JP2018191623A - 双性イオン、並びに双性イオンを含む培地用添加剤及び難溶性物質溶解剤 - Google Patents
双性イオン、並びに双性イオンを含む培地用添加剤及び難溶性物質溶解剤 Download PDFInfo
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- JP2018191623A JP2018191623A JP2017101161A JP2017101161A JP2018191623A JP 2018191623 A JP2018191623 A JP 2018191623A JP 2017101161 A JP2017101161 A JP 2017101161A JP 2017101161 A JP2017101161 A JP 2017101161A JP 2018191623 A JP2018191623 A JP 2018191623A
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Abstract
Description
(1)有機塩のカチオンと脂質二重膜(細胞膜)のリン酸が静電相互作用によって接近する。
(2)有機塩のカチオンのアルキル鎖と脂質二重膜の脂質部位が疎水性相互作用することでカチオンのアルキル鎖が脂質二重膜へ挿入され、細胞膜が破壊される。
本発明者らは、カチオンのアルキル鎖の末端に、非常に極性の高いアニオンを導入し双性イオンにすることで、毒性を抑えることが可能であると考えた。具体的には、アニオンを導入することでリン酸とアニオン間の静電反発が起こり、上記(1)を阻害することができる。また、アニオンを導入することで極性が非常に高くなり、上記(2)の疎水性相互作用も抑制することができる。そのため、イミダゾリウム、ホスホニウム、アンモニウム、スルホニウム、ピリジニウム、ピロリジニウム等をカチオンとする有機塩の毒性を大きく下げることができる。すなわち、本発明の要旨は以下のとおりである。
(2)前記双性イオンのカチオン部位が、イミダゾリウムカチオン、ホスホニウムカチオン、アンモニウムカチオン、スルホニウムカチオン、ピラゾリウムカチオン、ピリジニウムカチオン、ピロリジニウムカチオン、モルホリニウムカチオン、シクロプロペニリウムカチオン及びピペリジニウムカチオンからなる群から選択されるカチオンである上記(1)に記載の培地用添加剤。
(3)前記双性イオンのカチオン部位が、イミダゾリウムカチオン又はホスホニウムカチオンである上記(1)に記載の培地用添加剤。
(4)前記双性イオンのカチオン部位が、置換基として分子鎖中に1個以上のヘテロ原子を有していても良い炭素数1〜5個のアルキル基を1個以上有する上記(1)〜(3)のいずれか1つに記載の培地用添加剤。
(5)前記双性イオンのカチオン部位とアニオン部位との間が、分子鎖中に1個以上のヘテロ原子を有していても良い炭素数1〜5個の1個以上のアルキレン基を介して結合される上記(1)〜(4)のいずれか1つに記載の培地用添加剤。
(6)前記双性イオンが、下記式(1)
で表される上記(1)に記載の培地用添加剤。
(7)前記双性イオンが、下記式(2)
で表される上記(6)に記載の培地用添加剤。
(8)双性イオンを含む難溶性物質溶解剤。
(9)前記双性イオンのカチオン部位が、イミダゾリウムカチオン、ホスホニウムカチオン、アンモニウムカチオン、スルホニウムカチオン、ピラゾリウムカチオン、ピリジニウムカチオン、ピロリジニウムカチオン、モルホリニウムカチオン、シクロプロペニリウムカチオン及びピペリジニウムカチオンからなる群から選択されるカチオンである上記(8)に記載の難溶性物質溶解剤。
(10)前記双性イオンのカチオン部位が、イミダゾリウムカチオン又はホスホニウムカチオンである上記(8)に記載の難溶性物質溶解剤。
(11)
前記双性イオンのカチオン部位が、置換基として分子鎖中に1個以上のヘテロ原子を有していても良い炭素数1〜5個のアルキル基を1個以上有する上記(8)〜(10)のいずれか1つに記載の難溶性物質溶解剤。
(12)前記双性イオンのカチオン部位とアニオン部位との間が、分子鎖中に1個以上のヘテロ原子を有していても良い炭素数1〜5個の1個以上のアルキレン基を介して結合される上記(8)〜(11)のいずれか1つに記載の難溶性物質溶解剤。
(13)前記双性イオンが、下記式(1)
で表される上記(8)に記載の難溶性物質溶解剤。
(14)前記双性イオンが、下記式(2)
で表される上記(13)に記載の難溶性物質溶解剤。
(15)下記式(4)
本発明の培地用添加剤は、双性イオンを含む。双性イオンとしては、イオン液体様のカチオン部位とイオン液体様のアニオン部位とが共有結合により連結された物質を挙げることができる。好ましくは、双性イオンのカチオン部位とアニオン部位との間は、分鎖中に1個以上のヘテロ原子を有していても良い炭素数1〜5個の1個以上のアルキレン基を介して結合される。ここで、ヘテロ原子の例としては、酸素、窒素、イオウ、リン等が挙げられる。アルキレン基の炭素数を1〜5個にすることで、双性イオンの細胞に対する毒性をより弱めることができる。
(1)双性イオンOE2imC3Cの合成
15gのNaHを50mLのテトラヒドロフランと混合し、14gのイミダゾールを添加し、一日撹拌した。37gの1−ブロモ−2−(2−メトキシエトキシ)エタンを加え、70℃で6時間撹拌した。溶液を取り出し、蒸留によって精製した。それを250mLのアセトニトリルと混合し、29gのエチル−4−ブロモブチレートと混合し、80℃で16時間還流した。ジエチルエーテルで洗浄後、アニオン交換樹脂と混合し、ろ過後、溶媒を減圧留去することでOE2imC3Cを得た。
NMRデータ:δ=2.13-2.27 (4H, m, CH2CO and CH2CH2CO), 3.37 (3H, s, CH3O), 3.51-3.65 (4H, m, CH3OCH2CH2), 3.86 (2H, t, J = 3.6Hz, OCH2CH2N), 4.40 (2H, t, J=6.7Hz, NCH2CH2CH2COO), 4.66 (2H, t, J=3.7Hz, OCH2CH2N), 7.29 and 7.49 (2H, t, J= both 1.6 Hz, NCHCHN), 11.00 (1H, s, NCHN).
50mLのテトラヒドロフランと14gの1−エチルイミダゾール、26gの1−ブロモ−2−(2−メトキシエトキシ)エタンを加え、80℃で4時間撹拌した。イオン液体相を取り出し、ジエチルエーテルによって洗浄した。アニオン交換樹脂と混合し、イオン交換を行い、ろ過後、酢酸で中和した。小過剰の酢酸をアルミナで除き[OE2eim]OAcを得た。
NMRデータ:δ=1.58 (3H, t, J=7.4Hz, CH3CH2N), 1.98 (3H, s, CH3CO), 3.37 (3H, s, CH3O), 3.51-3.67 (4H, m, CH3OCH2CH2), 3.86 (2H, t, J=4.0Hz, OCH2CH2N), 4.36 (2H, quin, J=7.4Hz, CH3CH2N), 4.62 (2H, t, J=5.4Hz, OCH2CH2N), 7.34 and 7.55 (2H, t, J= both 1.6 Hz, NCHCHN), 11.23 (1H, s, NCHN).
上記のOE2imC3C、[C2mim]OAc、[OE2eim]OAc、又は有機溶媒としてジメチルスルホキシド(DMSO)を、5%仔牛血清含有ダルベッコ変法MEM培地に2重量%もしくは10重量%となるように添加し、ヒト線維芽細胞を24時間培養した。初期播種数は2.0×104細胞/ウェルとした。24時間培養後、ヒト線維芽細胞の生存率をナイルレッドを用いた方法で調べた。その結果を図1及び図2に示す。
上記1で合成したOE2imC3Cに対し、難溶性物質としてクロラムフェニコールを終濃度が100mg/Lになるように溶解させ、LB培地によって希釈した後(OE2imC3C終濃度:10重量%)、大腸菌の培養を行った。菌の濃度の指標であるOD600が、24時間の培養によって0.1から3.9まで増大した。このことから、双性イオンであるOE2imC3Cは大腸菌に対する細胞毒性が低く、難溶性物質を高濃度に溶解した状態で培地に添加し得ることが示された。
(1)双性イオンP8,8,8C3Sの合成
37gのトリオクチルホスフィン及び12gのブタンスルトンを、50mLのヘキサン中で200℃10時間還流し、ヘキサン及びジエチルエーテルで洗浄することでP8,8,8C3Sを得た。
P8,8,8C3Sを1重量%添加したLB培地で、大腸菌の培養を行った。菌の濃度の指標であるOD600が24時間の培養によって0.1から0.57まで増大し、P8,8,8C3S存在下でも菌が増殖できることが確認された。
上記1で合成したOE2imC3Cに対し、難溶性物質としてアシクロビル(Acyclovir)を溶解させた。
アシクロビルは、単純ヘルペスウイルスや水痘・帯状疱疹等に対して有効なウイルス感染症の治療薬である。単純ヘルペスウイルス感染症(単純疱疹)の治療や骨髄移植時における発症抑制、水痘、帯状疱疹の治療等に使われる。注射薬はこれらのウイルスに起因する脳炎・髄膜炎にも適応を持っている。化学的性状は、白色から微黄白色の結晶性の粉末でにおいはなく、味は苦い。ジメチルスルホキシド(DMSO)に溶けやすく、酢酸にはやや溶けにくい。水に溶けにくく、メタノール及びエタノールに極めて難溶である。アセトン、1−プロパノール、ジエチルエーテル、ヘキサンにほとんど溶けない。希塩酸、希水酸化ナトリウム試液又はアンモニア試液に溶ける。
上記1で合成したOE2imC3C、水、及びDMSOに対し、難溶性物質として、グリチルレチン酸、グリチルリチン酸二カリウム、クマリン、オノニン、グリチルリチン酸、リクイリチン、コラーゲン、キシラン、リグニン、及びクロラムフェニコールをそれぞれ溶解させた。クロラムフェニコール及びコラーゲン以外の構造式を以下に示す。
(1)双性イオンOE2imC5Cの合成
エチル-4-ブロモブチレートの代わりにエチル-6-ブロモヘキサノエートを用いた以外は、上記OE2imC3Cの場合と同様にして、OE2imC5Cを合成した。
1-ブロモ-2-(2-メトキシエトキシ)エタンの代わりに1-ブロモ-エチルメチルエーテルを用いた以外は、上記OE2imC3Cの場合と同様にしてOE1imC3Cを合成した。
12gの1-メチルイミダゾールを250mLのアセトニトリルと混合し、29gのエチル-4-ブロモブチレートと混合し、80℃で16時間還流した。ジエチルエーテルで洗浄後、アニオン交換樹脂と混合し、ろ過後、溶媒を減圧留去することでC1imC3Cを得た。
1-メチルイミダゾールの代わりに1-ブチルイミダゾールを用いた以外は、上記C1imC3Cの場合と同様にして、C4imC3Cを合成した。
12gの1-メチルイミダゾールを250mLのアセトニトリルと混合し、17gの1,3-プロパンスルトンと混合し、80℃で16時間還流した。ジエチルエーテルで洗浄後、溶媒を減圧留去することでC1imC3Sを得た。
プロパンスルトンの代わりに1,4-ブタンスルトンを用いた以外は、上記C1imC3Sの場合と同様にして、C1imC4Sを合成した。
合成した各双性イオンと、上記1で用いたOE2imC3C、並びにイオン液体である[C2mim]OAc及び[OE2eim]OAcを、LB培地にそれぞれ添加し(培地中の双性イオン又はイオン液体の濃度は0.5M)、大腸菌の成長について調べた。大腸菌の濃度の指標であるOD600が0.1となるようにLB培地中へ植菌し、37℃24時間培養後のOD600を調べた。その結果を表2に示す。
上記1で用いたOE2imC3Cを、LB培地に30重量%となるように添加し、大腸菌の成長について調べた。大腸菌の濃度の指標であるOD600が0.1となるようにLB培地中へ植菌し、−10℃で10日間培養後のOD600を調べたところ0.2であった。この結果から、本発明の双性イオンは、低温下でも、大腸菌の増殖を阻害しないことが明らかとなった。
Claims (15)
- 双性イオンを含む培地用添加剤。
- 前記双性イオンのカチオン部位が、イミダゾリウムカチオン、ホスホニウムカチオン、アンモニウムカチオン、スルホニウムカチオン、ピラゾリウムカチオン、ピリジニウムカチオン、ピロリジニウムカチオン、モルホリニウムカチオン、シクロプロペニリウムカチオン及びピペリジニウムカチオンからなる群から選択されるカチオンである請求項1に記載の培地用添加剤。
- 前記双性イオンのカチオン部位が、イミダゾリウムカチオン又はホスホニウムカチオンである請求項1に記載の培地用添加剤。
- 前記双性イオンのカチオン部位が、置換基として分子鎖中に1個以上のヘテロ原子を有していても良い炭素数1〜5個のアルキル基を1個以上有する請求項1〜3のいずれか1項に記載の培地用添加剤。
- 前記双性イオンのカチオン部位とアニオン部位との間が、分子鎖中に1個以上のヘテロ原子を有していても良い炭素数1〜5個の1個以上のアルキレン基を介して結合される請求項1〜4のいずれか1項に記載の培地用添加剤。
- 前記双性イオンが、下記式(1)
で表される請求項1に記載の培地用添加剤。 - 前記双性イオンが、下記式(2)
で表される請求項6に記載の培地用添加剤。 - 双性イオンを含む難溶性物質溶解剤。
- 前記双性イオンのカチオン部位が、イミダゾリウムカチオン、ホスホニウムカチオン、アンモニウムカチオン、スルホニウムカチオン、ピラゾリウムカチオン、ピリジニウムカチオン、ピロリジニウムカチオン、モルホリニウムカチオン、シクロプロペニリウムカチオン及びピペリジニウムカチオンからなる群から選択されるカチオンである請求項8に記載の難溶性物質溶解剤。
- 前記双性イオンのカチオン部位が、イミダゾリウムカチオン又はホスホニウムカチオンである請求項8に記載の難溶性物質溶解剤。
- 前記双性イオンのカチオン部位が、置換基として分子鎖中に1個以上のヘテロ原子を有していても良い炭素数1〜5個のアルキル基を1個以上有する請求項8〜10のいずれか1項に記載の難溶性物質溶解剤。
- 前記双性イオンのカチオン部位とアニオン部位との間が、分子鎖中に1個以上のヘテロ原子を有していても良い炭素数1〜5個の1個以上のアルキレン基を介して結合される請求項8〜11のいずれか1項に記載の難溶性物質溶解剤。
- 前記双性イオンが、下記式(1)
で表される請求項8に記載の難溶性物質溶解剤。 - 前記双性イオンが、下記式(2)
で表される請求項13に記載の難溶性物質溶解剤。 - 下記式(4)
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