JP2022188039A - 光増感剤分散物およびその使用 - Google Patents
光増感剤分散物およびその使用 Download PDFInfo
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- JP2022188039A JP2022188039A JP2022142961A JP2022142961A JP2022188039A JP 2022188039 A JP2022188039 A JP 2022188039A JP 2022142961 A JP2022142961 A JP 2022142961A JP 2022142961 A JP2022142961 A JP 2022142961A JP 2022188039 A JP2022188039 A JP 2022188039A
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- dispersion
- photosensitizer
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- microemulsion
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Abstract
Description
抗生物質治療に代わる治療の研究は、特にすでに2002年における日本およびアメリカ合衆国でのバンコマイシン耐性細菌系統(VRSA)の確認および増大する発生の結果、例えば細菌が原因となる感染症の処置に大きな意味を持つ。ヨーロッパでは2013年に最初のVRSA患者分離株がポルトガルで得られた。
また、真菌感染症における真菌感染症調合薬剤に対する耐性の増加も、表在性の感染症の処置において問題を先鋭化している。真菌感染症調合薬剤に対する耐性の臨床的帰結は、特に免疫が抑制された患者の処置の失敗によって示される。
耐性または多耐性の病原菌の撲滅のための新しい試みは、したがって、一方では新しい拮抗薬、例えば抗生物質または有糸分裂阻害剤の探索であり、他方では代替的な不活性化の可能性の探索である。
代替的な方法としては、微生物の光線力学的な不活性化が実証されている。微生物の光線力学的な不活性化においては、2つの光酸化プロセスが決定的な役割を果たす。
光増感剤は所定の波長の光によって励起される。励起された光増感剤は、活性酸素種(ROS)の生成を引き起こし、一方では、例えば、超酸化物アニオン、過酸化水素またはヒドロキシルラジカルのようなラジカル、および/または、他方では、例えば一重項酸素のような、励起された分子状酸素を生成させる。
いずれの反応においても、活性酸素種(ROS)と直接に接する特異的な生体分子の光酸化が重要である。ここでは、特に、微生物の細胞膜の成分として存在する、脂質およびタンパク質の酸化が起こる。細胞膜の破壊によっても、該当する微生物の不活性化が達成される。ウイルスおよび真菌に対しても類似の除去プロセスが採用される。
例えば、一重項酸素によって、好適には、酸化感受性の分子が攻撃される。酸化感受性の分子は、例えば、二重結合または酸化感受性の基を含む分子(フェノール、硫化物またはチオール)である。特に破壊されやすいのは、特に細菌の膜中の不飽和脂肪酸である。
しかし、従来技術に基づいて知られている多くの光増感剤は、不都合にも、不十分な濡れ性の疎水性表面を有している。
さらに、上記光増感剤を含む組成物は、上記光増感剤の向上した付着を、表面への塗布後に好ましく保証する。
さらに、上記光増感剤の有効性は、好ましく向上される。
しかし、上記光増感剤を含む組成物は、上記組成物に含まれる光増感剤分子の、特定の波長の光による刺激を、実質的に妨げない。
(a)少なくとも1つの光増感剤
(b)少なくとも1つの液体極性相、および
(c)少なくとも1つの界面活性剤
を含んでおり、当該分散物は、2~50℃の温度および600~1200mbrの圧力において、マイクロエマルション、ゲル、またはそれらの混合物を含み、好ましくはそれからなる。
(A)微生物を、請求項1~14のいずれか1項に係る光増感剤を含む分散物と接触させるステップ、および
(B)適切な周波数およびエネルギー密度の電磁放射線を上記微生物および上記少なくとも1つの光増感剤に照射するステップを含んでいる。
(a)少なくとも1つの光増感剤
(b)少なくとも1つの液体極性相、および
(c)少なくとも1つの界面活性剤
を含んでおり、かつ上記分散物は、2~50℃の温度および600~1200mbrの圧力において、マイクロエマルション、ゲル、またはそれらの混合物を含み、好ましくはそれからなる。
パテントブルーV (4-[4,4'-ビス(ジエチルアミノ)- α-ヒドロキシ-ベンズヒドリル]-6-ヒドロキシ-ベンゾール-1,3-ジスルホン酸)、マラカイトグリーン (N,N,N',N'-テトラメチル-4,4'-ジアミノトリフェニルカルベニウムクロリド)、フクシン (4-[(4-アミノフェニル)-(4-イミノ-1-シクロヘキサ-2,5-ジエニリデン)メチル]アニリン塩酸塩)、パラフクシン (4,4'-(4-イミノシクロヘキサ-2,5-ジエニリデン メチレン)ジアニリン塩酸塩)、クリスタルバイオレット ((4-(4,4'-ビス(ジメチルアミノフェニル)ベンズヒドリリデン)シクロヘキサ-2,5-ジエン-1-イリデン)ジメチルアンモニウムクロリド)である。
CH3-(CH2)m-(O-[CH2]x)n-OH, (I)
式中、 m = 8~20、好ましくは10 ~16 であり、n = 1 ~25、x = 1, 2, 3または4 である。
H3C-(CH3)a-CH2-COO-M+, (II)
式中、a = 5 ~21、好ましくは8~16であり、M+は水溶性カチオンであり、好ましくはアルカリ金属またはアンモニウムのカチオンであり、好ましくはLi+、Na+、K+、またはNH4 +である。
H3C-(CH3)d-CH2-O-SO3 -M+, (IV)
式中、d = 6 ~20、好ましくは8~18であり、M+は水溶性カチオン、好ましくは アルカリ金属またはアンモニウムのカチオンであり、好ましくはLi+、Na+、K+、またはNH4+である。
H3C-(CH3)e-CH2-O-PO3 2-2 x M+, (V)
式中、e = 6~20、好ましくは8~18であり、M+は水溶性カチオン、好ましくはアルカリ金属またはアンモニウムのカチオンであり、好ましくはLi+、Na+、K+、またはNH4+である。
(R1)(R2)(R3)(R4)N+Z- (VI)
式中、有機ラジカルR1はアルキル基を意味し、当該アルキル基は直鎖状または分岐鎖状でよく、好ましくは直鎖状であり、8個から20個の炭素原子、好ましくは10個から18個の炭素原子、より好ましくは12個から16個の炭素原子を有し、有機ラジカルR2、R3、およびR4はそれぞれ独立してアルキルラジカルを意味し、当該アルキルラジカルは直鎖状または分岐鎖状でよく、好ましくは直鎖状であり、1個から20個の炭素原子、好ましくは1個から16個の炭素原子、より好ましくは1個から12個のC原子を有し、Zはアニオンを意味し、当該アニオンは、好ましくは、フッ化物、塩化物、臭化物、ヨウ化物、硫酸塩、硫酸水素塩、リン酸塩、二水素リン酸塩、水素リン酸塩、トシル酸塩、メシル酸塩、蟻酸塩, 酢酸塩、プロピオン酸塩、ブタン酸塩、シュウ酸塩、酒石酸塩、フマル酸塩、安息香酸塩、クエン酸塩および/またはそれらの混合物からなる群から選択される。
(a)少なくとも1つの光増感剤であって、上記のフェナレノン、上記のクルクミン、上記のフラビン、上記のポルフィリン、上記のポルフィセン、上記のキサンチン色素、上記のクマリン、上記のフタロシアニン、上記のフェノチアジン化合物、上記のアントラセン色素、上記のピレン、上記のフラーレン、上記のペリレン、およびそれらの混合物からなる群から選択されることがより好ましく、上記のフェナレノン、上記のクルクミン、上記のフラビン、上記のポルフィリン、上記のフタロシアニン、上記のフェノチアジン化合物、およびそれらの混合物からなる群から選択されることが好ましく、上記のフェナレノン、上記のクルクミン、上記のフラビン、およびそれらの混合物からなる群から選択されることがより好ましく、式(2)から式(28)、式(32)から式(49)、式(51)から式(64)、式(75)から式(105)の化合物およびそれらの混合物からなる群から選択されることがより好ましい、少なくとも1つの光増感剤と、
(b)少なくとも1つの極性溶媒(好ましくは水)と、
(c)少なくとも1つの界面活性剤であって、上記の非イオン性界面活性剤、上記のアニオン性界面活性剤、上記のカチオン性界面活性剤、上記の両性界面活性剤およびこれらの混合物からなる群、好ましくは上記の非イオン性界面活性剤、上記のアニオン性界面活性剤およびそれらの混合物からなる群から選択される、少なくとも1つの界面活性剤と、
(d)少なくとも1つの非極性溶媒であって、上記の5個から30個の炭素原子を有する非環式アルカン、上記の5個から13個の炭素原子を有する環式アルカン、上記の5個から20個の炭素原子を有するペルフルオロアルカン、上記の4個から20個の炭素原子を有するモノカルボン酸エステル、上記の6個から20個の炭素原子を有するポリカルボン酸エステル、およびそれらの混合物からなる群から選択されることがより好ましい、少なくとも1つの非極性溶媒と、を含む。
(e)上記の2個から12個の炭素原子と、好ましくは1個から6個のOH基とを有するアルカノール、およびそれらの混合物からなる群から選択される、少なくとも1つのアルカノールをさらに含む。
(a)少なくとも1つの光増感剤であって、上記のフェナレノン、上記のクルクミン、上記のフラビン、上記のポルフィリン、上記のポルフィセン、上記のキサンチン色素、上記のクマリン、上記のフタロシアニン、上記のフェノチアジン化合物、上記のアントラセン色素、上記のピレン、上記のフラーレン、上記のペリレン、およびそれらの混合物からなる群から選択されることがより好ましく、上記のフェナレノン、上記のクルクミン、上記のフラビン、上記のポルフィリン、上記のフタロシアニン、上記のフェノチアジン化合物、およびそれらの混合物からなる群から選択されることが好ましく、上記のフェナレノン、上記のクルクミン、上記のフラビン、およびそれらの混合物からなる群から選択されることがより好ましく、式(2)から式(25)、式(32)から式(49)、式(51)から式(64)、式(75)から式(105)の化合物およびそれらの混合物からなる群から選択されることがより好ましい、少なくとも1つの光増感剤と、
(b)少なくとも1つの極性溶媒(好ましくは水)と、
(c)少なくとも1つの界面活性剤であって、上記の非イオン性界面活性剤、上記のアニオン性界面活性剤、上記のカチオン性界面活性剤、上記の両性界面活性剤およびこれらの混合物からなる群、好ましくは上記の非イオン性界面活性剤、上記のアニオン性界面活性剤およびそれらの混合物からなる群から選択される、少なくとも1つの界面活性剤と、
(d)少なくとも1つのゲル化剤と、を含む。
(e)好ましくは無機酸、有機酸、無機塩基、有機塩基、またはそれらの混合物である、少なくとも1つのpH調整物質をさらに含む。
(f)上記少なくとも1つの極性溶媒(好ましくは水)中に存在する、金属の少なくとも1つの可溶性塩であって、当該金属は、元素周期表の第1から第3主族の金属、好ましくはアルカリ金属またはアルカリ土類金属からなる群から選択される可溶性塩と、フッ化物、塩化物、臭化物、ヨウ化物、硫酸塩、硫酸水素塩、リン酸塩、二水素リン酸塩、水素リン酸塩、トシル酸塩、メシル酸塩、 蟻酸塩、 酢酸塩、プロピオン酸塩、ブタン酸塩、シュウ酸塩、酒石酸塩、フマル酸塩、安息香酸塩、クエン酸塩および/またはそれらの混合物からなる群、より好ましくは塩化物、硫酸塩、硫酸水素塩、蟻酸塩、酢酸塩、安息香酸塩, クエン酸塩、および/またはそれらの混合物からなる群から選択される少なくとも1つのアニオンと、をさらに含む。
(A)上記微生物を、請求項1~14のいずれか1項に記載の少なくとも1つの分散物と接触させるステップと、
(B) 適切な周波数およびエネルギー密度の電磁放射線を上記微生物および、上記分散物に含まれている少なくとも1つの光増感剤に照射するステップ。
(a)少なくとも1つの光増感剤、
(b)少なくとも1つの界面活性剤、および
(c)少なくとも1つの界面活性剤
を含んでいる。
(a)上述のフェナレノン、上述のクルクミン、上述のフラビン、上述のポルフィリン、上述のポルフィセン、上述のキサンチン色素、上述のクマリン、上述のフタロシアニン、上述のフェノチアジン化合物、上述のアントラセン色素、上述のピレン、上述のフラーレン、上述のペリレン、およびそれらの混合物、より好ましくは上述のフェナレノン、上述のクルクミン、上述のフラビン、上述のポルフィリン、上述のフタロシアニン、上述のフェノチアジン化合物、およびそれらの混合物、より好ましくは上述のフェナレノン、上述のクルクミン、上述のフラビン、およびそれらの混合物、より好ましくは式(2)~(25)、(32)~(49)、(51)~(64)、(75)~(105)を有している化合物およびそれらの混合物から、より好ましく選択される、少なくとも1つの光増感剤、
(b)少なくとも1つの極性溶媒、好ましくは水、
(c)上述の非イオン性界面活性剤、上述のアニオン性界面活性剤、上述のカチオン性界面活性剤、上述の両性界面活性剤およびこれらの混合物、好ましくは上述の非イオン性界面活性剤、上述のアニオン性界面活性剤およびこれらの混合物からなる群から選択される少なくとも1つの界面活性剤、ならびに
(d)5~30の炭素原子を有している上述の非環式アルカン、3~13の炭素原子を有している上述の環状アルカン、5~20の炭素原子を有している上述のパーフルオロアルカン、4~20の炭素原子を有している上述のモノカルボン酸エステル、6~20の炭素原子を有している上述のポリカルボン酸エステルおよびそれらの混合物からより好ましく選択される少なくとも1つの非極性溶媒、ならびに
(e)任意に、1~6のOH基を有していることが好ましい、2~12の炭素原子を有している、上述のアルカノールおよびそれらの混合物からなる群から選択される少なくとも1つのアルカノール
を含んでいる。
(A)上記微生物を、態様1~28のいずれか1項に記載の少なくとも1つの分散物と接触させるステップ;および
(B)適切な周波数およびエネルギー密度の電磁放射線を、上記微生物、および上記分散物に含まれている少なくとも1つの光増感剤に照射するステップ
を含んでいる。
図1は、光増感剤なしのマイクロエマルションE1~E4およびエタノール水溶液の、実施例1において示されている濃度にしたがって測定された接触角の平均値を示している。図2は、マイクロエマルションの、水による希釈物(DMS;TWEEN(登録商標) 20/1,2-ペンタンジオール(1:3);水)の、実施例1において測定された測定された接触角の平均値を示している。図3は、水(w)、マイクロエマルションE1(E1)またはマイクロエマルションE2(E2)における光増感剤TMPyPについて、実施例1において測定された時間分解一重項酸素スペクトルを示している。図4は、水(w)、マイクロエマルションE1(E1)またはマイクロエマルションE2(E2)における光増感剤SA-PN-01aについて、実施例1において測定された時間分解一重項酸素スペクトルを示している。図5は、水(w)、マイクロエマルションE1(E1)またはマイクロエマルションE2(E2)における光増感剤FL-AS-1aについて、実施例1において測定された時間分解一重項酸素スペクトルを示している。図6aは、示されている濃度の、水における光増感剤SA-PN-01aについて実施例1において測定された光毒性試験の結果を示している。図6bは、示されている濃度の、マイクロエマルションE2(E2)光増感剤SA-PN-01aについて実施例1において測定された光毒性試験の結果を示している。図7は、示されている界面活性剤の対応する量が加えられている、光増感剤なしのゲルG2およびG3の、実施例3において測定された接触角の平均値を示している。図8は、ゲルG3における光増感剤TMPyPについて実施例3において測定された、時間分解一重項酸素スペクトルを示している。図9は、ゲルG3における光増感剤TMPyPについて実施例3において測定された、波長分解一重項酸素スペクトルを示している。
(TMPyP、M=1363.65g/mol)
(SA-PN-01a、M = 307.78g/mol)、
条件5a)MeOH、メチルアミン、RT、一晩、50℃、2~10時間、60~75%;
5b)トリメチルアミン、エタノール、RT、一晩、50℃、5時間、83%;
条件5c)N,N’-ジ-Boc-N’’-トリフリルグアニジン、DCM、NEt3、0℃、その後RT、4時間、88%;
5d)Et2O中のHCl、DCM、RT、6時間、50℃、5時間、96%。
化学式(27)を有する化合物のクロライド
氷冷されたメタノール中のメチルアミン溶液(40mL、10%)をメタノール(10mL)中の2-クロロメチル-1H-フェナレン-1-オン(1)(113mg、0.5mmol)に滴状で1時間以上加えた。室温で30時間撹拌した後、余分なアミンおよび溶媒を窒素流中で除去した。残渣を、ジクロロメタン(DCM)/エタノール(4:1)に溶解し、ジエチルエーテルを加えることにより沈澱させた。生成物を遠心分離し(60分間、4400rpm、0℃)、上清を捨てた。この工程をもう1度繰り返した。そして、残渣をジエチルエーテル中に懸濁した。黄色の固体が沈殿した後、上清をデカンテーションして捨てた。この工程を2回繰り返した。生成物(101mg、0.39mmol)は、黄褐色の粉末であった。
1H-NMR(300MHz,CDCl3):δ[ppm]=8.66(d,J=7.4Hz,1H),8.28~8.20(m,2H),8.08(d,J=8.3Hz,1H),7.94(d,J=7.0Hz,1H),7.80(t,J=7.7Hz,1H)7.67~7.59(m,1H),4.20(s,2H),2.79(s,3H),
MS(ESI-MS,CH2Cl2/MeOH+10mmolNH4OAc):e/z(%)=224.1(MH+,100%),
分子量(MW)=224.28+35.45g/mol,分子式(MF)=C15H14NOCl.
(SA-PN-02a)
化学式(26)を有する化合物のクロライド
2-(クロロメチル)-1H-フェナレン-1-オン(1)(230mg、1mmol)-エタノール(60mL)をシュレンクフラスコに注いだ。エタノール中のトリエチルアミン(5mL、5.6M、23mmol)を、シリンジによって壁を伝わせて加えた。溶液を暗所で一晩撹拌した。それから、撹拌を50℃で30分間続けた。溶媒の体積を、3mLになるまで濃縮した。ジエチルエーテル(50mL)を加え、生成物を完全に沈殿させた。生成物を遠心分離し(60分間、4400rpm、0℃)、上清を捨てた。残渣をジエチルエーテルに懸濁した。黄色の固体が沈殿した後、上清をデカンテーションして捨てた。この工程を2回繰り返した。固体を減圧下で乾燥し、黄色の粉末を得た(210mg、0.73mmol)。
1H-NMR(600MHz,D2O):δ[ppm]=8.02(d,J=8Hz,1H),7.97(d,J=6.3Hz,1H),7.92(d,J=8.2Hz,1H),7.77(s,1H),7.62(d,J=7Hz,1H),7.50(t,J=7.8Hz,1H),7.45(t,J=7.8Hz,1H),4.12(s,2H),2.98(s,9H),
MS(ESI-MS,CH2Cl2/MeOH+10mmolNH4OAc):e/z(%)=252.1(100,M+),
MW=287.79g/mol,
MF=C17H18NOCl;
化学式(28a)を有する化合物
ジクロロメタン(10mL)中のN,N’-ジ-Boc-N’ ’-トリフリルグアニジン(0.41g、1.05mmol)を乾燥させた25mL丸底フラスコに注いだ。トリエチルアミン(0.3g、mL、0.39mL、3mmol)を、脱湿条件下2~5℃において、ゆっくりと加えた。化合物3(130mg、0.5mmol)を一度に加えた。室温で5時間撹拌した後、ジクロロメタン(30mL)で希釈し、その溶液を分液ロートへ移した。有機相を、硫酸水素カリウム水溶液、飽和重炭酸ナトリム溶液(10mL)および飽和食塩水で洗浄し、MgSO4上で乾燥させて濾過した。そして、回転蒸発によって濃縮した。粗生成物を、アセトン/石油エーテル(1:2)を用いたカラムクロマトグラフィーによって精製し、黄色の固体として生成物を得た(0.21g)。さらなる精製のため、その物質をアセトン(1mL)に溶解し、石油エーテル(14mL)を用いて沈殿させた。沈殿物を吸い上げ、石油エーテルで洗浄した。
1H-NMR(300MHz,CDCl3):δ[ppm]=8.63(d,J=7.3Hz,1H),8.21(d,J=7.9Hz,1H),8.03(d,J=8.2Hz,1H),7.85~7.70(m,3H),7.67~7.54(m,1H),4.59(s,2H),3.01(s,3H),1.50(s,9H),1.48(s,9H),
MS(ESI-MS,CH2Cl2/MeOH+10mmolNH4OAc):e/z(%)=466.1(MH+,100%),
MW=465.53g/mol,
MF=C26H31N3O5
(SA-PN-24d)
化学式(28)を有する化合物のクロライド
化合物の作製および精製を、光から保護する条件下で実施した。化合物5(200mg、0.45mmol)をジクロロメタン(20mL、CaCl CaCl2上で乾燥)に加えた。ジエチルエーテル(2mL)中のHCl飽和溶液を滴状で加えた。脱湿された条件下、室温で4時間撹拌した後、溶液を2つのブルーキャッップ(Blue Cap)に分け、ジエチルエーテルを15mLになるように注いだ。生成物を遠心分離し(60分間、4400rpm、0℃)、上清を捨てた。残渣をジエチルエーテルに懸濁した。黄色の固体が沈殿した後、上清をデカンテーションし、捨てた。この工程を2回繰り返した。これに続いて、生成物を減圧下で乾燥し、130mgの黄色の粉末を得た。
1H-NMR(300MHz,DMSO-d6):δ[ppm]=8.60~8.47(m,4H),8.33~8.24(m,2H),8.16~8.09(m,2H),7.98~7.89(m,2H),7.84~7.73(m,4H),7.57~7.48(m,7H),4.55~4.42(m,4H),3.05(s,6H),
MS(ESI-MS,CH2Cl2/MeOH+10mmolNH4OAc):e/z(%)=266.1(MH+,100%);
MW=266.3+35.45=301.75g/mol;
MF=C16H16N3OCl
A)異なる水含有マイクロエマルションの調製
以下に示されるマイクロエマルションE1~E4の成分のwt%は、それぞれ光増感剤を含まないそれぞれのマイクロエマルションの総重量に基づいている。
20.0wt%ジメチルコハク酸(DMS)
8.33wt%ドデシル硫酸ナトリウム(SDS)
16.67wt%1-ペンタノール
55.0wt%水
20.0wt%ジメチルコハク酸(DMS)
8.33wt%ドデシル硫酸ナトリウム(SDS)
16.67wt%1,2-ペンタンジオール
55.0wt%水
10.0wt%ジメチルコハク酸(DMS)
3.75wt%TWEEN(登録商標)20
11.25wt%1,2-ペンタンジオール
75.0wt%水
10.0wt%ジメチルコハク酸(DMS)
3.75wt%TWEEN(登録商標)20
11.25wt%1,2-プロパンジオール
75.0wt%水
使用するマイクロエマルションによる表面の濡れ性を、接触角試験を用いて測定した。
それぞれのマイクロエマルションE1~E4中において使用する光増感剤(TMPyP、SA-PN-01a、およびFL-AS-H-1a)の吸収を、250nm~600nmの波長域での吸収スペクトルを記録することで測定した。
本発明に係るマイクロエマルションの光毒性を調べるため、MTTアッセイを使用した。
A)様々な油含有マイクロエマルションの調製
さらに、油含有マイクロエマルションE5およびE6を調製した。
下記に示されるマイクロエマルションE5およびE6の成分のwt%は、光増感剤を含まないそれぞれのマイクロエマルションの総重量にそれぞれ基づいている。
66wt%ドデカン
29wt%ルテンソールAO7
5wt%水
66wt%パラフィンオイル
4wt%水
10wt%ルテンソールAO7
20wt%コステランSQ/OVH
それぞれのマイクロエマルションE5およびE6中において使用する光増感剤FL-AS-H-1aの吸収を、実施例1に記載したように、230nm~600nm波長域に対する吸収スペクトルを記録することで測定した。ここで、光増感剤FL-AS-H-2を、マイクロエマルションE5およびE6ならびに水中に10μMの濃度となるよう溶解した。
A)光増感剤を含むゲルの作製
以下に示すゲルG1~G3の成分のwt%は、使用されるゲルの総重量にそれぞれ基づいている。
成分/量[mL]
カルボポルSF-1(4wt%水溶液)/6.25
水酸化ナトリウム(2wt%水溶液)/2
塩化ナトリウム(10wt%水溶液/4
カルボポル水和物SF-1重合体、つまり、アクリル共重合体は、Lubrizol Corporation (Wickliffe, OH, USA)から購入し、ゲル化剤として使用した。
成分 量[mL]
カルボポルSF-1(4wt%水溶液) 6.25
水酸化ナトリウム(2wt%水溶液) 2
塩化ナトリウム(20wt%水溶液) 2
Brij35(6wt%水溶液) 2
Brij35、つまり、ポリオキシエチレン(23)ラウリルエーテルはMerck KGaA (Darmstadt, DE)から入手し、界面活性剤として使用した。
成分 量
カルボポルSF-1(4wt%水溶液) 6.25
水酸化ナトリウム(2wt%水溶液) 2
塩化ナトリウム(20wt%水溶液) 2
PLANTACARE 818 UP(6wt%水溶液) 2
PLANTACARE 818 UP、つまりC8~C17脂肪族アルコールグルコシドのD-グルコピラノースを、BASF SE (Ludwigshafen, DE)から購入し、界面活性剤として使用した。
C6 最大0.5%
C8 24~30%
C10 15~22%
C12 37~42%
C14 12~18%
C16 最大4%
作製されたゲルによる表面の濡れ性を、接触角試験によって測定した。
ゲルG1~G3のそれぞれ、ならびに水中で使用される光増感剤TMPyPの吸収を、実施例1に記載したように、250nm~600nmの波長域の吸収スペクトルを記録することで測定した。
光増感剤を含むマイクロエマルションにおいて照射した後の一重項酸素の形成を、実施例1に記載したように、時間分解一重項酸素蛍光測定を用いて測定した。
Butenandt J., Epple R., Wallenborn E.-U., Eker A.P.M., Gramlich V. und Carell T.: A comparative repair study of thymine- and uracil-photodimers with model compounds and a photolyase repair enzyme, Chem. Eur. J. 2000, Vol. 6, No. 1, pages 62 - 72,
Svoboda J., Schmaderer H. und Konig B.: Thiourea-enhanced flavin photooxidation of benzyl alcohol; Chem. Eur. J. 2008, 14, pages 1854 - 1865
Egorov S.Y., Krasnovsky A.A., Bashtanov M.Y., Mironov E.A., Ludnikova T.A. und Kritsky M.S.; Photosensitization of singlet oxygen formation by pterins and flavins. Time-resolved studies of oxygen phosphorescence under laser excitation. Biochemistry (Mosc)1999, 64 (10), p 1117 - 1121.
Claims (21)
- 分散物であって、
(a)少なくとも1つの光増感剤、
(b)少なくとも1つの界面活性剤、および
(c)少なくとも1つの界面活性剤
を含んでおり、
上記分散物が、マイクロエマルション、ゲルまたはそれらの混合物を、2~50℃の範囲の温度および800~1200ミリバールの範囲の圧力において、含んでいる、分散物。 - 上記光増感剤が、フェナレノン、クルクミン、フラビン、ポルフィリン、ポルフィセン、キサンチン色素、クマリン、フタロシアニン、フェノチアジン化合物、アントラセン色素、ピレン、フラーレン、ペリレン、およびそれらの混合物からなる群から選択される、請求項1に記載の分散物。
- 上記少なくとも1つの界面活性剤が、少なくとも1つの極性溶媒、好ましくは水である、請求項1または2に記載の分散物。
- 上記少なくとも1つの界面活性剤が、非イオン性界面活性剤、アニオン性界面活性剤、カチオン性界面活性剤、両性界面活性剤およびこれらの混合物、好ましくは非イオン性界面活性剤、アニオン性界面活性剤およびこれらの混合物からなる群から選択される、請求項1~3のいずれか1項に記載の分散物。
- カチオン性界面活性剤が、4級アルキルアンモニウム塩、エステルクアット、アシル化ポリアミン、ベンジルアンモニウム塩またはそれらの混合物からなる群から選択される、請求項4に記載の分散物。
- 非イオン性界面活性剤が、ポリアルキレングリコールエーテル、アルキルグルコシド、
アルキルポリグリコシド、アルキルグリコシドエステルおよびそれらの混合物からなる群から選択される、請求項4または5に記載の分散物。 - アニオン性界面活性剤が、アルキルカルボキシレート、アルキルスルホネート、アルキルサルフェート、アルキルホスハート(Alkylphoshaten)、アルキルポリグリコールエーテルサルフェート、アルキルカルボン酸のスルフォネート、N-アルキルサルコシネート、およびそれらの混合物からなる群から選択される、請求項4~6のいずれか1項に記載の分散物。
- 上記分散物が、少なくとも1つの液体非極性相をさらに含んでおり、当該少なくとも1つの液体非極性相が、6~30の炭素原子を有しているアルカン、4~20の炭素原子を好ましく有しているモノカルボン酸エステル、6~20の炭素原子を好ましく有しているポリカルボン酸エステル、およびそれらの混合物からなる群から好ましく選択される少なくとも1つの非極性溶媒を含んでいる、請求項1~7のいずれか1項に記載の分散物。
- 上記分散物が、1~6のOH基を有していることが好ましい、2~12の炭素原子を有している少なくとも1つのアルカノールをさらに含んでいる、請求項1~8のいずれか1項に記載の分散物。
- 800~1200ミリバールの範囲の圧力および2~50℃の範囲の温度における上記分散物が、マイクロエマルションを含んでいる、またはマイクロエマルションであり、当該マイクロエマルションが、1μm未満の液滴サイズを有している液滴を好ましく有している、請求項1~9のいずれか1項に記載の分散物。
- 上記マイクロエマルションが、O/Wマイクロエマルション、油中水型(W/O)マイクロエマルションまたは両連続マイクロエマルションである、請求項10に記載の分散物。
- 上記分散物が、無機酸、有機酸、無機塩基、有機塩基、それらの塩またはそれらの混合物であることが好ましい少なくとも1つのpH調整物質をさらに含んでいる、請求項1~7のいずれか1項に記載の分散物。
- 上記分散物が、カルボキシビニル重合体、ポリアクリルアミド、ポリビニルアルコール、アシル化ポリエチレンアミン、アルギナート、セルロースエーテルおよびそれらの混合物からなる群から選択される少なくとも1つのゲル化剤をさらに含んでいる、請求項1~7または12のいずれか1項に記載の分散物。
- 800~1200ミリバールの範囲の圧力および2~50℃の範囲の温度における上記分散物が、ゲルを含んでいる、またはゲルである、請求項1~7、12または13のいずれか1項に記載の分散物。
- ウイルス、古細菌、細菌、細菌胞子、真菌、真菌胞子、原性動物、藻類、および血液媒介寄生虫からなる群から好ましく選択される微生物の光力学的な不活性化のための、請求項1~14のいずれか1項に記載の分散物の、使用。
- 対象の表面清浄化および/または表面コーティングのための、請求項15に記載の使用。
- 医療品、食品包装、食品、飲料包装、飲料容器、繊維製品、建築材料、電子装置、家庭用装置、家具、窓、床、壁または衛生用品の表面清浄化および/または表面コーティングのための、請求項15または16に記載の使用。
- 液体の殺菌のための、請求項15または16に記載の使用。
- ウイルス、古細菌、細菌、細菌胞子、真菌、真菌胞子、原性動物、藻類、血液媒介寄生虫またはそれらの組み合わせを好ましく含んでいる微生物の光力学的な不活性化のための方法であって、当該方法が、以下のステップ:
(A)上記微生物を、請求項1~14のいずれか1項に記載の少なくとも1つの分散物と接触させるステップ;および
(B)適切な周波数およびエネルギー密度の電磁放射線を、上記微生物、および上記分散物に含まれている少なくとも1つの光増感剤に照射するステップ
を含んでいる、方法。 - ウイルス、古細菌、細菌、細菌胞子、真菌、真菌胞子、原性動物、藻類、および血液媒介寄生虫からなる群から好ましく選択される微生物の不活性化のための光力学的療法における使用のための、請求項1~14のいずれか1項に記載の分散物。
- 歯の組織および/または歯肉の疾患の処置および/または予防における請求項20に記載の使用のための、請求項1~14のいずれか1項に記載の分散物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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EP16163551.1 | 2016-04-01 | ||
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CN109152358A (zh) | 2019-01-04 |
KR20190015209A (ko) | 2019-02-13 |
US20190111168A1 (en) | 2019-04-18 |
AU2021221865A1 (en) | 2021-09-23 |
AU2017240185A1 (en) | 2018-11-22 |
JP7347798B2 (ja) | 2023-09-20 |
RU2019101968A3 (ja) | 2020-07-24 |
CN109152358B (zh) | 2023-07-07 |
KR102476983B1 (ko) | 2022-12-14 |
EP3225112A1 (de) | 2017-10-04 |
AU2024200362A1 (en) | 2024-02-08 |
ES2895851T3 (es) | 2022-02-22 |
WO2017167992A1 (de) | 2017-10-05 |
CA3019623A1 (en) | 2017-10-05 |
RU2766122C2 (ru) | 2022-02-08 |
SG11201808617UA (en) | 2018-11-29 |
PL3225112T3 (pl) | 2022-01-03 |
BR112018070133B1 (pt) | 2022-07-19 |
RU2019101968A (ru) | 2020-07-24 |
JP2019515946A (ja) | 2019-06-13 |
PT3225112T (pt) | 2021-09-16 |
BR112018070133A2 (pt) | 2019-02-12 |
EP3225112B1 (de) | 2021-08-18 |
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