Synthesis and cytotoxicity of new platinum(IV) complexes of mixed carboxylates

Rita Song; Sun Young Park; Yeong Sang Kim; Youngmee Kim; Sung Jin Kim; Byung Tae Ahn; Youn Soo Sohn

doi:10.1016/S0162-0134(03)00149-1

Synthesis and cytotoxicity of new platinum(IV) complexes of mixed carboxylates

Rita Song, Sun Young Park, Yeong Sang Kim, Youngmee Kim, Sung Jin Kim, Byung Tae Ahn, Youn Soo Sohn

Department of Chemistry & Nanoscience

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

27 Scopus citations

Abstract

In order to develop new antitumor platinum(IV) complexes with highly tuned lipophilicity, a series of (diamine)Pt(IV) complexes of the formula [Pt^IV(dach)L₃L′] or [Pt^IV(dach)L₂L″₂] (dach=trans-(±)-1,2-diaminocyclohexane; L=acetato, propionato; L′=acetato, propionato, valerato or pivalato; L″=trifluoroacetato) have been synthesized by electrophilic substitution of the tris(carboxylato)hydroxoplatinum(IV) complexes, [Pt^IV(dach)L₃OH] (L=acetato, propionato), with various carboxylic anhydrides such as acetic, trifluoroacetic, pivalic and valeric anhydrides. The present platinum(IV) complexes were fully characterized by means of elemental analyses, ¹H NMR, mass and IR spectroscopies. The complexes 8 and 10, satisfying the appropriate range of lipophilicity (logP=0.18-1.54), exhibited high activity (ED₅₀, 5.1 and 1.3 μM, respectively) compared with other complexes, which implies that the lipophilicity is an important factor for the antitumor activity of this series of complexes.

Original language	English
Pages (from-to)	339-345
Number of pages	7
Journal	Journal of Inorganic Biochemistry
Volume	96
Issue number	2-3
DOIs	https://doi.org/10.1016/S0162-0134(03)00149-1
State	Published - 1 Aug 2003

Bibliographical note

Funding Information:
This research was supported by the Basic Research Program of the Korea Science and Engineering Foundation (R03-2000-000-000080(2002)) and the Ministry of Science and Technology in Korea.

Keywords

Anticancer
Cytotoxicity
Lipophilicity
Platinum(IV)

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10.1016/S0162-0134(03)00149-1

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title = "Synthesis and cytotoxicity of new platinum(IV) complexes of mixed carboxylates",

abstract = "In order to develop new antitumor platinum(IV) complexes with highly tuned lipophilicity, a series of (diamine)Pt(IV) complexes of the formula [PtIV(dach)L3L′] or [PtIV(dach)L2L″2] (dach=trans-(±)-1,2-diaminocyclohexane; L=acetato, propionato; L′=acetato, propionato, valerato or pivalato; L″=trifluoroacetato) have been synthesized by electrophilic substitution of the tris(carboxylato)hydroxoplatinum(IV) complexes, [PtIV(dach)L3OH] (L=acetato, propionato), with various carboxylic anhydrides such as acetic, trifluoroacetic, pivalic and valeric anhydrides. The present platinum(IV) complexes were fully characterized by means of elemental analyses, 1H NMR, mass and IR spectroscopies. The complexes 8 and 10, satisfying the appropriate range of lipophilicity (logP=0.18-1.54), exhibited high activity (ED50, 5.1 and 1.3 μM, respectively) compared with other complexes, which implies that the lipophilicity is an important factor for the antitumor activity of this series of complexes.",

keywords = "Anticancer, Cytotoxicity, Lipophilicity, Platinum(IV)",

author = "Rita Song and Park, {Sun Young} and Kim, {Yeong Sang} and Youngmee Kim and Kim, {Sung Jin} and Ahn, {Byung Tae} and Sohn, {Youn Soo}",

note = "Funding Information: This research was supported by the Basic Research Program of the Korea Science and Engineering Foundation (R03-2000-000-000080(2002)) and the Ministry of Science and Technology in Korea.",

year = "2003",

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doi = "10.1016/S0162-0134(03)00149-1",

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pages = "339--345",

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T1 - Synthesis and cytotoxicity of new platinum(IV) complexes of mixed carboxylates

AU - Song, Rita

AU - Park, Sun Young

AU - Kim, Yeong Sang

AU - Kim, Youngmee

AU - Kim, Sung Jin

AU - Ahn, Byung Tae

AU - Sohn, Youn Soo

N1 - Funding Information: This research was supported by the Basic Research Program of the Korea Science and Engineering Foundation (R03-2000-000-000080(2002)) and the Ministry of Science and Technology in Korea.

PY - 2003/8/1

Y1 - 2003/8/1

N2 - In order to develop new antitumor platinum(IV) complexes with highly tuned lipophilicity, a series of (diamine)Pt(IV) complexes of the formula [PtIV(dach)L3L′] or [PtIV(dach)L2L″2] (dach=trans-(±)-1,2-diaminocyclohexane; L=acetato, propionato; L′=acetato, propionato, valerato or pivalato; L″=trifluoroacetato) have been synthesized by electrophilic substitution of the tris(carboxylato)hydroxoplatinum(IV) complexes, [PtIV(dach)L3OH] (L=acetato, propionato), with various carboxylic anhydrides such as acetic, trifluoroacetic, pivalic and valeric anhydrides. The present platinum(IV) complexes were fully characterized by means of elemental analyses, 1H NMR, mass and IR spectroscopies. The complexes 8 and 10, satisfying the appropriate range of lipophilicity (logP=0.18-1.54), exhibited high activity (ED50, 5.1 and 1.3 μM, respectively) compared with other complexes, which implies that the lipophilicity is an important factor for the antitumor activity of this series of complexes.

AB - In order to develop new antitumor platinum(IV) complexes with highly tuned lipophilicity, a series of (diamine)Pt(IV) complexes of the formula [PtIV(dach)L3L′] or [PtIV(dach)L2L″2] (dach=trans-(±)-1,2-diaminocyclohexane; L=acetato, propionato; L′=acetato, propionato, valerato or pivalato; L″=trifluoroacetato) have been synthesized by electrophilic substitution of the tris(carboxylato)hydroxoplatinum(IV) complexes, [PtIV(dach)L3OH] (L=acetato, propionato), with various carboxylic anhydrides such as acetic, trifluoroacetic, pivalic and valeric anhydrides. The present platinum(IV) complexes were fully characterized by means of elemental analyses, 1H NMR, mass and IR spectroscopies. The complexes 8 and 10, satisfying the appropriate range of lipophilicity (logP=0.18-1.54), exhibited high activity (ED50, 5.1 and 1.3 μM, respectively) compared with other complexes, which implies that the lipophilicity is an important factor for the antitumor activity of this series of complexes.

KW - Anticancer

KW - Cytotoxicity

KW - Lipophilicity

KW - Platinum(IV)

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U2 - 10.1016/S0162-0134(03)00149-1

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SN - 0162-0134

VL - 96

SP - 339

EP - 345

JO - Journal of Inorganic Biochemistry

JF - Journal of Inorganic Biochemistry

IS - 2-3

ER -

Synthesis and cytotoxicity of new platinum(IV) complexes of mixed carboxylates

Abstract

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Keywords

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