5-Carboxyfluorescein

5-Carboxyfluorescein 속성

5-Carboxyfluorescein C화학적 특성, 용도, 생산

개요

5-Carboxyfluorescein is a single isomer derivative of 5(6)-carboxyfluorescein that can be used to fluorescently label biomolecules through the interaction of carboxylic acid with primary amines. It demonstrates excitation/emission maxima of 492 and 518 nm, respectively.

화학적 성질

Orange Solid

용도

5-Carboxyfluorescein(5-FAM) contains a carboxylic acid that can be used to react with primary amines via carbodiimide activation of the carboxylic acid. It is a useful reagent for the preparation of hydrolytically stable fluorescent conjugates and is a useful starting material for the synthesis of other fluorescein-derives reagent. It has been principally used to develop a variety of green fluorescent reagents and small fluorescent molecules due to its relatively high absorbance characteristics, excellent fluorescence quantum yield, and good water solubility. The probe has also found application in studies of liposome-cell, cell-cell, and liposome-liposome interactions and in related studies on lipid bilayer structures.

정의

ChEBI: 5-carboxyfluorescein is a monocarboxylic acid. It has a role as a fluorochrome. It is functionally related to a fluorescein (lactone form).

Biochem/physiol Actions

5-Carboxyfluorescein is used for the staining of cells to differentiate between live and dead cells. It helps in monitoring the integrity and intactness of the cell membrane. It is also used for the measurement of intracellular pH. 5-Carboxyfluorescein diacetate is a non-fluorescent molecule which is cleaved by intracellular esterases, thereby giving a green fluorescent product 5-carboxyfluorescein. In viable cells, the fluorescent molecule is impermeable to the cellular membrane.

Synthesis

5-Carboxyfluorescein is a mixture of 5- and 6-isomers prepared by the reaction of benzotricarboxylic anhydride with resorcinol and zinc chloride.
Reaction: 1,2,4-Benzenetricarboxylic anhydride (also called 4-carboxyphthalic anhydride, 25.0 g, 0.13 mol) was added to a solution of 1,3-dihydroxybenzene (also called resorcinol, 28.6 g, 0.26 mol) in methane sulfonic acid (1M). An air condenser was attached to the flask and the reaction was heated at 85°C in an open vessel for 24 h. After cooling to room temperature, the reaction mixture was poured into 7 volumes of ice/water. An orange-yellow precipitate formed; this was collected by filtration and dried in an oven at 200°C. This residue was recrystallized two times from methanol/hexane to give 1.0 g of 6-carboxyfluorescein methanesulfonic acid adduct 2b. The mother liquors from this procedure were collected, the solvent was removed in vacuo, and the residues were recrystallized two times from ethanol/hexanes to give 3.2 g of 5-carboxyfluorescein methanesulfonic acid adduct 2a.

The methane sulfonic esters 2 are easily converted to the 5- and 6-carboxyfluoresceins 1 by treatment with sodium hydroxide solution then neutralizing with aqueous HCl.

5-Carboxyfluorescein 준비 용품 및 원자재

원자재

준비 용품

5-Carboxyfluorescein 공급 업체

공급자	전화	이메일	국가	제품 수	이점
Hongxiong	+undefined18915499068	Suzhouhongxiong@163.com	China	120	58
Henan Fengda Chemical Co., Ltd	+86-371-86557731 +86-13613820652	info@fdachem.com	China	7845	58
Henan Tianfu Chemical Co.,Ltd.	+86-0371-55170693 +86-19937530512	info@tianfuchem.com	China	21691	55
career henan chemical co	+86-0371-86658258	sales@coreychem.com	China	29914	58
Changzhou Ansciep Chemical Co., Ltd.	+86 519 86305871	sales@ansciepchem.com	CHINA	4242	58
Accela ChemBio Inc.	(+1)-858-699-3322	info@accelachem.com	United States	19965	58
Chongqing Chemdad Co., Ltd	+86-023-61398051 +8613650506873	sales@chemdad.com	China	39916	58
SHANGHAI T&W PHARMACEUTICAL CO., LTD.	+86-021-61551413 +8618813727289	contact@trustwe.com	China	5738	58
Xi'an Yutbon Pharmaceutical Technology Co., Ltd	029-81140587 +8618717328141	sales@yutbon.com	China	437	58
SIMAGCHEM CORP	+86-13806087780	sale@simagchem.com	China	17367	58

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