Nucleobase displacement from trans-diamineplatinum(II) complexes. A rationale for the inactivity of trans-DDP as an antitumor agent?

Krizanovic, Olga; Pesch, Ferdinand J.; Lippert, Bernhard

doi:10.1016/s0020-1693(00)83230-2

Cited by 23 publications

(5 citation statements)

References 10 publications

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“…For a = N H 3 or C H 3NH 2, the bis(l-M eC)-complex was the starting material of a series of heteronuclear complexes [14][15][16]. From its 'H NM R spectrum [14,19] the existence of two rotamers has been deduced.…”

Section: Resultsmentioning

confidence: 99%

Heteronuclear Nucleobase Complexes as Tools for the Isolation of the Minor Rotamer of the Parent Compound: Synthesis and Crystal Structure Determination of Head-Head and Head-Tail Forms of trans-[(CH₃NH₂)₂Pt(1-MeC-N3)₂]²⁺ (1-MeC = 1-methylcytosine)

Holthenrich

Sóvágó

Fusch

et al. 1995

Zeitschrift Für Naturforschung B

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Nucleobase rotation about bonds with transition metal ions has been intensively studied for purine complexes of d s-a2Pt(II) (with a = N H 3 or amine) [1][2][3][4][5][6][7][8][9]. Results obtained from these studies are considered meaningful with regard to the second step (chelate closure) of reactions of the antitum or agent d s-a2PtCl2 with DNA. Favorable or unfa vorable interactions between the am(m)ine li gands at the platinum atom and exocyclic groups of the nucleobases in the vicinity of the metal co ordination site are crucial as far as rotational b ar riers are concerned [5,7,8]. Although this aspect has been studied in detail for /V7-platinated p u rines only, it is of even greater significance to N3-platinated pyrimidine nucleobases. Qualitatively, we have dem onstrated in many instances that binding of a second metal ion to a TVJ-platinated pyrimidine base (uracil, thymine, cytosine) has a We have now applied the very same principle to a related system, namely to fra«s-[a2Pt(l-M eC -N3)2]2+ (1-MeC = 1-methylcytosine) for the following reasons: First, the aspect of nucleobase rotation has hardly been studied in complexes of trans-a2Pt(II) [13]; second, we have recently been able to characterize a series of heteronuclear com plexes of this compound with the two (deproto nated) nucleobases arranged head-head [14][15][16]; third, we found that removal of the heterom etal by a suitable nucleophile can be sufficiently fast, and subsequent ligand rotation sufficiently slow, to permit crystallization of the minor rotam er (headhead) of rra/7s-[a2Pt(l-MeC-/V3)2]2+ from aqueous solution. To the best of our knowledge, this is the

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Section: Resultsmentioning

confidence: 99%

Heteronuclear Nucleobase Complexes as Tools for the Isolation of the Minor Rotamer of the Parent Compound: Synthesis and Crystal Structure Determination of Head-Head and Head-Tail Forms of trans-[(CH₃NH₂)₂Pt(1-MeC-N3)₂]²⁺ (1-MeC = 1-methylcytosine)

Holthenrich

Sóvágó

Fusch

et al. 1995

Zeitschrift Für Naturforschung B

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“…A rationalization for formation of the bis(9MeA) complex with exclusive N1 coordination to Pt involves a dissociative pathway (Scheme ). Note that we have previously shown displacement of a nucleobase (nb=1‐methylcytosine) from a complex with the composition trans ‐[PtCl(NH 3 ) 2 (nb)] + under mild conditions, as a manifestation of the trans effect of chloride, and have proposed that this may be one reason for the lower tendency of trans ‐[PtCl 2 (NH 3 ) 2 ] versus cisplatin to bind to DNA 43. Subsequent attachment of two nucleobases to trans ‐[PtCl(D 2 O)(NH 3 ) 2 ] + is also seen in the case of 1‐methylcytosine.…”

Section: Resultsmentioning

confidence: 99%

“…Note that we have previously shown displacement of an ucleobase (nb = 1-methylcytosine) from ac omplex with the composition trans-[PtCl(NH 3 ) 2 (nb)] + under mild conditions, as am anifestation of the trans effect of chloride, and have proposed that this may be one reasonf or the lower tendency of trans-[PtCl 2 (NH 3 ) 2 ]v ersus cisplatin to bind to DNA. [43] Subsequent attachment of two nucleobases to trans-[PtCl(D 2 O)(NH 3 ) 2 ] + is also seen in the case of 1-methylcytosine. The higher thermodynamic stability of the (9MeA-N1)l inkage isomer [4] is certainly consistent with the proposed route to 5 (Scheme 3).…”

Section: Hn Mr Shift Rangesmentioning

confidence: 99%

The Challenge of Deciphering Linkage Isomers in Mixtures of Oligomeric Complexes Derived from 9‐Methyladenine and trans‐(NH₃)₂Pt^II Units

Mihály

Miguel

Steinborn

et al. 2015

Chemistry A European J

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Registro de acceso restringido Este recurso no está disponible en acceso abierto por política de la editorial. No obstante, se puede acceder al texto completo desde la Universitat Jaume I o si el usuario cuenta con suscripción. Registre d'accés restringit Aquest recurs no està disponible en accés obert per política de l'editorial. No obstant això, es pot accedir al text complet des de la Universitat Jaume I o si l'usuari compta amb subscripció. Restricted access item This item isn't open access because of publisher's policy. The full--text version is only available from Jaume I University or if the user has a running suscription to the publisher's contents.

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“…from NaCl) in order to prevent formation of the respective bis(nucleobase) compound. As to the behavior of the mono(nucleobase) complexes in water, two observations are worth mentioning: First, trans-[Pt(a) 2 (nb)Cl]Cl (with nb = 1MeC [181] and 9EtGH [182]) undergo a partial redistribution when dissolved in water, according to…”

Section: Examples and Propertiesmentioning

confidence: 99%

Beyond Sole Models for the First Steps of Pt-Dna Interactions: Fundamental Properties of Mono(Nucleobase) Adducts of Ptii Coordination Compounds

Lippert¹,

Miguel²

2022

SSRN Journal

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Nucleobase displacement from trans-diamineplatinum(II) complexes. A rationale for the inactivity of trans-DDP as an antitumor agent?

Cited by 23 publications

References 10 publications

Heteronuclear Nucleobase Complexes as Tools for the Isolation of the Minor Rotamer of the Parent Compound: Synthesis and Crystal Structure Determination of Head-Head and Head-Tail Forms of trans-[(CH₃NH₂)₂Pt(1-MeC-N3)₂]²⁺ (1-MeC = 1-methylcytosine)

Heteronuclear Nucleobase Complexes as Tools for the Isolation of the Minor Rotamer of the Parent Compound: Synthesis and Crystal Structure Determination of Head-Head and Head-Tail Forms of trans-[(CH₃NH₂)₂Pt(1-MeC-N3)₂]²⁺ (1-MeC = 1-methylcytosine)

The Challenge of Deciphering Linkage Isomers in Mixtures of Oligomeric Complexes Derived from 9‐Methyladenine and trans‐(NH₃)₂Pt^II Units

Beyond Sole Models for the First Steps of Pt-Dna Interactions: Fundamental Properties of Mono(Nucleobase) Adducts of Ptii Coordination Compounds

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Nucleobase displacement from trans-diamineplatinum(II) complexes. A rationale for the inactivity of trans-DDP as an antitumor agent?

Cited by 23 publications

References 10 publications

Heteronuclear Nucleobase Complexes as Tools for the Isolation of the Minor Rotamer of the Parent Compound: Synthesis and Crystal Structure Determination of Head-Head and Head-Tail Forms of trans-[(CH3NH2)2Pt(1-MeC-N3)2]2+ (1-MeC = 1-methylcytosine)

Heteronuclear Nucleobase Complexes as Tools for the Isolation of the Minor Rotamer of the Parent Compound: Synthesis and Crystal Structure Determination of Head-Head and Head-Tail Forms of trans-[(CH3NH2)2Pt(1-MeC-N3)2]2+ (1-MeC = 1-methylcytosine)

The Challenge of Deciphering Linkage Isomers in Mixtures of Oligomeric Complexes Derived from 9‐Methyladenine and trans‐(NH3)2PtII Units

Beyond Sole Models for the First Steps of Pt-Dna Interactions: Fundamental Properties of Mono(Nucleobase) Adducts of Ptii Coordination Compounds

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Heteronuclear Nucleobase Complexes as Tools for the Isolation of the Minor Rotamer of the Parent Compound: Synthesis and Crystal Structure Determination of Head-Head and Head-Tail Forms of trans-[(CH₃NH₂)₂Pt(1-MeC-N3)₂]²⁺ (1-MeC = 1-methylcytosine)

Heteronuclear Nucleobase Complexes as Tools for the Isolation of the Minor Rotamer of the Parent Compound: Synthesis and Crystal Structure Determination of Head-Head and Head-Tail Forms of trans-[(CH₃NH₂)₂Pt(1-MeC-N3)₂]²⁺ (1-MeC = 1-methylcytosine)

The Challenge of Deciphering Linkage Isomers in Mixtures of Oligomeric Complexes Derived from 9‐Methyladenine and trans‐(NH₃)₂Pt^II Units