JP7010700B2 - 修飾コラーゲン、その製造方法 - Google Patents
修飾コラーゲン、その製造方法 Download PDFInfo
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- JP7010700B2 JP7010700B2 JP2017554518A JP2017554518A JP7010700B2 JP 7010700 B2 JP7010700 B2 JP 7010700B2 JP 2017554518 A JP2017554518 A JP 2017554518A JP 2017554518 A JP2017554518 A JP 2017554518A JP 7010700 B2 JP7010700 B2 JP 7010700B2
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- collagen
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- wound dressing
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- 238000010908 decantation Methods 0.000 description 1
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- SKQUUKNCBWILCD-UHFFFAOYSA-J dicopper;chloride;trihydroxide Chemical compound [OH-].[OH-].[OH-].[Cl-].[Cu+2].[Cu+2] SKQUUKNCBWILCD-UHFFFAOYSA-J 0.000 description 1
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Images
Classifications
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- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
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Description
第1段階:止血。
第2段階:炎症。
第3段階:増殖。
第4段階:リモデリング。
・ 血管拡張
・ 血管新生の刺激
・ 免疫応答の調節
・ 強力な抗菌活性
を含む数種の効果を発揮する。
・ 関連する感染症を低減させる際の臨床的有用性を提供すること
・ 病変領域への血流を刺激する能力を提供すること
・ 創傷治癒を促進すること
・ DFUの治療のための、より安全でより効果的な製品への高まる市場の需要を満たすこと
が望ましい。
- S-S結合を含むコラーゲンを提供するステップと、
- S-S結合の還元により、S-S結合を含む前記コラーゲンに-SH基を導入して-SH基を含むコラーゲンチオールを提供するステップと、
- コラーゲンチオールの-SH基をニトロソ化して修飾コラーゲンを提供するステップであって、前記修飾コラーゲンがS-ニトロソ基を含むステップと
を含む、修飾コラーゲンを生成する方法が提供される。
- リシンおよびヒドロキシリシン残基のうちの一方または両方を含むコラーゲン供給源を提供するステップと、
- コラーゲン供給源を、ジスルフィド基を含む活性化されたジカルボン酸誘導体と反応させて、活性化されたジカルボン酸誘導体のカルボニル官能基と、リシンおよびヒドロキシリシン残基のうちの一方または両方のε-NH2基との間にアミド結合を形成し、それにより、S-S結合を含むコラーゲンを提供するステップと
を含む。
ZN-C(O)-R3-C(O)-NH-R1-S-S-R2-NH-C(O)-R3-C(O)-NZ (I)
[式中、R1、R2およびR3は、独立して、二価の連結基を表し、
ZNは、一緒に、窒素含有ヘテロ環式基を表す]
の化合物である。
- -SH基を含むシステイン残基を含むコラーゲン結合タンパク質を提供するステップと、
- コラーゲン結合タンパク質のシステイン残基-SH基を、光反応性架橋剤と反応させて、S-S基を含む光反応性架橋剤修飾コラーゲン結合タンパク質を提供するステップと、
- 光反応性架橋剤修飾コラーゲン結合タンパク質を、コラーゲンと組み合わせて、光反応性架橋剤修飾コラーゲン結合タンパク質およびコラーゲンの複合体を提供するステップと、
- 複合体に電磁放射を照射し、光反応性架橋剤をコラーゲンと架橋させて、S-S結合を含むコラーゲンを提供するステップと
を含む。
- S-S結合を含むコラーゲンを、ジチオスレイトールと反応させること
を含む。
- コラーゲンチオールの-SH基を、酸性化亜硝酸塩の溶液と反応させること、
- コラーゲンチオールの-SH基を、ガス状のNOと反応させること、および
- コラーゲンチオールの-SH基を、S-ニトロソチオールと反応させること
のうちの1つまたは複数を含む。
- 修飾コラーゲンを、II型コラーゲン、V型コラーゲンおよびゼラチン・マトリックスを含む群のうちの1つもしくは複数に組み込むステップ、または
- 修飾コラーゲンを、ポリマー、好ましくは、フィルム形成ポリマー、膜形成ポリマー、ヒドロゲル形成ポリマー、もしくはフィルム、膜、ヒドロゲル、および安定なゲルもしくは膜ベースの足場を生成できる他の構築物を製作することができるポリマーに組み込むステップ
をさらに含む。
R5は、HまたはOHであり、
Xは、OH基 または化学結合から選択され、Yは、Hまたは化学結合から選択され、但し、XおよびYのうちの一方または両方は、修飾コラーゲン内でペプチド結合を形成する化学結合である]
のリシンまたはヒドロキシリシン残基を含む。
Xは、OH基 および化学結合から選択され、Yは、Hおよび化学結合から選択され、但し、XおよびYのうちの一方または両方は、コラーゲン内でペプチド結合を形成する化学結合である。修飾コラーゲンのペプチド鎖形成部は、式(XI)において「[]」によって括弧で囲んで示されている。残基は、例えばXおよびYのうちの一方または他方がそれぞれOHおよびHであるならば、ペプチドの末端位置にあり得る。XおよびYの両方がペプチド結合であるならば、リシン残基は、コラーゲンのペプチド鎖形成部内の非末端である]
の残基を含み得る。
ZN-C(O)-R3-C(O)-NH-R1-S-S-R2-NH-C(O)-R3-C(O)-NZ (I)
[式中、R1、R2およびR3は、独立して、二価の連結基、好ましくは二価の有機連結基、より好ましくは、1から6個までの炭素原子を有するアルカンジイル基または2から6個までの炭素原子を有するアルケンジイル(alkendiyl)もしくはアルキンジイル(alkyndiyl)基等の二価の炭化水素連結基を表す。なお一層好ましくは、R1、R2およびR3は、独立して、エタンジイルまたはプロパンジイル基、最も好ましくはエタンジイル、すなわち-CH2CH2-を表す。基R1、R2およびR3は、独立して、1から4個の水素原子をヒドロキシル基またはFもしくはCl等のハロゲンで置き換えることによって場合により置換されていてよい。好ましい実施形態において、R1およびR2は、同一であり、
ZNは、一緒に、窒素含有ヘテロ環式基、好ましくは、N原子が式(I)の化合物のカルボニル基と直接結合している、ヘテロ環式環中に5~6個の原子を有する窒素含有ヘテロ環式基を表し、そのため、Zは、2つの原子価が窒素と結合している二価の連結基を表す。ヘテロ環式基は飽和または不飽和であってよく、そのため、Zは、特に2から4個の炭素原子を有する、アルカンジイル、アルケンジイルまたはアルキンジイルを表し得る。Zは、O、SおよびNから選択される1または2個のヘテロ原子を場合により含み得る]
の化合物である。
1-イミダゾール、すなわち
のジカルボン酸ジアミドを提供することができる。
HO-C(O)-R3-C(O)-NH-R1-S-S-R2-NH-C(O)-R3-C(O)-OH (VI)→
ZN-C(O)-R3-C(O)-NH-R1-S-S-R2-NH-C(O)-R3-C(O)-NZ (I)
[式中、R1、R2、R3およびNZは、上記で定義した通りである]。
の化合物等のカルボジイミドであってよい。
のN-ヒドロキシヘテロ環式化合物であってよい。
ZN-C(O)-R3-C(O)-NH-R1-S-S-R2-NH-C(O)-R3-C(O)-NZ(I)+コラーゲン-NH2→
ZN-C(O)-R3-C(O)-NH-R1-S-S-R2-NH-C(O)-R3-C(O)-NH-コラーゲン+HNZ
によって表すことができる。
ZN-C(O)-R3-C(O)-NH-R1-S-S-R2-NH-C(O)-R3-C(O)-NH-コラーゲン+コラーゲン-NH2→
コラーゲン-HN-C(O)-R3-C(O)-NH-R1-S-S-R2-NH-C(O)-R3-C(O)-NH-コラーゲン+HNZ
Xは、OH基 および化学結合から選択され、Yは、Hおよび化学結合から選択され、但し、XおよびYのうちの一方または両方は、コラーゲン内でペプチド結合を形成する化学結合である。修飾コラーゲンのペプチド鎖形成部は、式(X)において「[]」によって括弧で囲んで示されている。残基は、例えばXおよびYのうちの一方または他方がそれぞれOHおよびHであるならば、ペプチドの末端位置にあり得る。XおよびYの両方がペプチド結合であるならば、リシン残基は、コラーゲンのペプチド鎖形成部内の非末端である]。
Xは、OH基 および化学結合から選択され、Yは、Hおよび化学結合から選択され、但し、XおよびYのうちの一方または両方は、コラーゲン内でペプチド結合を形成する化学結合である。修飾コラーゲンのペプチド鎖形成部は、式(X)において「[]」によって括弧で囲んで示されている。残基は、例えばXおよびYのうちの一方または他方がそれぞれOHおよびHであるならば、ペプチドの末端位置にあり得る。XおよびYの両方がペプチド結合であるならば、リシン残基は、修飾コラーゲンのペプチド鎖形成部内の非末端である]。
下記の実験例は、クラゲ供給源からのS-ニトロソ基を含む修飾コラーゲンの合成を記述するものである。S-ニトロソ基を含む修飾コラーゲンの半減期についても調査する。
Claims (28)
- 少なくとも、
- S-S結合を含むコラーゲンを提供するステップと、
- S-S結合の還元により、S-S結合を含む前記コラーゲンに-SH基を導入して-SH基を含むコラーゲンチオールを提供するステップと、
- コラーゲンチオールの-SH基をニトロソ化して修飾コラーゲンを提供するステップ
であって、前記修飾コラーゲンがS-ニトロソ基を含むステップと
を含む、修飾コラーゲンを生成する方法。 - S-S結合を含む前記コラーゲンが、S-S結合を含むI、II、III、IV、V、VI、IX、XおよびXI型のうちの1つまたは複数から選択される、請求項1に記載の
方法。 - S-S結合を含むコラーゲンを提供するステップが、少なくとも、
- リシンおよびヒドロキシリシン残基のうちの一方または両方を含むコラーゲン供給源を提供するステップと、
- コラーゲン供給源を、ジスルフィド基を含む活性化されたジカルボン酸誘導体と反応させて、活性化されたジカルボン酸誘導体のカルボニル官能基と、リシンおよびヒドロキシリシン残基のうちの一方または両方のε-NH2基との間にアミド結合を形成し、それにより、S-S結合を含むコラーゲンを提供するステップと
を含む、請求項1または2に記載の方法。 - 活性化されたジカルボン酸誘導体が、式:
ZN-C(O)-R3-C(O)-NH-R1-S-S-R2-NH-C(O)-R3-C(O)-NZ (I)
[式中、R1、R2およびR3は、独立して、二価の連結基を表し、
ZNは、一体的に、窒素含有ヘテロ環式基を表す]
の化合物である、請求項3に記載の方法。 - S-S結合の還元により、S-S結合を含む前記コラーゲンに-SH基を導入して-SH基を有するコラーゲンチオールを提供するステップが、
- S-S結合を含むコラーゲンを、ジチオスレイトールと反応させること
を含む、請求項1から5のいずれか一項に記載の方法。 - -SH基のニトロソ化が、
- コラーゲンチオールの-SH基を、酸性化亜硝酸塩の溶液と反応させること、
- コラーゲンチオールの-SH基を、ガス状のNOと反応させること、および
- コラーゲンチオールの-SH基を、S-ニトロソチオールと反応させることのうちの1つまたは複数を含む、請求項1から6のいずれか一項に記載の方法。 - - 修飾コラーゲンを、II型コラーゲン、V型コラーゲンおよびゼラチン・マトリックスを含む群のうちの1つもしくは複数に組み込むステップ、または、
- 修飾コラーゲンをポリマーに組み込むステップをさらに含む、請求項1から7のいずれか一項に記載の方法。 - コラーゲンが、哺乳動物または非哺乳動物供給源に由来する、請求項1から8のいずれか一項に記載の方法。
- 非哺乳動物供給源が、クラゲ、海洋無脊椎動物および魚類から選択される1つまたは複数である、請求項9に記載の方法。
- S-ニトロソ基を含む修飾コラーゲンであって、前記修飾コラーゲンが、クラゲ、海洋無脊椎動物および魚類から選択される1つまたは複数の供給源に由来し、Sーニトロソ基を含むリシンおよびヒドロキシリシン残基のうちの一方または両方を含み、前記リシンまたはヒドロキシリシン残基は、式(IX):
R5は、HまたはOHであり、
Xは、OH基または化学結合から選択され、Yは、Hまたは化学結合から選択され、但し、XおよびYのうちの一方または両方は、修飾コラーゲン内でペプチド結合を形成する化学結合である]
のリシンまたはヒドロキシリシン残基である、修飾コラーゲン。 - I、II、III、IV、V、VI、IX、XおよびXI型コラーゲンのうちのいずれか1つである、請求項11に記載の修飾コラーゲン。
- R 1 およびR 3 は、独立して、エタンジイルまたはプロパンジイル基を表す、請求項11または12に記載の修飾コラーゲン。
- R 1 およびR 3 は、エタンジイル、すなわち-CH 2 CH 2 -を表す、請求項13に記載の修飾コラーゲン。
- 医薬として使用するための、請求項11から14のいずれか一項に記載の修飾コラーゲン。
- 創傷治癒において使用するための、請求項11から15のいずれか一項に記載の修飾コラーゲン。
- クラゲに由来するII型コラーゲン、クラゲに由来するV型コラーゲンおよびゼラチン・マトリックスを含む群のうちの1つまたは複数に組み込まれた、請求項11から13のいずれか一項に記載の修飾コラーゲンを含む配合組成物を含む、創傷被覆材。
- 請求項11から13のいずれか一項に記載の修飾コラーゲンを含む配合組成物を含む創傷被覆材であって、当該修飾コラーゲンが任意のポリマー・マトリックスに組み込まれた、創傷被覆材。
- 前記配合組成物が、フィルム、膜またはヒドロゲル複合物である、請求項18に記載の創傷被覆材。
- 前記フィルム、膜またはヒドロゲル複合物が、5から1000マイクロメートルまでの範囲内の厚さを有する、請求項19に記載の創傷被覆材。
- 前記フィルム、膜またはヒドロゲル複合物が滅菌される、請求項19または20に記載の創傷被覆材。
- 前記フィルム、膜またはヒドロゲル複合物が、多孔質構造を有する、請求項19から21のいずれか一項に記載の創傷被覆材。
- クラゲに由来する前記コラーゲンが、Rhizostoma pulmoクラゲ組織を含む、請求項17から21のいずれか一項に記載の創傷被覆材。
- 食品グレードの作用物質をさらに含む、請求項17から23のいずれか一項に記載の創傷被覆材。
- 医療グレードの作用物質をさらに含む、請求項17から22に記載の創傷被覆材。
- 血管拡張剤として使用するための、請求項17から25に記載の創傷被覆材。
- 消毒剤として使用するための、請求項17から25に記載の創傷被覆材。
- 細菌、酵母、真菌およびウイルスに対して抗菌特性を有する、請求項27に記載の創傷被覆材。
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CN105008611A (zh) | 2012-12-20 | 2015-10-28 | 康沃特克科技公司 | 化学改性的纤维素纤维的处理 |
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