A Tridentate Cu(II) Complex with a 2-(4′-Aminophenyl)Benzothiazole Derivative: Crystal Structure and Biological Evaluation for Anticancer Activity

Herein, the synthesis, structural characterization and in vitro biological evaluation of a novel Cu(II) complex with the 2-(4-aminophenyl)benzothiazole pharmacophore conjugated with the (2-pyridinyl)methylamino chelating moiety is reported for the first time. A full characterization of the Cu(II) co...

Full description

Saved in:
Bibliographic Details
Published inInorganics Vol. 11; no. 3; p. 132
Main Authors Mavroidi, Barbara, Sagnou, Marina, Halevas, Eleftherios, Mitrikas, George, Kapiris, Fotis, Bouziotis, Penelope, Hatzidimitriou, Antonios G., Pelecanou, Maria, Methenitis, Constantinos
Format Journal Article
LanguageEnglish
Published Basel MDPI AG 01.03.2023
Subjects
2-(4-aminophenyl)benzothiazole
Anticancer properties
Antitumor activity
Apoptosis
Benzothiazole
Biological activity
Cancer
Cell cycle
Chelation
Circular dichroism
Clinical trials
Copper
copper(II) complex
Crystal structure
Crystallography
Cytotoxicity
Dichroism
DNA binding studies
Ethidium bromide
Fibroblasts
Glioblastoma
in vitro evaluation
Intracellular
Ligands
Lung cancer
Nitrates
Nitrogen
Palladium
Prostate
Prostate cancer
Spectroscopy
Spectrum analysis
Structural analysis
Thermal denaturation
Toxicity
Tumor cell lines
Viscometry
X-ray crystallography
Online AccessGet full text

Cover

Abstract Herein, the synthesis, structural characterization and in vitro biological evaluation of a novel Cu(II) complex with the 2-(4-aminophenyl)benzothiazole pharmacophore conjugated with the (2-pyridinyl)methylamino chelating moiety is reported for the first time. A full characterization of the Cu(II) complex was conducted by X-ray crystallography, EPR, IR, elemental and MS analysis, and its binding to CT-DNA was investigated by UV-vis spectroscopy, ethidium bromide competition studies, circular dichroism, viscometry and thermal denaturation. The data clearly indicate that the Cu(II) complex interacts with CT-DNA via intercalation, registering a difference compared to previously reported Pt(II) and Pd(II) analogues. To evaluate the anticancer activity of the complex, a series of in vitro experiments against breast, glioblastoma, prostate and lung cancer cell lines along with healthy fibroblasts were implemented. Cytotoxicity, cellular uptake, intracellular ROS production, cell cycle and apoptosis analysis revealed an increased anticancer activity towards breast cancer cells that is accompanied by an induction in intracellular ROS levels and a significant G2/M arrest followed by apoptosis.
AbstractList Herein, the synthesis, structural characterization and in vitro biological evaluation of a novel Cu(II) complex with the 2-(4-aminophenyl)benzothiazole pharmacophore conjugated with the (2-pyridinyl)methylamino chelating moiety is reported for the first time. A full characterization of the Cu(II) complex was conducted by X-ray crystallography, EPR, IR, elemental and MS analysis, and its binding to CT-DNA was investigated by UV-vis spectroscopy, ethidium bromide competition studies, circular dichroism, viscometry and thermal denaturation. The data clearly indicate that the Cu(II) complex interacts with CT-DNA via intercalation, registering a difference compared to previously reported Pt(II) and Pd(II) analogues. To evaluate the anticancer activity of the complex, a series of in vitro experiments against breast, glioblastoma, prostate and lung cancer cell lines along with healthy fibroblasts were implemented. Cytotoxicity, cellular uptake, intracellular ROS production, cell cycle and apoptosis analysis revealed an increased anticancer activity towards breast cancer cells that is accompanied by an induction in intracellular ROS levels and a significant G2/M arrest followed by apoptosis.
Author Methenitis, Constantinos
Mitrikas, George
Bouziotis, Penelope
Pelecanou, Maria
Hatzidimitriou, Antonios G.
Mavroidi, Barbara
Sagnou, Marina
Kapiris, Fotis
Halevas, Eleftherios
Author_xml – sequence: 1
  givenname: Barbara
  orcidid: 0000-0002-4453-5758
  surname: Mavroidi
  fullname: Mavroidi, Barbara
– sequence: 2
  givenname: Marina
  orcidid: 0000-0002-4231-6658
  surname: Sagnou
  fullname: Sagnou, Marina
– sequence: 3
  givenname: Eleftherios
  orcidid: 0000-0002-6803-5395
  surname: Halevas
  fullname: Halevas, Eleftherios
– sequence: 4
  givenname: George
  orcidid: 0000-0001-7874-2846
  surname: Mitrikas
  fullname: Mitrikas, George
– sequence: 5
  givenname: Fotis
  surname: Kapiris
  fullname: Kapiris, Fotis
– sequence: 6
  givenname: Penelope
  orcidid: 0000-0001-6778-2201
  surname: Bouziotis
  fullname: Bouziotis, Penelope
– sequence: 7
  givenname: Antonios G.
  surname: Hatzidimitriou
  fullname: Hatzidimitriou, Antonios G.
– sequence: 8
  givenname: Maria
  orcidid: 0000-0002-7669-2424
  surname: Pelecanou
  fullname: Pelecanou, Maria
– sequence: 9
  givenname: Constantinos
  surname: Methenitis
  fullname: Methenitis, Constantinos
BookMark eNplUctu2zAQJIoUaJrmB3oi0EtyUMOHREq9OWrSGAiQQ3wX1uQqpiGTLkU5dU79iH5JPqlfUqYuigLdyw52BzOD3bfkyAePhLzn7KOUDbtwPsQH8M6MnDPJuBSvyLGQrCyULtnRP_gNOR3HNcvVcFnL-pj8mNFFdBZ9goS0nc7m83Pahs12wG_00aUVBSqKs_Ln9-ditslO2xX6_XB-if4ppJWDpzAg_YzR7SC5HX6ibdyPCQZ6n-Jk0hSRgrf00oUhPDiTF1c7GKZMDp72IdKZT3nsDWZosoRL-3fkdQ_DiKd_-glZXF8t2pvi9u7LvJ3dFkZKlQpVl6JiprfYVKXUtuZCNkurl7zHspagVVXxvjdY69Ja1oPQZslUhQJshUaekPlB1gZYd9voNhD3XQDX_R7ko3YQc7gBO86tAsNACVuVirFaWhQlM0ZA_YKz1oeD1jaGrxOOqVuHKfqcvhO64ariQuvMEgeWiWEcI_Z_XTnrXn7Z_f9L-Quoc5h5
Cites_doi 10.1016/j.jtemb.2018.01.011
10.1007/s00280-006-0364-9
10.1007/s10895-017-2151-x
10.1016/S0022-2836(61)80004-1
10.3390/molecules23040721
10.1016/j.jphotobiol.2016.06.022
10.1016/0022-2836(74)90031-X
10.1186/s12929-019-0518-9
10.1016/j.jinorgbio.2020.111083
10.1016/0003-9861(74)90298-7
10.1016/S1367-5931(03)00018-8
10.1186/1471-2407-14-527
10.1021/jm1001293
10.1016/j.jinorgbio.2006.09.014
10.1021/bi00617a002
10.1016/j.ijbiomac.2017.10.131
10.1080/00958972.2016.1250153
10.1016/j.ica.2016.01.012
10.1021/ja01640a067
10.1016/j.cbpa.2007.11.013
10.1007/s10895-013-1211-0
10.1385/089603447X
10.1107/S0021889803021800
10.1016/j.jinorgbio.2021.111692
10.1016/j.semcdb.2017.07.012
10.1089/154545703322860825
10.1039/C9DT04540F
10.1016/0022-2836(67)90353-1
10.1039/b801549j
10.1039/c3dt52518j
10.1002/bip.360311405
10.1016/S0162-0134(01)00344-0
10.1016/j.jphotobiol.2016.06.030
10.2174/187152009787313837
10.1016/j.leukres.2016.11.001
10.1107/S0021889807029238
10.3390/molecules26134028
10.1016/j.ica.2020.120062
10.1007/s10895-012-1038-0
10.1039/c0dt00292e
10.1039/D1DT01358K
10.1016/j.jmr.2005.08.013
10.1016/j.jinorgbio.2012.09.019
10.1016/j.ejmech.2017.10.058
10.1016/j.jinorgbio.2013.10.023
10.1016/0006-2952(90)90065-S
10.1007/s10637-022-01211-z
10.1016/S0006-2952(02)00918-8
10.3389/fonc.2022.837373
10.1007/s10534-012-9578-y
10.2174/0929867013373714
10.1021/ic981100x
10.1002/bip.360320910
10.3389/fchem.2021.716771
10.1158/1535-7163.MCT-08-0840
10.3390/molecules27196485
10.1021/acsomega.0c00275
10.1080/00958972.2020.1793966
10.1021/bi00371a023
10.1073/pnas.0708143105
10.1007/s00775-015-1298-7
10.3390/cancers12102863
10.1007/s11356-019-05345-1
10.3390/polym8020051
10.7554/eLife.04630
10.3390/M1114
10.1038/bjc.1998.122
10.1007/s10895-016-1818-z
10.2116/analsci.17.1031
ContentType Journal Article
Copyright 2023 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.
Copyright_xml – notice: 2023 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.
DBID AAYXX
CITATION
3V.
7XB
8FE
8FG
8FH
8FK
8G5
ABJCF
ABUWG
AFKRA
AZQEC
BBNVY
BENPR
BGLVJ
BHPHI
CCPQU
D1I
DWQXO
GNUQQ
GUQSH
HCIFZ
KB.
LK8
M2O
M7P
MBDVC
PADUT
PDBOC
PIMPY
PQEST
PQQKQ
PQUKI
PRINS
Q9U
DOA
DOI 10.3390/inorganics11030132
DatabaseName CrossRef
ProQuest Central (Corporate)
ProQuest Central (purchase pre-March 2016)
ProQuest SciTech Collection
ProQuest Technology Collection
ProQuest Natural Science Collection
ProQuest Central (Alumni) (purchase pre-March 2016)
Research Library (Alumni Edition)
Materials Science & Engineering Collection
ProQuest Central (Alumni)
ProQuest Central UK/Ireland
ProQuest Central Essentials
Biological Science Collection
AUTh Library subscriptions: ProQuest Central
Technology Collection
ProQuest Natural Science Collection
ProQuest One Community College
ProQuest Materials Science Collection
ProQuest Central
ProQuest Central Student
Research Library Prep
SciTech Premium Collection (Proquest) (PQ_SDU_P3)
ProQuest Materials Science Database
Biological Sciences
ProQuest research library
Biological Science Database
Research Library (Corporate)
Research Library China
Materials Science Collection
Access via ProQuest (Open Access)
ProQuest One Academic Eastern Edition (DO NOT USE)
ProQuest One Academic
ProQuest One Academic UKI Edition
ProQuest Central China
ProQuest Central Basic
Directory of Open Access Journals
DatabaseTitle CrossRef
Publicly Available Content Database
Research Library Prep
ProQuest Central Student
Technology Collection
ProQuest Central Essentials
Materials Science Collection
ProQuest Central (Alumni Edition)
SciTech Premium Collection
ProQuest One Community College
Research Library (Alumni Edition)
ProQuest Natural Science Collection
ProQuest Central China
ProQuest Central
Natural Science Collection
ProQuest Central Korea
Biological Science Collection
Materials Science Database
ProQuest Research Library
Research Library China
ProQuest Materials Science Collection
ProQuest Biological Science Collection
ProQuest Central Basic
ProQuest One Academic Eastern Edition
ProQuest Technology Collection
Biological Science Database
ProQuest SciTech Collection
ProQuest One Academic UKI Edition
Materials Science & Engineering Collection
ProQuest One Academic
ProQuest Central (Alumni)
DatabaseTitleList Publicly Available Content Database

CrossRef
Database_xml – sequence: 1
  dbid: DOA
  name: DOAJ Directory of Open Access Journals
  url: https://www.doaj.org/
  sourceTypes: Open Website
– sequence: 2
  dbid: 8FG
  name: ProQuest Technology Collection
  url: https://search.proquest.com/technologycollection1
  sourceTypes: Aggregation Database
DeliveryMethod fulltext_linktorsrc
Discipline Chemistry
EISSN 2304-6740
ExternalDocumentID oai_doaj_org_article_11d6ac0a62d5460083de240cc2a883de
10_3390_inorganics11030132
GroupedDBID 3V.
5VS
8FE
8FG
8FH
8G5
AADQD
AAFWJ
AAYXX
ABDBF
ABJCF
ABUWG
ACIWK
ACPRK
ADBBV
ADFRT
AFKRA
AFPKN
AFZYC
ALMA_UNASSIGNED_HOLDINGS
AZQEC
BBNVY
BCNDV
BENPR
BGLVJ
BHPHI
BPHCQ
CCPQU
CITATION
D1I
DWQXO
GNUQQ
GROUPED_DOAJ
GUQSH
GX1
HCIFZ
IAO
ITC
KB.
KQ8
LK8
M2O
M7P
MODMG
M~E
OK1
PADUT
PDBOC
PIMPY
PQQKQ
PROAC
7XB
8FK
MBDVC
PQEST
PQUKI
PRINS
Q9U
ID FETCH-LOGICAL-c336t-684250cfde95437d81239bd7b1fe483a76551ffce874dd0fa27cb065e2ad5ec3
IEDL.DBID DOA
ISSN 2304-6740
IngestDate Tue Oct 22 15:07:00 EDT 2024
Thu Oct 10 17:44:29 EDT 2024
Thu Sep 26 15:53:41 EDT 2024
IsDoiOpenAccess true
IsOpenAccess true
IsPeerReviewed true
IsScholarly true
Issue 3
Language English
LinkModel DirectLink
MergedId FETCHMERGED-LOGICAL-c336t-684250cfde95437d81239bd7b1fe483a76551ffce874dd0fa27cb065e2ad5ec3
ORCID 0000-0002-4453-5758
0000-0001-7874-2846
0000-0002-4231-6658
0000-0002-6803-5395
0000-0002-7669-2424
0000-0001-6778-2201
OpenAccessLink https://doaj.org/article/11d6ac0a62d5460083de240cc2a883de
PQID 2791651277
PQPubID 2032382
ParticipantIDs doaj_primary_oai_doaj_org_article_11d6ac0a62d5460083de240cc2a883de
proquest_journals_2791651277
crossref_primary_10_3390_inorganics11030132
PublicationCentury 2000
PublicationDate 2023-03-01
PublicationDateYYYYMMDD 2023-03-01
PublicationDate_xml – month: 03
  year: 2023
  text: 2023-03-01
  day: 01
PublicationDecade 2020
PublicationPlace Basel
PublicationPlace_xml – name: Basel
PublicationTitle Inorganics
PublicationYear 2023
Publisher MDPI AG
Publisher_xml – name: MDPI AG
References Gaal (ref_8) 2018; 47
Lyng (ref_39) 1992; 32
Leon (ref_65) 2015; 20
LePecq (ref_41) 1967; 27
Jakusch (ref_24) 2022; 228
Stoll (ref_27) 2006; 178
Reichmann (ref_29) 1954; 76
ref_14
Lyng (ref_40) 1991; 31
ref_13
Mavroidi (ref_75) 2022; 40
McWhinney (ref_10) 2009; 8
Molinaro (ref_66) 2022; 12
Huy (ref_4) 1990; 39
Qin (ref_12) 2018; 143
Mavroidi (ref_22) 2016; 444
Chen (ref_55) 2020; 73
Han (ref_17) 2007; 101
Peisach (ref_28) 1974; 165
Ester (ref_56) 2014; 30
Tzanopoulou (ref_23) 2010; 53
Halevas (ref_26) 2021; 515
Halevas (ref_25) 2020; 208
Bolos (ref_64) 2002; 88
Jullian (ref_51) 2020; 5
Li (ref_38) 2013; 119
ref_68
Banerjee (ref_43) 2013; 23
ref_67
ref_20
Husain (ref_62) 2019; 26
ref_63
Loganathan (ref_37) 2014; 43
He (ref_50) 2008; 24
Szymanski (ref_7) 2012; 25
Shi (ref_59) 2018; 73
Weder (ref_6) 1999; 38
Sunita (ref_30) 2012; 22
Goodwin (ref_54) 2008; 105
Liu (ref_53) 2001; 17
Bruijnincx (ref_18) 2008; 12
ref_71
Sangeetha (ref_15) 2018; 107
Brewer (ref_2) 2003; 7
Marzano (ref_16) 2009; 9
Joseph (ref_31) 2016; 162
Lerman (ref_52) 1961; 3
ref_73
Palatinus (ref_70) 2007; 40
Devi (ref_74) 2017; 27
McGhee (ref_72) 1974; 86
Betteridge (ref_69) 2003; 36
Chiniforoshan (ref_48) 2016; 162
Bradshaw (ref_57) 1998; 77
(ref_21) 2007; 60
Lebon (ref_3) 2002; 63
Bradshaw (ref_58) 2001; 8
Wheate (ref_11) 2010; 39
ref_46
ref_45
Vamsikrishna (ref_33) 2016; 26
Iqbal (ref_5) 1990; 40
Mallam (ref_34) 2014; 3
ref_1
Volarevic (ref_9) 2019; 26
Gaugain (ref_42) 1978; 17
Halevas (ref_76) 2020; 49
Romo (ref_61) 2021; 50
ref_49
Mayani (ref_19) 2017; 52
Mergny (ref_44) 2003; 13
Saraswathi (ref_47) 2021; 9
Joseph (ref_32) 2016; 70
Pakravan (ref_36) 2015; 14
Kwon (ref_60) 2014; 131
Kuwabara (ref_35) 1986; 25
References_xml – volume: 47
  start-page: 79
  year: 2018
  ident: ref_8
  article-title: Metal transport capabilities of anticancer copper chelators
  publication-title: J. Trace Elem. Med. Biol.
  doi: 10.1016/j.jtemb.2018.01.011
  contributor:
    fullname: Gaal
– volume: 60
  start-page: 219
  year: 2007
  ident: ref_21
  article-title: Induction of oxidative damage by copper-based antineoplastic drugs (Casiopeinas)
  publication-title: Cancer Chemother. Pharmacol.
  doi: 10.1007/s00280-006-0364-9
– volume: 27
  start-page: 2119
  year: 2017
  ident: ref_74
  article-title: Analytical Techniques Used to Detect DNA Binding Modes of Ruthenium(II) Complexes with Extended Phenanthroline Ring
  publication-title: J. Fluoresc.
  doi: 10.1007/s10895-017-2151-x
  contributor:
    fullname: Devi
– ident: ref_68
– volume: 3
  start-page: 18
  year: 1961
  ident: ref_52
  article-title: Structural considerations in the interaction of DNA and acridines
  publication-title: J. Mol. Biol.
  doi: 10.1016/S0022-2836(61)80004-1
  contributor:
    fullname: Lerman
– ident: ref_63
  doi: 10.3390/molecules23040721
– volume: 162
  start-page: 34
  year: 2016
  ident: ref_48
  article-title: A novel Schiff base derived from the gabapentin drug and copper (II) complex: Synthesis, characterization, interaction with DNA/protein and cytotoxic activity
  publication-title: J. Photochem. Photobiol. B
  doi: 10.1016/j.jphotobiol.2016.06.022
  contributor:
    fullname: Chiniforoshan
– volume: 86
  start-page: 469
  year: 1974
  ident: ref_72
  article-title: Theoretical aspects of DNA-protein interactions: Co-operative and non-co-operative binding of large ligands to a one-dimensional homogeneous lattice
  publication-title: J. Mol. Biol.
  doi: 10.1016/0022-2836(74)90031-X
  contributor:
    fullname: McGhee
– volume: 26
  start-page: 25
  year: 2019
  ident: ref_9
  article-title: Molecular mechanisms of cisplatin-induced nephrotoxicity: A balance on the knife edge between renoprotection and tumor toxicity
  publication-title: J. Biomed. Sci.
  doi: 10.1186/s12929-019-0518-9
  contributor:
    fullname: Volarevic
– volume: 208
  start-page: 111083
  year: 2020
  ident: ref_25
  article-title: Synthesis, physicochemical characterization and biological properties of two novel Cu(II) complexes based on natural products curcumin and quercetin
  publication-title: J. Inorg. Biochem.
  doi: 10.1016/j.jinorgbio.2020.111083
  contributor:
    fullname: Halevas
– volume: 165
  start-page: 691
  year: 1974
  ident: ref_28
  article-title: Structural implications derived from the analysis of electron paramagnetic resonance spectra of natural and artificial copper proteins
  publication-title: Arch. Biochem. Biophys.
  doi: 10.1016/0003-9861(74)90298-7
  contributor:
    fullname: Peisach
– ident: ref_1
– volume: 7
  start-page: 207
  year: 2003
  ident: ref_2
  article-title: Copper in medicine
  publication-title: Curr. Opin. Chem. Biol.
  doi: 10.1016/S1367-5931(03)00018-8
  contributor:
    fullname: Brewer
– ident: ref_71
– ident: ref_14
  doi: 10.1186/1471-2407-14-527
– volume: 53
  start-page: 4633
  year: 2010
  ident: ref_23
  article-title: Evaluation of Re and (99m)Tc complexes of 2-(4′-aminophenyl)benzothiazole as potential breast cancer radiopharmaceuticals
  publication-title: J. Med. Chem.
  doi: 10.1021/jm1001293
  contributor:
    fullname: Tzanopoulou
– volume: 101
  start-page: 214
  year: 2007
  ident: ref_17
  article-title: DNA cleavage mediated by copper superoxide dismutase via two pathways
  publication-title: J. Inorg. Biochem.
  doi: 10.1016/j.jinorgbio.2006.09.014
  contributor:
    fullname: Han
– volume: 17
  start-page: 5078
  year: 1978
  ident: ref_42
  article-title: DNA Bifunctional intercalators. 2. Fluorescence properties and DNA binding interaction of an ethidium homodimer and an acridine ethidium heterodimer
  publication-title: Biochemistry
  doi: 10.1021/bi00617a002
  contributor:
    fullname: Gaugain
– volume: 107
  start-page: 2501
  year: 2018
  ident: ref_15
  article-title: Non-covalent DNA binding, protein interaction, DNA cleavage and cytotoxicity of [Cu(quamol)Cl].H(2)O
  publication-title: Int. J. Biol. Macromol.
  doi: 10.1016/j.ijbiomac.2017.10.131
  contributor:
    fullname: Sangeetha
– volume: 70
  start-page: 242
  year: 2016
  ident: ref_32
  article-title: Antimicrobial, antioxidant and SOD activities of copper(II) complexes derived from 2-aminobenzothiazole derivatives
  publication-title: J. Coord. Chem.
  doi: 10.1080/00958972.2016.1250153
  contributor:
    fullname: Joseph
– volume: 444
  start-page: 63
  year: 2016
  ident: ref_22
  article-title: Palladium(II) and platinum(II) complexes of derivatives of 2-(4′-aminophenyl)benzothiazole as potential anticancer agents
  publication-title: Inorg. Chim. Acta
  doi: 10.1016/j.ica.2016.01.012
  contributor:
    fullname: Mavroidi
– volume: 76
  start-page: 3047
  year: 1954
  ident: ref_29
  article-title: A Further Examination of the Molecular Weight and Size of Desoxypentose Nucleic Acid
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/ja01640a067
  contributor:
    fullname: Reichmann
– volume: 12
  start-page: 197
  year: 2008
  ident: ref_18
  article-title: New trends for metal complexes with anticancer activity
  publication-title: Curr. Opin. Chem. Biol.
  doi: 10.1016/j.cbpa.2007.11.013
  contributor:
    fullname: Bruijnincx
– volume: 23
  start-page: 745
  year: 2013
  ident: ref_43
  article-title: Fluorescence spectroscopic and calorimetry based approaches to characterize the mode of interaction of small molecules with DNA
  publication-title: J. Fluoresc.
  doi: 10.1007/s10895-013-1211-0
  contributor:
    fullname: Banerjee
– ident: ref_49
  doi: 10.1385/089603447X
– volume: 36
  start-page: 1487
  year: 2003
  ident: ref_69
  article-title: Software for guided crystal structure analysis
  publication-title: J. Appl. Cryst.
  doi: 10.1107/S0021889803021800
  contributor:
    fullname: Betteridge
– volume: 228
  start-page: 111692
  year: 2022
  ident: ref_24
  article-title: Characterization of copper(II) specific pyridine containing ligands: Potential metallophores for Alzheimer’s disease therapy
  publication-title: J. Inorg. Biochem.
  doi: 10.1016/j.jinorgbio.2021.111692
  contributor:
    fullname: Jakusch
– volume: 73
  start-page: 31
  year: 2018
  ident: ref_59
  article-title: The structure and function of cell membranes studied by atomic force microscopy
  publication-title: Semin. Cell Dev. Biol.
  doi: 10.1016/j.semcdb.2017.07.012
  contributor:
    fullname: Shi
– volume: 13
  start-page: 515
  year: 2003
  ident: ref_44
  article-title: Analysis of thermal melting curves
  publication-title: Oligonucleotides
  doi: 10.1089/154545703322860825
  contributor:
    fullname: Mergny
– volume: 49
  start-page: 2734
  year: 2020
  ident: ref_76
  article-title: Structurally characterized gallium-chrysin complexes with anticancer potential
  publication-title: Dalton Trans.
  doi: 10.1039/C9DT04540F
  contributor:
    fullname: Halevas
– volume: 27
  start-page: 87
  year: 1967
  ident: ref_41
  article-title: A fluorescent complex between ethidium bromide and nucleic acids. Physical-chemical characterization
  publication-title: J. Mol. Biol.
  doi: 10.1016/0022-2836(67)90353-1
  contributor:
    fullname: LePecq
– volume: 24
  start-page: 3207
  year: 2008
  ident: ref_50
  article-title: Double-strand DNA cleavage by copper complexes of 2,2′-dipyridyl with guanidinium/ammonium pendants
  publication-title: Dalton Trans.
  doi: 10.1039/b801549j
  contributor:
    fullname: He
– volume: 43
  start-page: 6177
  year: 2014
  ident: ref_37
  article-title: Mixed ligand mu-phenoxo-bridged dinuclear copper(II) complexes with diimine co-ligands: Efficient chemical nuclease and protease activities and cytotoxicity
  publication-title: Dalton Trans.
  doi: 10.1039/c3dt52518j
  contributor:
    fullname: Loganathan
– volume: 31
  start-page: 1709
  year: 1991
  ident: ref_40
  article-title: The CD of ligand-DNA systems. I. Poly(dG-dC) B-DNA
  publication-title: Biopolymers
  doi: 10.1002/bip.360311405
  contributor:
    fullname: Lyng
– volume: 88
  start-page: 25
  year: 2002
  ident: ref_64
  article-title: Antiproliferative activity of mixed-ligand dien-Cu(II) complexes with thiazole, thiazoline and imidazole derivatives
  publication-title: J. Inorg. Biochem.
  doi: 10.1016/S0162-0134(01)00344-0
  contributor:
    fullname: Bolos
– volume: 162
  start-page: 86
  year: 2016
  ident: ref_31
  article-title: Copper complexes bearing 2-aminobenzothiazole derivatives as potential antioxidant: Synthesis, characterization
  publication-title: J. Photochem. Photobiol. B
  doi: 10.1016/j.jphotobiol.2016.06.030
  contributor:
    fullname: Joseph
– volume: 9
  start-page: 185
  year: 2009
  ident: ref_16
  article-title: Copper complexes as anticancer agents
  publication-title: Anticancer Agents Med. Chem.
  doi: 10.2174/187152009787313837
  contributor:
    fullname: Marzano
– volume: 52
  start-page: 8
  year: 2017
  ident: ref_19
  article-title: Casiopeina III-Ea, a copper-containing small molecule, inhibits the in vitro growth of primitive hematopoietic cells from chronic myeloid leukemia
  publication-title: Leuk. Res.
  doi: 10.1016/j.leukres.2016.11.001
  contributor:
    fullname: Mayani
– volume: 40
  start-page: 786
  year: 2007
  ident: ref_70
  article-title: SUPERFLIP—A Computer Program for the Solution of Crystal Structures by Charge Flipping in Arbitrary Dimensions
  publication-title: J. Appl. Crystallogr.
  doi: 10.1107/S0021889807029238
  contributor:
    fullname: Palatinus
– ident: ref_73
  doi: 10.3390/molecules26134028
– volume: 515
  start-page: 120062
  year: 2021
  ident: ref_26
  article-title: Structurally characterized copper-chrysin complexes display genotoxic and cytotoxic activity in human cells
  publication-title: Inorg. Chim. Acta
  doi: 10.1016/j.ica.2020.120062
  contributor:
    fullname: Halevas
– volume: 22
  start-page: 1003
  year: 2012
  ident: ref_30
  article-title: Synthesis, characterization, DNA binding and cleavage studies of mixed-ligand Cu(II) complexes of 2,6-bis(benzimidazol-2-yl)pyridine
  publication-title: J. Fluoresc.
  doi: 10.1007/s10895-012-1038-0
  contributor:
    fullname: Sunita
– volume: 39
  start-page: 8113
  year: 2010
  ident: ref_11
  article-title: The status of platinum anticancer drugs in the clinic and in clinical trials
  publication-title: Dalton Trans.
  doi: 10.1039/c0dt00292e
  contributor:
    fullname: Wheate
– volume: 14
  start-page: 111
  year: 2015
  ident: ref_36
  article-title: Study on the Interaction between Isatin-beta-Thiosemicarbazone and Calf Thymus DNA by Spectroscopic Techniques
  publication-title: Iran. J. Pharm. Res.
  contributor:
    fullname: Pakravan
– volume: 50
  start-page: 11931
  year: 2021
  ident: ref_61
  article-title: Synergy of DNA intercalation and catalytic activity of a copper complex towards improved polymerase inhibition and cancer cell cytotoxicity
  publication-title: Dalton Trans.
  doi: 10.1039/D1DT01358K
  contributor:
    fullname: Romo
– volume: 178
  start-page: 42
  year: 2006
  ident: ref_27
  article-title: EasySpin, a comprehensive software package for spectral simulation and analysis in EPR
  publication-title: J. Magn. Reason.
  doi: 10.1016/j.jmr.2005.08.013
  contributor:
    fullname: Stoll
– volume: 119
  start-page: 43
  year: 2013
  ident: ref_38
  article-title: Synthesis, crystal structure, DNA interaction and anticancer activity of tridentate copper(II) complexes
  publication-title: J. Inorg. Biochem.
  doi: 10.1016/j.jinorgbio.2012.09.019
  contributor:
    fullname: Li
– volume: 143
  start-page: 1597
  year: 2018
  ident: ref_12
  article-title: Synthesis, crystal structure and biological evaluation of a new dasatinib copper(II) complex as telomerase inhibitor
  publication-title: Eur. J. Med. Chem.
  doi: 10.1016/j.ejmech.2017.10.058
  contributor:
    fullname: Qin
– volume: 131
  start-page: 79
  year: 2014
  ident: ref_60
  article-title: DNA cleavage induced by [Cu(L)x(NO3)2] (L = 2,2′-dipyridylamine, 2,2′-bipyridine, dipicolylamine, x = 1 or 2): Effect of the ligand structure
  publication-title: J. Inorg. Biochem.
  doi: 10.1016/j.jinorgbio.2013.10.023
  contributor:
    fullname: Kwon
– volume: 39
  start-page: 569
  year: 1990
  ident: ref_4
  article-title: Non-steroidal anti-inflammatory drug-copper complex modulation of polymorphonuclear leukocyte migration
  publication-title: Biochem. Pharmacol.
  doi: 10.1016/0006-2952(90)90065-S
  contributor:
    fullname: Huy
– volume: 40
  start-page: 497
  year: 2022
  ident: ref_75
  article-title: Biological evaluation of complexes of cyclopentadienyl M(CO)(3)(+) (M = Re, (99m)Tc) with high blood-brain barrier penetration potential as brain cancer agents
  publication-title: Investig. New Drugs
  doi: 10.1007/s10637-022-01211-z
  contributor:
    fullname: Mavroidi
– volume: 63
  start-page: 1863
  year: 2002
  ident: ref_3
  article-title: Metal-organic compounds: A new approach for drug discovery. N1-(4-methyl-2-pyridyl)-2,3,6-trimethoxybenzamide copper(II) complex as an inhibitor of human immunodeficiency virus 1 protease
  publication-title: Biochem. Pharmacol.
  doi: 10.1016/S0006-2952(02)00918-8
  contributor:
    fullname: Lebon
– volume: 12
  start-page: 837373
  year: 2022
  ident: ref_66
  article-title: A Novel Copper(II) Indenoisoquinoline Complex Inhibits Topoisomerase I, Induces G2 Phase Arrest, and Autophagy in Three Adenocarcinomas
  publication-title: Front. Oncol.
  doi: 10.3389/fonc.2022.837373
  contributor:
    fullname: Molinaro
– volume: 25
  start-page: 1089
  year: 2012
  ident: ref_7
  article-title: Development of copper based drugs, radiopharmaceuticals and medical materials
  publication-title: Biometals
  doi: 10.1007/s10534-012-9578-y
  contributor:
    fullname: Szymanski
– ident: ref_67
– volume: 8
  start-page: 203
  year: 2001
  ident: ref_58
  article-title: The discovery of the potent and selective antitumour agent 2-(4-amino-3-methylphenyl)benzothiazole (DF 203) and related compounds
  publication-title: Curr. Med. Chem.
  doi: 10.2174/0929867013373714
  contributor:
    fullname: Bradshaw
– volume: 38
  start-page: 1736
  year: 1999
  ident: ref_6
  article-title: Anti-Inflammatory Dinuclear Copper(II) Complexes with Indomethacin. Synthesis, Magnetism and EPR Spectroscopy. Crystal Structure of the N,N-Dimethylformamide Adduct
  publication-title: Inorg. Chem.
  doi: 10.1021/ic981100x
  contributor:
    fullname: Weder
– volume: 32
  start-page: 1201
  year: 1992
  ident: ref_39
  article-title: The CD of ligand-DNA systems. 2. Poly(dA-dT) B-DNA
  publication-title: Biopolymers
  doi: 10.1002/bip.360320910
  contributor:
    fullname: Lyng
– volume: 9
  start-page: 716771
  year: 2021
  ident: ref_47
  article-title: DNA Condensation Triggered by the Synergistic Self-Assembly of Tetraphenylethylene-Viologen Aggregates and CT-DNA
  publication-title: Front. Chem.
  doi: 10.3389/fchem.2021.716771
  contributor:
    fullname: Saraswathi
– volume: 8
  start-page: 10
  year: 2009
  ident: ref_10
  article-title: Platinum neurotoxicity pharmacogenetics
  publication-title: Mol. Cancer Ther.
  doi: 10.1158/1535-7163.MCT-08-0840
  contributor:
    fullname: McWhinney
– ident: ref_20
  doi: 10.3390/molecules27196485
– volume: 5
  start-page: 6928
  year: 2020
  ident: ref_51
  article-title: Influence of DMbetaCD on the Interaction of Copper(II) Complex of 6-Hydroxychromone-3-carbaldehyde-3-hydroxybenzoylhydrazine with ctDNA
  publication-title: ACS Omega
  doi: 10.1021/acsomega.0c00275
  contributor:
    fullname: Jullian
– volume: 73
  start-page: 1817
  year: 2020
  ident: ref_55
  article-title: Biological properties of a benzothiazole-based mononuclear platinum(II) complex as a potential anticancer agent
  publication-title: J. Coord. Chem.
  doi: 10.1080/00958972.2020.1793966
  contributor:
    fullname: Chen
– volume: 40
  start-page: 221
  year: 1990
  ident: ref_5
  article-title: Antibacterial activity of copper-amino acid complexes
  publication-title: J. Pak. Med. Assoc.
  contributor:
    fullname: Iqbal
– volume: 25
  start-page: 7401
  year: 1986
  ident: ref_35
  article-title: Nuclease activity of 1, 10-phenanthroline-copper ion: Reaction with CGCGAATTCGCG and its complexes with netropsin and EcoRI
  publication-title: Biochemistry
  doi: 10.1021/bi00371a023
  contributor:
    fullname: Kuwabara
– volume: 105
  start-page: 5052
  year: 2008
  ident: ref_54
  article-title: Crystal structure of DNA-bound Co(III) bleomycin B2: Insights on intercalation and minor groove binding
  publication-title: Proc. Natl. Acad. Sci. USA
  doi: 10.1073/pnas.0708143105
  contributor:
    fullname: Goodwin
– volume: 20
  start-page: 1175
  year: 2015
  ident: ref_65
  article-title: Oxidovanadium(IV) complexes with chrysin and silibinin: Anticancer activity and mechanisms of action in a human colon adenocarcinoma model
  publication-title: J. Biol. Inorg. Chem.
  doi: 10.1007/s00775-015-1298-7
  contributor:
    fullname: Leon
– ident: ref_13
  doi: 10.3390/cancers12102863
– volume: 26
  start-page: 20654
  year: 2019
  ident: ref_62
  article-title: Copper(II) generates ROS and RNS, impairs antioxidant system and damages membrane and DNA in human blood cells
  publication-title: Environ. Sci. Pollut. Res. Int.
  doi: 10.1007/s11356-019-05345-1
  contributor:
    fullname: Husain
– ident: ref_46
  doi: 10.3390/polym8020051
– volume: 3
  start-page: e04630
  year: 2014
  ident: ref_34
  article-title: Molecular insights into RNA and DNA helicase evolution from the determinants of specificity for a DEAD-box RNA helicase
  publication-title: eLife
  doi: 10.7554/eLife.04630
  contributor:
    fullname: Mallam
– volume: 30
  start-page: 4935
  year: 2014
  ident: ref_56
  article-title: Interactions with polynucleotides and antitumor activity of amidino and imidazolinyl substituted 2-phenylbenzothiazole mesylates
  publication-title: Eur J. Med. Chem.
  contributor:
    fullname: Ester
– ident: ref_45
  doi: 10.3390/M1114
– volume: 77
  start-page: 745
  year: 1998
  ident: ref_57
  article-title: 2-(4-Aminophenyl)benzothiazoles: Novel agents with selective profiles of in vitro anti-tumour activity
  publication-title: Br. J. Cancer
  doi: 10.1038/bjc.1998.122
  contributor:
    fullname: Bradshaw
– volume: 26
  start-page: 1317
  year: 2016
  ident: ref_33
  article-title: DNA Binding, Cleavage and Antibacterial Activity of Mononuclear Cu(II), Ni(II) and Co(II) Complexes Derived from Novel Benzothiazole Schiff Bases
  publication-title: J. Fluoresc.
  doi: 10.1007/s10895-016-1818-z
  contributor:
    fullname: Vamsikrishna
– volume: 17
  start-page: 1031
  year: 2001
  ident: ref_53
  article-title: Fluorescence spectral study of interaction of water-soluble metal complexes of Schiff-base and DNA
  publication-title: Anal. Sci.
  doi: 10.2116/analsci.17.1031
  contributor:
    fullname: Liu
SSID ssj0000913838
Score 2.2643633
Snippet Herein, the synthesis, structural characterization and in vitro biological evaluation of a novel Cu(II) complex with the 2-(4-aminophenyl)benzothiazole...
SourceID doaj
proquest
crossref
SourceType Open Website
Aggregation Database
StartPage 132
SubjectTerms 2-(4-aminophenyl)benzothiazole
Anticancer properties
Antitumor activity
Apoptosis
Benzothiazole
Biological activity
Cancer
Cell cycle
Chelation
Circular dichroism
Clinical trials
Copper
copper(II) complex
Crystal structure
Crystallography
Cytotoxicity
Dichroism
DNA binding studies
Ethidium bromide
Fibroblasts
Glioblastoma
in vitro evaluation
Intracellular
Ligands
Lung cancer
Nitrates
Nitrogen
Palladium
Prostate
Prostate cancer
Spectroscopy
Spectrum analysis
Structural analysis
Thermal denaturation
Toxicity
Tumor cell lines
Viscometry
X-ray crystallography
SummonAdditionalLinks – databaseName: ProQuest Technology Collection
  dbid: 8FG
  link: http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwfV3NSgMxEA5aD3oRf7FaJQcPiix2k-xm60Xa2loFvVjB25LNDxTqVlsrticfwifxkXwSZ3a3FRG8hU0OS-bvm0kyHyGHlkvhIC57zk-MJxLJwKSY8zTHl5o6MjWHJ7o3t2HnXlw_BA9FwW1UXKuc-cTMUZuBxhr5KZMAZCA6SXn-9OwhaxSerhYUGotkCWcw-Yral_MaC_a8jHiUv5XhkN2f9tKcLEmPfOTX8jn7FY-ytv1_vHIWatprZLXAiLSeC3WdLNh0gyw3Z9Rsm-SjTrtDZANFpEib46Orq2OKlt23bxQrq1RR5h2Jr_dPr_4If4MXuSb944ZNpyCZnpoO-pZegPK9Zn2_z2hzOAGY2Kd3WTvZ8dBSlRqaE1WiGGlr3hWcAsyl9RRr4KAwMNQ5AcUW6bZb3WbHK-gVQBA8fPGyE7iqdsbWAsGlgVDPa4mRie-siLiSIaAp57SNpDCm6hSTOgHEYpkygdV8m5TSQWp3CHUwF-GLVykC4WtXqyoNDl0YoZjztS2Tk9kex095E40Ykg-USPxXImXSQDHMV2ID7OwDLIwLe4LExYRKV1XITCBCBJLGAjjRmqkIx2VSmQkxLqxyFP_o0O7_03tkBWnl87tmFVKCvbf7AD5ekoNMw74B1JPd9w
  priority: 102
  providerName: ProQuest
Title A Tridentate Cu(II) Complex with a 2-(4′-Aminophenyl)Benzothiazole Derivative: Crystal Structure and Biological Evaluation for Anticancer Activity
URI https://www.proquest.com/docview/2791651277
https://doaj.org/article/11d6ac0a62d5460083de240cc2a883de
Volume 11
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwrV3JTuQwELVYDsMFwcCIHpiWD3MAjSLiJXHCrbvpZpFAaOiRuEWOFwmpCaNmEXDiI_gSPokvmSq7GzHiwIVblFiK5VeueuWlHiE_nVDSQ1xOPKttImvFYUpxnxiBNzVNYUuPO7pHx_n-H3l4lp29kfrCM2GxPHAcuG3GbK5NqnNuM5kjY7AOopAxXBf4HLxvWr5JpoIPLhmkXkW8JSMgr98-b6JMkrliqKzFBP8vEoWC_e_8cQgygyWyOGGHtBN7tUxmXPOVfOlNRdlWyFOHDseoA4ockfZuNg8OtijO6ZG7o7imSjXlyaZ8eXxOOhfQGzzCdT_a6rrmATA51w-XI0d3wexuQ8XvHdob3wNBHNHTUEj2ZuyobiyNEpUIIO2_1gOnQHBpp8HVbzAVeDRRemKVDAf9YW8_mQgrAAQiv07C3ltqvHVlJoWyEORFWVtVM-9kIbTKgUd5b1yhpLWp11yZGriK49pmzohvZK65bNwaoR6-FXjXVclMMuPLVBtw5dJKzT0zrkV-Tce4-hvLZ1SQdiAi1XtEWqSLMLy2xNLX4QU0rCYGUX1kEC2yMQWxmszHq4oroMHAbZT6_hn_WCcLKDsfz6JtkDlAyP0AcnJdt8lsMdhrk_lu__jkdztY5T9jX-jW
link.rule.ids 315,783,787,867,2109,12777,21400,27936,27937,33385,33756,43612,43817,74363,74630
linkProvider Directory of Open Access Journals
linkToHtml http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwfV3JTsMwELVYDnBBrKKsPnBohSIa24lTLqgUSst2oUjcIseLhFRSaAHRnvgIvoRP4kuYSdIihMQtin2I8jwzz2PPPEL2LJfCQVz2nJ8YTySSgUkx52mOlZo6MjWHJ7pX12HrVpzfBXdFwm1QXKsc-8TMUZuexhz5AZNAZCA6SXn0-OShahSerhYSGtNkVnCI1Vgp3jyb5Fiw52XEo7xWhsPu_uA-zcWS9MBHfS2fs1_xKGvb_8crZ6GmuUgWCo5I6zmoS2TKpstkrjGWZlshH3Xa6aMaKDJF2ngpt9sVipbdtW8UM6tUUeaVxdf7p1d_gK_Bi1zDbuXYpiNA5l6Nel1LT2DxvWZ9vw9poz8EmtilN1k72Ze-pSo1NBeqRBjp6aQrOAWaS-sp5sBhwcCjzgUoVkmnedpptLxCXgGA4OGzl53AVbUzthYILg2Eel5LjEx8Z0XElQyBTTmnbSSFMVWnmNQJMBbLlAms5mtkJu2ldp1QB2MRVrxKEQhfu1pVaXDowgjFnK9tieyP_3H8mDfRiGHzgYjEfxEpkWOEYTITG2BnL2BiXNgTbFxMqHRVhcwEIkQiaSyQE62ZivC5RLbGIMaFVQ7inzW08f_wLplrda4u48v29cUmmUeJ-fze2RaZARzsNhCR52QnW23fS03g2Q
linkToPdf http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwfV3LSsNAFB20groRn1ifs3ChSGgzM8mkbqRWq_WFYAV3YTIPEGqqrYp15Uf4JX6SX-K9SVoRwV3IzCLk3MeZmTv3ELJluRQO8rLn_MR4IpEMXIo5T3O8qakjU3N4ontxGZ7ciNPb4Laof-oXZZXDmJgFatPVuEdeYRKIDGQnKSuuKIu4OmzuPzx6qCCFJ62FnMY4mYCsGKLNR83j0X4L9r-MeJTfm-Gw0q_cpblwku77qLXlc_YrN2Ut_P9E6CztNGfJTMEXaT0HeI6M2XSeTDWGMm0L5KNO2z1UBkXWSBvP263WDkUv79hXirusVFHmbYuv90-vfg9fg0Vdg87OgU3fAKU79dbtWHoIhviS9QDfo43eAChjh15nrWWfe5aq1NBctBIhpUejDuEUKC-tp7gfDsYDjzoXo1gk7eZRu3HiFVILAAoPn7zsNK6qnbG1QHBpIO3zWmJk4jsrIq5kCMzKOW0jKYypOsWkToC9WKZMYDVfIqW0m9plQh2MRXj7VYpA-NrVqkpDcBdGKOZ8bctkd_iP44e8oUYMCxFEJP6LSJkcIAyjmdgMO3sBE-PCt2ARY0KlqypkJhAhkkpjgahozVSEz2WyNgQxLjy0H__Y08r_w5tkEgwtPm9dnq2SaVSbz0vQ1kgJYLDrwEmeko3M2L4BfcnlEQ
openUrl ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=A+Tridentate+Cu%28II%29+Complex+with+a+2-%284%E2%80%B2-Aminophenyl%29Benzothiazole+Derivative%3A+Crystal+Structure+and+Biological+Evaluation+for+Anticancer+Activity&rft.jtitle=Inorganics&rft.au=Barbara+Mavroidi&rft.au=Marina+Sagnou&rft.au=Eleftherios+Halevas&rft.au=George+Mitrikas&rft.date=2023-03-01&rft.pub=MDPI+AG&rft.eissn=2304-6740&rft.volume=11&rft.issue=3&rft.spage=132&rft_id=info:doi/10.3390%2Finorganics11030132&rft.externalDBID=DOA&rft.externalDocID=oai_doaj_org_article_11d6ac0a62d5460083de240cc2a883de
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=2304-6740&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=2304-6740&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=2304-6740&client=summon