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Unexpected formation of [M]2+from [M+CuCl+H]2+ions under CID conditions, where M is a molecule of 3,5-bis(2,2’-bipyridin-4-ylethynyl)benzoic acid or its methyl ester

100%

Frański R., Zalas M., Gierczyk B., Cegłowski M., Schroeder G., Kozik T., Hoffmann M.

Open Chemistry

2015

vol. 13

issue 1

[M+CuCl+H]2+ ions were generated using electrospray ionization (ESI); where M is a molecule of 3,5-bis(2,2’-bipyridin-4-ylethynyl)benzoic acid or its methyl ester (1 and 2, respectively). The ions were subjected to CID-MS/MS analysis. It was found that their gas phase decomposition lead to the formation of rare di-cations [M]2+, namely [1]2+ and [2]2+ ions. The formation of [1]2+ ion from [3+H+CuCl]2+ ion in the second fragmentation, where 3 is ethyl ester of 3,5-bis(2,2-bipyridin-4-ylethynyl)benzoic acid, was also observed since in the first fragmentation step the loss of ethylene molecule from [3+H+CuCl]2+ ion took place. To the best of our knowledge, it is the first time that [M]2+ ions formation from respective metal complexes has been reported. It is also unusual that formation of [M]2+ ions is not accompanied by formation of [M]+∙ ions. Furthermore, as expected, theoretical calculation and electron ionization mass spectra show that 1 and 2 are not especially prone to form [M]2+ ions. Thus formation of [M]2+ ions under CID conditions is very surprising.

Phenylcopper(I) clusters in the gas phase obtained by laser desorption/ionization from bis(dibenzoylmethane)copper(II)

88%

Frański R., Kozik T., Staniszewski B., Urbaniak W.

Open Chemistry

2010

vol. 8

issue 3

508-512

It has been demonstrated that phenylcopper(I)-containing clusters are generated in the gas phase from bis(dibenzoylmethane) copper(II) (Cu(dbm)2) by laser desorption/ ionization (LDI) method. For example, the [Cu5dbm2(C6H5)2]+ ion can be considered as consisting of two Cudbm molecules, two CuC6H5 molecules and a Cu+ cation. The [Cu5(C6H5)4]+ ion can be considered as phenylcopper(I) cluster (consisting of four phenylcopper molecules) ionized by additional Cu+ cation. Results from MS/MS (tandem mass spectrometry) experiments have confirmed the presence of phenylcopper molecules in the analyzed clusters. Ease of preparation of dibenzoylmethane-metal complexes and straightforward method to obtain LDI mass spectra offer a wide range of possibilities to study similar organometallic clusters in the gas phase. [...]

Changes in expression of genes related to caspases and BCL-2 family in RPTEC treated with amphotericin B and its modified forms

63%

Gola J. M., Simka K., Strzałka-Mrozik B., Kruszniewska-Rajs C., Gagoś M., Mazurek U.

Annales Academiae Medicae Silesiensis

2018

issue 72

62-68

INTRODUCTION: The main limitation of the use of amphotericin B (AmB) – effective in the treatment of systemic fungal infections – is its high toxicity to human cells. The mechanism of AmB toxicity is not clear. Caspase-related and BCL-2 proteins participate in the regulation of apoptosis. Thus, they may be involved in drug toxicity. In this study we evaluated the influence of AmB on the transcriptional activity of genes related to caspases and the BCL-2 family. We also tested the influence of modified forms of AmB: AmB-Cu2+ (the complex with copper(II) ions) and the AmB-ox (oxidized form). MATERIAL AND METHODS: Human RPTECs (Renal Proximal Tubule Epithelial Cells) were treated with AmB, AmB-Cu2+ and AmB-ox. Total RNA was extracted using the phenol-chloroform method. The expression profiles of genes related to caspase activity and BCL-2 were determined using oligonucleotide microarrays (HG-U133A 2.0, Affymetrix). Analysis included 67 ID related to caspases and 32 ID associated with BCL-2, according to the Affymetrix database. RESULTS: The analysis revealed upregulation of the BCL-2 and BCL2L1genes in the cells treated with AmB-Cu2+, in comparison to the control. In both the AmB and AmB-Cu2+ -treated cells, differentiating genes were associated with inflammation and mitophagy activated by intrinsic signals. In the cells treated with AmB-ox, the BCL-2 genes were downregulated. CONCLUSIONS: The results suggest that AmB and AmB-Cu2+ activate genes involved in the regulation of inflam-mation and autophagy induced by intrinsic signals, but overexpression of BCL-2 and BCL2L1 may protect AmB-Cu2+--treated cells from death. In the cells treated with AmB-ox extrinsic signals prevail, indicating the distinct molecular mechanism of its cytotoxicity.

WSTĘP: Głównym ograniczeniem stosowania amfoterycyny B (AmB) – skutecznej w leczeniu grzybic układowych – jest jej wysoka toksyczność wobec komórek ludzkich. Mechanizm cytotoksyczności nie został wyjaśniony. Białka związane z aktywnością kaspaz oraz białka należące do rodziny BCL-2 uczestniczą w regulacji apoptozy, mogą być zatem zaangażowane w procesy odpowiedzialne za toksyczność leku. W pracy oceniono wpływ AmB na aktywność transkrypcyjną genów kodujących białka związane z aktywnością kaspaz oraz białka z rodziny BCL-2. Zbadano również wpływ modyfikowanych form AmB: AmB-Cu2+ (kompleks z jonami miedzi (II)) i AmB-ox (formy utlenione). MATERIAŁ I METODY: Ludzkie komórki RPTECs (Human Renal Proximal Tubule Epithelial Cells) inkubowano z AmB, AmB-Cu2+ i AmB-ox. Całkowity RNA wyekstrahowano metodą fenolowo-chloroformową. Profil ekspresji genów wyznaczono techniką mikromacierzy oligonukleotydowych (HG-U133A 2.0, Affymetrix). Analiza obejmowała 67 ID genów związanych z aktywnością kaspaz i 32 ID geny kodujące białka z rodziny BCL-2, zaproponowane przez bazę Affymetrix. WYNIKI: Analiza wykazała nadekspresję genów BCL-2 i BCL2L1 w komórkach traktowanych AmB-Cu2+, w porównaniu z kontrolą. Zarówno w komórkach traktowanych AmB, jak i AmB-Cu2+ geny różnicujące związane były z za-paleniem i mitofagią aktywowanymi w odpowiedzi na sygnały wewnątrzkomórkowe. W komórkach traktowanych AmB-ox geny z rodziny BCL-2 były wyciszone. WNIOSKI: Wyniki sugerują, że AmB i AmB-Cu2+ aktywują geny zaangażowane w regulację zapalenia i mitofagii aktywowanych sygnałami wewnątrzkomórkowymi, jednak nadekspresja genów BCL-2 i BCL2L1 może chronić komórki traktowane AmB-Cu2+ przed śmiercią. W komórkach traktowanych AmB-ox przeważa sygnał zewnątrzkomórkowy, co wskazuje na odrębny mechanizm cytotoksyczności tej formy antybiotyku.

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2 Open Chemistry

1 Annales Academiae Medicae Silesiensis

1 2018

1 2015

1 2010

2 Frański R.

2 Kozik T.

1 Cegłowski M.

1 Gagoś M.

1 Gierczyk B.

1 Gola J. M.

1 Hoffmann M.

1 Kruszniewska-Rajs C.

1 Mazurek U.

1 Schroeder G.

1 Simka K.

1 Staniszewski B.

1 Strzałka-Mrozik B.

1 Urbaniak W.

1 Zalas M.

Search results

Unexpected formation of [M]2+from [M+CuCl+H]2+ions under CID conditions, where M is a molecule of 3,5-bis(2,2’-bipyridin-4-ylethynyl)benzoic acid or its methyl ester

Phenylcopper(I) clusters in the gas phase obtained by laser desorption/ionization from bis(dibenzoylmethane)copper(II)

Changes in expression of genes related to caspases and BCL-2 family in RPTEC treated with amphotericin B and its modified forms