Adriamycin Complexes of Pd(II) and Pt(II)

Tim Allman; R. E. Lenkinski

doi:10.1016/0162-0134(87)80042-9

Adriamycin Complexes of Pd(II) and Pt(II)

Tim Allman, R. E. Lenkinski

Research output: Contribution to journal › Article › peer-review

9 Scopus citations

Abstract

Perturbations of the ¹H NMR spectrum of the free base of Adriamycin in DMF solution were found when MCl₂(DMF)₂ (M = Pd or Pt) was added to the Adriamycin solutions. These perturbations were greatest for the 3' proton on the sugar ring and the effect decreased as the distance from this site increased. No changes were observed in the NMR spectrum of the rest of the molecule nor was there any color change when the metal solutions were added. This is interpreted as evidence that Adriamycin binds to these metals at the 3 ' amino group in DMF solution and that there is no reaction at the chromophore. The complexes were found to be in the fast exchange regime on the NMR time scale. As well, some products were isolated from reactions of Adriamycin with MCl₂(DMF)₂ in 20% MeOH/CH₂Cl₂ and MCl₂ in DMF solution. They were characterized by their elemental analyses, as well as by ¹H NMR and infrared spectroscopies.

Original language	English (US)
Pages (from-to)	35-43
Number of pages	9
Journal	Journal of Inorganic Biochemistry
Volume	30
Issue number	1
DOIs	https://doi.org/10.1016/0162-0134(87)80042-9
State	Published - May 1987

ASJC Scopus subject areas

Biochemistry
Inorganic Chemistry

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10.1016/0162-0134(87)80042-9

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@article{d6a6255f2f7042d78dd70f4997d64429,

title = "Adriamycin Complexes of Pd(II) and Pt(II)",

abstract = "Perturbations of the 1H NMR spectrum of the free base of Adriamycin in DMF solution were found when MCl2(DMF)2 (M = Pd or Pt) was added to the Adriamycin solutions. These perturbations were greatest for the 3' proton on the sugar ring and the effect decreased as the distance from this site increased. No changes were observed in the NMR spectrum of the rest of the molecule nor was there any color change when the metal solutions were added. This is interpreted as evidence that Adriamycin binds to these metals at the 3 ' amino group in DMF solution and that there is no reaction at the chromophore. The complexes were found to be in the fast exchange regime on the NMR time scale. As well, some products were isolated from reactions of Adriamycin with MCl2(DMF)2 in 20% MeOH/CH2Cl2 and MCl2 in DMF solution. They were characterized by their elemental analyses, as well as by 1H NMR and infrared spectroscopies.",

author = "Tim Allman and Lenkinski, {R. E.}",

note = "Funding Information: We thank the Natural Sciencesa nd Engineering Research Council of supporting this work and Adria Laboratories, MississaugaO ntario for Adriamycin.",

year = "1987",

month = may,

doi = "10.1016/0162-0134(87)80042-9",

language = "English (US)",

volume = "30",

pages = "35--43",

journal = "Journal of Inorganic Biochemistry",

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publisher = "Elsevier Inc.",

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}

TY - JOUR

T1 - Adriamycin Complexes of Pd(II) and Pt(II)

AU - Allman, Tim

AU - Lenkinski, R. E.

N1 - Funding Information: We thank the Natural Sciencesa nd Engineering Research Council of supporting this work and Adria Laboratories, MississaugaO ntario for Adriamycin.

PY - 1987/5

Y1 - 1987/5

N2 - Perturbations of the 1H NMR spectrum of the free base of Adriamycin in DMF solution were found when MCl2(DMF)2 (M = Pd or Pt) was added to the Adriamycin solutions. These perturbations were greatest for the 3' proton on the sugar ring and the effect decreased as the distance from this site increased. No changes were observed in the NMR spectrum of the rest of the molecule nor was there any color change when the metal solutions were added. This is interpreted as evidence that Adriamycin binds to these metals at the 3 ' amino group in DMF solution and that there is no reaction at the chromophore. The complexes were found to be in the fast exchange regime on the NMR time scale. As well, some products were isolated from reactions of Adriamycin with MCl2(DMF)2 in 20% MeOH/CH2Cl2 and MCl2 in DMF solution. They were characterized by their elemental analyses, as well as by 1H NMR and infrared spectroscopies.

AB - Perturbations of the 1H NMR spectrum of the free base of Adriamycin in DMF solution were found when MCl2(DMF)2 (M = Pd or Pt) was added to the Adriamycin solutions. These perturbations were greatest for the 3' proton on the sugar ring and the effect decreased as the distance from this site increased. No changes were observed in the NMR spectrum of the rest of the molecule nor was there any color change when the metal solutions were added. This is interpreted as evidence that Adriamycin binds to these metals at the 3 ' amino group in DMF solution and that there is no reaction at the chromophore. The complexes were found to be in the fast exchange regime on the NMR time scale. As well, some products were isolated from reactions of Adriamycin with MCl2(DMF)2 in 20% MeOH/CH2Cl2 and MCl2 in DMF solution. They were characterized by their elemental analyses, as well as by 1H NMR and infrared spectroscopies.

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DO - 10.1016/0162-0134(87)80042-9

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SN - 0162-0134

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EP - 43

JO - Journal of Inorganic Biochemistry

JF - Journal of Inorganic Biochemistry

IS - 1

ER -

Adriamycin Complexes of Pd(II) and Pt(II)

Abstract

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