ArticleAMB Express2020
Synthesis of cyclophosphamide metabolites by a peroxygenase from Marasmius rotula for toxicological studies on human cancer cells.
Article in AMB Express, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed, 28 citations in OpenAlex.
- Engineering peroxygenases for pharmaceutical applications: recent advances and future perspectives.Chemical science · 2026Review
- N-Glycosylation Influences the Heterologous Expression of an Unspecific Peroxygenase From Marasmius rotula in Saccharomyces cerevisiae.Microbial biotechnology · 2026Article
- Telmisartan protects male reproductive function by modulating biochemical, oxidative stress, apoptosis, and DNA integrity in cyclophosphamide-exposed rats.Toxicology reports · 2026Article
- Hematopoietic and T-lymphopoiesis-stimulating effects of a fluorinated pyrazolopiperidine β-cyclodextrin complex in cyclophosphamide-induced hematopoietic suppression.Frontiers in pharmacology · 2026Article
- Molecular mechanisms underlying cyclophosphamide-induced ovarian injury and protective strategies.Naunyn-Schmiedeberg's archives of pharmacology · 2026Review
- Protective effects and metabolomics analysis of dihydromyricetin on cyclophosphamide-induced hepatotoxicity in mice.Pharmaceutical science advances · 2025Article
- Characterization of Pharmaceutical Transformation Products by High-Field Asymmetric Waveform Ion Mobility and Infrared Ion Spectroscopy Coupled to Mass Spectrometry.Journal of the American Society for Mass Spectrometry · 2025Article
- Zebrafish Avatar testing preclinical study predicts chemotherapy response in breast cancer.NPJ precision oncology · 2025Article
- Association of pharmacokinetic biomarkers with early immune recovery following HLA-haploidentical hematopoietic cell transplantation.Frontiers in immunology · 2025Article
- Therapeutic effect of notoginseng saponins before and after fermentation on blood deficiency rats.Experimental and therapeutic medicine · 2024Article
- Direct immunoactivation by chemotherapeutic drugs in cancer treatment.Advanced therapeutics · 2023Article
- The protective effect of hydroalcoholic extract ofInternational journal of reproductive biomedicine · 2023Article
- Therapeutic Potential of Capsaicin against Cyclophosphamide-Induced Liver Damage.Journal of clinical medicine · 2023Article
- Investigation of Radiotracer Metabolic Stability In Vitro with CYP-Overexpressing Hepatoma Cell Lines.Cells · 2022Article
- Oxygenating Biocatalysts for Hydroxyl Functionalisation in Drug Discovery and Development.ChemMedChem · 2022Review
- Cell-Free Protein Synthesis with Fungal Lysates for the Rapid Production of Unspecific Peroxygenases.Antioxidants (Basel, Switzerland) · 2022Article
- Vesicle-based cell-free synthesis of short and long unspecific peroxygenases.Frontiers in bioengineering and biotechnology · 2022Article
- Hemoprotein Catalyzed Oxygenations: P450s, UPOs, and Progress toward Scalable Reactions.JACS Au · 2021Review
- Biocatalytic Syntheses of Antiplatelet Metabolites of the Thienopyridines Clopidogrel and Prasugrel Using Fungal Peroxygenases.Journal of fungi (Basel, Switzerland) · 2021Article
- Identification and Expression of New Unspecific Peroxygenases - Recent Advances, Challenges and Opportunities.Frontiers in bioengineering and biotechnology · 2021Review
Corrections and comments
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Authors and funding
8 authors at 2 institutions in 1 country.
Funding
Abstract
Cyclophosphamide (CPA) represents a widely used anti-cancer prodrug that is converted by liver cytochrome P450 (CYP) enzymes into the primary metabolite 4-hydroxycyclophosphamide (4-OH-CPA), followed by non-enzymatic generation of the bioactive metabolites phosphoramide mustard and acrolein. The use of human drug metabolites as authentic standards to evaluate their toxicity is essential for drug development. However, the chemical synthesis of 4-OH-CPA is complex and leads to only low yields and undesired side products. In past years, fungal unspecific peroxygenases (UPOs) have raised to powerful biocatalysts. They can exert the identical selective oxyfunctionalization of organic compounds and drugs as known for CYP enzymes with hydrogen peroxide being used as sole cosubstrate. Herein, we report the efficient enzymatic hydroxylation of CPA using the unspecific peroxygenase from Marasmius rotula (MroUPO) in a simple reaction design. Depending on the conditions used the primary liver metabolite 4-OH-CPA, its tautomer aldophosphamide (APA) and the overoxidized product 4-ketocyclophosphamide (4-keto-CPA) could be obtained. Using a kinetically controlled approach 4-OH-CPA was isolated with a yield of 32% (purity > 97.6%). Two human cancer cell lines (HepG2 and MCF-7) were treated with purified 4-OH-CPA produced by MroUPO (4-OH-CPA
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.