Methods for asymmetric cis-dihydroxylation (“AD”) of quinones to produce cis-diols of quinones with high yield (i.e. a yield ≥30%) and high enantioselectivity (i.e. an enantiometric excess ≥30%) are disclosed. The method uses an iron-based catalyst, such as one or more Fe(II) complexes, as the catalyst, and can be performed under mild reaction conditions (e.g. a temperature ≤50° C. at 1 atom in open air). The method generally includes: (i) maintaining a reaction mixture at a temperature for a period of time sufficient to form a product, where the reaction mixture contains a quinone, one or more iron-based catalyst(s), and a solvent, and where the product contains a chiral cis-diol. Optionally, the method also includes adding an oxidant into the reaction mixture prior to and/or during step (i), such as a hydrogen peroxide solution.

Methods for asymmetric cis-dihydroxylation (“AD”) of quinones to produce cis-diols of quinones with high yield (i.e. a yield ≥30%) and high enantioselectivity (i.e. an enantiometric excess ≥30%) are disclosed. The method uses an iron-based catalyst, such as one or more Fe(II) complexes, as the catalyst, and can be performed under mild reaction conditions (e.g. a temperature ≤50° C. at 1 atom in open air). The method generally includes: (i) maintaining a reaction mixture at a temperature for a period of time sufficient to form a product, where the reaction mixture contains a quinone, one or more iron-based catalyst(s), and a solvent, and where the product contains a chiral cis-diol. Optionally, the method also includes adding an oxidant into the reaction mixture prior to and/or during step (i), such as a hydrogen peroxide solution.

The invention discloses a monosubstituted or polysubstituted amphiphilic hypocrellin derivative, and a preparation method and application thereof. The amphiphilic hypocrellin derivative substituted by a group containing PEG, a quaternary ammonium salt or the like prepared according to the invention has an obvious red shift in its absorption spectrum and a significantly enhanced molar extinction coefficient, compared with the parent hypocrellin, can efficiently produce singlet state oxygen and other reactive oxygen species under photosensitive conditions; has different amphiphilicities and increased biocompatibility with cells or tissues by regulating its hydrophilicity and hydrophobicity; can meet the requirements of different clinical drugs, and solves the requirements of different drug delivery methods for different drug hydrophilicity and lipophilicity. Under identical conditions, the amphiphilic hypocrellin derivative photosensitizer according to the invention has higher ability to photodynamically inactivate tumor cells than the first and second generation commercial photosensitizers.

The invention discloses a monosubstituted or polysubstituted amphiphilic hypocrellin derivative, and a preparation method and application thereof. The amphiphilic hypocrellin derivative substituted by a group containing PEG, a quaternary ammonium salt or the like prepared according to the invention has an obvious red shift in its absorption spectrum and a significantly enhanced molar extinction coefficient, compared with the parent hypocrellin, can efficiently produce singlet state oxygen and other reactive oxygen species under photosensitive conditions; has different amphiphilicities and increased biocompatibility with cells or tissues by regulating its hydrophilicity and hydrophobicity; can meet the requirements of different clinical drugs, and solves the requirements of different drug delivery methods for different drug hydrophilicity and lipophilicity. Under identical conditions, the amphiphilic hypocrellin derivative photosensitizer according to the invention has higher ability to photodynamically inactivate tumor cells than the first and second generation commercial photosensitizers.

A topical therapeutic hydrophobic breakable composition includes a carrier comprising (a) about 60% to about 99% by weight of at least one hydrophobic oil; (b) at least one viscosity-modifying agents selected from the group consisting of a fatty alcohol, a fatty acid and a wax; and (c) a tetracycline antibiotic, characterized in that at least part of the tetracycline antibiotic is suspended in the composition; the viscosity of the composition is at least about 30% higher than the viscosity of the carrier without the tetracycline antibiotic; and is higher than the viscosity of the hydrophobic oil and the tetracycline antibiotic without the viscosity modifying agents. The tetracycline is chemically stable in the composition for at least six months; wherein more than about 90% of the tetracycline has not broken down. The composition is packaged as a breakable foam that breaks easily upon application of shear force.

Improved systems and methods for producing synthetic hypericin at high volume and high purity. In particular, systems and methods of preparing a purified synthetic hypericin resulting from irradiation, wherein the irradiation step is performed in a continuous flow micro-reactor. The process of manufacturing purified synthetic hypericin results in the synthetic yield of 30-100% of the dry product.

Improved systems and methods for producing synthetic hypericin at high volume and high purity. In particular, systems and methods of preparing a purified synthetic hypericin resulting from irradiation, wherein the irradiation step is performed in a continuous flow micro-reactor. The process of manufacturing purified synthetic hypericin results in the synthetic yield of 30-100% of the dry product.

A topical therapeutic hydrophobic breakable composition includes a carrier comprising (a) about 60% to about 99% by weight of at least one hydrophobic oil; (b) at least one viscosity-modifying agents selected from the group consisting of a fatty alcohol, a fatty acid and a wax; and (c) a tetracycline antibiotic, characterized in that at least part of the tetracycline antibiotic is suspended in the composition; the viscosity of the composition is at least about 30% higher than the viscosity of the carrier without the tetracycline antibiotic; and is higher than the viscosity or the hydrophobic oil and the tetracycline antibiotic without the viscosity modifying agents. The tetracycline is chemically stable in the composition for at least six months; wherein more than about 90% of the tetracycline has not broken down. The composition is packaged as a breakable foam that breaks easily upon application of shear force.

A topical therapeutic hydrophobic breakable composition includes a carrier comprising (a) about 60% to about 99% by weight of at least one hydrophobic oil; (b) at least one viscosity-modifying agents selected from the group consisting of a fatty alcohol, a fatty acid and a wax; and (c) a tetracycline antibiotic, characterized in that at least part of the tetracycline antibiotic is suspended in the composition; the viscosity of the composition is at least about 30% higher than the viscosity of the carrier without the tetracycline antibiotic; and is higher than the viscosity or the hydrophobic oil and the tetracycline antibiotic without the viscosity modifying agents. The tetracycline is chemically stable in the composition for at least six months; wherein more than about 90% of the tetracycline has not broken down. The composition is packaged as a breakable foam that breaks easily upon application of shear force.

Improved systems and methods for producing synthetic hypericin at high volume and high purity.