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Biosynthesis of doxorubicin - Wikipedia

Biosynthesis of doxorubicin ..

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Chemical structure of doxorubicin

Cells were plated onto a 96-well dish (5,000cells/well) and incubated overnight at 37°C. The following day,cells were treated with increasing dosages (3–100 μM) of eachcompound, which had been dissolved in DMSO. The DMSO concentrationof treatments was limited to 0.5%, and cells were treated with DMSOalone (0.5%) or 10 μM doxorubicin as negative and positive controlsfor cytotoxicity, respectively. After 48 h, cells were fixed andcell viability was analyzed using the Sulforhodamine B colorimetricassay as previously described (). Absorbance of SRB was measuredutilizing a SpextraMaxM5 plate reader and absorbance values werenormalized to non-treated cells. The normalized cell viability withincreasing drug doses was plotted on a four-parameter logisticalcurve, and the IC of each compound in each cell linewas calculated using SigmaPlot software (Systat Software, Inc.,Chicago, IL, USA). Each compound was synthesized in two independentreactions and used in cell viability assays to generatedose-response curves. The mean IC (in μM), with thecorresponding standard deviation of the two independent synthesisreactions, was then calculated.

Doxorubicin/chemical synthesis;

Banik BK, Banik I and Becker FF:Asymmetric synthesis of anticancer β-lactams via Staudingerreaction: utilization of chiral ketene from carbohydrate. Eur J MedChem. 45:846–848. 2010.

Synthesis of Doxorubicin α-Linolenic Acid …

Banik BK, Samajdar S and Becker FF:Asymmetric synthesis of anticancer β-lactams via Staudingerreaction. Mol Med Reports. 3:319–321. 2010.

PAH-containing anticancer compounds were firstreported to be present in either the anthracene (–) orthe pyrene ring systems (,–).DNA-binding molecules are considered to be an important class ofdrugs in anticancer therapy ().Although it is well-established that DNA binding is not sufficientto confer cytotoxic activities, interaction with DNA is oftenconsidered a necessary criterion for maintaining a cytotoxiceffect. The antitumoral anthracyclines daunorubicin and doxorubicinand the synthetic anthracene-9,10-dione mitoxantrone are potentagents in clinical use at present, with broad application in thetreatment of several leukemias and lymphomas as well as incombination chemotherapy of solid tumors (,).

The following materials were obtained for the study:PAH (chrysene and pyrene), bismuth nitrate pentahydrate,montmorillonite KSF clay, indium, ammonium chloride, isobutylchloroformate, 1.0 M borane in tetrahydrofuran, reagent gradesolvents (Aldrich Chemical Co., St. Louis, MO, USA),dimethylsulfoxide (DMSO; Sigma-Aldrich Corp., St. Louis, MO, USA),phosphate-buffered saline (PBS), Dulbecco's modified Eagle's medium(DMEM) (Invitrogen, Carlsbad, CA, USA), fetal bovine serum (FBS;Invitrogen), McCoy's media (Invitrogen) and doxorubicin (FisherScientific, Pittsburgh, PA, USA).

Synthesis of [14-14C] daunorubicin and doxorubicin.

[Synthesis and antitumor properties of 3'-desamino- dimethylformamidine doxorubicin]

Banik BK, Banik I and Becker FF:Stereocontrolled synthesis of anticancer β-lactams via theStaudinger reaction. Biorg Med Chem. 13:3611–3622. 2005.

Banik BK and Becker FF: Synthesis,electrophilic substitution and structure-activity relationshipstudies of polycyclic aromatic compounds towards the development ofanticancer agents. Curr Med Chem. 8:1513–1533. 2001. :

Synthesis of Doxorubicin α-Linolenic Acid Conjugate and Evaluation of Its Antitumor Activity
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  • and more reproducible alternative to chemical synthesis of metal ..

    The Synthesis of a Prodrug of Doxorubicin Designed to Provide Reduced Systemic Toxicity and Greater ..

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    Synthesis of a new hapten for generating catalytic antibodies that activate doxorubicin prodrugs

  • synthesis: Intercalation of the doxorubicin ..

    Robust, Efficient, and Orthogonal Synthesis of Dendrimers via Thiol-ene “Click” Chemistry

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Synthesis Of Doxorubicin Loaded And Glucose…

Dendrimers up to the fourth generation were successfully prepared via the divergent growth strategy using a combination of thiol-ene “click” chemistry and traditional esterification reactions. The thiol-ene reactions were conducted under solvent-free, ambient conditions at room temperature by irradiating with UV light. The fourth-generation dendrimers were subsequently functionalized with carboxylic acid, pyrene, and Fmoc-protected cysteine moieties via thiol-ene reactions.

Synthesis, characterization and in vitro studies of doxorubicin …

Doxorubicin (Dox) can provide some stabilization in prostate cancer; however, its use is limited because of systemic toxicities, primarily cardiotoxicity and immunosuppression. The administration of a prodrug of doxorubicin, designed to permit selective activation by the tumor, would reduce general systemic exposure to the active drug and would thereby increase the therapeutic index. Prostate specific antigen (PSA) is a serine protease with chymotrypsin-like activity that is a member of the kallikrein gene family. PSA's putative physiological role is the liquefaction of semen by virtue of its ability to cleave the seminal fluid proteins semenogelins I and II. Serum PSA levels have been found to correlate well with the number of malignant prostate cells. The use of a prodrug which is cleaved by the enzyme PSA in the prostate should in principle produce high localized concentrations of the cytotoxic agent at the tumor site while limiting systemic exposure to the active drug. Cleavage maps following PSA treatment of human semenogelin were constructed. Systematic modification of the amino acid residues flanking the primary cleavage site led to the synthesis of a series of short peptides which were efficiently hydrolyzed by PSA. Subsequent coupling of selected peptides to doxorubicin provided a series of doxorubicin-peptide conjugates which were evaluated in vitro and in vivo as targeted prodrugs for PSA-secreting tumor cells. From these studies we selected Glutaryl-Hyp-Ala-Ser-Chg-Gln-Ser-Leu-Dox, 27, as the peptide-doxorubicin conjugate with the best profile of physical and biological properties. Compound 27 has a greater than 20-fold selectivity against human prostate PSA-secreting LNCaP cells relative to the non-PSA-secreting DuPRO cell line. In nude mouse xenograft studies, 27 reduced PSA levels by 95% and tumor weight by 87% at a dose below its MTD. Both doxorubicin and Leu-Dox (13) were ineffective in reducing circulating PSA and tumor burden at their maximum tolerated doses. On the basis of these results, we selected 27 for further study to assess its ability to inhibit human prostate cancer cell growth and tumorigenesis.

Synthesis of 4-demethoxy-11-deoxy-analogs of …

Dr. Qiang Wang is currently a postdoctoral associate in the University of Oxford. He received his BSc (2003) and MSc (2005) from Harbin Institute of Technology (HIT) in China, and his PhD (2009) from Pohang University of Science and Technology (POSTECH) in South Korea. Before moving to Oxford, he had worked in the Institute of Chemical and Engineering Sciences (ICES) under A*STAR, Singapore for two years. His research interests are heterogeneous catalysis and materials chemistry, with a particular focus on energy and environmental issues. He was awarded the Chinese Government Award for Outstanding Self-Financed Students Abroad in 2008.

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