Fluorescent Sugar and Uridine Conjugates of 1,8-Naphthalimides with Methyl and Ferrocenyl Headgroups
Giorgio Cavigiolio A B , Joy L. Morgan A , Brian H. Robinson A C and Jim Simpson AA Department of Chemistry, University of Otago, Dunedin, New Zealand.
B Current address: Children’s Hospital Oakland Research Institute, 5700 Martin Luther King Jr Way, Oakland, CA 94609-1673, USA.
C Author to whom correspondence should be addressed (e-mail: brobinson@alkali.otago.ac.nz).
Australian Journal of Chemistry 57(9) 885-894 https://doi.org/10.1071/CH04020
Submitted: 3 February 2004 Accepted: 12 March 2004 Published: 1 September 2004
Abstract
The first amphiphilic sugar and deoxyuridine conjugates with a 4-ethynyl-1,8-N-methylnaphthalimide linker, a 4-ethynyldeoxyuridine conjugate with a N-undecylferrocenyl headgroup, and a 1,8-naphthalimide with a 2,3,4,6-tetra-O-acetate-β-d-glucopyranoside headgroup have been synthesized. A novel acrylate monomeric precursor for sugar–ethynylnaphthalimide polymers is also reported. The ethynyl tether forms complexes with Co2(CO)8 and Co2(CO)6dppm. The single-crystal X-ray structures of 2′-propynyl-2,3,4,6-tetra-O-acetate-β-d-glucopyranoside 4 and 4-(2′-propynyl-2,3,4,6-tetra-O-acetate-β-d-glucopyranoside)-N-methyl-1,8-naphthalimide 6 are also reported. With the exception of the Co2 complexes, the sugar and deoxyuridine conjugates are strongly fluorescent. ‘On–off’ fluorescent switching is achieved in the deoxyuridine conjugate with an undecylferrocenyl headgroup.
Acknowledgments
We thank the University of Otago for financial support, Professor Ward T. Robinson and Dr Jan Wikaira (University of Canterbury) for X-ray data collection, and Dr C. Nervi (Turin) and Dr D. S. Larsen (Otago) for useful discussions.
[1]
(a) J. M. Prober,
G. L. Trainor,
R. J. Dam,
F. W. Hobbs,
C. W. Robertson,
R. J. Zagursky,
A. J. Cocuzza,
M. A. Jensen,
et al.
Science 1987, 238, 336.
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
[42]
[43]
[44]
