Near-infrared (NIR) photosensitizers have great potential to develop various fields of photochemistry, such as photodynamic therapy (PDT) and photocatalysts. Organelle-targeted PDT using NIR light attracts considerable attention to high-efficiency phototherapy. Although drug delivery system (DDS) carriers are often combined with NIR photosensitizers for effective PDT, the systematic correlations between the cargo and DDS carriers are still unclear. In this study, we develop NIR-photosensitizers from a π-extended porphyrin-type sensitizer (rTPA) that allows us to modify the structure and properties with a one-touch operation for the systematic study. Single-step amidations give five rTPA derivatives readily, facilitating comprehensive information about the properties according to their molecular structure and electric charge of the photosensitizer and DDS carriers prepared using a microfluidic device. One of the combinations, rTPA-NH₂@MP, demonstrates the highest ability among the derivatives to kill pancreatic cancer cells, which are known to be highly lethal. The present study provides a guideline for inventing effective DDS-based NIR-PDT compounds for future photodrugs.

近红外（NIR）光敏剂在光化学的各个领域具有巨大的发展潜力，例如光动力疗法（PDT）和光催化剂。使用近红外光的细胞器靶向 PDT 引起了人们对高效光疗的广泛关注。尽管药物输送系统（DDS）载体通常与近红外光敏剂结合用于有效的PDT，但货物和DDS载体之间的系统相关性仍不清楚。在本研究中，我们利用 π 延伸卟啉型敏化剂 (rTPA) 开发了近红外光敏剂，使我们能够通过一键式操作，系统学习。单步酰胺化很容易得到五种rTPA衍生物，根据光敏剂和DDS载体的分子结构和电荷，有助于全面了解其性质微流体装置。其中一种组合 rTPA-NH₂@MP 演示了衍生物中杀死胰腺癌细胞的能力最高，已知胰腺癌细胞具有高度致死性。本研究为未来光药物发明有效的基于 DDS 的 NIR-PDT 化合物提供了指导。