“…These bis-indole derivatives have been previously identified as anticancer agents. 37 Figure 9 Binding modes of metabolites 3 and 9 together with the co-crystallized inhibitor ( A – C , respectively) inside the binding site of Pin-1. …”
Introduction
Sponge-
Coscinoderma
sp. (Family: Spongiidae) is a coastal sponge that possesses a broad variety of natural-products. However, the exact chemical constituents and cytotoxic activity of the extract are still undefinable.
Methodology
In the present study, the metabolomic profiling of
Coscinoderma
sp. dereplicated 20 compounds, utilizing liquid chromatography coupled with high-resolution mass spectrometry (LC-HRESIMS).
Coscinoderma-
derived crude extract, before and after encapsulation within nanosized liposomes, was in vitro screened against hepatic, breast, and colorectal carcinoma human cell lines (HepG2, MCF-7, and Caco-2, respectively).
Results
The identified metabolites were fit to diverse chemical classes, covering diterpenes, an indole alkaloid, sesterterpenoid, sterol, and methylherbipoline salt. Comprehensive in silico experiments predicted several compounds in the sponge-derived extract (eg, compounds
1
–
15
) to have an anticancer potential via targeting multiple targets. The crude extract showed moderate antiproliferative activities towards studied cell lines with IC
50
values range from 10.7 to 12.4 µg/mL. The formulated extract-containing liposomes (size 141±12.3nm, PDI 0.222, zeta potential 20.8 ± 2.3), significantly enhanced the in vitro anticancer activity of the entrapped extract (IC
50
values ranged from 1.7 to 4.1 µg/mL).
Discussion
Encapsulation of both the hydrophilic and the lipophilic components of the extract within the lipid-based nanovesicles enhanced the cellular uptake and accessibility of the entrapped cargo. This study introduces liposomal nano-vesicles as a promising approach to improve the therapeutic potential of sponge-derived extracts.
“…These bis-indole derivatives have been previously identified as anticancer agents. 37 Figure 9 Binding modes of metabolites 3 and 9 together with the co-crystallized inhibitor ( A – C , respectively) inside the binding site of Pin-1. …”
Introduction
Sponge-
Coscinoderma
sp. (Family: Spongiidae) is a coastal sponge that possesses a broad variety of natural-products. However, the exact chemical constituents and cytotoxic activity of the extract are still undefinable.
Methodology
In the present study, the metabolomic profiling of
Coscinoderma
sp. dereplicated 20 compounds, utilizing liquid chromatography coupled with high-resolution mass spectrometry (LC-HRESIMS).
Coscinoderma-
derived crude extract, before and after encapsulation within nanosized liposomes, was in vitro screened against hepatic, breast, and colorectal carcinoma human cell lines (HepG2, MCF-7, and Caco-2, respectively).
Results
The identified metabolites were fit to diverse chemical classes, covering diterpenes, an indole alkaloid, sesterterpenoid, sterol, and methylherbipoline salt. Comprehensive in silico experiments predicted several compounds in the sponge-derived extract (eg, compounds
1
–
15
) to have an anticancer potential via targeting multiple targets. The crude extract showed moderate antiproliferative activities towards studied cell lines with IC
50
values range from 10.7 to 12.4 µg/mL. The formulated extract-containing liposomes (size 141±12.3nm, PDI 0.222, zeta potential 20.8 ± 2.3), significantly enhanced the in vitro anticancer activity of the entrapped extract (IC
50
values ranged from 1.7 to 4.1 µg/mL).
Discussion
Encapsulation of both the hydrophilic and the lipophilic components of the extract within the lipid-based nanovesicles enhanced the cellular uptake and accessibility of the entrapped cargo. This study introduces liposomal nano-vesicles as a promising approach to improve the therapeutic potential of sponge-derived extracts.
“…A significant part among thousands of new biologically active compounds synthesized each year by medicinal chemists around the world belongs to the group of hydrazide‐hydrazones (Bala, Uppal, Kajal, Kamboj, & Sharma, ; Popiołek, ; Rollas & Küçükgüzel, ). This is due to the fact that this group of compounds possesses very interesting and broad spectrum of biological properties (Bala et al, ; Popiołek, ; Rollas & Küçükgüzel, ), which include antimicrobial (Backes, Neumann, & Jursic, ; Manikandan et al, ; Metwally, Abdel‐Aziz, Lashine, Husseiny, & Badawy, ; Rollas, Gulerman, & Erdeniz, ; Zha et al, ), anticancer (Kumar, Kumar, Ghosh, & Shah, ; Nasr et al, ; Nasr, Bondock, & Youns, ; Nikolova‐Mladenova, Momekov, Ivanov, & Bakalova, ; Sreenivasulu, Reddy, Sujitha, Kumar, & Raju, ; Tantak et al, ), anti‐inflammatory (Gökçe, Utku, & Küpeli, ; Moldovan et al, ; Sondhi, Dinodia, & Kumar, ), anticonvulsant (Dehestani et al, ) and analgesic activity (Navidpour, Shafaroodi, Saeedi‐Motahar, & Shafiee, ).…”
In this research, we synthesized and evaluated for in vitro antimicrobial activity a new series of hydrazide-hydrazones obtained from 5-nitrofuran-2-carboxylic acid.New compounds were identified and characterized by spectral methods ( 1 H NMR and 13 C NMR). All tested hydrazide-hydrazones proved to be promising antimicrobial agents. Antimicrobial activity and antifungal activity of new derivatives of 5-nitrofuran-2-carboxylic acid were revealed in many cases to be higher than the activity of reference substances (nitrofurantoin, cefuroxime and ampicillin). Yield: 47%; M.p.: 126°C; 1 H NMR (DMSO-d 6 ) δ (ppm): 2.09 (s, 3H, CH 3 ), 2.57-2.61 (t, 2H, CH 2 , J = 6 Hz), 2.68-2.74 (q, 2H, CH 2 , J = 6 Hz), 7.50-7.51 (d, 1H, ArH, J = 3 Hz), 7.78-7.79 (d, 1H, ArH, J = 3 Hz), 7.79-7.83 (t, 1H, =CH, J = 9 Hz, J = 3 Hz), 11.95 (s, 1H, NH); 13 C NMR (DMSO-d 6 ) δ (ppm): 14.6 (SCH 3 ), 30.3 (CH 2 ), 33.6 (CH 2 ), 115.4, 123.6, 138.2, 150.1 (4C ar ), 154.8 (=CH), 156.2 (C = O); For 262 | POPIOŁEK Et al.
“…Also, a series of 7-azaindolyl hydrazones are characterized as antiproliferative against MCF-7 breast carcinoma cell line [25]. N-methyl and N,N-dimethyl bis(indolyl)hydrazide hydrazone analog derivatives had anti-proliferative activity against cervical (HeLa) and breast cancer (MCF-7) [31]. The series of (E)-N1-((2-chloro-7-methoxyquinolin-3-yl)methylene)-3-(phenylthio)propanehydrazide derivatives had a greater cytotoxic effect on the neuroblastoma cells (SH-SY5Y and Kelly) compared to the breast cancer cell lines (MCF-7 and MDA-MB-231) [32].…”
Thanks to the progress in oncology, pharmacological treatment of cancer is gaining in importance and in the near future anti-cancer chemotherapeutics are expected to be the main method of treatment for cancer diseases. What is more, the search for new anti-cancer compounds with the desired application properties is constantly underway. As a result of designed syntheses, we obtained some new N’-substituted 5-chloro-3-methylisothiazole-4-carboxylic acid hydrazide derivatives with anticancer activity. The structure of new compounds was determined by mass spectrometry (MS), elemental analysis, proton nuclear magnetic resonance spectroscopy (1H-NMR), carbon nuclear magnetic resonance spectroscopy (13C-NMR), 1H-13C NMR correlations and infrared spectroscopy (IR). Moreover, the structures of the compounds were confirmed by crystallographic examination. The antiproliferative MTT tests for 11 prepared compounds was conducted towards human biphenotypic B cell myelomonocytic leukemia MV4-11. SRB test was used to examine their potential anticancer activity towards human colon adenocarcinoma cell lines sensitive LoVo, resistant to doxorubicin LoVo/DX, breast adenocarcinoma MCF-7 and normal non-tumorigenic epithelial cell line derived from mammary gland MCF-10A. The most active compound was 5-chloro-3-methyl-N′-[(1E,2E)-(3-phenyloprop-2-en-1-ylidene]isothiazole-4-carbohydrazide, which showed the highest antiproliferative activity against all tested cell lines.
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