Specifically Glyco-Substituted Porphyrins and Chlorins for Photodynamic Therapy

Simple SummaryContent extracted from patent full text and abstract with AI.

This patent presents a new class of specifically glycosylated porphyrin and chlorin compounds—molecules in which precise sugar groups (glyco-substituents) are attached to certain positions on the tetrapyrrole structure. These compounds are designed as improved photosensitizers for photodynamic therapy (PDT): a treatment where light, absorbed by the photosensitizer, produces reactive oxygen species to selectively destroy diseased cells such as cancer cells. The invention focuses on structures that combine well-chosen glycosyl and lipophilic groups in specific configurations, increasing their effectiveness, controllable synthesis, and the ability to target diseased tissue.

Use CasesContent extracted from patent full text and abstract with AI.

• Photodynamic therapy (PDT) for treating cancers and other hyperproliferative diseases (e.g., skin, colon, bladder tumors)
• Targeted destruction of diseased tissue using light-activated therapy
• Treatment of dermatological disorders using selective cell killing
• Ophthalmological disorders (e.g., age-related macular degeneration) where abnormal cells need to be targeted and destroyed
• Urological applications (e.g., bladder cancer PDT)
• Anti-inflammatory therapy, such as treatment for arthritis
• Diagnostic fluorescence imaging to localize tumors or abnormal tissue
• Drug formulations in liposomes or nanoparticles for enhanced delivery of photosensitizers

BenefitsContent extracted from patent full text and abstract with AI.

• Increased selectivity for tumor or diseased cells due to glyco-substituents that can interact with overexpressed receptors on these cells (such as lectins)
• Stronger absorption in the red/near-infrared spectrum, allowing deeper tissue penetration and thus ability to target internal tumors more effectively
• Enhanced photodynamic activity, even against resistant cancer cell lines
• More efficient accumulation in cell membranes and diseased tissues due to amphiphilicity of the compounds
• Flexible and straightforward synthesis methods for a variety of tailored structures
• Better formulation options (e.g., liposomes, nanoparticles), reducing side effects, improving pharmacokinetics, and potentially enabling oral or injectable therapies
• Potential to be conjugated to antibodies or targeting agents to further enhance specificity
• Utility in both therapeutic (cell-killing) and diagnostic (imaging) contexts

Technical Classifications (CPCs)

Inventors & Applicants

Patent Abstract

The present invention provides certain tetrapyrrolic compounds having a structure of Formula (1), (2), or (3) wherein B is (I), (II) (III) or (IV), O-R1 is a substituent in the meta or para position of the phenyl ring, R1 is a glyco-substituent derived from a mono-, di-, or trisaccharide group, and each R2 is independently selected from the group consisting of a linear or branched (fluoro-)alkyl group with 3 to 8 carbon atoms, phenyl, pentafluorophenyl, 3,5-bis(trifluoromethyl)phenyl, 4-(1'-thio-β-D-glucosyl)-2,3,5,6-tetrafluorophenyl, 4-(1'-thio-β- D-galactosyl)-2,3,5,6-tetrafluorophenyl, meta- or para-hydroxyphenyl, meta- or para- carboxyphenyl, and meta- or para-YO-phenyl with Y being a polyethyleneglycol-residue with (CH2CH2O)nCH3 with n = 1-30.