Title:
CYANINE COMPOUND, DYE CONTAINING CYANINE COMPOUND, AND APPLICATION OF CYANINE COMPOUND
Document Type and Number:
WIPO Patent Application WO/2022/099658
Kind Code:
A1
Abstract:
Disclosed in the present invention are a cyanine compound, a dye containing the cyanine compound, and an application of the cyanine compound. The cyanine compound has the structure of general formula I. X is selected from a group consisting of C(CH3)2, O, S, and Se. R1 and R2 are independently selected from a group consisting of H, C1-C18 alkyl groups, a phenyl group, OR6, and a halogen, respectively; R3 and R4 are independently selected from a group consisting of C1-C18 alkyl groups, C1-C18 carboxyl groups, C1-C18 hydroxyl groups, C1-C18NR5R6, a benzyl group, and a substituted benzyl group, respectively, wherein a substituent of the substituted benzyl group is selected from a group consisting of C1-C18 alkyl groups, CN, COOH, NH2, NO2, OH, SH, C1-C6 alkoxy groups, C1-C6 alkylamino groups, C1-C6 acylamino groups, a halogen, and C1-C6 haloalkyl groups. R5 and R6 are independently selected from a group consisting of H and C1-C18 alkyl groups, respectively. Y- is an anion. The cyanine compound according to the present invention has good permeability for living cells, and can enter a cell to dye a nucleic acid without destroying the cell membrane; moreover, the excitation light is blue-green light having a smaller wavelength.
Inventors:
FAN JIANGLI (CN)
CHEN GENGWEN (CN)
XIA TIANPING (CN)
YE YI (CN)
ZHANG ZIQIAN (CN)
YAO QICHAO (CN)
CHEN GENGWEN (CN)
XIA TIANPING (CN)
YE YI (CN)
ZHANG ZIQIAN (CN)
YAO QICHAO (CN)
Application Number:
PCT/CN2020/128838
Publication Date:
May 19, 2022
Filing Date:
November 13, 2020
Export Citation:
Assignee:
UNIV DALIAN TECH (CN)
SHENZHEN MINDRAY BIOMEDICAL ELECTRONICS CO LTD (CN)
SHENZHEN MINDRAY BIOMEDICAL ELECTRONICS CO LTD (CN)
International Classes:
C09B23/02; C07D413/06; C07D417/06
Domestic Patent References:
| WO1996013552A2 | 1996-05-09 | |||
| WO1994024213A1 | 1994-10-27 |
Foreign References:
| US20060263844A1 | 2006-11-23 | |||
| CN102112875A | 2011-06-29 | |||
| CN1226928A | 1999-08-25 | |||
| US5321130A | 1994-06-14 | |||
| FR1242962A | 1960-10-07 |
Other References:
TARITA BIVER ET AL.: "Influence of cyanine dye structure on self-aggregation and interaction with nucleic acids: A kinetic approach to TO and BO binding", ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, vol. 465, no. 1, 15 May 2007 (2007-05-15), XP022211409, ISSN: 0003-9861, DOI: 10.1016/j.abb.2007.04.034
JENNIE ISACSSON ET AL.: "Solid-phase synthesis of asymmetric cyanine dyes", TETRAHEDRON LETTERS, vol. 42, no. 18, 30 April 2001 (2001-04-30), XP004234076, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(01)00365-3
NETZEL THOMAS L., NAFISI KAMBIZ, ZHAO MIN, LENHARD JEROME R., JOHNSON IAIN: "Base-Content Dependence of Emission Enhancements, Quantum Yields, and Lifetimes for Cyanine Dyes Bound to Double-Strand DNA: Photophysical Properties of Monomeric and Bichromomphoric DNA Stains", THE JOURNAL OF PHYSICAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 99, no. 51, 1 December 1995 (1995-12-01), pages 17936 - 17947, XP055929526, ISSN: 0022-3654, DOI: 10.1021/j100051a019
LEE L. G., CHEN C.-H., CHIU L. A.: "THIAZOLE ORANGE: A NEW DYE FOR RETICULOCYTE ANALYSIS.", CYTOMETRY, ALAN LISS, NEW YORK., US, vol. 07., 1 January 1986 (1986-01-01), US , pages 508 - 517., XP000613662, ISSN: 0196-4763, DOI: 10.1002/cyto.990070603
XIANG-FENG ZHOU ET AL.: "Blue sensitizing dyes: synthesis, spectroscopy, and performance in photographic emulsions", JOURNAL OF IMAGING SCIENCE AND TECHNOLOGY, vol. 39, no. 3, 30 June 1995 (1995-06-30), XP000541067, ISSN: 1062-3701
JENNIE ISACSSON ET AL.: "Solid-phase synthesis of asymmetric cyanine dyes", TETRAHEDRON LETTERS, vol. 42, no. 18, 30 April 2001 (2001-04-30), XP004234076, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(01)00365-3
NETZEL THOMAS L., NAFISI KAMBIZ, ZHAO MIN, LENHARD JEROME R., JOHNSON IAIN: "Base-Content Dependence of Emission Enhancements, Quantum Yields, and Lifetimes for Cyanine Dyes Bound to Double-Strand DNA: Photophysical Properties of Monomeric and Bichromomphoric DNA Stains", THE JOURNAL OF PHYSICAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 99, no. 51, 1 December 1995 (1995-12-01), pages 17936 - 17947, XP055929526, ISSN: 0022-3654, DOI: 10.1021/j100051a019
LEE L. G., CHEN C.-H., CHIU L. A.: "THIAZOLE ORANGE: A NEW DYE FOR RETICULOCYTE ANALYSIS.", CYTOMETRY, ALAN LISS, NEW YORK., US, vol. 07., 1 January 1986 (1986-01-01), US , pages 508 - 517., XP000613662, ISSN: 0196-4763, DOI: 10.1002/cyto.990070603
XIANG-FENG ZHOU ET AL.: "Blue sensitizing dyes: synthesis, spectroscopy, and performance in photographic emulsions", JOURNAL OF IMAGING SCIENCE AND TECHNOLOGY, vol. 39, no. 3, 30 June 1995 (1995-06-30), XP000541067, ISSN: 1062-3701
Attorney, Agent or Firm:
P. C. & ASSOCIATES (CN)
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