Inhibition of Vesicular Glutamate Uptake by Rose Bengal-Related Compounds: Structure–Activity Relationship

Content Provider	Semantic Scholar
Author	Bole, David G. Ueda, Tetsufumi
Copyright Year	2005
Abstract	Synaptic vesicular accumulation of glutamate is a vital initial step in glutamate transmission. We have previously shown that Rose Bengal, a polyhalogenated fluorescein analog, is a potent inhibitor of glutamate uptake into synaptic vesicles. Here, we report the structural features of Rose Bengal required for this inhibition. Various Rose Bengal-related compounds, with systematic structural variations, were tested. Results indicate that the four iodo groups and the phenyl group attached to the xanthene moiety are critical for potent inhibitory activity. Replacement of these groups with two iodo groups and an alkyl group, respectively, results in substantial reduction in potency. Of further interest in creating high potency is the critical nature of the oxygen atom which links the two benzene rings of xanthene. Thus, the phenyl group and multiple iodo groups, as well as the bridging oxygen of xanthene, are crucial elements of Rose Bengal required for its potent inhibitory action.
Starting Page	363
Ending Page	369
Page Count	7
File Format	PDF HTM / HTML
DOI	10.1007/s11064-005-2610-7
PubMed reference number	16018580
Journal	Medline
Volume Number	30
Alternate Webpage(s)	https://deepblue.lib.umich.edu/bitstream/handle/2027.42/45424/11064_2005_Article_2610.pdf;sequence=1
Alternate Webpage(s)	https://deepblue.lib.umich.edu/bitstream/handle/2027.42/45424/11064_2005_Article_2610.pdf?isAllowed=y&sequence=1
Alternate Webpage(s)	https://deepblue.lib.umich.edu/bitstream/handle/2027.42/45424/11064_2005_Article_2610.pdf?sequence=1
Journal	Neurochemical Research
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article