JP2014520900A - 疎水性セラゲニン化合物、及びそれを組み込む装置 - Google Patents
疎水性セラゲニン化合物、及びそれを組み込む装置 Download PDFInfo
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- JP2014520900A JP2014520900A JP2014521854A JP2014521854A JP2014520900A JP 2014520900 A JP2014520900 A JP 2014520900A JP 2014521854 A JP2014521854 A JP 2014521854A JP 2014521854 A JP2014521854 A JP 2014521854A JP 2014520900 A JP2014520900 A JP 2014520900A
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Abstract
【選択図】 なし
Description
本出願は、米国仮出願第61/572,714号(2011年7月20日出願、タイトル"Ceragenin−Containing Hydrogels For Prevention of Bacterial Biofilm Formation")、及び米国仮出願第61/642,431号(2012年5月3日出願、タイトル"Hydrogel Materials Incorporating Eluting Ceragenin Compound")からの利益を主張し、それらは本参照により本願に組み込まれるものである。
一実施形態では、本明細書で開示する疎水性セラゲニン化合物は、(i)4個の縮合炭素環を有するステロール構造と、(ii)疎水性のステロール面と親水性のカチオン性面とを有する両親媒性化合物を形成するために前記4個の縮合炭素環の少なくとも3個にそれぞれ結合する少なくとも1個のカチオン性置換基と、(iii)前記縮合炭素環のうち少なくとも1個の縮合炭素環に結合する少なくとも1個の疎水性置換基とを有し、(iv)前記CSA化合物が6.5以上のCLogP値を有する。
セラゲニン化合物がポリマー素材に組み込まれる場合、ポリマーの疎水性/親水性とセラゲニン化合物は、セラゲニン化合物がヒドロゲルポリマーに非共有結合で結合するように選択される。非共有結合は、溶媒の存在下でセラゲニン化合物が一度に全部放出されることを防ぐ。逆に、非共有結合は、溶媒の存在下でセラゲニン化合物が時間をかけて溶出されることを可能にする。
疎水性セラゲニン化合物を取り込むのに特に有用なポリマーの一種は、ヒドロゲルポリマーである。
本明細書で記述されるポリマーは、医療装置、被覆材、包帯、インプラント、組織の足場、及びその類似物、が含まれるがこれに限定されない、多様な用途で用いられうる。図2は、基材110とポリマー被覆材120を含む医療装置100の略図である。
疎水性セラゲニン化合物が細菌のコロニー形成を防止しうる仕組みをより良く理解すべく、CSA−138とコンタクトレンズに使われるヒドロゲルとの間の結合を評価した。1個目の例では、コンタクトレンズに用いるのに適切なヒドロゲルからのCSA−138の溶出率を測定した。ヒドロゲルから溶出するセラゲニン量の定量には、質量標識化された内部標準を用いた液体クロマトグラフ質量分析(LC/MS)を使用した。しかしながら、この手法では検出限界はおよそ2μg/mlでしかなく、我々は、検出限界以下の一定溶出率で効果的に細菌を殺すことができた。例えば、CSA−138が1%の割合で組み込まれたレンズからの溶出は、溶出5日以内で検出限界以下に低下するが、それでもまだセラゲニン類は適切な殺菌率を示すようだった。
Claims (15)
- 疎水性のカチオン性ステロイド系抗微生物性(CSA)化合物であって、
4個の縮合炭素環を有するステロール構造と、
疎水性のステロール面と親水性のカチオン性面とを有する両親媒性化合物を形成するために前記4個の縮合炭素環の少なくとも3個にそれぞれ結合する少なくとも1個のカチオン性置換基と、
少なくとも1個の前記縮合炭素環に結合する少なくとも1個の疎水性置換基とを有し、
前記CSA化合物は6.5以上のCLogP値を有する、CSA化合物。 - 請求項1記載の疎水性CSA化合物において、前記CLogP値が7.5以上である、化合物。
- 請求項1記載の疎水性CSA化合物において、前記CLogP値が8.5以上である、化合物。
- 請求項1記載の疎水性CSA化合物において、前記疎水性置換基がトリメチルシランを含む、化合物。
- 請求項1記載の疎水性CSA化合物において、前記疎水性置換基がステロイド構造のC17の位置に結合されている、化合物。
- 請求項1記載の疎水性CSA化合物において、前記疎水性置換基がヘテロ原子と、前記ヘテロ原子から離れた位置にある少なくとも9個の炭素原子を有する炭化水素基とを含む、化合物。
- 請求項6記載の疎水性CSA化合物において、前記炭化水素基が直鎖状炭化水素である、化合物。
- 請求項7記載の疎水性CSA化合物において、前記炭化水素基が少なくとも11個の原子を含む、化合物。
- 請求項9記載の疎水性CSA化合物において、構造が、CSA−131、CSA−132、CSA−133、CSA−134、CSA−135、CSA−137、CSA−138、CSA−144、及びCSA−145からなる群から選択されるものである、化合物。
- ポリマー構造を有する装置であって、請求項1記載の疎水性セラゲニン化合物が非共有結合性相互作用により前記ポリマーに組み込まれるものである、装置。
- 請求項11記載の装置において、前記ポリマー構造が、ポリビニルアルコール、ポリアクリル酸ナトリウム、アクリレートポリマー、ポリエチレンオキシド、ポリAMPS、ポリビニルピロリドン、ポリアクリルアミド、シリコーン、アガロース、メチルセルロース、ヒアルロン酸、またはこれらの組み合わせを含むものである、装置。
- 請求項11記載の装置において、医療装置が、骨インプラント、骨ピン、骨ねじ、移植組織片、気管内チューブ、冠動脈ステント、末梢ステント、カテーテル、動静脈グラフト、バイパス移植片、ペースメーカーまたは除細動器リード線、吻合用クリップ、動脈閉鎖デバイス、卵円孔開存閉鎖デバイス、及び薬物輸送バルーンからなる群から選択されるものである、装置。
- 請求項11記載の装置において、前記ポリマーが基材を被覆している、装置。
- 請求項11記載の装置において、前記疎水性セラゲニン化合物が過剰量の生理食塩水中において、3日、1週間、あるいは1ヶ月で、及び/または3日、1週間、及び/または1ヶ月の期間にわたって、0.1〜100μg/ml、0.5〜50μg/ml、あるいは1〜10μg/mlの割合で前記ポリマーから溶出するものである、装置。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201161572714P | 2011-07-20 | 2011-07-20 | |
US61/572,714 | 2011-07-20 | ||
US201261642431P | 2012-05-03 | 2012-05-03 | |
US61/642,431 | 2012-05-03 | ||
PCT/US2012/047746 WO2013013221A1 (en) | 2011-07-20 | 2012-07-20 | Hydrophobic ceragenin compounds and devices incorporating same |
Publications (3)
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US11739116B2 (en) | 2013-03-15 | 2023-08-29 | Brigham Young University | Methods for treating inflammation, autoimmune disorders and pain |
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US11286276B2 (en) | 2014-01-23 | 2022-03-29 | Brigham Young University | Cationic steroidal antimicrobials |
US11253634B2 (en) | 2016-03-11 | 2022-02-22 | Brigham Young University | Cationic steroidal antibiotic compositions for the treatment of dermal tissue |
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