Salaam Al-Baker

The University of Texas at Austin

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Abdul R. Khokhar

Holy Family Hospital

Román Pérez-Soler

Montefiore Medical Center

Zahid H. Siddik

The University of Texas MD Anderson Cancer Center

James C. Dabrowiak

Syracuse University

Jean F. Vollano

Johnson Matthey (United States)

Quanyun Xu

Scripps MD Anderson Cancer Center

Charles A. McAuliffe

University of Manchester

W. E. HILL

Auburn University

Insook Han

Kyungpook National University

Gregg J. Lumetta

Pacific Northwest National Laboratory

Cooperative Institutions

The University of Texas MD Anderson Cancer Center

The University of Texas Health Science Center at Houston

University of Houston

Institute of Cancer Research

Anderson Hospital

The University of Texas System

The University of Texas at Austin

Bristol-Myers Squibb (United States)

Montefiore Medical Center

Syracuse University

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SYNTHESIS AND CHARACTERIZATION OF NEW ANTITUMORTRANS-R,R-, TRANS-S,S- ANDCIS-1,2-DIAMINOCYCLOHEXANE PLATINUM (IV) COMPLEXES

Journal of Coordination Chemistry (1994)

Salaam Al-Baker Zahid H. Siddik Abdul R. Khokhar

Abstract A series of isomeric 1, 2-diaminocyclohexane platinum (IV) complexes of the type DACH-PtIV-trans(X)2 cis(Y) (where DACH = trans-R,R-, trans-S,S- or cis-1,2-diaminocyclohexane, X = chloro, bromo, acetato, or trifluoroacetato, and Y = dichloro, dibromo, 1,1-cyclobutanedicarboxylato, tartronato, ketomalonato, or methylmalonato) has been synthesized. The isomeric DACH-PtIV-trans(X)2 cis(Y) complexes were prepared by first oxidizing the corresponding DACH-dihaloplatinum(II) or DACH-dicarboxylato-platinum(II) [DACH-PtIIY] with hydrogen peroxide to DACH-PtIV-trans(OH)2Y, and then replacing the axial hydroxo groups with chloro, bromo, or monocarboxylato ligands. These complexes were characterized by elemental analysis, and infrared and nuclear magnetic resonance (195Pt{1H}) spectroscopic techniques. Key Words: Platinum1,2-diaminocyclohexaneisomercarboxylatesynthesis

Oxidizing agent

Cis–trans isomerism

10.1080/00958979408024206

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Citations (21)

ChemInform Abstract: Exchange Kinetics of Gold(I) Phosphine Complexes by NMR Line Shape Analysis (rate constants of the exchanging species, which have one, two, and three coordinated phosphine (PPhMe₂, PBu₃)ligands; thermodynamic parameters for the exchange process.

Chemischer Informationsdienst (1986)

Salaam Al-Baker W. E. HILL Charles A. McAuliffe

Line (geometry)

10.1002/chin.198640278

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Toxicity and anti-tumor activity of hydrophobic diammine and diaminocyclohexane platinum complexes entrapped in multilamellar vesicles.

PubMed (1988)

Khokhar Ar Salaam Al-Baker Román Pérez-Soler

The toxicity and anti-tumor activity of a lipophilic diaminocyclohexane (DACH) platinum complex entrapped in liposomes (liposomal-cis-bis-neodecanoato-trans-R, R-1, 2-DACH platinum II-L-NDDP) were compared with those of the liposomal preparation of the same compound without the DACH group (liposomal-cis-bis-neodecanoato-(diammine) platinum II-L-CNDP). Both liposomal preparations had the same liposome size distribution, drug entrapment efficiency (greater than 95%), and liposome stability (greater than 95%). Although no differences were observed in the mouse LD50 (60.2 mg/kg for L-NDDP vs 67.8 mg/kg for L-CNDP), the liposome entrapped non-DACH compound (L-CNDP) was more nephrotoxic than the liposome entrapped DACH compound (L-NDDP), but much less than cisplatin (CDDP) (mean BUN elevation 4 days after the administration of the LD50 dose 67 mg% for L-CNDP vs 30 mg% for L-NDDP vs 255 mg% for CDDP). L-NDDP was not cross-resistant with CDDP against L1210/CDDP leukemia while L-CNDP was cross-resistant (%T/C 200 for L-NDDP, 112 for CDDP, and 100 for L-CNDP). In addition, L-NDDP was slightly more active than L-CNDP against i.p. L1210/0 leukemia and i.v. M5076 reticulosarcoma. These studies suggest that the attachment of a cyclohexane group to the amino functions of lipophilic platinum complexes results in a decrease of the nephrotoxicity and a lack of cross-resistance with CDDP. The lack of cross-resistance is preserved when the compounds are entrapped and delivered in a liposomal carrier but not when they are delivered in a micellar suspension.

Nephrotoxicity

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Chemical and biological studies on a series of lipid-soluble (trans-(R,R)- and -(S,S)-1,2-diaminocyclohexane)platinum(II) complexes incorporated in liposomes

Journal of Medicinal Chemistry (1991)

Abdul R. Khokhar Salaam Al-Baker Trellis Brown Román Pérez-Soler

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTChemical and biological studies on a series of lipid-soluble (trans-(R,R)- and -(S,S)-1,2-diaminocyclohexane)platinum(II) complexes incorporated in liposomesAbdul R. Khokhar, Salaam Al-Baker, Trellis Brown, and Roman Perez-SolerCite this: J. Med. Chem. 1991, 34, 1, 325–329Publication Date (Print):January 1, 1991Publication History Published online1 May 2002Published inissue 1 January 1991https://pubs.acs.org/doi/10.1021/jm00105a051https://doi.org/10.1021/jm00105a051research-articleACS PublicationsRequest reuse permissionsArticle Views219Altmetric-Citations54LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts

10.1021/jm00105a051

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Citations (62)

X-ray crystal structure of tetrachloro(trans-d,l-1,2-diaminocyclohexane) platinum(IV) complex: A potential anticancer agent

Journal of Inorganic Biochemistry (1993)

Abdul R. Khokhar Quanyun Xu Salaam Al-Baker

Crystal (programming language)

10.1016/0162-0134(93)85622-f

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Citations (21)

Chemical and pharmacological studies of lipophilic platinum complexes entrapped in liposomes.

Journal of Inorganic Biochemistry (1991)

Abdul R. Khokhar Salaam Al-Baker Irwin H. Krakoff Román Pérez-Soler

10.1016/0162-0134(91)84572-q

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Synthesis and antitumor activity of ammine/amine platinum(II) and (IV) complexes

Journal of Inorganic Biochemistry (1993)

Abdul R. Khokhar Yuanjian Deng Salaam Al-Baker Motofumi Yoshida Zahid H. Siddik

Cyclohexylamine

Alicyclic compound

Dimethyl formamide

10.1016/0162-0134(93)85039-b

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Citations (53)

ChemInform Abstract: Synthesis and Structure of Dinuclear Complexes of Platinum(IV) Having cis‐Diamine Geometry.

ChemInform (1987)

Salaam Al-Baker Jean F. Vollano James C. Dabrowiak

Abstract H 2 O 2 ‐oxidation of the binuclear cis‐diamine‐Pt(II) complexes (I) yields the Pt(IV) products (II) having also cis‐diamine geometry.

10.1002/chin.198702298

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Synthesis and antitumor activity of 1,2-diaminocyclohexane platinum(IV) complexes

Journal of Inorganic Biochemistry (1994)

Abdul R. Khokhar Salaam Al-Baker Zahid H. Siddik

Proton NMR

10.1016/0162-0134(94)85122-0

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Citations (22)

SYNTHESIS AND CHARACTERIZATION OF NEW ETHYLENEDIAMINE AND 1,1-BIS(AMINOMETHYL)CYCLOHEXANEPLATINUM(II) COMPLEXES CONTAINING DISUBSTITUTED SULFIDE AS A LEAVING GROUP

Journal of Coordination Chemistry (1995)

Abdul R. Khokhar Shamsuddin Salaam Al-Baker Chirayu Shah

Abstract A series of cationic platinum(II) complexes of the type [Pt(en)(R′R″S)Cl]NO3 and [Pt(BAMCH)(R′R″S)Cl]NO3 (where en = ethylenediamine; BAMCH = 1,1-bis(aminomethyl)cyclohexane; and R′R″S = dimethylsulfide, diethysulfide, dipropylsulfide, diisopropylsulfide, diphenylsulfide, dibenzylsulfide, thioanisole, and methyl-p-tolylsulfide) has been synthesized and characterized by elemental analysis, infrared, and 195Pt nuclear magnetic resonance spectroscopic techniques.

Thioanisole

Ethylene diamine

Cationic polymerization

Tetrahydrothiophene

10.1080/00958979508022214

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Citations (7)