荧光物质，其具有高双光子吸收荧光物质的阿登丹的光稳定性和双光子吸收截面积大，并具有高荧光 作为单光子吸收荧光物质的香豆素的效率，同时具有比现有的氨基和香豆素更长的波长的吸收和发射特性，因此在体内成像方面是有利的。 根据本发明的化合物可以用作对各种底物高度敏感和选择性的荧光传感器，更具体地可以用于研究和治疗涉及MAO酶的疾病，例如使用MAO的情绪障碍 酶活性和抑制剂筛选。