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Targeting of mitochondria by 10-N-alkyl acridine orange analogues: role of alkyl chain length in determining cellular uptake and localization.
- Source :
-
Mitochondrion [Mitochondrion] 2008 Jun; Vol. 8 (3), pp. 237-46. Date of Electronic Publication: 2008 Apr 25. - Publication Year :
- 2008
-
Abstract
- 10-N-Nonyl acridine orange (NAO) is used as a mitochondrial probe because of its high affinity for cardiolipin (CL). Targeting of NAO may also depend on mitochondrial membrane potential. As the nonyl group has been considered essential for targeting, a systematic study of alkyl chain length was undertaken; three analogues (10-methyl-, 10-hexyl-, and 10-hexadecyl-acridine orange) were synthesized and their properties studied in phospholipid monolayers and breast cancer cells. The shortest and longest alkyl chains reduced targeting, whereas the hexyl group was superior to the nonyl group, allowing very clear and specific targeting to mitochondria at concentrations of 20-100 nM, where no evidence of toxicity was apparent. Additional studies in wild-type and cardiolipin-deficient yeast cells suggested that cellular binding was not absolutely dependent upon cardiolipin.
- Subjects :
- Acridine Orange chemical synthesis
Acridine Orange chemistry
Acridine Orange pharmacology
Breast Neoplasms pathology
Cardiolipins metabolism
Cell Line, Tumor
Dose-Response Relationship, Drug
Female
Fluorescent Dyes chemical synthesis
Fluorescent Dyes chemistry
Fluorescent Dyes pharmacology
Humans
Molecular Structure
Saccharomyces cerevisiae genetics
Saccharomyces cerevisiae metabolism
Temperature
Time Factors
Acridine Orange analogs & derivatives
Acridine Orange metabolism
Cells metabolism
Fluorescent Dyes metabolism
Mitochondria metabolism
Subjects
Details
- Language :
- English
- ISSN :
- 1567-7249
- Volume :
- 8
- Issue :
- 3
- Database :
- MEDLINE
- Journal :
- Mitochondrion
- Publication Type :
- Academic Journal
- Accession number :
- 18514589
- Full Text :
- https://doi.org/10.1016/j.mito.2008.04.003