Preparation and Biological Activity of Amino Acid and Peptide Conjugates of Antitumor Hydroxymethylacylfulvene

The primary hydroxyl group in hydroxymethylacylfulvene, a potent antitumor drug, is readily replaced by thiols including cysteine, N-acetylcysteine, homocysteine, and glutathione. Best yields are obtained when reaction is carried out in the presence of dilute sulfuric acid. A variety of sulfur-conta...

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Published inJournal of medicinal chemistry Vol. 43; no. 19; pp. 3577 - 3580
Main Authors McMorris, Trevor C, Yu, Jian, Ngo, Huan-Tony, Wang, Haixia, Kelner, Michael J
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.09.2000
Amer Chemical Soc
Subjects
Amino Acids - chemistry
Animals
Antineoplastic agents
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Biological and medical sciences
Chemistry, Medicinal
Drug Screening Assays, Antitumor
General aspects
Inhibitory Concentration 50
Life Sciences & Biomedicine
Medical sciences
Peptides - chemistry
Pharmacology & Pharmacy
Pharmacology. Drug treatments
Rats
Science & Technology
Sesquiterpenes - chemistry
Sesquiterpenes - pharmacology
Tumor Cells, Cultured
METABOLISM
EFFICACY
RAT
MGI-114
TRADITIONAL ANTICANCER AGENTS
ACYLFULVENE
ILLUDINS
MODEL
HMAF
Antineoplastic agent
Lung
Ketol
Combinatorial chemistry
Cytotoxicity
Spiran
Cell line
Structure activity relation
Tetrapeptide
Sulfur peptide
Peptide synthesis
Chemical synthesis
Tumor cell
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Abstract The primary hydroxyl group in hydroxymethylacylfulvene, a potent antitumor drug, is readily replaced by thiols including cysteine, N-acetylcysteine, homocysteine, and glutathione. Best yields are obtained when reaction is carried out in the presence of dilute sulfuric acid. A variety of sulfur-containing analogues have been prepared, and their toxicity to tumor cells was examined.
AbstractList The primary hydroxyl group in hydroxymethylacylfulvene, a potent antitumor drug, is readily replaced by thiols including cysteine, N-acetylcysteine, homocysteine, and glutathione. Best yields are obtained when reaction is carried out in the presence of dilute sulfuric acid. A variety of sulfur-containing analogues have been prepared, and their toxicity to tumor cells was examined.
Author Yu, Jian
Wang, Haixia
Kelner, Michael J
Ngo, Huan-Tony
McMorris, Trevor C
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  surname: Kelner
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Cites_doi 10.1016/S0140-6736(78)92703-4
10.1007/BF00210787
10.3109/00498259609046713
10.1016/S0006-2952(98)00273-1
10.1021/tx00018a013
10.1021/np960450y
10.1016/S0040-4020(97)01064-8
10.1007/BF01922420
10.1126/science.279.5349.377
10.1021/ja00889a052
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Issue 19
Keywords METABOLISM
EFFICACY
RAT
MGI-114
TRADITIONAL ANTICANCER AGENTS
ACYLFULVENE
ILLUDINS
MODEL
HMAF
Antineoplastic agent
Lung
Ketol
Combinatorial chemistry
Cytotoxicity
Spiran
Cell line
Structure activity relation
Tetrapeptide
Sulfur peptide
Peptide synthesis
Chemical synthesis
Tumor cell
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Snippet The primary hydroxyl group in hydroxymethylacylfulvene, a potent antitumor drug, is readily replaced by thiols including cysteine, N-acetylcysteine,...
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SubjectTerms Amino Acids - chemistry
Animals
Antineoplastic agents
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Biological and medical sciences
Chemistry, Medicinal
Drug Screening Assays, Antitumor
General aspects
Inhibitory Concentration 50
Life Sciences & Biomedicine
Medical sciences
Peptides - chemistry
Pharmacology & Pharmacy
Pharmacology. Drug treatments
Rats
Science & Technology
Sesquiterpenes - chemistry
Sesquiterpenes - pharmacology
Tumor Cells, Cultured
Title Preparation and Biological Activity of Amino Acid and Peptide Conjugates of Antitumor Hydroxymethylacylfulvene
URI http://dx.doi.org/10.1021/jm0000315
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