Synthesis and in vitro biochemical evaluation of oxime bond-linked daunorubicin–GnRH-III conjugates developed for targeted drug delivery

• Sabine Schuster,
• Beáta Biri-Kovács,
• Bálint Szeder,
• Viktor Farkas,
• László Buday,
• Zsuzsanna Szabó,
• Gábor Halmos and
• Gábor Mező

Beilstein J. Org. Chem. 2018, 14, 756–771, doi:10.3762/bjoc.14.64

• novel compounds to the GnRH-receptor, an in vitro ligand competition assay has been performed on human pituitary and GnRH-R positive human prostate cancer tissues. Hereby, the displacement of radiolabeled triptorelin by the unlabeled bioconjugates 1, 2, 4 and 5 was determined. For a better comparison

• slightly higher binding affinity on human prostate cancer (3.0–10.4 nM) than on human pituitary tissue (3.9–23.5 nM) being in accordance with our previous observations [29]. The lowest ligand concentration causing 50% inhibition of radioligand binding was obtained for K2 with 3.9 nM on pituitary and 3.0 nM

• on prostate cancer tissues which is only slightly higher than the reported values for GnRH-I–[D-Lys6(Dau=Aoa)] (1.6 nM and 0.9 nM) and GnRH-II–[D-Lys6(Dau=Aoa)] (4.2 nM and 2.1 nM) [29][50]. Nevertheless, it has to be considered that the determined IC50 values are within a narrow, low nanomolar range

Synthesis and evaluation of anti-oxidant and cytotoxic activities of novel 10-undecenoic acid methyl ester based lipoconjugates of phenolic acids

• Naganna Narra,
• Shiva Shanker Kaki,
• Rachapudi Badari Narayana Prasad,
• Sunil Misra,
• Koude Dhevendar,
• Venkateshwarlu Kontham and
• Padmaja V. Korlipara

Beilstein J. Org. Chem. 2017, 13, 26–32, doi:10.3762/bjoc.13.4

• different cancer cell lines viz., MDA-MB-231, breast cancer (ATCC® HTB-26™); SKOV3, ovarian cancer (ATCC® HTB-77™); MCF7, breast cancer (ATCC® HTB-22™); DU 145, prostate cancer (ATCC® HTB-81™); HepG2, liver hepatocellular carcinoma (ATCC® HB-8065™) were obtained from the ATCC (Bethesda, MD, USA) and

Synthesis of acylhydrazino-peptomers, a new class of peptidomimetics, by consecutive Ugi and hydrazino-Ugi reactions

• Angélica de Fátima S. Barreto,
• Veronica Alves dos Santos and
• Carlos Kleber Z. Andrade

Beilstein J. Org. Chem. 2016, 12, 2865–2872, doi:10.3762/bjoc.12.285

• peptomers by Ostergaard and Holm [45]) prodrugs that can be selectively activated by prostate cancer cells. Peptidomimetics can be conveniently synthesized using the so called "submonomer approach" either in solution [41] or in solid-phase [46][47]. However, some disadvantages have been reported for long or

Synthesis and in vitro cytotoxicity of acetylated 3-fluoro, 4-fluoro and 3,4-difluoro analogs of D-glucosamine and D-galactosamine

• Štěpán Horník,
• Lucie Červenková Šťastná,
• Petra Cuřínová,
• Jan Sýkora,
• Kateřina Káňová,
• Roman Hrstka,
• Ivana Císařová,
• Martin Dračínský and
• Jindřich Karban

Beilstein J. Org. Chem. 2016, 12, 750–759, doi:10.3762/bjoc.12.75

• by fluoridolysis of 1,6:3,4-dianhydro-2-azido-β-D-galactopyranose with KHF2. The amino group was introduced and masked as an azide in the synthesis. The 1-O-deacetylated 3-fluoro and 4-fluoro analogs of acetylated D-galactosamine inhibited proliferation of the human prostate cancer cell line PC-3

• leukemia cells in micromolar range (IC50 27–35 μM). Compound 5 also inhibited the proliferation of the human pancreatic cancer cell line KP1-NL (IC50 30 μM) [20] and 4-fluoro-D-glucosamine analogs 1 and 2 were reported to inhibit the proliferation of the human prostate cancer cell line PC-3 (IC50 61 µm for

• ][29]. Herein we also report on the cytotoxicity of prepared fluoro analogs in the human ovarian cancer A2780 and prostate cancer PC-3 cell lines. Preliminary results for the synthesis of compounds 5 and 6 were communicated earlier in a letter [30]. Results and Discussion Synthesis The synthesis

Self and directed assembly: people and molecules

• Tony D. James

Beilstein J. Org. Chem. 2016, 12, 391–405, doi:10.3762/bjoc.12.42

• , Defence Science and Technology Laboratory (DSTL), the Nuffield Foundation, Prostate Cancer UK, Dunhill Medical Trust, Alzheimer's Research UK (ARUK), Beckman-Coulter Inc, Zeneca Group PLC, Unipath Ltd, Smart Holograms, Glysure Ltd, Quotient Diagnostics, the Royal Society and the Royal Society of Chemistry

Synthesis, antimicrobial and cytotoxicity evaluation of new cholesterol congeners

• Mohamed Ramadan El Sayed Aly,
• Hosam Ali Saad and
• Shams Hashim Abdel-Hafez

Beilstein J. Org. Chem. 2015, 11, 1922–1932, doi:10.3762/bjoc.11.208

• antifungal activities against the filamentous fungal strain Aspergillus flavus (Link) and the yeast forming fungal strain Candida albicans (ATCC 7102) were moderate compared with amphotericin B in vitro. In the cytotoxicity study, this derivative was the most cytotoxic one against the prostate cancer PC3

• microbial organisms and the prostate cancer PC3 cell line. It is worth mentioning that the bacterial [27][28] and fungal [29][30] strains in this consideration were elected as they represent the main microbial classes for our in vitro antimicrobial evaluation. On the other hand, prostate cancer was

• group of target cholesterols were screened in vitro as cytotoxic agents against the human prostate cancer cell line PC3 using the sulforhodamine B colorimetric (SRB) assay and doxorubicin as positive control (IC50 = 8.8 μM) (Figure 3) [48]. As shown in Figure 3, cholesterol–lactoside conjugate 27

Glycodendrimers: tools to explore multivalent galectin-1 interactions

• Jonathan M. Cousin and
• Mary J. Cloninger

Beilstein J. Org. Chem. 2015, 11, 739–747, doi:10.3762/bjoc.11.84

• are quite homogeneous, we used these nanoparticles in cellular aggregation assays with galectin-1 and DU145 human prostate cancer cells. The DU145 cell line was chosen because it expresses a putative galectin-1 ligand – the Thomsen Friedenreich (TF) antigen on Mucin-1 [34][35]. As shown in Figure 7

Natural phenolic metabolites with anti-angiogenic properties – a review from the chemical point of view

• Qiu Sun,
• Jörg Heilmann and
• Burkhard König

Beilstein J. Org. Chem. 2015, 11, 249–264, doi:10.3762/bjoc.11.28

• . For example, it can inhibit androgen receptor signaling and tumor growth in athymic nude mice [87], it can cause apoptosis and cell-cycle arrest in human prostate cancer LNCaP cells [88] and in HCT-116 human colon cancer cells, and it can induce apoptosis associated with an increased level of p53 [89

The chemistry of isoindole natural products

• Klaus Speck and
• Thomas Magauer

Beilstein J. Org. Chem. 2013, 9, 2048–2078, doi:10.3762/bjoc.9.243

• yielding synthesis, ample quantities could be obtained for a preliminary evaluation of the biological activity of 79. In a first screen against A2058 melanoma and DU145 prostate cancer cell lines, 79 showed to be inactive [73]. Isoindolinones derived from isoquinoline alkaloids: The aporhoeadane alkaloids

Design and synthesis of tag-free photoprobes for the identification of the molecular target for CCG-1423, a novel inhibitor of the Rho/MKL1/SRF signaling pathway

• Jessica L. Bell,
• Andrew J. Haak,
• Susan M. Wade,
• Yihan Sun,
• Richard R. Neubig and
• Scott D. Larsen

Beilstein J. Org. Chem. 2013, 9, 966–973, doi:10.3762/bjoc.9.111

• functional activity in a PC-3 prostate cancer cell model of migration. Cells (5.0 × 105) were plated in DMEM containing 10% FBS and grown to confluence in a 12-well plate. After 24 h, a scratch was made using a 200 µL pipette tip. Medium was replaced with DMEM containing 0.5% FBS and varying concentrations

• photolabeling studies with 24 were undertaken in PC-3 prostate cancer cells. Intact cells were treated with 0.3 µM 24 for 30 min. To facilitate the identification of specifically labeled proteins, a parallel competition experiment was also performed by treating cells with 0.3 µM 24 and a large excess (10 µM) of

• with the most potent photoprobe 24 in whole prostate cancer cells was successful at detecting specific binding to one or more proteins at 24 kDa. Future work will focus on identifying the labeled protein(s). We first plan to repeat the photolabeling study with 24 and tag the labeled proteins by

Cyclodextrin-based nanosponges as drug carriers

• Francesco Trotta,
• Marco Zanetti and
• Roberta Cavalli

Beilstein J. Org. Chem. 2012, 8, 2091–2099, doi:10.3762/bjoc.8.235

• effective nanotechnology for the treatment of both androgen-sensitive and castrate-refractory prostate cancer in cell-line experiments [42]. Nanosponges can be used to store and prolong the release of volatile molecules, such as essential oils, following their encapsulation. Linalool, a liquid component of

Synthesis and characterization of Sant-75 derivatives as Hedgehog-pathway inhibitors

• Chao Che,
• Song Li,
• Bo Yang,
• Shengchang Xin,
• Zhixiong Yu,
• Taofeng Shao,
• Chuanye Tao,
• Shuo Lin and
• Zhen Yang

Beilstein J. Org. Chem. 2012, 8, 841–849, doi:10.3762/bjoc.8.94

• cancers was first confirmed through a study of Gorlin syndrome predisposing to basal cell carcinoma, arising from autosomal dominant mutations in Ptch [3]. Indeed, aberrant Hh signaling has been reported in a variety of other malignancy diseases, such as small-cell lung cancer, pancreatic cancer, prostate

• cancer, breast cancer and multiple myeloma [4][5][6][7][8][9]. Taken together, the development of Hh pathway antagonists has thus represented an attractive strategy for anticancer therapy [10][11]. Because mutated Ptch or Smo proteins are mostly responsible for the abnormal activation of Hh related to

Multiple hydride reduction pathways in isoflavonoids

• Auli K. Salakka,
• Tuija H. Jokela and
• Kristiina Wähälä

Beilstein J. Org. Chem. 2006, 2, No. 16, doi:10.1186/1860-5397-2-16

• possible cancer preventing agents, particularly in hormone based cancers such as breast and prostate cancer. [57][58][59] Epidemiological studies have shown that they decrease the risk of colon cancer, osteoporosis, and coronary heart disease. [1][2][3] Significantly, health claims of soy foods, rich in