Document Detail


A series of naphthalimide derivatives as intra and extracellular pH sensors.
MedLine Citation:
PMID:  20619451     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
A series of new naphthalimide derivatives were synthesized and studied. Three of the materials (SM1, SM2, and SM3) possess methacrylate(s) moieties as pH sensor monomers, enabling these compounds to be polymerized with other monomers for thin film preparation for extracellular pH sensing. Herein, poly(2-hydroxyethyl methacrylate)-co-poly(acrylamide) (PHEMA-co-PAM) was chosen as the polymer matrix. Structure influences on pH responses and pK(a) values were studied. The film P3 composed of the sensing moiety SM3 has a pK(a) close to the usual biological environmental pH of approximately 7. It was used as an extracellular pH sensor to monitor pH change during the metabolism of prokaryotic Escherichia coli (E. coil). On the other hand, the three sensor monomers are new intracellular biomarkers to sense lysosomes of eukaryotic cells since (1) their pK(a) values are in a range of 5.9-6.8; (2) their emission intensities at acidic conditions (such as at pH 5) are much stronger than those at a neutral condition of pH 7; (3) lysosomes range in size from 0.1 to 1.2 mum in diameter with pH ranging from 4.5 to 5.0, which is much more acidic than the pH value of the cytoplasm (usually with a pH value of approximately 7.2); and (4) the acidity of lysosomes enables a protonation of the amino groups of the pH probes making the sensors emit brightly in acidic organelles by inhibiting the photo-induced electron transfer from the amino groups to the fluorophores. Lysosome sensing was demonstrated using live human brain glioblastoma U87MG cell line, human cervical cancer HeLa cell line, and human esophagus premalignant CP-A and CP-D cell lines by observations of small acidic spherical organelles (lysosomes) and significant colocalizations (82-95%) of the sensors with a commercially available lysosome-selective staining probe LysoTracker Red under confocal fluorescence microscopy.
Authors:
Yanqing Tian; Fengyu Su; Warner Weber; Vivek Nandakumar; Bradley R Shumway; Yuguang Jin; Xianfeng Zhou; Mark R Holl; Roger H Johnson; Deirdre R Meldrum
Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural     Date:  2010-07-08
Journal Detail:
Title:  Biomaterials     Volume:  31     ISSN:  1878-5905     ISO Abbreviation:  Biomaterials     Publication Date:  2010 Oct 
Date Detail:
Created Date:  2010-08-03     Completed Date:  2010-11-16     Revised Date:  2013-05-29    
Medline Journal Info:
Nlm Unique ID:  8100316     Medline TA:  Biomaterials     Country:  England    
Other Details:
Languages:  eng     Pagination:  7411-22     Citation Subset:  IM    
Copyright Information:
2010 Elsevier Ltd. All rights reserved.
Affiliation:
Center for Biosignatures Discovery Automation, Biodesign Institute, Arizona State University, 1001 McAllister Ave, Tempe, AZ 85287, USA. yanqing.tian@asu.edu
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MeSH Terms
Descriptor/Qualifier:
Cell Line, Tumor
HeLa Cells
Humans
Hydrogen-Ion Concentration
Models, Theoretical
Naphthalimides / chemistry*
Optical Devices*
Grant Support
ID/Acronym/Agency:
5 P50 HG002360/HG/NHGRI NIH HHS
Chemical
Reg. No./Substance:
0/Naphthalimides
Comments/Corrections

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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