Wydział Chemii

Małgorzata Ostrowska

Yuliya Toporivska

Monika Pyrkosz-Bulska

Elżbieta Gumienna-Kontecka

2018

Wiadomości Chemiczne

72

449-467

Naukowa

Polski

Artykuł

Thiosemicarbazones are considered to be potential therapeutics, because they
possess a broad range of biological properties including antitumor, antimalarial and
antimicrobial activity. Generally, the tiosemicarbazones coordinate to the metal
centre by means of an (N,S) bidentate mode, and when an additional coordinating
group is present, more diversified binding modes can occur such as a tridentate
(X,N,S) coordination fashion. The stability of the metal complexes formed with the
tiosemicarbazoness strongly depends on the character of the metal ion, the X-donor
atom of the additional functional group and the position and type of the substituents
at the tiosemicarbazones.
The most prominent representative of this family is the α(N)-heterocyclic Triapine
(3-aminopyridine- 2-carbaldehyde thiosemicarbazone; 3-AP), which is currently
undergoing different phase-I and -II clinical trials as an antitumor agent, and
demonstrates promising activity. Triapine is a very strong inhibitor of ribonucleotide
reductase, the rate determining enzyme in the supply of deoxyribonucleotides
for DNA synthesis required for cell proliferation. The mechanism of action involves
most probably the formation of an iron(II)–Triapine complex, which reacts with
molecular oxygen to result in the generation of reactive oxygen species. Subsequently,
these reactive oxygen species are responsible for the quenching of the active-site
tyrosyl radical of ribonucleotide reductase required for the enzymatic activity. As
a result, the coordination chemistry of iron complexes of tiosemicarbazones has
been receiving considerable attention.
This review describes the coordination chemistry of tiosemicarbazones, in particular
analogs of Triapine. The coordination compounds of d-block elements are
discussed with respect to their bonding and structures. Several of complexes are
mononuclear, with distorted tetrahedral, square planar, square pyramid or octahedral
as their common geometries. The metal-binding ability of STSC at physiological
pH was compared and shown.
Further, various biological applications with emphasis an anticancer activity
of the ligands/complexes are discussed in brief so as to indicate the importance of
ligands under consideration.

thiosemicarbazones, antitumor agents, biological activity, stability constants, transition metals

tiosemikarbazony, czynniki przeciwnowotworowe, aktywność biologiczna, stałe trwałości, metale przejściowe

OTHER

https://www.dbc.wroc.pl/dlibra/publication/66676/edition/45212