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Photooxidation Responsive Elastin-Like Polypeptide Conjugates for Photodynamic Therapy Application
Bioconjugate Chemistry ( IF 4.0 ) Pub Date : 2021-07-09 , DOI: 10.1021/acs.bioconjchem.1c00251 Vusala Ibrahimova 1 , José A González-Delgado 2 , Manon Levêque 1 , Tomas Torres 2, 3, 4 , Elisabeth Garanger 1 , Sébastien Lecommandoux 1
Bioconjugate Chemistry ( IF 4.0 ) Pub Date : 2021-07-09 , DOI: 10.1021/acs.bioconjchem.1c00251 Vusala Ibrahimova 1 , José A González-Delgado 2 , Manon Levêque 1 , Tomas Torres 2, 3, 4 , Elisabeth Garanger 1 , Sébastien Lecommandoux 1
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Stimuli-responsive recombinant elastin-like polypeptides (ELPs) are artificial protein polymers derived from the hydrophobic domain of tropoelastin that have attracted significant interest for drug delivery and tissue engineering applications. In the present study, we have conjugated a photosensitizer (PS) to a hydrophobic methionine-containing ELP scaffold, which upon reaction with singlet oxygen (1O2) is transformed into a hydrophilic sulfoxide derivative facilitating the disassembly of photosensitizer-delivery particles during the photodynamic therapy (PDT) process. A peripherally substituted carboxy-Zn(II)-phthalocyanine derivative (TT1) bearing a carboxyl group directly linked to the Pc-ring, and presenting an absorption maximum around 680 nm, was selected as PS which simultaneously acted as a photooxidation catalyst. A TT1-ELP[M1V3-40] conjugate was prepared from ELP[M1V3-40] modified with an alkyne group at the N-terminal chain end, and from TT1-amide-C3-azide by copper(I)-catalyzed alkyne–azide cycloaddition (CuAAC) reaction. This innovative model photooxidation sensitive PS delivery technology offers promising attributes in terms of temperature-controlled particle formation and oxidation-triggered release, narrow molar mass distribution, reproducibility, scalability, non-immunogenicity, biocompatibility, and biodegradability for pharmaceutical applications in an effort to improve the clinical effectiveness of PDT treatments.
中文翻译：
用于光动力疗法应用的光氧化反应性弹性蛋白样多肽缀合物
刺激响应性重组弹性蛋白样多肽 (ELP) 是源自弹性蛋白原疏水域的人工蛋白质聚合物，已引起药物递送和组织工程应用的极大兴趣。在本研究中，我们将光敏剂 (PS) 与疏水性含蛋氨酸 ELP 支架结合，该支架在与单线态氧 ( 1 O 2) 转化为亲水性亚砜衍生物，促进光动力疗法 (PDT) 过程中光敏剂递送颗粒的分解。外围取代的羧基-Zn(II)-酞菁衍生物 (TT1) 带有直接连接到 Pc 环的羧基，在 680 nm 附近具有最大吸收，被选为 PS，同时充当光氧化催化剂。甲TT1 -ELP [M 1 V 3 - 40 ]缀合物从ELP [M制备1 V 3 - 40 ]与在炔基改性Ñ-末端链端，并通过铜（I）催化的炔-叠氮环加成（CuAAC）反应从TT1-酰胺-C3-叠氮化物。这种创新的模型光氧化敏感 PS 递送技术在温度控制的颗粒形成和氧化触发释放、窄摩尔质量分布、再现性、可扩展性、非免疫原性、生物相容性和生物降解性方面为制药应用提供了有希望的属性，以努力改善PDT 治疗的临床有效性。
更新日期：2021-08-19
中文翻译：
用于光动力疗法应用的光氧化反应性弹性蛋白样多肽缀合物
刺激响应性重组弹性蛋白样多肽 (ELP) 是源自弹性蛋白原疏水域的人工蛋白质聚合物，已引起药物递送和组织工程应用的极大兴趣。在本研究中，我们将光敏剂 (PS) 与疏水性含蛋氨酸 ELP 支架结合，该支架在与单线态氧 ( 1 O 2) 转化为亲水性亚砜衍生物，促进光动力疗法 (PDT) 过程中光敏剂递送颗粒的分解。外围取代的羧基-Zn(II)-酞菁衍生物 (TT1) 带有直接连接到 Pc 环的羧基，在 680 nm 附近具有最大吸收，被选为 PS，同时充当光氧化催化剂。甲TT1 -ELP [M 1 V 3 - 40 ]缀合物从ELP [M制备1 V 3 - 40 ]与在炔基改性Ñ-末端链端，并通过铜（I）催化的炔-叠氮环加成（CuAAC）反应从TT1-酰胺-C3-叠氮化物。这种创新的模型光氧化敏感 PS 递送技术在温度控制的颗粒形成和氧化触发释放、窄摩尔质量分布、再现性、可扩展性、非免疫原性、生物相容性和生物降解性方面为制药应用提供了有希望的属性，以努力改善PDT 治疗的临床有效性。
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