Bio-Catalytic Structural Transformation of Anti-cancer Steroid, Drostanolone Enanthate with Cephalosporium aphidicola and Fusarium lini, and Cytotoxic Potential Evaluation of Its Metabolites against Certain Cancer Cell Lines

Choudhary, M. Iqbal; Siddiqui, Mahwish; Wahab, Atia‐tul; Yousuf, Sammer; Fatima, Narjis; Ahmad, Malik Shoaib; Choudhry, Hani

doi:10.3389/fphar.2017.00900

Cited by 18 publications

(8 citation statements)

References 46 publications

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“…Drostanolone (Figure 2) has secondary antiestrogenic activity 19 and does not cause a significant virilizing effect 20 . Therefore, its therapeutic use includes treatment of breast cancer in women as a propionate ester 21 . It is one of the most frequently detected AASs, 1–7 and its misuse is monitored by GC–MS focusing on the 3α‐hydroxy‐2α‐methyl‐5α‐androstan‐17‐one metabolite after the hydrolysis of the glucuronide with E. coli –derived β‐glucuronidase 22 .…”

Section: Introductionmentioning

confidence: 99%

Searching for new long‐term urinary metabolites of metenolone and drostanolone using gas chromatography–mass spectrometry with a focus on non‐hydrolysed sulfates

Albertsdóttir

Gansbeke

Coppieters

et al. 2020

Drug Testing and Analysis

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Sulfated metabolites have been shown to have potential as long‐term markers of anabolic–androgenic steroid (AAS) abuse. In 2019, the compatibility of gas chromatography–mass spectrometry (GC–MS) with non‐hydrolysed sulfated steroids was demonstrated, and this approach allowed the incorporation of these compounds in a broad GC–MS initial testing procedure at a later stage. However, research is needed to identify which are beneficial. In this study, a search for new long‐term metabolites of two popular AAS, metenolone and drostanolone, was undertaken through two excretion studies each. The excretion samples were analysed using GC–chemical ionization–triple quadrupole MS (GC–CI–MS/MS) after the application of three separate sample preparation methodologies (i.e. hydrolysis with Escherichia coli–derived β‐glucuronidase, Helix pomatia–derived β‐glucuronidase/arylsulfatase and non‐hydrolysed sulfated steroids). For metenolone, a non‐hydrolysed sulfated metabolite, 1β‐methyl‐5α‐androstan‐17‐one‐3ζ‐sulfate, was documented for the first time to provide the longest detection time of up to 17 days. This metabolite increased the detection time by nearly a factor of 2 in comparison with the currently monitored markers for metenolone in a routine doping control initial testing procedure. In the second excretion study, it prolonged the detection window by 25%. In the case of drostanolone, the non‐hydrolysed sulfated metabolite with the longest detection time was the sulfated analogue of the main drostanolone metabolite (3α‐hydroxy‐2α‐methyl‐5α‐androstan‐17‐one) with a detection time of up to 24 days. However, the currently monitored main drostanolone metabolite in routine doping control, after hydrolysis of the glucuronide with E.coli, remained superior in detection time (i.e. up to 29 days).

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Section: Introductionmentioning

confidence: 99%

Searching for new long‐term urinary metabolites of metenolone and drostanolone using gas chromatography–mass spectrometry with a focus on non‐hydrolysed sulfates

Albertsdóttir

Gansbeke

Coppieters

et al. 2020

Drug Testing and Analysis

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show abstract

“…Similarly, OH group at C-14 was deduced as α on the basis of reported chemical shift for 14α-OH in similar steroidal compound. 18 Thus the structure of a new compound was deduced as 2α-methyl-3β,14α,17β-trihydroxy-5α-androstane (8).…”

Section: Resultsmentioning

confidence: 99%

“…12 Similarly, several metabolites of drostanolone on incubation with cryopreserved human hepatocytes are also reported. 13 In continuation of our structural transformation studies on steroidal drugs, [14][15][16][17][18][19][20] biotransformation of drostanolone heptanoate (1) was carried out. Based on small scale screening results, compound 1 was subjected to biotransformation by using two microbial cell cultures, Beauveria bassiana, and Macrophomina phaseolina, for the rst time, yielding seven new, and two known compounds.…”

Section: Introductionmentioning

confidence: 99%

Seven new metabolites of drostanolone heptanoate by using Beauveria bassiana, and Macrophomina phaseolina cell suspension cultures

et al. 2020

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“…PCF11 was positively correlated with nelarabine and vorinostat (Figure 7). All these drugs modulate the tumor immune microenvironment to induce cancer cell death (33)(34)(35)(36)(37)(38)(39)(40)(41)(42)(43)(44)(45)(46).…”

Section: Drug Sensitivitymentioning

confidence: 99%

Development of multivariable risk signature based on four immune-related RNA-binding proteins to predict survival and immune status in lung adenocarcinoma

You¹,

Shen²

2022

Transl Cancer Res TCR

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Background: This study aimed to construct a risk signature with predictive power based on immunerelated RNA-binding proteins (RBPs) for lung adenocarcinoma (LUAD) patients. Methods:The Cancer Genome Atlas (TCGA) database was used as the data source. Immune genes (IGs)were obtained from the Immunology Database and Analysis Portal (immPort) database. Differentially expressed RBPs and IGs between tumor and normal tissues were screened. For external validation, an independent cohort from the Gene-Expression Omnibus (GEO) database was used. The accuracy of the risk signature prediction was evaluated using Cox regression analysis and the receiver operating characteristic (ROC) curve. Results:The risk signature was constructed from four immune-related and prognostic RBPs (OAS3, PCF11, TLR7, and EXO1). The patients were divided into the low-and high-risk groups, with the low-risk group having a higher survival rate than the high-risk group. The risk signature outperformed other clinical parameters, with a multivariable hazard ratio of 1.862 (95% confidence interval: 1.292-2.683). The tumor immune microenvironment, stemness index, immune checkpoint, immune infiltration, and proportion of immune cells were significantly different between the low-and high-risk groups (all P<0.05). Conclusions:The risk signature of immune-related RBPs can provide the basis for clinical decisions regarding diagnosis, prognosis, and immunotherapy in LUAD patients.

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Bio-Catalytic Structural Transformation of Anti-cancer Steroid, Drostanolone Enanthate with Cephalosporium aphidicola and Fusarium lini, and Cytotoxic Potential Evaluation of Its Metabolites against Certain Cancer Cell Lines

Cited by 18 publications

References 46 publications

Searching for new long‐term urinary metabolites of metenolone and drostanolone using gas chromatography–mass spectrometry with a focus on non‐hydrolysed sulfates

Searching for new long‐term urinary metabolites of metenolone and drostanolone using gas chromatography–mass spectrometry with a focus on non‐hydrolysed sulfates

Seven new metabolites of drostanolone heptanoate by using Beauveria bassiana, and Macrophomina phaseolina cell suspension cultures

Development of multivariable risk signature based on four immune-related RNA-binding proteins to predict survival and immune status in lung adenocarcinoma

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