Sciencemadness Discussion Board

Seeking for general information on fluorescein derivatives

Deathtillation - 19-7-2014 at 21:57

Hello!

I'm looking for a way to produce a fluorescein-like compound with a functional reactive group in position 5 or 6 (but actully ANY group that can serve a linker will fit). These cost a fortune at commercial stores, over 100 euro for 100 mg.

Can you please recommend some general reading on 5-/6- substituted fluoresceins?
I have a seen a chapter "Fluoresceins, Rhodamines" in Elderfield's "Heterocyclic compounds". v.2 but the information on production of "phthalic" ring substited compounds is limited. It only raised more questions.
I have also seen a paper of Y.Ueno et al that directly condenses carboxyphthalate with resorcinol in methanesulfonic acid.
I wonder if there are cheaper methods, and I also have no idea how to convert the carboxyfluorescein to acid chloride, since chlorinating agents like SOCl2 react with aromatic hydroxyls in fluorescein ring system.

As for the purpose, It came to my knowledge that our peroxidase enzyme can be detected with fluorescent labelled phenols. The peroxidase (in presence of hydrogen peroxide) oxidizes phenols to radical species that bind covalently to the surrounding of reaction site. The fluorescent dye can be attached to a phenol moeity, thus making reaction visually detectable. This technique is widely used to detect various biomolecules.
I'm planning to use a self made fluoresecent substrate to detect peroxisomes in daphnia.

There are millions of paperson fluorescein but I need alink on a review or a book that covers common chemistry of fluorescein derivatives.
Thank you in advance

[Edited on 20-7-2014 by Deathtillation]

forgottenpassword - 20-7-2014 at 04:12

http://www.ingentaconnect.com/content/ben/mroc/2009/00000006...

Deathtillation - 21-7-2014 at 08:16

Maybe someone has an access to that inspiring reading? Pleeease? :) ^_^

forgottenpassword - 21-7-2014 at 11:49

Here:

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