Cancer Chemotherapy: A Paclitaxel Prodrug for ADEPT (Antibody-Directed Enzyme Prodrug Therapy)
A glucuronide‐based prodrug of paclitaxel (taxol®) has been synthesized for use in antibody‐directed enzyme prodrug therapy (ADEPT). This three‐component prodrug was obtained by coupling a glucuronyl derivative of N‐methylamino 4‐nitrophenol (10) to the 2′‐hydroxy group of the side‐chain of paclitax...
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| Veröffentlicht in: | European journal of organic chemistry 2001-06, Vol.2001 (11), p.2129-2134 |
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| container_end_page | 2134 |
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| container_issue | 11 |
| container_start_page | 2129 |
| container_title | European journal of organic chemistry |
| container_volume | 2001 |
| creator | Schmidt, Frédéric Ungureanu, Ioana Duval, Romain Pompon, Alain Monneret, Claude |
| description | A glucuronide‐based prodrug of paclitaxel (taxol®) has been synthesized for use in antibody‐directed enzyme prodrug therapy (ADEPT). This three‐component prodrug was obtained by coupling a glucuronyl derivative of N‐methylamino 4‐nitrophenol (10) to the 2′‐hydroxy group of the side‐chain of paclitaxel through an aromatic carbamate. Once deprotected, prodrug 2 was shown to be relatively stable in human serum, and to be significantly less cytotoxic (IC50 = 65 μM and 90 nM, respectively) than the parent drug. As expected, compound 2 efficiently releases taxol in the presence of β‐glucuronidase. |
| doi_str_mv | 10.1002/1099-0690(200106)2001:11<2129::AID-EJOC2129>3.0.CO;2-# |
| format | Article |
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| ispartof | European journal of organic chemistry, 2001-06, Vol.2001 (11), p.2129-2134 |
| issn | 1434-193X 1099-0690 |
| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Antitumor agents Bioorganic chemistry Chemical Sciences Drug research Life Sciences Natural products |
| title | Cancer Chemotherapy: A Paclitaxel Prodrug for ADEPT (Antibody-Directed Enzyme Prodrug Therapy) |
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