JP2015120708A - ビス[チオヒドラジドアミド]化合物の遷移金属錯体 - Google Patents
ビス[チオヒドラジドアミド]化合物の遷移金属錯体 Download PDFInfo
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- JP2015120708A JP2015120708A JP2015003335A JP2015003335A JP2015120708A JP 2015120708 A JP2015120708 A JP 2015120708A JP 2015003335 A JP2015003335 A JP 2015003335A JP 2015003335 A JP2015003335 A JP 2015003335A JP 2015120708 A JP2015120708 A JP 2015120708A
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- XLQGICHHYYWYIU-UHFFFAOYSA-N veramine Natural products O1C2CC3C4CC=C5CC(O)CCC5(C)C4CC=C3C2(C)C(C)C21CCC(C)CN2 XLQGICHHYYWYIU-UHFFFAOYSA-N 0.000 description 1
- ZQFGRJWRSLZCSQ-ZSFNYQMMSA-N verteporfin Chemical compound C=1C([C@@]2([C@H](C(=O)OC)C(=CC=C22)C(=O)OC)C)=NC2=CC(C(=C2C=C)C)=NC2=CC(C(=C2CCC(O)=O)C)=NC2=CC2=NC=1C(C)=C2CCC(=O)OC ZQFGRJWRSLZCSQ-ZSFNYQMMSA-N 0.000 description 1
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- 208000024523 vestibulocochlear nerve neoplasm Diseases 0.000 description 1
- AQTQHPDCURKLKT-JKDPCDLQSA-N vincristine sulfate Chemical compound OS(O)(=O)=O.C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C=O)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 AQTQHPDCURKLKT-JKDPCDLQSA-N 0.000 description 1
- 229960002110 vincristine sulfate Drugs 0.000 description 1
- 229960004355 vindesine Drugs 0.000 description 1
- UGGWPQSBPIFKDZ-KOTLKJBCSA-N vindesine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(N)=O)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1N=C1[C]2C=CC=C1 UGGWPQSBPIFKDZ-KOTLKJBCSA-N 0.000 description 1
- 229960004854 viral vaccine Drugs 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- 201000007790 vitelliform macular dystrophy Diseases 0.000 description 1
- 208000020938 vitelliform macular dystrophy 2 Diseases 0.000 description 1
- 210000003905 vulva Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
- 229940051021 yellow-fever virus Drugs 0.000 description 1
- 229960000523 zalcitabine Drugs 0.000 description 1
- 229950005561 zanoterone Drugs 0.000 description 1
- 229950003017 zeniplatin Drugs 0.000 description 1
- 229960002555 zidovudine Drugs 0.000 description 1
- HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- 150000003952 β-lactams Chemical class 0.000 description 1
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Abstract
Description
本出願は2008年10月22日出願の米国仮出願第61/196,932号の恩典を主張し、その全体が参照により本明細書に組み入れられる。
米国特許第6,800,660号(特許文献1); 第6,762,204号(特許文献2); 第7,037,940号(特許文献3); 第7,001,923号(特許文献4); および第6,924,312号(特許文献5)において、ある種のビス[チオ-ヒドラジドアミド]化合物がパクリタキセルおよびパクリタキセル類似体の抗がん活性を著しく増強することが報告された。特に、N-マロニル-ビス(N'-メチル-N'-チオベンゾイルヒドラジド)とパクリタキセルとの組み合わせは、ステージIV転移性黒色腫に罹患する患者の進行までの時間を、パクリタキセル単独で処置する患者に比べて増加させることがわかった。さらに活性の高いビス[チオヒドラジドアミド]抗がん化合物を有することが有利であると考えられる。
式中、
R1〜R4は独立して、-H、置換されていてもよい脂肪族基、置換されていてもよいアリール基であり、あるいは、R1およびR3は、それらが結合している炭素原子および窒素原子と一緒になって、かつ/または、R2およびR4は、それらが結合している炭素原子および窒素原子と一緒になって、アリール基に縮合していてもよい非芳香族複素環を形成し;
Yは共有結合、または置換もしくは非置換の直鎖ヒドロカルビル基であり、あるいは、Yは、それが結合している両>C=Z基と一緒になって、置換もしくは非置換のアリール基となり;
R7およびR8は独立して、-H、置換されていてもよい脂肪族基または置換されていてもよいアリール基であり;
ZはOまたはSである。
式中、
R5およびR6は各々独立して、-H、脂肪族または置換脂肪族基であり、あるいは、R5は-Hであり、R6は置換されていてもよいアリール基であり、あるいは、R5およびR6は一緒になって、置換されていてもよいC2〜C6アルキレン基となり;
Xは+2の電荷を有する遷移金属カチオンであり; 変動要素の残りは構造式(I)について先に記載の通りである。
[本発明1001]
遷移金属カチオンと錯体を形成している、下記構造式で表されるビス[チオヒドラジドアミド]またはその脱プロトン化形態を含む、化合物:
式中、
R1〜R4は独立して、-H、置換されていてもよい脂肪族基、置換されていてもよいアリール基であり、あるいは、R1およびR3は、それらが結合している炭素原子および窒素原子と一緒になって、かつ/または、R2およびR4は、それらが結合している炭素原子および窒素原子と一緒になって、アリール基に縮合していてもよい非芳香族複素環を形成し;
Yは、置換もしくは非置換の直鎖ヒドロカルビル基の共有結合であり、あるいは、Yは、それが結合している両>C=Z基と一緒になって、置換もしくは非置換のアリール基となり;
R7およびR8は独立して、-H、置換されていてもよい脂肪族基、または置換されていてもよいアリール基であり; かつ
各Zは独立して、OまたはSである。
[本発明1002]
50重量%を超えて純粋である、本発明1001の化合物。
[本発明1003]
90重量%を超えて純粋である、本発明1001の化合物。
[本発明1004]
遷移金属カチオンがNi2+、Cu2+、Co2+、Fe2+、Zn2+、Pt2+またはPd2+である、本発明1001の化合物。
[本発明1005]
遷移金属カチオンがCu2+である、本発明1004の化合物。
[本発明1006]
遷移金属カチオンに対するビス[チオヒドラジドアミド]またはその脱プロトン化形態のモル比が0.5以上および2.0以下である、本発明1001〜1006のいずれかの化合物。
[本発明1007]
ビス[チオヒドラジドアミド]またはその脱プロトン化形態対遷移金属カチオンのモル比が1:1である、本発明1008の化合物。
[本発明1008]
下記構造式で表される、本発明1009の化合物:
式中、R5およびR6は各々独立して、-H、脂肪族または置換脂肪族基であり、あるいは、R5は-Hであり、かつR6は置換されていてもよいアリール基であり、あるいは、R5およびR6は一緒になって、置換されていてもよいC2〜C6アルキレン基となる。
[本発明1009]
R1およびR2が各々、置換されていてもよいフェニル基であり;
R3およびR4が各々、置換されていてもよいアルキル基であり; かつ
R5が-Hであり、かつR6が-H、アルキルまたは置換アルキル基である、
本発明1008の化合物。
[本発明1010]
R1およびR2が各々、置換されていてもよい脂肪族基であり; かつ
R3およびR4が各々、置換されていてもよい脂肪族基である、
本発明1008の化合物。
[本発明1011]
R1およびR2がいずれも、少なくとも1個のアルキル基で置換されていてもよいC3〜C8シクロアルキル基であり、
R3およびR4が各々、置換されていてもよいアルキル基であり; かつ
R5が-Hであり、かつR6が-H、アルキルまたは置換アルキル基である、
本発明1010の化合物。
[本発明1012]
R1およびR2がいずれもシクロプロピルまたは1-メチルシクロプロピルである、本発明1011の化合物。
[本発明1013]
ビス[チオヒドラジドアミド]が、以下より選択される構造式で表される、本発明1001〜1012のいずれかの化合物:
。
[本発明1014]
下記構造式で表される化合物:
式中、
Xは+2の電荷を有する遷移金属カチオンであり;
R1〜R4は独立して、-H、置換されていてもよい脂肪族基、置換されていてもよいアリール基であり、あるいは、R1およびR3は、それらが結合している炭素原子および窒素原子と一緒になって、かつ/または、R2およびR4は、それらが結合している炭素原子および窒素原子と一緒になって、アリール基に縮合していてもよい非芳香族複素環を形成し;
R5およびR6は各々独立して、-H、脂肪族または置換脂肪族基であり、あるいは、R5は-Hであり、かつR6は置換されていてもよいアリール基であり、あるいは、R5およびR6は一緒になって、置換されていてもよいC2〜C6アルキレン基となり; かつ
各Zは独立して、OまたはSである。
[本発明1015]
50重量%を超えて純粋である、本発明1014の化合物。
[本発明1016]
90重量%を超えて純粋である、本発明1014の化合物。
[本発明1017]
XがNi2+、Cu2+、Co2+、Fe2+、Zn2+、Pt2+またはPd2+である、本発明1014〜1016のいずれかの化合物。
[本発明1018]
XがCu2+である、本発明1014の化合物。
[本発明1019]
XがNi2+である、本発明1014の化合物。
[本発明1020]
R1およびR2が各々、置換されていてもよいフェニル基であり;
R3およびR4が各々、置換されていてもよいアルキル基であり; かつ
R5が-Hであり、かつR6が-H、アルキルまたは置換アルキル基である、
本発明1014の化合物。
[本発明1021]
R1およびR2が各々、置換されていてもよい脂肪族基であり; かつ
R3およびR4が各々、置換されていてもよい脂肪族基である、
本発明1014の化合物。
[本発明1022]
R1およびR2がいずれも、少なくとも1個のアルキル基で置換されていてもよいC3〜C8シクロアルキル基であり、
R3およびR4が各々、置換されていてもよいアルキル基であり; かつ
R5が-Hであり、かつR6が-H、アルキルまたは置換アルキル基である、
本発明1021の化合物。
[本発明1023]
R1およびR2がいずれもシクロプロピルまたは1-メチルシクロプロピルである、本発明1014の化合物。
[本発明1024]
以下より選択される構造式で表される、本発明1014〜1023のいずれかの化合物:
。
[本発明1025]
本発明1001〜1024のいずれか一項より選択される化合物と、薬学的に許容される担体または希釈剤とを含む、薬学的組成物。
[本発明1026]
がんを有する対象を処置する方法であって、有効量の本発明1001〜1024のいずれかの化合物または本発明1025の薬学的組成物を対象に投与する段階を含む方法。
[本発明1027]
さらなる抗がん剤を対象に投与する段階をさらに含む、本発明1026の方法。
[本発明1028]
前記さらなる抗がん剤が、パクリタキセル、パクリタキセル類似体、ディスコデルモリド、エポチロンA、エポチロンB、エポチロンC、エポチロンD、エポチロンE、エポチロンF、エポチロンB N-オキシド、エポチロンA N-オキシド、16-アザ-エポチロンB、21-アミノエポチロンB、21-ヒドロキシエポチロンD、FR-182877、BSF-223651、AC-7739、AC-7700、フィジアノリド(Fijianolide)B、ラウリマリド、カリベオシド、カリベオリン、タッカロノリド、エロイテロビン、サルコジクチイン; ラウリマリド、ジクチオスタチン-1、ジャトロファンエステル、またはその類似体および誘導体からなる群より選択される微小管安定化剤である、本発明1027の方法。
[本発明1029]
パクリタキセル類似体がドセタキソールである、本発明1028の方法。
[本発明1030]
がんが黒色腫である、本発明1026〜1029のいずれかの方法。
本発明は、構造式(I)で表されるビス[チオヒドラジドアミド]またはそのプロドラッグ、異性体、エステル、塩、水和物、溶媒和物、多形もしくは脱プロトン化形態の遷移金属錯体(配位体またはキレート)に関する。この種類の錯体の一例は、先に記載の構造式(II)で表される。
式中、変動要素は先に記載の通りである。Xの例としてはNi2+、Cu2+、Co2+、Fe2+、Zn2+、Pt2+およびPd2+が挙げられる。
構造式(III)の変動要素は、構造式(II)について定義の通りである。好ましくは、構造式(IIa)および(IIb)を含む構造式(I)〜(III)では、ZはOであり、R1およびR2は同一であり、かつR3およびR4は同一である。
変動要素は構造式(II)について先に記載の通りであるが、但し、R1およびR2がいずれもフェニルであり、両Z原子がOであり、R3およびR4がいずれもメチルである場合、R5およびR6がいずれも-Hであるということはない。構造式(IV)の別の態様では、XはCu2+またはNi2+ではない。
構造式(V)の変動要素は構造式(II)について定義の通りであるが、但し、R1およびR2がいずれもフェニルであり、両Z原子がOであり、かつR3およびR4がいずれもメチルである場合、R5およびR6がいずれも-Hであるということはない。
R1およびR2はいずれもフェニルであり、R3およびR4はいずれもメチルであり、かつR5およびR6はいずれも-Hであり;
R1およびR2はいずれもフェニルであり、R3およびR4はいずれもエチルであり、かつR5およびR6はいずれも-Hであり;
R1およびR2はいずれも4-シアノフェニルであり、R3およびR4はいずれもメチルであり、R5はメチルであり、かつR6は-Hであり;
R1およびR2はいずれも4-メトキシフェニルであり、R3およびR4はいずれもメチルであり、かつR5およびR6はいずれも-Hであり;
R1およびR2はいずれもフェニルであり、R3およびR4はいずれもメチルであり、R5はメチルであり、かつR6は-Hであり;
R1およびR2はいずれもフェニルであり、R3およびR4はいずれもエチルであり、R5はメチルであり、かつR6は-Hであり;
R1およびR2はいずれも4-シアノフェニルであり、R3およびR4はいずれもメチルであり、かつR5およびR6はいずれも-Hであり;
R1およびR2はいずれも2,5-ジメトキシフェニルであり、R3およびR4はいずれもメチルであり、かつR5およびR6はいずれも-Hであり;
R1およびR2はいずれも2,5-ジメトキシフェニルであり、R3およびR4はいずれもメチルであり、R5はメチルであり、かつR6は-Hであり;
R1およびR2はいずれも3-シアノフェニルであり、R3およびR4はいずれもメチルであり、かつR5およびR6はいずれも-Hであり;
R1およびR2はいずれも3-フルオロフェニルであり、R3およびR4はいずれもメチルであり、かつR5およびR6はいずれも-Hであり;
R1およびR2はいずれも4-クロロフェニルであり、R3およびR4はいずれもメチルであり、R5はメチルであり、かつR6は-Hであり;
R1およびR2はいずれも2-メトキシフェニルであり、R3およびR4はいずれもメチルであり、かつR5およびR6はいずれも-Hであり;
R1およびR2はいずれも3-メトキシフェニルであり、R3およびR4はいずれもメチルであり、かつR5およびR6はいずれも-Hであり;
R1およびR2はいずれも2,3-ジメトキシフェニルであり、R3およびR4はいずれもメチルであり、かつR5およびR6はいずれも-Hであり;
R1およびR2はいずれも2,3-ジメトキシフェニルであり、R3およびR4はいずれもメチルであり、R5はメチルであり、かつR6は-Hであり;
R1およびR2はいずれも2,5-ジフルオロフェニルであり、R3およびR4はいずれもメチルであり、かつR5およびR6はいずれも-Hであり;
R1およびR2はいずれも2,5-ジフルオロフェニルであり、R3およびR4はいずれもメチルであり、R5はメチルであり、かつR6は-Hであり;
R1およびR2はいずれも2,5-ジクロロフェニルであり、R3およびR4はいずれもメチルであり、かつR5およびR6はいずれも-Hであり;
R1およびR2はいずれも2,5-ジメチルフェニルであり、R3およびR4はいずれもメチルであり、かつR5およびR6はいずれも-Hであり;
R1およびR2はいずれもシクロプロピルであり、R3およびR4はいずれもメチルであり、かつR5およびR6はいずれも-Hであり;
R1およびR2はいずれもシクロプロピルであり、R3およびR4はいずれもエチルであり、かつR5およびR6はいずれも-Hであり;
R1およびR2はいずれもシクロプロピルであり、R3およびR4はいずれもメチルであり、R5はメチルであり、かつR6は-Hであり;
R1およびR2はいずれも1-メチルシクロプロピルであり、R3およびR4はいずれもメチルであり、かつR5およびR6はいずれも-Hであり;
R1およびR2はいずれも1-メチルシクロプロピルであり、R3およびR4はいずれもメチルであり、R5はメチルであり、かつR6は-Hであり;
R1およびR2はいずれも1-メチルシクロプロピルであり、R3およびR4はいずれもメチルであり、R5はエチルであり、かつR6は-Hであり;
R1およびR2はいずれも1-メチルシクロプロピルであり、R3およびR4はいずれもメチルであり、R5はn-プロピルであり、かつR6は-Hであり;
R1およびR2はいずれも1-メチルシクロプロピルであり、R3およびR4はいずれもメチルであり、かつR5およびR6はいずれもメチルであり;
R1およびR2はいずれも1-メチルシクロプロピルであり、R3およびR4はいずれもエチルであり、かつR5およびR6はいずれも-Hであり;
R1およびR2はいずれも1-メチルシクロプロピルであり、R3はメチルであり、R4はエチルであり、かつR5およびR6はいずれも-Hであり;
R1およびR2はいずれも2-メチルシクロプロピルであり、R3およびR4はいずれもメチルであり、かつR5およびR6はいずれも-Hであり;
R1およびR2はいずれも2-フェニルシクロプロピルであり、R3およびR4はいずれもメチルであり、かつR5およびR6はいずれも-Hであり;
R1およびR2はいずれも1-フェニルシクロプロピルであり、R3およびR4はいずれもメチルであり、かつR5およびR6はいずれも-Hであり;
R1およびR2はいずれもシクロブチルであり、R3およびR4はいずれもメチルであり、かつR5およびR6はいずれも-Hであり;
R1およびR2はいずれもシクロペンチルであり、R3およびR4はいずれもメチルであり、かつR5およびR6はいずれも-Hであり;
R1およびR2はいずれもシクロヘキシルであり、R3およびR4はいずれもメチルであり、かつR5およびR6はいずれも-Hであり;
R1およびR2はいずれもシクロヘキシルであり、R3およびR4はいずれもフェニルであり、かつR5およびR6はいずれも-Hであり;
R1およびR2はいずれもメチルであり、R3およびR4はいずれもメチルであり、かつR5およびR6はいずれも-Hであり;
R1およびR2はいずれもメチルであり、R3およびR4はいずれもt-ブチルであり、かつR5およびR6はいずれも-Hであり;
R1およびR2はいずれもメチルであり、R3およびR4はいずれもフェニルであり、かつR5およびR6はいずれも-Hであり;
R1およびR2はいずれもt-ブチルであり、R3およびR4はいずれもメチルであり、かつR5およびR6はいずれも-Hであり;
R1およびR2はエチルであり、R3およびR4はいずれもメチルであり、かつR5およびR6はいずれも-Hであり; あるいは
R1およびR2はいずれもn-プロピルであり、R3およびR4はいずれもメチルであり、かつR5およびR6はいずれも-Hである。
アリーレン基の置換基は、アリール基について以下に記載の通りである。
R14は、-H、-CH2SCH3または-CH2-O-P(O)(OH)2であり; R15は、CH3CO-であり;
R16は、フェニルであり; R17は、-Hであり、あるいは、R17およびR18は、一緒になって-O-CO-O-となり;
R18は、-Hであり; R20は、-Hまたは-Fであり; R21は、-H、-C(O)-CHBr-(CH2)13-CH3もしくは-C(O)-(CH2)14-CH3; -C(O)-CH2-CH(OH)-COOH、-C(O)-CH2-O-C(O)-CH2CH(NH2)-CONH2、-C(O)-CH2-O-CH2CH2OCH3または-C(O)-O-C(O)-CH2CH3である。
実施例1:化合物の合成
化合物1の合成
ビス[チオヒドラジドアミド] A (800mg、2.0mmol)のEtOH (10.0mL)溶液に、塩化銅(II) (277mg、2.0mmol)を加えた。混合物を室温で20分間攪拌した。水を加えた。固体を濾取した。固体を塩化メチレン中に取り込んだ。得られた溶液を水(2X)で洗浄し、乾燥させ(Na2SO4)、濾過し、濃縮して粗固体を得た。固体をアセトンで洗浄して純粋な化合物1 (600mg)を得た。アセトニトリルからの再結晶により単結晶固体を得ることができる。MS (ESI) [M+H+]: 462. 融点: 198〜202℃(分解). C19H18CuN4O2S2の分析計算値: C, 49.39; H, 3.93; N, 12.13; 実測値: C, 49.36; H, 3.68; N, 11.92.
化合物1の調製についての記載と同様にして、ビス[チオヒドラジドアミド] Aおよび塩化ニッケル(II)六水和物を使用して、化合物2を調製した。MS (ESI) [M+H+]: 457. 1H NMR (300 MHz, CDCl3) δ 7.58-7.44 (m, 10H), 3.61 (s, 6H), 3.59 (s, 2H).
10%ウシ胎仔血清を補充したダルベッコ最小必須培地(DMEM) 100μl中に、M14黒色腫細胞を、96ウェルプレートの1ウェル当たり細胞50,000個で播種した。細胞を5% CO2-95%空気下、37℃で培養した。16時間のインキュベーション後、試験化合物を細胞培養液に加えた。最初に化合物を、100%ジメチルスルホキシド(DMSO)中に、アッセイに実際に使用する終濃度の400倍に希釈した。次に、DMSO溶液を培地で20倍希釈し、最後にさらに20倍希釈してアッセイウェルに加えた。アッセイ培地は、指示された濃度を有する試験化合物と0.25% DMSOとを含んでいた。試験化合物と共に48時間インキュベートした後の最後の15分において、CCK8アッセイ(the Technical Manual for Cell Counting Kit-8, Product #CK04-11, CK04-13 and CK04-20, Dojindo Molecular Technologies, Inc. MD; Tantular, I.S. et al. Tropical Medicine and International Health, 8(6), 569-574, 2003に記載の)を用いて、細胞生存率を測定した。図25に示すように、化合物1〜7のデータを化合物Aのそれと比較する。図の各棒線は、媒体(0.25% DMSO)対照に対する平均阻害パーセントを表す(n=4)。誤差棒線は標準偏差を示す。化合物1〜7のIC50値を表1に列挙する。
熱ショックタンパク質(Hsp)を、種々のストレス条件下で誘導し、他のタンパク質に結合させてそれらの変性を防止する。Hspは細胞をアポトーシス死より保護することができる。Hsp70の産生を誘導する薬剤は、広範な侵襲に対する保護活性を有し得るものであり、神経障害において特別な有用性を有し得る。本発明のHsp70誘導化合物の神経保護活性を、種々の動物神経疾患モデルにおいて評価することができる。具体的には、脳卒中、筋萎縮性側索硬化症、ハンチントン病、パーキンソン病およびアルツハイマー病の動物モデルが、有効性の試験に適切な設定である。いくつかの例示的動物モデルを以下に示す。
本発明のHsp70誘導化合物を用いる、開示される処置の利点を、脳卒中のげっ歯類モデルにおいて評価することができる。例えばLongaら(Longa, E.Z., Weinstein, P.R., Carlson, S., and Cummins, R. (1989) Reversible middle cerebral artery occlusion without craniectomy in rats. Stroke 20:84-91)に記載の脳卒中モデルを利用することができる。
ALSの処置における本発明の化合物の有効性を、SOD1遺伝子導入マウスモデルを使用してモデリングすることができる(Gurney, M.E., Pu, H., Chiu, A.Y., Dal Canto, M.C., Polchow, C.Y., Alexander, D.D., Caliendo, J., Hentati, A., Kwon, Y.W., and Deng, H.X. (1994) Motor neuron degeneration in mice that express a human CuZn superoxide dismutase mutation. Science 264:1772-1775)。ヒトCuZnスーパーオキシドジスムターゼ(SOD)の変異は、家族性ALSを有する患者にみられる。アミノ酸93でのグリシンからアラニンへの置換を含むヒトSOD遺伝子の発現は、遺伝子導入マウスにおける運動ニューロン疾患を導く。脊髄からの運動ニューロン喪失の結果として、マウスは麻痺し、5〜6月齢までに死亡する。
HDの遺伝子導入マウスモデルが存在し、この疾患設定における有効性に関する本発明のHsp70誘導化合物の試験を可能にする(Mangiarini, L., Sathasivam, K., Seller, M., Cozens, B., Harper, A., Hetherington, C., Lawton, M., Trottier, Y., Lehrach, H., Davies, S.W., and Bates, G.P. (1996) Exon 1 of the HD gene with an expanded CAG repeat is sufficient to cause a progressive neurological phenotype in transgenic mice. Cell 87:493-506; Carter, R.J., Lione, L.A., Humby, T., Mangiarini, L., Mahal, A., Bates, G.P., Dunnett, S.B., and Morton, A.J. (1999) Characterization of progressive motor deficits in mice transgenic for the human Huntington's disease mutation. J. Neuroscience 19:3248-3257)。HDは、CAG/ポリグルタミンの反復伸長が引き起こす。これらの遺伝子導入マウス(R6/2遺伝子導入)は、(CAG)115〜(CAG)150反復伸長を有するヒトHD遺伝子の5'末端を有する。マウスは、異常かつ不随意の運動、振戦およびてんかん発作を含む、HDと同様の進行性神経病理を示す。
疾患が化学的処理により誘導される、PDの2つの広く使用されるモデルが存在する。これらは6-OHDA (Zigmond, M.J. and Stricker, E.M. (1984) Parkinson's disease: studies with an animal model. Life Sci. 35:5-18; Sauer, H. and Oertel, W.H. (1994) Progressive degeneration of nigrostriatal dopamine neurons following intrastriatal terminal lesions with 6-hydroxydopamine: a combined retrograde tracing and immunocytochemical study in the rat. Neuroscience 59:401-415)およびMPTP (Langston, J.W., Forno, L.S., Rebert, C.S., and Irwin, I. (1984) Selective nigral toxicity after systemic administration of 1-methyl-4-phenyl-1,2,5,6-tetrahydropyrine (MPTP) in the squirrel monkey. Brain Res. 292:390-4)モデルである。6-OHDAを使用する本発明のHsp70誘導化合物の試験の一例を記載する。
ADのいくつかの遺伝子導入マウスモデルが存在する。ADでの薬剤の有効性を試験するために広く使用されるそのような1つのモデルは、Holcombらが記述した(Holcomb, L., Gordon, M.N., McGowan, E., Yu, X., Benkovic, S., Jantzen, P., Wright, K., Saad, I., Mueller, R., Morgan, D., Sanders, S., Zehr, C., O'Campo, K., Hardy, J., Prada, C.M., Eckman, C., Younkin, S., Hsiao, K., and Duff, K. (1998) Accelerated Alzheimer-type phenotype in transgenic mice carrying both mutant amyloid precursor protein and presenilin 1 transgenes. Nature Medicine 4:97-100)。このモデルは、ADに関連する2つの異なる遺伝子を含む。1つはアミロイド前駆体タンパク質(APP)の変異である。変異体APP (K670N、M671L)遺伝子導入系Tg2576は、若年齢では上昇したアミロイドβタンパク質レベルを有し、後には細胞外AD-Aβ型沈着物を脳内に発生させる。もう1つの遺伝子は変異プレセニリン-1 (PS1)遺伝子である。Tg2576とPS1変異体PS1M146L遺伝子導入系との間の交雑種による二重遺伝子導入後代は、それらの単独遺伝子導入Tg2576マウスよりもはるかに早期に、多数の原線維Aβ沈着物を大脳皮質および海馬内に発生させる。
血漿Hsp70を、サンドイッチELISAキット(カナダ・ブリティッシュコロンビア州ビクトリア、Stressgen Bioreagents)により、室内用に修正したプロトコールに従って測定することができる。要するに、血漿検体中のHsp70、および段階濃度のHsp70標準物質を捕捉して、抗Hsp70抗体をコーティングした96ウェルプレート上に置く。次に、捕捉したHsp70をビオチン化抗Hsp70抗体で検出した後、ユーロピウム抱合ストレプトアビジンと共にインキュベートする。各インキュベーション後、未結合材料を洗浄により除去する。最後に、抗体-Hsp70複合体を、ユーロピウムの時間分解蛍光光度法により測定する。Hsp70の濃度を標準曲線より算出する。
以下の手順を使用して、対象におけるNK細胞活性をアッセイすることができる。この手順はKantakamalakul W, Jaroenpool J, Pattanapanyasat K. A novel enhanced green fluorescent protein (EGFP)-K562 flow cytometric method for measuring natural killer (NK) cell cytotoxic activity. J Immunol Methods. 2003 Jan 15; 272:189-197を適応させたものであり、その教示全体が参照により本明細書に組み入れられる。
ヒト赤白血病細胞系K562を、American Type Culture Collection (CCL-243、バージニア州マナサス、American Type Culture Collection)より得て、10%熱不活化ウシ胎仔血清(Gibco)、2mM L-グルタミン、100μg/mlストレプトマイシンおよび100IU/mlペニシリンを補充したRPMI-1640培地(カタログ番号11875-093、カリフォルニア州カールスバッド、Gibco Invitrogen Corp)中にて、37℃および5% CO2で培養する。緑色蛍光タンパク質(eGFP)をコードするレトロウイルスベクターをK562細胞に形質導入する。抗生物質G418を用いて安定な細胞系を選択する。約99.6%のG418耐性細胞が、薄切後にeGFP陽性である。
本発明の化合物が内皮細胞機能に影響するか否かを検査するために、本発明の化合物の存在下でインビトロヒト臍静脈内皮細胞(HUVEC)遊走アッセイを行う。HUVEC細胞(継代数4)を12ウェルプレート上で培養し、6〜7% CO2が供給される倒立顕微鏡上の生細胞イメージングシステムを用いて微速度イメージングを行う。温度を37℃に保持する。30分ごとに2X対物レンズを使用して最大106時間、または60秒ごとに20X対物レンズを使用して30分間、画像を撮影する。コンフルエントHUVEC培養物を同様に掻き取ってブランク領域を作製し、続いてHUVEC培地中で処理せずに15時間培養する。各ウェルについて微速度シーケンスとして画像形成される遊走領域を、遊走速度を標準化/補正する基礎として使用する。次に、異なる処理下での細胞の遊走を同時に画像形成して、各ウェルについて微速度画像シーケンスを生成する。遊走細胞が覆う領域を測定することで、微速度動画をさらに分析する。実験中、HUVEC細胞をVEGFおよび塩基性FGFの存在により活性化する。本発明の化合物(例えば100nMおよび1μM)は、ブランク領域へのHUVEC細胞の遊走を完全に遮断すると予測され、このことは、VEGFおよび塩基性FGFがインビトロで誘導する活性化HUVEC細胞の遊走に対する強力な阻害作用を本発明の化合物が有することを示している。
抗VE-カドヘリン抗体を使用して免疫蛍光試験を行うことで、HUVEC細胞間のVE-カドヘリン接合部を検査する。HUVEC細胞を、DMSOまたは本発明の化合物(例えば10、100および1000nM)で24時間処理し、免疫染色用に固定する。DMSO濃度はすべての処理で1:100とする。免疫蛍光シグナルを増進するために、細胞を2つのポリクローナル抗ヒトVE-カドヘリンAbの混合物で染色した後、蛍光二次抗体の混合物で染色する。本発明の化合物を用いる場合、VE-カドヘリン染色は、DMSO処理培養物におけるそれに比べて、細胞-細胞接合区域では非常に強いが、非接触区域ではそうではないと予測される。本発明の化合物は、おそらくは接合部でのVE-カドヘリン分子の蓄積の誘導を通じて、活性化ヒト内皮細胞の細胞-細胞接合部の集合を増強すると予測される。この作用は、細胞の限定された運動性および内皮の浸透性の減少を生じさせ、したがって本発明の化合物の細胞遊走阻害および潜在的な抗血管新生作用に寄与する可能性がある。
Claims (30)
- 遷移金属カチオンと錯体を形成している、下記構造式で表されるビス[チオヒドラジドアミド]またはその脱プロトン化形態を含む、配位錯体:
式中、
R1〜R4は独立して、−H、置換されていてもよい脂肪族基、置換されていてもよいアリール基であり、あるいは、R1およびR3は、それらが結合している炭素原子および窒素原子と一緒になって、かつ/または、R2およびR4は、それらが結合している炭素原子および窒素原子と一緒になって、アリール基に縮合していてもよい非芳香族複素環を形成し;
Yは、共有結合または置換もしくは非置換の直鎖ヒドロカルビル基であり、あるいは、Yは、それが結合している両>C=Z基と一緒になって、置換もしくは非置換のアリール基となり;
R7およびR8は独立して、−H、置換されていてもよい脂肪族基、または置換されていてもよいアリール基であり;かつ
各Zは独立して、OまたはSである。 - 50重量%を超えて純粋である、請求項1記載の錯体。
- 90重量%を超えて純粋である、請求項1記載の錯体。
- 遷移金属カチオンがNi2+、Cu2+、Co2+、Fe2+、Zn2+、Pt2+またはPd2+である、請求項1記載の錯体。
- 遷移金属カチオンがCu2+である、請求項4記載の錯体。
- 遷移金属カチオンに対するビス[チオヒドラジドアミド]またはその脱プロトン化形態のモル比が0.5以上および2.0以下である、請求項1〜5のいずれか一項記載の錯体。
- ビス[チオヒドラジドアミド]またはその脱プロトン化形態対遷移金属カチオンのモル比が1:1である、請求項6記載の錯体。
- R1およびR2が各々、置換されていてもよいフェニル基であり;
R3およびR4が各々、置換されていてもよいアルキル基であり;かつ
R5が−Hであり、かつR6が−H、アルキルまたは置換アルキル基である、
請求項8記載の錯体。 - R1およびR2が各々、置換されていてもよい脂肪族基であり;かつ
R3およびR4が各々、置換されていてもよい脂肪族基である、
請求項8記載の錯体。 - R1およびR2がいずれも、少なくとも1個のアルキル基で置換されていてもよいC3〜C8シクロアルキル基であり、
R3およびR4が各々、置換されていてもよいアルキル基であり;かつ
R5が−Hであり、かつR6が−H、アルキルまたは置換アルキル基である、
請求項10記載の錯体。 - R1およびR2がいずれもシクロプロピルまたは1−メチルシクロプロピルである、請求項11記載の錯体。
- 下記構造式で表される配位錯体:
式中、
Xは+2の電荷を有する遷移金属カチオンであり;
R1〜R4は独立して、−H、置換されていてもよい脂肪族基、置換されていてもよいアリール基であり、あるいは、R1およびR3は、それらが結合している炭素原子および窒素原子と一緒になって、かつ/または、R2およびR4は、それらが結合している炭素原子および窒素原子と一緒になって、アリール基に縮合していてもよい非芳香族複素環を形成し;
R5およびR6は各々独立して、−H、脂肪族または置換脂肪族基であり、あるいは、R5は−Hであり、かつR6は置換されていてもよいアリール基であり、あるいは、R5およびR6は一緒になって、置換されていてもよいC2〜C6アルキレン基となり;かつ
各Zは独立して、OまたはSである。 - 50重量%を超えて純粋である、請求項14記載の錯体。
- 90重量%を超えて純粋である、請求項14記載の錯体。
- XがNi2+、Cu2+、Co2+、Fe2+、Zn2+、Pt2+またはPd2+である、請求項14〜16のいずれか一項記載の錯体。
- XがCu2+である、請求項14記載の錯体。
- XがNi2+である、請求項14記載の錯体。
- R1およびR2が各々、置換されていてもよいフェニル基であり;
R3およびR4が各々、置換されていてもよいアルキル基であり;かつ
R5が−Hであり、かつR6が−H、アルキルまたは置換アルキル基である、
請求項14記載の錯体。 - R1およびR2が各々、置換されていてもよい脂肪族基であり;かつ
R3およびR4が各々、置換されていてもよい脂肪族基である、
請求項14記載の錯体。 - R1およびR2がいずれも、少なくとも1個のアルキル基で置換されていてもよいC3〜C8シクロアルキル基であり、
R3およびR4が各々、置換されていてもよいアルキル基であり;かつ
R5が−Hであり、かつR6が−H、アルキルまたは置換アルキル基である、
請求項21記載の錯体。 - R1およびR2がいずれもシクロプロピルまたは1−メチルシクロプロピルである、請求項14記載の錯体。
- 請求項1〜24のいずれか一項より選択される配位錯体と、薬学的に許容される担体または希釈剤とを含む、薬学的組成物。
- 有効量の請求項1〜24のいずれか一項記載の錯体または請求項25記載の薬学的組成物を含む、がんを有する対象の処置に用いるための薬学的組成物。
- さらなる抗がん剤をさらに含む、請求項26記載の薬学的組成物。
- 前記さらなる抗がん剤が、パクリタキセル、パクリタキセル類似体、ディスコデルモリド、エポチロンA、エポチロンB、エポチロンC、エポチロンD、エポチロンE、エポチロンF、エポチロンB N−オキシド、エポチロンA N−オキシド、16−アザ−エポチロンB、21−アミノエポチロンB、21−ヒドロキシエポチロンD、FR−182877、BSF−223651、AC−7739、AC−7700、フィジアノリド(Fijianolide)B、ラウリマリド、カリベオシド、カリベオリン、タッカロノリド、エロイテロビン、サルコジクチイン;ラウリマリド、ジクチオスタチン−1、ジャトロファンエステル、またはその類似体および誘導体からなる群より選択される微小管安定化剤である、請求項27記載の薬学的組成物。
- パクリタキセル類似体がドセタキソールである、請求項28記載の薬学的組成物。
- がんが黒色腫である、請求項26〜29のいずれか一項記載の薬学的組成物。
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EP2349991A4 (en) | 2014-06-04 |
AU2009308502A1 (en) | 2010-04-29 |
NZ592400A (en) | 2013-09-27 |
MX2011004276A (es) | 2011-06-27 |
CN102256937A (zh) | 2011-11-23 |
JP2012506443A (ja) | 2012-03-15 |
IL212439A (en) | 2015-01-29 |
KR20110073613A (ko) | 2011-06-29 |
BRPI0919720A2 (pt) | 2015-12-08 |
US9174935B2 (en) | 2015-11-03 |
CA2741189A1 (en) | 2010-04-29 |
WO2010048284A1 (en) | 2010-04-29 |
JP5886986B2 (ja) | 2016-03-16 |
EP2349991A1 (en) | 2011-08-03 |
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