Synthesis and evaluation of novel daunomycin-phosphate -sulfate -beta-glucuronide and -beta-glucoside prodrugs for application in ADEPT.

RGG Leenders; HW Scheeren; PHJ Houba; E Boven; HJ Haisma

Synthesis and evaluation of novel daunomycin-phosphate -sulfate -beta-glucuronide and -beta-glucoside prodrugs for application in ADEPT.

RGG Leenders, HW Scheeren, PHJ Houba, E Boven, HJ Haisma

Biopharmaceuticals, Discovery, Design and Delivery (BDDD)

Research output: Contribution to journal › Article › Academic › peer-review

21 Citations (Scopus)

Abstract

The synthesis, antiproliferative effect and enzymatic hydrolysis of daunomycin-3'-N- and -4'-O-phosphate and -sulfate derivatives and of daunomycin-3'-N-CO-beta-glucuronide and -beta-glucoside, designed to be prodrugs in ADEPT are described. The phosphate derivatives were almost as toxic as the parent drug whereas the sulfates were not hydrolyzed by aryl sulfatases, Glucuronyl and glucosyl prodrugs were found to be useful for application in ADEPT.

Original language	English
Pages (from-to)	2975-2980
Number of pages	6
Journal	Bioorganic & Medicinal Chemistry Letters
Volume	5
Issue number	24
Publication status	Published - 21-Dec-1995

Keywords

BIOLOGICAL EVALUATION
ADRIAMYCIN ANALOGS
ANTIBODY
CONJUGATE
CANCER
COMBINATION
DERIVATIVES
ENZYMES
INVITRO

Cite this

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title = "Synthesis and evaluation of novel daunomycin-phosphate -sulfate -beta-glucuronide and -beta-glucoside prodrugs for application in ADEPT.",

abstract = "The synthesis, antiproliferative effect and enzymatic hydrolysis of daunomycin-3'-N- and -4'-O-phosphate and -sulfate derivatives and of daunomycin-3'-N-CO-beta-glucuronide and -beta-glucoside, designed to be prodrugs in ADEPT are described. The phosphate derivatives were almost as toxic as the parent drug whereas the sulfates were not hydrolyzed by aryl sulfatases, Glucuronyl and glucosyl prodrugs were found to be useful for application in ADEPT.",

keywords = "BIOLOGICAL EVALUATION, ADRIAMYCIN ANALOGS, ANTIBODY, CONJUGATE, CANCER, COMBINATION, DERIVATIVES, ENZYMES, INVITRO",

author = "RGG Leenders and HW Scheeren and PHJ Houba and E Boven and HJ Haisma",

year = "1995",

month = dec,

day = "21",

language = "English",

volume = "5",

pages = "2975--2980",

journal = "Bioorganic & Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "American Chemical Society",

number = "24",

}

Synthesis and evaluation of novel daunomycin-phosphate -sulfate -beta-glucuronide and -beta-glucoside prodrugs for application in ADEPT. / Leenders, RGG; Scheeren, HW; Houba, PHJ; Boven, E; Haisma, HJ.

In: Bioorganic & Medicinal Chemistry Letters, Vol. 5, No. 24, 21.12.1995, p. 2975-2980.

Research output: Contribution to journal › Article › Academic › peer-review

TY - JOUR

T1 - Synthesis and evaluation of novel daunomycin-phosphate -sulfate -beta-glucuronide and -beta-glucoside prodrugs for application in ADEPT.

AU - Leenders, RGG

AU - Scheeren, HW

AU - Houba, PHJ

AU - Boven, E

AU - Haisma, HJ

PY - 1995/12/21

Y1 - 1995/12/21

N2 - The synthesis, antiproliferative effect and enzymatic hydrolysis of daunomycin-3'-N- and -4'-O-phosphate and -sulfate derivatives and of daunomycin-3'-N-CO-beta-glucuronide and -beta-glucoside, designed to be prodrugs in ADEPT are described. The phosphate derivatives were almost as toxic as the parent drug whereas the sulfates were not hydrolyzed by aryl sulfatases, Glucuronyl and glucosyl prodrugs were found to be useful for application in ADEPT.

AB - The synthesis, antiproliferative effect and enzymatic hydrolysis of daunomycin-3'-N- and -4'-O-phosphate and -sulfate derivatives and of daunomycin-3'-N-CO-beta-glucuronide and -beta-glucoside, designed to be prodrugs in ADEPT are described. The phosphate derivatives were almost as toxic as the parent drug whereas the sulfates were not hydrolyzed by aryl sulfatases, Glucuronyl and glucosyl prodrugs were found to be useful for application in ADEPT.

KW - BIOLOGICAL EVALUATION

KW - ADRIAMYCIN ANALOGS

KW - ANTIBODY

KW - CONJUGATE

KW - CANCER

KW - COMBINATION

KW - DERIVATIVES

KW - ENZYMES

KW - INVITRO

M3 - Article

VL - 5

SP - 2975

EP - 2980

JO - Bioorganic & Medicinal Chemistry Letters

JF - Bioorganic & Medicinal Chemistry Letters

SN - 0960-894X

IS - 24

ER -