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Design and synthesis of paclitaxel-containing aminoester phosphate and phosphoamidate

Reuben Jih-Ru Hwu 1
Reuben Jih-Ru Hwu
, 
Shwu-Chen Tsay 2
Shwu-Chen Tsay
, 
Thota Sambaiah 1
Thota Sambaiah
, 
Yiu-Kay Lai 3
Yiu-Kay Lai
, 
Chien-Hui Lieu 3
Chien-Hui Lieu
, 
Gholam H Hakimelahi 2
Gholam H Hakimelahi
, 
Ke-Yung King 2
Ke-Yung King
10.1070/MC2001v011n06ABEH001498
Published 2001-12-18
Communication , Volume 11, Issue 6, 216-217
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Hwu R. J. et al. Design and synthesis of paclitaxel-containing aminoester phosphate and phosphoamidate // Mendeleev Communications. 2001. Vol. 11. No. 6. pp. 216-217.
GOST all authors (up to 50) Copy
Hwu R. J., Tsay S., Sambaiah T., Lai Y., Lieu C., Hakimelahi G. H., King K. Design and synthesis of paclitaxel-containing aminoester phosphate and phosphoamidate // Mendeleev Communications. 2001. Vol. 11. No. 6. pp. 216-217.
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TY - JOUR
DO - 10.1070/MC2001v011n06ABEH001498
UR - https://mendcomm.colab.ws/publications/10.1070/MC2001v011n06ABEH001498
TI - Design and synthesis of paclitaxel-containing aminoester phosphate and phosphoamidate
T2 - Mendeleev Communications
AU - Hwu, Reuben Jih-Ru
AU - Tsay, Shwu-Chen
AU - Sambaiah, Thota
AU - Lai, Yiu-Kay
AU - Lieu, Chien-Hui
AU - Hakimelahi, Gholam H
AU - King, Ke-Yung
PY - 2001
DA - 2001/12/18
PB - Mendeleev Communications
SP - 216-217
IS - 6
VL - 11
ER -
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@article{2001_Hwu,
author = {Reuben Jih-Ru Hwu and Shwu-Chen Tsay and Thota Sambaiah and Yiu-Kay Lai and Chien-Hui Lieu and Gholam H Hakimelahi and Ke-Yung King},
title = {Design and synthesis of paclitaxel-containing aminoester phosphate and phosphoamidate},
journal = {Mendeleev Communications},
year = {2001},
volume = {11},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1070/MC2001v011n06ABEH001498},
number = {6},
pages = {216--217},
doi = {10.1070/MC2001v011n06ABEH001498}
}
MLA
Cite this
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Hwu, Reuben Jih-Ru, et al. “Design and synthesis of paclitaxel-containing aminoester phosphate and phosphoamidate.” Mendeleev Communications, vol. 11, no. 6, Dec. 2001, pp. 216-217. https://mendcomm.colab.ws/publications/10.1070/MC2001v011n06ABEH001498.

Abstract

Paclitaxel-containing aminoester phosphate 4 and phosphoamidate 9 were synthesised and found to possess anticancer activity against HL-60 leukemia cells; their solubility in a phosphate buffer solution was about 16 times higher than that of paclitaxel.

References

1.
Taxol, a molecule for all seasons
Kingston D.G.
Chemical Communications, 2001
2.
Taxol Resistance
Sangrajrang S., Fellous A.
Chemotherapy, 2000
3.
10.1070/MC2001v011n06ABEH001498_bib1_3
Hudis
Semin. Oncol., 1999
4.
10.1070/MC2001v011n06ABEH001498_bib1_4
Shin
Semin. Oncol., 1999
5.
10.1070/MC2001v011n06ABEH001498_bib1_5
Weiner
Semin. Oncol., 1999
6.
10.1070/MC2001v011n06ABEH001498_bib1_6
Younes
Semin. Oncol., 1999
7.
Paclitaxel (taxol)
Rowinsky E.K., Donehower R.C.
New England Journal of Medicine, 1995
8.
Promotion of microtubule assembly in vitro by taxol
SCHIFF P.B., FANT J., HORWITZ S.B.
Nature, 1979
9.
Taxol stabilizes microtubules in mouse fibroblast cells.
Schiff P.B., Horwitz S.B.
Proceedings of the National Academy of Sciences of the United States of America, 1980
10.
Taxol: a novel investigational antimicrotubule agent.
Rowinsky E.K., Cazenave L.A., Donehower R.C.
Journal of the National Cancer Institute, 1990
11.
Phase II Trial of Taxol, an Active Drug in the Treatment of Metastatic Breast Cancer
Holmes F.A., Walters R.S., Theriault R.L., Buzdar A.U., Frye D.K., Hortobagyi G.N., Forman A.D., Newton L.K., Raber M.N.
Journal of the National Cancer Institute, 1991
12.
Prodrugs of Peptides and Proteins for Improved Formulation and Delivery
Oliyai R., Stella V.J.
Annual Review of Pharmacology and Toxicology, 1993
13.
Drug Delivery Systems:  Water Soluble Taxol 2‘-Poly(ethylene glycol) Ester ProdrugsDesign and in Vivo Effectiveness
Greenwald R.B., Gilbert C.W., Pendri A., Conover C.D., Xia J., Martinez A.
Journal of Medicinal Chemistry, 1996
14.
Ein wasserlösliches Prodrug von Taxol mit der Fähigkeit zur Selbstorganisation
Nicolaou K.C., Guy R.K., Pitsinos E.N., Wrasidlo W.
Angewandte Chemie, 1994
15.
Design, Synthesis, and Structure-Activity Relationship of Novel Dinucleotide Analogs as Agents against Herpes and Human Immunodeficiency Viruses
Hakimelahi G.H., Moosavi-Movahedi A.A., Sadeghi M.M., Tsay S., Hwu J.R.
Journal of Medicinal Chemistry, 1995
16.
M A. Jordon and L. Wilson, in Taxane Anticancer Agents, eds. G. I. Georg, T. T. Chen, I. Ojima and D. M. Vyas, ACS Symposium Series 583, American Chemical Society, Washington, DC, 1995, p. 124.
17.
Synthesis and antitumor evaluation of paclitaxel phosphonooxymethyl ethers: a novel class of water soluble paclitaxel pro-drugs
Golik J., Wong H.S., Chen S.H., Doyle T.W., Kim Wright J.J., Knipe J., Rose W.C., Casazza A.M., Vyas D.M.
Bioorganic and Medicinal Chemistry Letters, 1996
19.
Design, synthesis and biological activity of protaxols
Nicolaou K.C., Riemer C., Kerr M.A., Rideout D.R., Wrasidlo W.W.
Nature, 1993
20.
Synthesis of congeners and prodrugs. 3. Water-soluble prodrugs of taxol with potent antitumor activity
Deutsch H.M., Glinski J.A., Hernandez M., Haugwitz R.D., Narayanan V.L., Suffness M., Zalkow L.H.
Journal of Medicinal Chemistry, 1989
21.
Biologically active taxol analogs with deleted A-ring side chain substituents and variable C-2' configurations
Swindell C.S., Krauss N.E., Horwitz S.B., Ringel I.
Journal of Medicinal Chemistry, 1991
22.
Synthesis and evaluation of some water-soluble prodrugs and derivatives of taxol with antitumor activity
Mathew A.E., Mejillano M.R., Nath J.P., Himes R.H., Stella V.J.
Journal of Medicinal Chemistry, 1992
23.
Highly water soluble taxol derivatives: 2′-polyethyleneglycol esters as potential prodrugs
Greenwald R.B., Pendri A., Bolikal D., Gilbert C.W.
Bioorganic and Medicinal Chemistry Letters, 1994
24.
Synthesis and antitumor evaluation of 2′-oxycarbonylpaclitaxels (paclitaxel-2′-carbonates)
Ueda Y., Wong H., Matiskella J.D., Mikkilineni A.B., Farina V., Fairchild C., Rose W.C., Mamber S.W., Long B.H., Kerns E.H., Casazza A.M., Vyas D.M.
Bioorganic and Medicinal Chemistry Letters, 1994
25.
Synthesis and biological activity of beta-glucuronyl carbamate-based prodrugs of paclitaxel as potential candidates for ADEPT.
de Bont D.B., Leenders R.G., Haisma H.J., van der Meulen-Muileman I., Scheeren H.W.
Bioorganic and Medicinal Chemistry, 1997
26.
Synthesis of Water-Soluble Paclitaxel Derivatives by Enzymatic Acylation
Khmelnitsky Y.L., Budde C., Arnold J.M., Usyatinsky A., Clark D.S., Dordick J.S.
Journal of the American Chemical Society, 1997
27.
Paclitaxel esters of malic acid as prodrugs with improved water solubility
Damen E.W., Wiegerinck P.H., Braamer L., Sperling D., de Vos D., Scheeren H.W.
Bioorganic and Medicinal Chemistry, 2000
28.
Synthesis and antitumor evaluation of water soluble taxol phosphates
Vyas D.M., Wong H., Crosswell A.R., Casazza A.M., Knipe J.O., Mamber S.W., Doyle T.W.
Bioorganic and Medicinal Chemistry Letters, 1993
29.
Highly Water Soluble Taxol Derivatives: 7-Polyethylene Glycol Carbamates and Carbonates
Greenwald R.B., Pendri A., Bolikal D.
Journal of Organic Chemistry, 1995
30.
Novel, water-soluble phosphate derivatives of 2′-ethoxy carbonylpaclitaxel as potential prodrugs of paclitaxel: Synthesis and antitumor evaluation
Ueda Y., Matiskella J.D., Mikkilineni A.B., Farina V., Knipe J.O., Rose W.C., Casazza A.M., Vyas D.M.
Bioorganic and Medicinal Chemistry Letters, 1995
31.
Design and synthesis of a water-soluble taxol analogue : Taxol-sialyl conjugate
Takahashi T., Tsukamoto H., Yamada H.
Bioorganic and Medicinal Chemistry Letters, 1998
32.
10.1070/MC2001v011n06ABEH001498_bib26
Dugas
Bioorganic Chemistry, A Chemical Approach to Enzyme Action, 1981
33.
Design and synthesis of new taxol-containing aminophosphates as protaxols
Jih Ru Hwu, Hakimelahi G.H., Sambaiah T., Patel H.V., Shwu-Chen Tsay, Yiu-Kay Lai, Chien-Hui Lieu
Bioorganic and Medicinal Chemistry Letters, 1997
34.
New detritylation method for nucleosides and nucleotides by ceric ammonium nitrate
Hwu J.R., Jain M.L., Tsay S., Hakimelahi G.H.
Chemical Communications, 1996
35.
Feasibility of a High-Flux Anticancer Drug Screen Using a Diverse Panel of Cultured Human Tumor Cell Lines
Monks A., Scudiero D., Skehan P., Shoemaker R., Paull K., Vistica D., Hose C., Langley J., Cronise P., Vaigro-Wolff A., Gray-Goodrich M., Campbell H., Mayo J., Boyd M.
Journal of the National Cancer Institute, 1991
36.
New Colorimetric Cytotoxicity Assay for Anticancer-Drug Screening
Skehan P., Storeng R., Scudiero D., Monks A., McMahon J., Vistica D., Warren J.T., Bokesch H., Kenney S., Boyd M.R.
Journal of the National Cancer Institute, 1990