skip to main content
DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information

This content will become publicly available on August 28, 2021

Title: Synthesis and antiproliferative activity of hindered, chiral 1,2-diaminodiamantane platinum( ii ) complexes

Abstract

Platinum-based antineoplastic agents play a major role in the treatment of numerous types of cancer.

Authors:
 [1];  [2];  [3];  [1]; ORCiD logo [4]; ORCiD logo [4];  [1]; ORCiD logo [1]
  1. Institute of Organic Chemistry, Justus Liebig University, Heinrich-Buff-Ring 17, 35392 Giessen, Germany and Center for Materials Research (LaMa)
  2. Department of Organic Chemistry, Igor Sikorsky Kiev Polytechnic Institute, 03056 Kiev, Ukraine, Leiden Institute of Chemistry
  3. Institute of Inorganic and Analytical Chemistry, Justus-Liebig-Universität, 35392 Giessen, Germany
  4. Leiden Institute of Chemistry, Leiden University, 2300RA Leiden, The Netherlands
Publication Date:
Sponsoring Org.:
USDOE
OSTI Identifier:
1657623
Grant/Contract Number:  
AC02-76SF00515
Resource Type:
Publisher's Accepted Manuscript
Journal Name:
Dalton Transactions
Additional Journal Information:
Journal Name: Dalton Transactions Journal Volume: 49 Journal Issue: 40; Journal ID: ISSN 1477-9226
Publisher:
Royal Society of Chemistry (RSC)
Country of Publication:
United Kingdom
Language:
English

Citation Formats

Bakhonsky, Vladyslav V., Pashenko, Aleksander A., Becker, Jonathan, Hausmann, Heike, De Groot, Huub J. M., Overkleeft, Herman S., Fokin, Andrey A., and Schreiner, Peter R. Synthesis and antiproliferative activity of hindered, chiral 1,2-diaminodiamantane platinum( ii ) complexes. United Kingdom: N. p., 2020. Web. https://doi.org/10.1039/D0DT02391D.
Bakhonsky, Vladyslav V., Pashenko, Aleksander A., Becker, Jonathan, Hausmann, Heike, De Groot, Huub J. M., Overkleeft, Herman S., Fokin, Andrey A., & Schreiner, Peter R. Synthesis and antiproliferative activity of hindered, chiral 1,2-diaminodiamantane platinum( ii ) complexes. United Kingdom. https://doi.org/10.1039/D0DT02391D
Bakhonsky, Vladyslav V., Pashenko, Aleksander A., Becker, Jonathan, Hausmann, Heike, De Groot, Huub J. M., Overkleeft, Herman S., Fokin, Andrey A., and Schreiner, Peter R. Tue . "Synthesis and antiproliferative activity of hindered, chiral 1,2-diaminodiamantane platinum( ii ) complexes". United Kingdom. https://doi.org/10.1039/D0DT02391D.
@article{osti_1657623,
title = {Synthesis and antiproliferative activity of hindered, chiral 1,2-diaminodiamantane platinum( ii ) complexes},
author = {Bakhonsky, Vladyslav V. and Pashenko, Aleksander A. and Becker, Jonathan and Hausmann, Heike and De Groot, Huub J. M. and Overkleeft, Herman S. and Fokin, Andrey A. and Schreiner, Peter R.},
abstractNote = {Platinum-based antineoplastic agents play a major role in the treatment of numerous types of cancer.},
doi = {10.1039/D0DT02391D},
journal = {Dalton Transactions},
number = 40,
volume = 49,
place = {United Kingdom},
year = {2020},
month = {10}
}

Journal Article:
Free Publicly Available Full Text
This content will become publicly available on August 28, 2021
Publisher's Version of Record

Save / Share:

Works referenced in this record:

Cytotoxic, antioxidant activities and structure activity relationship of some newly synthesized terpenoidal oxaliplatin analogs
journal, February 2009

  • Amr, Abd El-Galil E.; Ali, Korany A.; Abdalla, Mohamed M.
  • European Journal of Medicinal Chemistry, Vol. 44, Issue 2
  • DOI: 10.1016/j.ejmech.2008.05.024

The resurgence of platinum-based cancer chemotherapy
journal, July 2007

  • Kelland, Lloyd
  • Nature Reviews Cancer, Vol. 7, Issue 8
  • DOI: 10.1038/nrc2167

Potent Anticancer Activity and Possible Low Toxicity of Platinum(II) Complexes with Functionalized 1,1-Cyclobutanedicarboxylate as a Leaving Ligand
journal, September 2014

  • Zhao, Jian; Gou, Shaohua; Liu, Fengfan
  • Chemistry - A European Journal, Vol. 20, Issue 46
  • DOI: 10.1002/chem.201404090

Comparison of silver and molybdenum microfocus X-ray sources for single-crystal structure determination
journal, January 2015

  • Krause, Lennard; Herbst-Irmer, Regine; Sheldrick, George M.
  • Journal of Applied Crystallography, Vol. 48, Issue 1
  • DOI: 10.1107/S1600576714022985

Say No to DMSO: Dimethylsulfoxide Inactivates Cisplatin, Carboplatin, and Other Platinum Complexes
journal, May 2014


Pharmaceuticals that contain polycyclic hydrocarbon scaffolds
journal, January 2015

  • Stockdale, Tegan P.; Williams, Craig M.
  • Chemical Society Reviews, Vol. 44, Issue 21
  • DOI: 10.1039/C4CS00477A

Octanol‐Water Partition Coefficients of Simple Organic Compounds
journal, July 1989

  • Sangster, James
  • Journal of Physical and Chemical Reference Data, Vol. 18, Issue 3
  • DOI: 10.1063/1.555833

Revisiting [PtCl 2 ( cis -1,4-DACH)]: An Underestimated Antitumor Drug with Potential Application to the Treatment of Oxaliplatin-Refractory Colorectal Cancer
journal, August 2012

  • Margiotta, Nicola; Marzano, Cristina; Gandin, Valentina
  • Journal of Medicinal Chemistry, Vol. 55, Issue 16
  • DOI: 10.1021/jm3006838

Unique Properties of DNA Interstrand Cross-Links of Antitumor Oxaliplatin and the Effect of Chirality of the Carrier Ligand
journal, January 2008

  • Kasparkova, Jana; Vojtiskova, Marie; Natile, Giovanni
  • Chemistry - A European Journal, Vol. 14, Issue 4
  • DOI: 10.1002/chem.200701352

Effect of chirality in platinum drugs
journal, February 2015

  • Arnesano, Fabio; Pannunzio, Alessandra; Coluccia, Mauro
  • Coordination Chemistry Reviews, Vol. 284
  • DOI: 10.1016/j.ccr.2014.07.016

Chemotherapy-induced peripheral neurotoxicity and complementary and alternative medicines: progress and perspective
journal, October 2015


Correlation of Octanol/Water Solubility Ratios and Partition Coefficients
journal, May 1995

  • Pinsuwan, Sirirat; Li, An; Yalkowsky, Samuel H.
  • Journal of Chemical & Engineering Data, Vol. 40, Issue 3
  • DOI: 10.1021/je00019a019

The formation, isolation and characterization of DNA adducts produced by anticancer platinum complexes
journal, January 1987


Molecular mechanisms of resistance and toxicity associated with platinating agents
journal, February 2007


Cisplatin: Polymorphism and Structural Insights into an Important Chemotherapeutic Drug
journal, October 2010

  • Ting, Valeska P.; Schmidtmann, Marc; Wilson, Chick C.
  • Angewandte Chemie International Edition, Vol. 49, Issue 49
  • DOI: 10.1002/anie.201003185

2.4 Å Crystal Structure of an Oxaliplatin 1,2-d(GpG) Intrastrand Cross-Link in a DNA Dodecamer Duplex
journal, October 2001

  • Spingler, Bernhard; Whittington, Douglas A.; Lippard, Stephen J.
  • Inorganic Chemistry, Vol. 40, Issue 22
  • DOI: 10.1021/ic010790t

Hydrophobicity parameters for platinum complexes
journal, February 1991

  • Souchard, Jean Pierre; Ha, Tam T. B.; Cros, S.
  • Journal of Medicinal Chemistry, Vol. 34, Issue 2
  • DOI: 10.1021/jm00106a056

Oxaliplatin
journal, January 2004

  • Graham, Joanne; Muhsin, Mohamed; Kirkpatrick, Peter
  • Nature Reviews Drug Discovery, Vol. 3, Issue 1
  • DOI: 10.1038/nrd1287

Synthesis, biological evaluation and SAR studies of novel bicyclic antitumor platinum(IV) complexes
journal, August 2014


SHELXT – Integrated space-group and crystal-structure determination
journal, January 2015

  • Sheldrick, George M.
  • Acta Crystallographica Section A Foundations and Advances, Vol. 71, Issue 1, p. 3-8
  • DOI: 10.1107/S2053273314026370

State of the art and prospects of methods for determination of lipophilicity of chemical compounds
journal, April 2019

  • Kempińska, Dagmara; Chmiel, Tomasz; Kot-Wasik, Agata
  • TrAC Trends in Analytical Chemistry, Vol. 113
  • DOI: 10.1016/j.trac.2019.01.011

Chemotherapy-induced peripheral neurotoxicity (CIPN): An update
journal, April 2012


Mechanisms of resistance to cisplatin and carboplatin
journal, July 2007


Improved potency of cisplatin by hydrophobic ion pairing
journal, July 2004

  • Feng, Lixin; De Dille, Alexandra; Jameson, Vicky J.
  • Cancer Chemotherapy and Pharmacology, Vol. 54, Issue 5
  • DOI: 10.1007/s00280-004-0840-z

Anticancer kiteplatin pyrophosphate derivatives show unexpected target selectivity for DNA
journal, January 2017

  • Kasparkova, Jana; Kostrhunova, Hana; Novohradsky, Vojtech
  • Dalton Trans., Vol. 46, Issue 41
  • DOI: 10.1039/C7DT02633A

Platinum Compounds: A Hope for Future Cancer Chemotherapy
journal, January 2013

  • Ali, Imran; A. Wani, Waseem; Saleem, Kishwar
  • Anti-Cancer Agents in Medicinal Chemistry, Vol. 13, Issue 2
  • DOI: 10.2174/1871520611313020016

Relation of conformation to antitumor activity of platinum(II) complexes of 1,2-cyclohexanediamine and 2-(aminomethyl)cyclohexylamine isomers against leukemia P388
journal, May 1981

  • Noji, Masahide; Okamoto, Koji; Kidani, Yoshinori
  • Journal of Medicinal Chemistry, Vol. 24, Issue 5
  • DOI: 10.1021/jm00137a007

The Rational Design of Anticancer Platinum Complexes: The Importance of the Structure-Activity Relationship
journal, June 2009


Toward a better understanding of the oxaliplatin mode of action upon the steric hindrance of 1,2-diaminocyclohexane and its analogue
journal, April 2016


Comparative Adverse Effect Profiles of Platinum Drugs
journal, January 1995


In Vitro Anticancer Activity of cis -Diammineplatinum(II) Complexes with β-Diketonate Leaving Group Ligands
journal, May 2012

  • Wilson, Justin J.; Lippard, Stephen J.
  • Journal of Medicinal Chemistry, Vol. 55, Issue 11
  • DOI: 10.1021/jm3002857

Use of intensity quotients and differences in absolute structure refinement
journal, May 2013

  • Parsons, Simon; Flack, Howard D.; Wagner, Trixie
  • Acta Crystallographica Section B Structural Science Crystal Engineering and Materials, Vol. 69, Issue 3
  • DOI: 10.1107/S2052519213010014

Platinum-based drugs: past, present and future
journal, February 2016


Oxaliplatin: A review of preclinical and clinical studies
journal, October 1998


Crystal structure refinement with SHELXL
journal, January 2015

  • Sheldrick, George M.
  • Acta Crystallographica Section C Structural Chemistry, Vol. 71, Issue 1, p. 3-8
  • DOI: 10.1107/S2053229614024218

Cisplatin Resistance: A Cellular Self-Defense Mechanism Resulting from Multiple Epigenetic and Genetic Changes
journal, June 2012

  • Shen, Ding-Wu; Pouliot, Lynn M.; Hall, Matthew D.
  • Pharmacological Reviews, Vol. 64, Issue 3
  • DOI: 10.1124/pr.111.005637

Synthetic Methods for the Preparation of Platinum Anticancer Complexes
journal, November 2013

  • Wilson, Justin J.; Lippard, Stephen J.
  • Chemical Reviews, Vol. 114, Issue 8
  • DOI: 10.1021/cr4004314

Synthesis, characterization and antiproliferative studies of the enantiomers of cis-[(1,2-camphordiamine)dichloro]platinum(II) complexes
journal, February 2008

  • Montaña, Ángel M.; Bernal, Francisco J.; Lorenzo, Julia
  • Bioorganic & Medicinal Chemistry, Vol. 16, Issue 4
  • DOI: 10.1016/j.bmc.2007.11.021

Antitumor activity of 1,2-diaminocyclohexaneplatinum complexes against Sarcoma-180 ascites form
journal, December 1978

  • Kidani, Yoshinori; Inagaki, Kenji; Iigo, Masaaki
  • Journal of Medicinal Chemistry, Vol. 21, Issue 12
  • DOI: 10.1021/jm00210a029

Conformation of DNA GG Intrastrand Cross-Link of Antitumor Oxaliplatin and Its Enantiomeric Analog
journal, December 2007


The Lipophilic Bullet Hits the Targets: Medicinal Chemistry of Adamantane Derivatives
journal, February 2013

  • Wanka, Lukas; Iqbal, Khalid; Schreiner, Peter R.
  • Chemical Reviews, Vol. 113, Issue 5
  • DOI: 10.1021/cr100264t

Biological activity of platinum complexes containing chiral centers on the nitrogen or carbon atoms of a chelate diamine ring
journal, July 1987


Influence of pyridine versus piperidine ligands on the chemical, DNA binding and cytotoxic properties of light activated trans,trans,trans-[Pt(N3)2(OH)2(NH3)(L)]
journal, May 2011


Cisplatin: mode of cytotoxic action and molecular basis of resistance
journal, October 2003


Cisplatin nephrotoxicity
journal, September 2003


Cisplatin in cancer therapy: Molecular mechanisms of action
journal, October 2014


New trends in platinum and palladium complexes as antineoplastic agents
journal, March 2016


Synthesis, Biophysical Studies, and Antiproliferative Activity of Platinum(II) Complexes Having 1,2-Bis(aminomethyl)carbobicyclic Ligands
journal, February 2008

  • de Mier-Vinué, Jordi; Gay, Marina; Montaña, Ángel M.
  • Journal of Medicinal Chemistry, Vol. 51, Issue 3
  • DOI: 10.1021/jm070844u

Oxaliplatin and Its Enantiomer Induce Different Condensation Dynamics of Single DNA Molecules
journal, August 2013


Development and Validation of Liquid Chromatography-Based Methods to Assess the Lipophilicity of Cytotoxic Platinum(IV) Complexes
journal, December 2018


Pt(IV) Bifunctional Prodrug Containing 2-(2-Propynyl)octanoato Axial Ligand: Induction of Immunogenic Cell Death on Colon Cancer
journal, February 2019


Metal complex interactions with DNA
journal, January 2015

  • Pages, Benjamin J.; Ang, Dale L.; Wright, Elisé P.
  • Dalton Transactions, Vol. 44, Issue 8
  • DOI: 10.1039/C4DT02700K

Chemotherapy-induced peripheral neurotoxicity: A critical analysis: CIPN: A Critical Analysis
journal, November 2013

  • Park, Susanna B.; Goldstein, David; Krishnan, Arun V.
  • CA: A Cancer Journal for Clinicians, Vol. 63, Issue 6
  • DOI: 10.3322/caac.21204

Molecular mechanisms of cisplatin resistance
journal, September 2011


Study on Antitumor Platinum(II) Complexes of Chiral Diamines with Dicyclic Species as Steric Hindrance
journal, August 2015

  • Liu, Fengfan; Gou, Shaohua; Chen, Feihong
  • Journal of Medicinal Chemistry, Vol. 58, Issue 16
  • DOI: 10.1021/jm501952r

The status of platinum anticancer drugs in the clinic and in clinical trials
journal, January 2010

  • Wheate, Nial J.; Walker, Shonagh; Craig, Gemma E.
  • Dalton Transactions, Vol. 39, Issue 35
  • DOI: 10.1039/c0dt00292e

Chiral Building Blocks Based on 1,2-Disubstituted Diamantanes
journal, February 2017

  • Fokin, Andrey; Pashenko, Alexander; Bakhonsky, Vladyslav
  • Synthesis, Vol. 49, Issue 09
  • DOI: 10.1055/s-0036-1588694

Chemotherapy-induced peripheral neuropathy
journal, January 2002

  • Quasthoff, Stefan; Hartung, Hans Peter
  • Journal of Neurology, Vol. 249, Issue 1
  • DOI: 10.1007/PL00007853