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4. Juli 2025 am IPB
IPB-Newsletter | April 2025
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Die Chemie der Natur – Basis für Wirkstoffe zur Gesunderhaltung von Mensch und Pflanze.
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Prof. Dr. Tina Romeis
Wechselwirkungen in, von und mit Pflanzen.
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Prof. Dr. Alain Tissier
Sekundär jedoch nicht zweitrangig - Die biologischen Funktionen pflanzlicher Sekundärmetaboliten.
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Dr. Mariana Schuster

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Im Rahmen der Wirkstofftage am 9. April 2025 verlieh das Leibniz-Forschungsnetzwerk Wirkstoffe den Preis „Leibniz-Wirkstoff des Jahres“ 2025 an Dr. Ibrahim Morgan, Dr. Robert Rennert, Dr. Tuvshinjargal Budragchaa und Prof.…

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Laborantin bzw. Technischer Assistent*in (m/w/d) (9/2025)

Datum: 08.04.2025 Referenznummer: 9/2025

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Chaudhuri, S. R.; Kaluđerović, G. N.; Bette, M.; Schmidt, J.; Schmidt, H.; Paschke, R.; Steinborn, D.; Synthesis, characterization and cytotoxicity studies of platinum(II) complexes with amino acid ligands in various coordination modes Inorg. Chim. Acta 394 472-480 (2013) DOI: 10.1016/j.ica.2012.08.034

Reactions of [Pt(CO3)(PPh3)2]·CH2Cl2 (1) with non-substituted and alkyl substituted amino acids, NH(R)CH(R′)CO2H (R/R′ = H/Me, L1; H/iPr, L2; H/CH2CHMe2, L3; Me/H, L4; Et/H, L5), in the presence of Tl[PF6] in methanol afforded with liberation of CO2 the formation of platinum(II) complexes of the type [Pt(PPh3)2{NHR–CHR′–C(O)O-κN,κO}][PF6] (R/R′ = H/Me, 2; H/iPr, 3; H/CH2CHMe2, 4; Me/H, 5; Et/H, 6). Single-crystal X-ray diffraction analysis of complex 4 exhibited a square-planar coordination of the platinum atom having coordinated two triphenylphosphane ligands and a deprotonated κN,κO-coordinated leucine ligand (L3−H). On varying the pKa value of the amino group, platinum(II) complexes with different coordination modes of amino acid ligands were obtained. Thus, treatment of complex 1 with N-acetyl l-alanine (L6), possessing a comparatively highly acidic NH proton, in 1:1 ratio in methanol resulted in the formation of [Pt(PPh3)2{N(COMe)–CHMe–C(O)O-κN,κO}] (7), while reacting N-phenyl glycine (L7) having a moderately acidic NH proton with complex 1 afforded a mixture of complexes [Pt(PPh3)2{NPh–CH2–C(O)O-κN,κO}] (8) and [Pt(PPh3)2{NHPh–CH2–C(O)O-κO}2] (10). Treatment of complex 1 with two equivalents of L6/L7 in dichloromethane resulted in the formation of [Pt(PPh3)2{NHR–CHR′–C(O)O-κO}2] (R/R′ = COMe/Me, 9; Ph/H, 10). An analogous reactivity was observed for l-lactic acid on treating with complex 1 in 1:1 and 2:1 ratio resulting in [Pt(PPh3)2{O–CHMe–C(O)O-κO,κO′}] (11) and [Pt(PPh3)2{HO–CHMe–C(O)O-κO}2] (12). The identities of all complexes have been proven by NMR (1H, 13C, 31P) spectroscopic and high-resolution ESI mass-spectrometric investigations. In vitro cytotoxicity studies against human tumor cell lines (8505C, A2780, HeLa, SW480, and MCF-7) showed the highest activities for the neutral complex 7. Furthermore, complexes 7 and 9 against the A2780 cell line induced an apoptotic mode of cell death, which was further supported by morphological investigation and DNA laddering. Cell cycle perturbation studies showed that both complexes induced faster cell death than cisplatin.

Publikation

Vetter, C.; Kaluđerović, G. N.; Paschke, R.; Kluge, R.; Schmidt, J.; Steinborn, D.; Synthesis, characterization and in vitro cytotoxicity studies of platinum(IV) complexes with thiouracil ligands Inorg. Chim. Acta 363 2452-2460 (2010) DOI: 10.1016/j.ica.2010.03.079

Reactions of [PtMe3(bpy)(Me2CO)][BF4] (2) with the thionucleobases 2-thiouracil (s2Ura), 4-thiouracil (s4Ura) and 2,4-dithiouracil (s2s4Ura) resulted in the formation of complexes of the type [PtMe3(bpy)(L-κS)][BF4] (L = s2Ura, 3; s4Ura, 4; s2s4Ura, 5). The complexes were characterized by NMR spectroscopy (1H, 13C, 195Pt), IR spectroscopy as well as microanalyses. The coordination through the C4S groups (4, 5) was additionally confirmed by DFT calculations, where it was shown that these complexes [PtMe3(bpy)(L-κS4)]+ (L = s4Ura, s2s4Ura) are about 5.8 (4b) and 3.3 kcal/mol (5b), respectively, more stable than the respective complexes, having thiouracil ligands bound through the C2X groups (X = O, 4a; S, 5a). For [PtMe3(bpy)(s2Ura-κS2)][BF4] (3) no preferred coordination mode could be assigned solely based on DFT calculations. Analysis of NMR spectra showed the κS2 coordination. In vitro cytotoxic studies of complexes 3−5 on nine different cell lines (8505C, A253, FaDu, A431, A549, A2780, DLD-1, HCT-8, HT-29) revealed in most cases moderate activities. However, 3 and 5 showed significant activity towards A549 and A2780, respectively, possessing IC50 values comparable to those of cisplatin. Cell cycle perturbations and trypan blue exclusion test on cancer cell line A431 using [PtMe3(bpy)(s2s4Ura-κS4)][BF4] (5) showed induction of apoptotic cell death. Furthermore, the reaction of [PtMe3(OAc-κ2O,O′)(Me2CO)] (6) with 4-thiouracil yielded the dinuclear complex [(PtMe3)2(μ-s4Ura–H)2] (7), which has been characterized by microanalysis, NMR (1H, 13C, 195Pt) and IR spectroscopy as well as ESI mass spectrometry. X-ray diffraction analysis of crystals yielded in an isolated case exhibited the presence of a hexanuclear thiouracilato platinum(IV) complex, possessing each three different kinds of methyl platinum(IV) moieties and 4-thiouracilato ligands. This exhibited the ability of 4-thiouracil platinum(IV) complexes to form multinuclear complexes.

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Lange Nacht, die Wissen schafft

IPB-Newsletter | April 2025

Wir verstehen Pflanzen!

Molekulare Signalverarbeitung

Natur- und Wirkstoffchemie

Biochemie pflanzlicher Interaktionen

Stoffwechsel- und Zellbiologie

Unabhängige Nachwuchsgruppe

Aktuelles

+++ Newsticker Wissenschaft #181 +++ Maschinelles Lernen +++

Preisverleihung zu den Wirkstofftagen: “Leibniz-Wirkstoff des Jahres 2025” geht an IPB-Team für Krebsforschungsprojekt

Pilzsachverständige in Sachsen-Anhalt: Jubiläumsstimmung zur Frühjahrstagung

Stellenausschreibungen

Laborantin bzw. Technischer Assistent*in (m/w/d) (9/2025)

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