Abstract
Isopentenyladenosine (iPA), a member of the cytokinin family of plant hormones, exerts a marked antiproliferative activity on some leukemic and epithelial cancer cell lines. To characterize the molecular moieties required for the in vitro antitumor activity of the molecule and to obtain cytostatic iPA derivatives potentially useful as chemotherapeutic agents, N9-acyclic analogues have been synthesized using regioselective Mitsunobu reaction and characterized by elemental analyses, 1H and 13C NMR. These compounds were analyzed for their activity on human bladder cancer cell lines. In this study, we report that iPA inhibited the proliferation but not the migration of human bladder cancer cells, while the newly synthesized analogues revealed no significant cytostatic activity apart from the compound with a saturated double bond of the isopentenyl chain. These results indicate that the integrity of the ribose ring is required for the cytostatic activity of iPA.
| Original language | English |
|---|---|
| Pages (from-to) | 736-751 |
| Number of pages | 16 |
| Journal | Nucleosides, Nucleotides and Nucleic Acids |
| Volume | 28 |
| Issue number | 8 |
| DOIs | |
| Publication status | Published - Aug 2009 |
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Keywords
- Acyclic nucleosides
- Antitumor agents
- Bladder carcinoma cells
- Isopentenyladenosine
ASJC Scopus subject areas
- Biochemistry
- Genetics
- Molecular Medicine
Cite this
Novel isopentenyladenosine analogues : Synthesis, characterization, and evaluation of antiproliferative activity on bladder carcinoma cells. / Ottria, Roberta; Casati, Silvana; Maier, J. A M; Mariotti, Massimo; Ciuffreda, Pierangela.
In: Nucleosides, Nucleotides and Nucleic Acids, Vol. 28, No. 8, 08.2009, p. 736-751.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Novel isopentenyladenosine analogues
T2 - Synthesis, characterization, and evaluation of antiproliferative activity on bladder carcinoma cells
AU - Ottria, Roberta
AU - Casati, Silvana
AU - Maier, J. A M
AU - Mariotti, Massimo
AU - Ciuffreda, Pierangela
PY - 2009/8
Y1 - 2009/8
N2 - Isopentenyladenosine (iPA), a member of the cytokinin family of plant hormones, exerts a marked antiproliferative activity on some leukemic and epithelial cancer cell lines. To characterize the molecular moieties required for the in vitro antitumor activity of the molecule and to obtain cytostatic iPA derivatives potentially useful as chemotherapeutic agents, N9-acyclic analogues have been synthesized using regioselective Mitsunobu reaction and characterized by elemental analyses, 1H and 13C NMR. These compounds were analyzed for their activity on human bladder cancer cell lines. In this study, we report that iPA inhibited the proliferation but not the migration of human bladder cancer cells, while the newly synthesized analogues revealed no significant cytostatic activity apart from the compound with a saturated double bond of the isopentenyl chain. These results indicate that the integrity of the ribose ring is required for the cytostatic activity of iPA.
AB - Isopentenyladenosine (iPA), a member of the cytokinin family of plant hormones, exerts a marked antiproliferative activity on some leukemic and epithelial cancer cell lines. To characterize the molecular moieties required for the in vitro antitumor activity of the molecule and to obtain cytostatic iPA derivatives potentially useful as chemotherapeutic agents, N9-acyclic analogues have been synthesized using regioselective Mitsunobu reaction and characterized by elemental analyses, 1H and 13C NMR. These compounds were analyzed for their activity on human bladder cancer cell lines. In this study, we report that iPA inhibited the proliferation but not the migration of human bladder cancer cells, while the newly synthesized analogues revealed no significant cytostatic activity apart from the compound with a saturated double bond of the isopentenyl chain. These results indicate that the integrity of the ribose ring is required for the cytostatic activity of iPA.
KW - Acyclic nucleosides
KW - Antitumor agents
KW - Bladder carcinoma cells
KW - Isopentenyladenosine
UR - http://www.scopus.com/inward/record.url?scp=75149161883&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=75149161883&partnerID=8YFLogxK
U2 - 10.1080/15257770903155550
DO - 10.1080/15257770903155550
M3 - Article
C2 - 20183613
AN - SCOPUS:75149161883
VL - 28
SP - 736
EP - 751
JO - Nucleosides and Nucleotides
JF - Nucleosides and Nucleotides
SN - 0732-8311
IS - 8
ER -