Terpene conjugates of diaminedichloridoplatinum(II) complexes: antiproliferative effects in HL-60 leukemia, 518A2 melanoma, and HT-29 colon cancer cells

Chemistry & Biodiversity
Günther BernhardtMiroslava Zoldakova

Abstract

Twenty-eight [6-(aminomethyl)nicotinate]dichloridoplatinum(II) complexes 1 esterified with various terpene alcohols either directly or via alkyl spacers were tested for antiproliferative activity in human 518A2 melanoma and HL-60 leukemia cells. Generally, conjugates with menthanes and polycyclic sesquiterpenes attached via propane-1,2-diyl spacers were most active. In the melanoma cells, the propane-1,2-diyl-spacered conjugates of (-)-menthol (1a(2')), (+)-neomenthol (1b(2')), (-)-carvomenthol (1h(2')), and (-)-isolongifolol (1n(2')) displayed growth inhibition at IC(50)<4 microM which is ten times smaller than that of cisplatin. The stationary diamino ligand was also crucial. The (-)-menthyl ester complexes with 2,3-diaminopropanoate (9a) and 2,4-diaminobutanoate (10a) ligands caused a greater and persistent growth inhibition in HT-29 colon cancer cells upon long-term exposure when compared to the 6-(aminomethyl)nicotinate analogue 1a. The cedrenyl ester 1l and the menthoxyisopropyl ester 1a(2') proved most efficacious in all three tumor cell lines. The DNA binding of complexes 1 was assessed by electrophoretic band-shift experiments and found correlated to the terpene structure but not to the observed antiproliferative activ...Continue Reading

References

Jan 1, 1992·Journal of Cancer Research and Clinical Oncology·G BernhardtH Schönenberger
Mar 13, 1999·Biochemical Pharmacology·I R HardcastleM Jarman
Feb 15, 2001·Cell Death and Differentiation·Y Tsujimoto, S Shimizu
Dec 26, 2001·Chemical Reviews·E Wong, C M Giandomenico
Dec 26, 2001·Chemical Reviews·E R Jamieson, S J Lippard
Feb 28, 2003·Reviews of Physiology, Biochemistry and Pharmacology·M A JakupecB K Keppler
Mar 26, 2003·Proceedings of the National Academy of Sciences of the United States of America·Jan Reedijk
Apr 3, 2003·Journal of Lipid Research·Sarah A Holstein, Raymond J Hohl
Nov 1, 2003·Bioorganic & Medicinal Chemistry Letters·Caroline DescôteauxGervais Bérubé
Mar 18, 2004·Breast Cancer Research and Treatment·Takashi YuriAiro Tsubura
Apr 26, 2005·Cancer Treatment Reviews·D M KweekelH-J Guchelaar
May 27, 2005·Antimicrobial Agents and Chemotherapy·Domenico TrombettaGiuseppe Bisignano
Apr 6, 2006·Pharmazie in unserer Zeit·Wieland VoigtHans-Joachim Schmoll

❮ Previous
Next ❯

Citations

Jun 1, 2011·Tobacco Induced Diseases·Allison C Hoffman
Nov 11, 2011·Journal of Inorganic Biochemistry·Bernhard BiersackThomas Mueller
Mar 27, 2009·ChemMedChem·Sandra BreyerRainer Schobert
Jan 21, 2010·Chemistry & Biodiversity·Katharina EffenbergerRainer Schobert
Sep 16, 2016·Cancer Epidemiology, Biomarkers & Prevention : a Publication of the American Association for Cancer Research, Cosponsored by the American Society of Preventive Oncology·Ping-Ching HsuPeter G Shields
May 6, 2021·International Journal of Molecular Sciences·Mariola Zielińska-BłajetJoanna Feder-Kubis
Feb 6, 2010·European Journal of Medicinal Chemistry·K EffenbergerR Schobert

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.