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3 protocols using diethyl ether

1

Transition Metal Catalyst Synthesis

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All solvents were of analytical grade and used without further purification. [Rh(η6-C5Me5)(μ-Cl)Cl]2, [Ru(η6-p-cymene)(μ-Cl)Cl]2, 5-nitro-8-hydroxyquinoline, L-proline, aqueous formaldehyde (30% (v/v)), bpy, tetrabutylammonium nitrate (TBAN), KH-phthalate, n-octanol, D2O, doxorubicin, 2-(N-morpholino)ethanesulfonic acid (MES), human serum, Dulbecco’s Modified Eagle Medium (DMEM) and RPMI media, HSA (A8763, essentially globulin free), DG, 1-methylimidazole, 4,4-dimethyl-4-silapentane-1-sulfonic acid (DSS) were Sigma-Aldrich (Darmstadt, Germany) products and were used without further purification. Ac-Ala-His-Ala-NH2 (AHA) and Ac-Phe-His-Ala-NH2 (FHA) peptides were purchased from GenScript (Piscataway, NJ, USA). HQCl-L-Pro was prepared according to our former report [12 (link)]. NaH2PO4, Na2HPO4, KH2PO4, KCl, KNO3, NaCl, KOH, HNO3, ethanol, ethyl acetate, dichloromethane, n-hexane, diethyl-ether, and methanol were purchased from Molar Chemicals (Halásztelek, Hungary) or VWR (Budapest, Hungary).
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2

Synthesis of Daunorubicin Conjugates

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All amino acid derivatives and Rink-Amide MBHA resin were purchased from Iris Biotech GmBH (Marktredwitz, Germany). Boc-aminooxyacetic acid (Boc-Aoa-OH), coupling agents and cleavage reagents (1-hydroxybenzotriazole hydrate (HOBt), N,N′-diisopropylcarbodiimide (DIC), triisopropylsilane (TIS), piperidine, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), trifluoroacetic acid (TFA)), diisopropylethylamine (DIPEA), n-butyric anhydride, and acetonitrile (MeCN) for HPLC were obtained from Sigma-Aldrich Kft. (Budapest, Hungary). Daunorubicin hydrochloride was a gift from IVAX (Budapest, Hungary). Dimethylformamide (DMF), dichloromethane (DCM) and diethyl ether were purchased from Molar Chemicals Kft (Budapest, Hungary). All reagents and solvents were of analytical grade or highest available purity.
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3

Cytotoxic Metal Complexes: Synthesis and Evaluation

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All solvents were of analytical grade and used without further purification (except the solutions used for the DNA cleavage assay, vide infra). [RhCp*(μ-Cl)Cl]2, [Ru(η6-p-cymene)(μ-Cl)Cl]2, 5-chloro-8-hydroxyquinoline, D-proline, D-homoproline, aqueous formaldehyde (30% (v/v)), pic, phen, KNO3, HNO3, KOH, n-octanol, CD3OD, D2O, doxorubicin, EB, HSA (A8763, essentially globulin free), ct-DNA, DG, 4,4-dimethyl-4-silapentane-1-sulfonic acid (DSS) were Sigma-Aldrich (St. Louis, MO, USA) products and were used without further purification. FHA was purchased from GenScript (Piscataway, NJ, USA). NaH2PO4, Na2HPO4, KH2PO4, KCl, NaCl, diethyl-ether, n-hexane, ethanol, ethyl acetate and methanol were purchased from Molar Chemicals (Halásztelek, Hungary) or Reanal (Budapest, Hungary). [RuCym(HQCl-L-Pro)Cl]Cl and [RhCp*(HQCl-L-Pro)Cl]Cl were used in some cases due to comparative reasons, and their preparation and characterization were reported in our previous work [25 (link)].
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