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Azo and diaza derivatives and uses thereof in phototherapy

A compound, stand-alone technology, applied in the field of azo and diazo derivatives and their use in phototherapy, able to solve the problem of dyes not preferentially localizing malignant tissue

Inactive Publication Date: 2011-05-04
MALLINCKRODT INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it has been recognized that in some cases many dyes do not localize preferentially in malignant tissue

Method used

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  • Azo and diaza derivatives and uses thereof in phototherapy
  • Azo and diaza derivatives and uses thereof in phototherapy
  • Azo and diaza derivatives and uses thereof in phototherapy

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0178] Example 1: Compounds for Phototherapy

[0179] 1.a Type 1 phototherapeutic agent

[0180] The present invention provides Type 1 phototherapeutic agents (including compositions, articles, and formulations) and methods of using and preparing Type 1 phototherapeutic agents. Type 1 phototherapeutic agents of the present invention include compounds comprising a first ring A, a second unsaturated ring B, and a third aromatic ring having an intracyclic azo or intracyclic diazo group, so The rings are in a condensed ring configuration in which ring A is fused to both unsaturated ring B and aromatic ring C, and in which unsaturated ring B and aromatic ring C are also fused to each other. The incorporation of unsaturated ring B in a fused-ring configuration in some compounds can enhance stability prior to photoactivation and can extend the conjugation of the fused-ring azo or diazo compounds, allowing light to Activation and internal energy transfer processes are carried out,...

Embodiment 1b

[0242] Example 1.b(iv): Phototherapy and Cell Viability Measurements

[0243] A general procedure was performed for measuring cell viability upon exposure of tumor cells to a fused ring diazo compound of formula (FX33) and electromagnetic radiation. The compound of formula (FX33) has an absorption maximum (λ max ). Cell viability was measured by the standard WST-1 assay using the human myelogenous leukemia U937 cell line. In this operation, U397 leukemia cells (0.5×10 6 ) were plated on standard T-25 cell culture dishes and exposed to 4 control conditions and a series of experimental conditions corresponding to a series of fused ring diazo compound concentrations, summarized in Table 1.

[0244] Table 1: Control and experimental conditions for cell viability measurements

[0245] Control 1

No electromagnetic radiation, no photosensitizer

Control 2

Electromagnetic radiation, no photosensitizers

Control 3

No electromagnetic radiation, pho...

Embodiment 2

[0250] Example 2: Light Therapy

[0251] Phototherapy, such as photodynamic therapy (PDT), typically employs a photosensitizer (PS) in combination with visible or near-infrared electromagnetic radiation to produce active species that kill or otherwise degrade target cells, such as tumors or other lesions . The present invention provides phototherapeutic agents useful in phototherapy.

[0252] The present invention includes phototherapy wherein a phototherapeutic agent comprising a compound of any of Formulas (FX1)-(FX40) is administered to a patient, eg, wherein a therapeutically effective amount of such a component is administered to a patient in need of treatment. In some embodiments, compounds of the invention provide photoreagents that can be selectively targeted and delivered to target tissues such as tumors, sites of inflammation, or other lesions. Upon administration, the phototherapeutic agent is optionally allowed to accumulate in a target area of ​​interest (eg, ...

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Abstract

The invention relates generally to optical agents, including Type 1 phototherapeutic agents, for biomedical applications, such as phototherapy. Provided are fused ring azo and diaza compounds comprising a plurality of fused rings including a first ring having an intra-ring azo or intra-ring diaza group capable of activation upon exposure to electromagnetic radiation in visible and / or infrared regions of the electromagnetic spectrum. Optical agents of the invention enable a versatile phototherapy platform for treatment of a range of pathological conditions, including the treatment of cancers, stenosis and inflammation. The invention further provides preparations and formulations comprising the fused ring azo and diaza compounds and methods of making and using the fused ring azo and diaza compounds as optical agents in in vivo or ex vivo biomedical procedures.

Description

[0001] Cross references to related patent applications [0002] This application claims priority based on US Provisional Patent Application 61 / 117,310, filed November 24, 2008, which is hereby incorporated by reference in its entirety to the extent not inconsistent with this specification. Background technique [0003] Today, photoreagents play an important role in a large number of in vivo, in vitro and ex vivo clinical procedures, including important diagnostic and therapeutic procedures. For example, photodiagnostic and phototherapeutic agents include a class of molecules that absorb, emit or scatter electromagnetic radiation applied to biological materials, particularly in the visible and near-infrared regions of the electromagnetic spectrum. This property of photoreagents is used in a range of biomedical applications to visualize, image, or characterize biological materials and / or to achieve desired therapeutic outcomes. Recent developments in targeted drug delivery and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/06A61K41/00A61K31/5025A61P35/00
CPCA61K41/0057A61K49/0021C07D491/06A61P29/00A61P35/00
Inventor R·拉杰戈帕兰
Owner MALLINCKRODT INC
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