Northern-southern route to synthesis of bacteriochlorins

Liu, Yizhou; Lindsey, Jonathan S.; Allu, Srinivasa Rao; Fujita, Hikaru

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Title: Northern-southern route to synthesis of bacteriochlorins

Abstract

Described herein are chlorins, bacteriochlorins, methods and intermediates for the synthesis of bacteriochlorins, and methods of using such bacteriochlorins for, among other things, diagnostic and therapeutic purposes such as luminescent compounds in flow cytometry, and as active agents in photodynamic therapy (PDT).

Inventors:: Liu, Yizhou; Lindsey, Jonathan S.; Allu, Srinivasa Rao; Fujita, Hikaru

Issue Date:: 2021-02-16

Research Org.:: North Carolina State University, Raleigh, NC (United States)

Sponsoring Org.:: USDOE

OSTI Identifier:: 1805505

Patent Number(s):: 10919904

Application Number:: 16/323,607

Assignee:: North Carolina State University (Raleigh, NC)

Patent Classifications (CPCs):: A - HUMAN NECESSITIES A61 - MEDICAL OR VETERINARY SCIENCE A61K - PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES

A - HUMAN NECESSITIES A61 - MEDICAL OR VETERINARY SCIENCE A61P - SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

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A - HUMAN NECESSITIES A61 - MEDICAL OR VETERINARY SCIENCE A61K - PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
A61K31/409 - having four such rings, e.g. porphine derivatives, bilirubin, biliverdine
A61K41/0071 - {PDT with porphyrins having exactly 20 ring atoms, i.e. based on the non-expanded tetrapyrrolic ring system, e.g. bacteriochlorin, chlorin-e6, or phthalocyanines}
A61K9/0019 - {Injectable compositions

A - HUMAN NECESSITIES A61 - MEDICAL OR VETERINARY SCIENCE A61P - SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
A61P35/00 - Antineoplastic agents

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07D - HETEROCYCLIC COMPOUNDS
C07D487/22 - in which the condensed system contains four or more hetero rings

G - PHYSICS G01 - MEASURING G01N - INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
G01N15/14 - Electro-optical investigation, e.g. flow cytometers
G01N15/1459 - {the analysis being performed on a sample stream}
G01N33/483 - Physical analysis of biological material

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DOE Contract Number:: FG02-05ER15661; SC0001035

Resource Type:: Patent

Resource Relation:: Patent File Date: 08/17/2017

Country of Publication:: United States

Language:: English

Citation Formats


                    Liu, Yizhou, Lindsey, Jonathan S., Allu, Srinivasa Rao, and Fujita, Hikaru. Northern-southern route to synthesis of bacteriochlorins.  United States: N. p., 2021. 
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                    Liu, Yizhou, Lindsey, Jonathan S., Allu, Srinivasa Rao, & Fujita, Hikaru. Northern-southern route to synthesis of bacteriochlorins.  United States.

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                    Liu, Yizhou, Lindsey, Jonathan S., Allu, Srinivasa Rao, and Fujita, Hikaru. Tue .  
        "Northern-southern route to synthesis of bacteriochlorins".  United States.  https://www.osti.gov/servlets/purl/1805505.

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@article{osti_1805505,

  title        = {Northern-southern route to synthesis of bacteriochlorins},

  author       = {Liu, Yizhou and Lindsey, Jonathan S. and Allu, Srinivasa Rao and Fujita, Hikaru},

  abstractNote = {Described herein are chlorins, bacteriochlorins, methods and intermediates for the synthesis of bacteriochlorins, and methods of using such bacteriochlorins for, among other things, diagnostic and therapeutic purposes such as luminescent compounds in flow cytometry, and as active agents in photodynamic therapy (PDT).},

  doi          = {},

  journal      = {},
number       = ,

  volume       = ,

  place        = {United States},

  year         = {2021},

  month        = {2}

}

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Described herein are bacteriochlorins comprising an annulated isocyclic ring such as a compound Formula I: or a metal conjugate thereof, wherein: R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, and Z are each as defined herein. Also described are methods and intermediates for the synthesis of bacteriochlorins comprising an annulated isocyclic ring, and methods of using such bacteriochlorins for, among other things, diagnostic and therapeutic purposes such as, e.g., luminescent compounds in flow cytometry, and/or as active agents in photodynamic therapy (PDT).
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Method and apparatus for routing data in an inter-nodal communications lattice of a massively parallel computer system by dynamically adjusting local routing strategies

Patent Archer, Charles Jens [Rochester, MN]; Musselman, Roy Glenn [Rochester, MN]; Peters, Amanda [Rochester, MN]; ...

A massively parallel computer system contains an inter-nodal communications network of node-to-node links. Each node implements a respective routing strategy for routing data through the network, the routing strategies not necessarily being the same in every node. The routing strategies implemented in the nodes are dynamically adjusted during application execution to shift network workload as required. Preferably, adjustment of routing policies in selective nodes is performed at synchronization points. The network may be dynamically monitored, and routing strategies adjusted according to detected network conditions.
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Method and apparatus for routing data in an inter-nodal communications lattice of a massively parallel computer system by semi-randomly varying routing policies for different packets

Patent Archer, Charles Jens [Rochester, MN]; Musselman, Roy Glenn [Rochester, MN]; Peters, Amanda [Rochester, MN]; ...

A massively parallel computer system contains an inter-nodal communications network of node-to-node links. Nodes vary a choice of routing policy for routing data in the network in a semi-random manner, so that similarly situated packets are not always routed along the same path. Semi-random variation of the routing policy tends to avoid certain local hot spots of network activity, which might otherwise arise using more consistent routing determinations. Preferably, the originating node chooses a routing policy for a packet, and all intermediate nodes in the path route the packet according to that policy. Policies may be rotated on a round-robinmore » « less
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Title: Northern-southern route to synthesis of bacteriochlorins

Abstract

Citation Formats

Drug-Delivery Device with Stretched, Rate-Controlling Membrane patent, January 1973

Propylene glycol diester solutions of PGE-type compounds patent, October 1983

Polymerized liposomes targeted to M cells and useful for oral or mucosal drug delivery patent, May 2000

High density non-volatile memory device incorporating thiol-derivatized porphyrins patent, March 2001

Dialkylated glycol compositions and medicament preparations containing same patent, May 1976

Carbonate diester solutions of PGE-type compounds patent, October 1983

Single polypeptide chain binding molecules patent, August 1990

Method for enhancing target specificity of antibody localization and clearance of non-target diagnostic and therapeutic principles patent, November 1986

Synthesis of Phosphono-substituted Porphyrin Compounds for Attachment to Metal Oxide Surfaces patent-application, May 2005

Macromolecular environment control in specific receptor assays patent, February 1983

Electrophoretic cuff apparatus drug delivery system patent, November 1999

Tightly coupled porphyrin macrocycles for molecular memory storage patent, November 2001

Photovoltaic cell interconnection patent, March 2004

Pressure sensitive adhesive matrix patches for transdermal delivery of salts of pharmaceutical agents patent, November 1999

Recombinant monoclonal antibodies patent, October 1984

Targeted gas and gaseous precursor-filled liposomes patent, June 2000

Photovoltaic fibers patent, July 2005

Chemical compounds patent, December 1982

High-density non-volatile memory devices incorporating sandwich coordination compounds patent, April 2001

Tissue-specific and pathogen-specific toxic agents and ribozymes patent, August 2001

Hybrid polypeptides with enhanced pharmacokinetic properties patent, December 2003

Targeted polymerized liposomes for improved drug delivery patent, December 1999

Conjugation-stabilized therapeutic agent compositions, delivery and diagnostic formulations comprising same, and method of making and using the same patent, October 1997

Child resistant package assembly for dispensing pharmaceutical medications patent, June 1994

Covalent microparticle-drug conjugates for biological targeting patent, November 1998

Charged lipids and uses for the same patent, September 2000

High density non-volatile memory device patent, April 2002

Serial injection of muramyldipeptides and liposomes enhances the anti-infective activity of muramyldipeptides patent, June 1985

De novo synthesis of bacteriochlorins patent, March 2014

Tumor localization and therapy with labeled antibody fragments specific to tumor-associated markers patent, May 1982

Colon targeted delivery system patent, March 2000

Substrates carrying polymers of linked sandwich coordination compounds and methods of use thereof patent, September 2002

Transdermal drug patch with attached pocket for controlled heating device patent, July 2001

Method of transdermally administering high molecular weight drugs with a polymer skin enhancer patent, February 2000

Photovoltaic cell patent, August 2005

Swallowtail motifs for imparting water solubility to porphyrinic compounds patent, September 2013

CEA-family antigens, Anti-CEA antibodies and CEA immunoassay patent, April 1989

Packaged pharmaceutical product patent, October 1991

Tumor localization and therapy with labeled antibodies specific to intracellular tumor-associated markers patent, November 1982

Compounds having affinity for the granulocyte-colony stimulating factor receptor (G-CSFR) and associated uses patent, April 2004

Method of packaging and sterilizing a pharmaceutical product patent, July 1991

Pulseless liquid supply system for flow cytometry patent, June 1999

Gel electrolytes for dye sensitized solar cells patent, May 2005

Enzyme Amplification Assay patent, June 1974

Tetrapartate prodrugs patent, April 2004

Multipathway electronically-controlled drug delivery system patent, January 1999

Fluorinated Photosensitizers Related to Chlorins and Bacteriochlorins for Photodynamic Therapy patent-application, March 2004

Method and apparatus for flow cytometry patent, June 2001

Apparatus and method for using an intracutaneous microneedle array patent, July 2001

Cyclodextrin polymers for carrying and releasing drugs patent, April 2000

Iontophoretic drug delivery device having high-efficiency DC-to-DC energy conversion circuit patent, December 2000

Tumor localization and therapy with labeled anti-CEA antibody patent, September 1982

Carbonate diester solutions of PGE-type compounds patent, May 1982

Low temperature interconnection of nanoparticles patent, February 2005

Flow cytometry for high throughput screening patent, May 2005

Method for diagnostically imaging lesions in the brain inside a blood-brain barrier patent, October 1991

Taste-masked microcapsule compositions and methods of manufacture patent, October 2000

Solar cells incorporating light harvesting arrays patent, June 2002

Method and apparatus for flow cytometry patent, July 2003

Compositions and methods for the delivery of drugs by platelets for the treatment of cardiovascular and other diseases patent, June 1998

Localization of tumors by radiolabelled antibodies patent, December 1975

Dermatological patch and process for producing thereof patent, July 2001

Wire interconnects for fabricating interconnected photovoltaic cells patent, August 2005

Micronized aerosol steroids patent, November 1983

Alkyl ether analogs of chlorins having an N-substituted imide ring patent, September 1999

Polyethylene glycol modified interferon therapy patent, February 2003

Track soundproofing arrangement patent, July 2001

Non-immunogenic polypeptides patent, December 1979

Composition and method for delivery of biologically-active factors patent, August 2001

Steroidal aerosol compositions and process for the preparation thereof patent, August 1977

Transparent regenerating photoelectrochemical cell patent, August 1995

High density non-volatile memory device patent, December 2003

Device for local drug delivery and methods for using the same patent, January 1998

Transdermal patch patent, September 1999

Multistate triple-decker dyads in three distinct architectures for information storage applications patent, April 2004

Device and method for non-occlusive localized drug delivery patent, November 1999

Method for targeted and controlled release of drugs in the intestinal tract and more particularly in the colon patent, May 1999

Drug-Delivery Device with Stretched, Rate-Controlling Membrane
patent, January 1973

Propylene glycol diester solutions of PGE-type compounds
patent, October 1983

Polymerized liposomes targeted to M cells and useful for oral or mucosal drug delivery
patent, May 2000

High density non-volatile memory device incorporating thiol-derivatized porphyrins
patent, March 2001

Dialkylated glycol compositions and medicament preparations containing same
patent, May 1976

Carbonate diester solutions of PGE-type compounds
patent, October 1983

Single polypeptide chain binding molecules
patent, August 1990

Method for enhancing target specificity of antibody localization and clearance of non-target diagnostic and therapeutic principles
patent, November 1986

Synthesis of Phosphono-substituted Porphyrin Compounds for Attachment to Metal Oxide Surfaces
patent-application, May 2005

Macromolecular environment control in specific receptor assays
patent, February 1983

Electrophoretic cuff apparatus drug delivery system
patent, November 1999

Tightly coupled porphyrin macrocycles for molecular memory storage
patent, November 2001

Photovoltaic cell interconnection
patent, March 2004

Pressure sensitive adhesive matrix patches for transdermal delivery of salts of pharmaceutical agents
patent, November 1999

Recombinant monoclonal antibodies
patent, October 1984

Targeted gas and gaseous precursor-filled liposomes
patent, June 2000

Photovoltaic fibers
patent, July 2005

Chemical compounds
patent, December 1982

High-density non-volatile memory devices incorporating sandwich coordination compounds
patent, April 2001

Tissue-specific and pathogen-specific toxic agents and ribozymes
patent, August 2001

Hybrid polypeptides with enhanced pharmacokinetic properties
patent, December 2003

Targeted polymerized liposomes for improved drug delivery
patent, December 1999

Conjugation-stabilized therapeutic agent compositions, delivery and diagnostic formulations comprising same, and method of making and using the same
patent, October 1997

Child resistant package assembly for dispensing pharmaceutical medications
patent, June 1994

Covalent microparticle-drug conjugates for biological targeting
patent, November 1998

Charged lipids and uses for the same
patent, September 2000

High density non-volatile memory device
patent, April 2002

Serial injection of muramyldipeptides and liposomes enhances the anti-infective activity of muramyldipeptides
patent, June 1985

De novo synthesis of bacteriochlorins
patent, March 2014

Tumor localization and therapy with labeled antibody fragments specific to tumor-associated markers
patent, May 1982

Colon targeted delivery system
patent, March 2000

Substrates carrying polymers of linked sandwich coordination compounds and methods of use thereof
patent, September 2002

Transdermal drug patch with attached pocket for controlled heating device
patent, July 2001

Method of transdermally administering high molecular weight drugs with a polymer skin enhancer
patent, February 2000

Photovoltaic cell
patent, August 2005

Swallowtail motifs for imparting water solubility to porphyrinic compounds
patent, September 2013

CEA-family antigens, Anti-CEA antibodies and CEA immunoassay
patent, April 1989

Packaged pharmaceutical product
patent, October 1991

Tumor localization and therapy with labeled antibodies specific to intracellular tumor-associated markers
patent, November 1982

Compounds having affinity for the granulocyte-colony stimulating factor receptor (G-CSFR) and associated uses
patent, April 2004

Method of packaging and sterilizing a pharmaceutical product
patent, July 1991

Pulseless liquid supply system for flow cytometry
patent, June 1999

Gel electrolytes for dye sensitized solar cells
patent, May 2005

Enzyme Amplification Assay
patent, June 1974

Tetrapartate prodrugs
patent, April 2004

Multipathway electronically-controlled drug delivery system
patent, January 1999

Fluorinated Photosensitizers Related to Chlorins and Bacteriochlorins for Photodynamic Therapy
patent-application, March 2004

Method and apparatus for flow cytometry
patent, June 2001

Apparatus and method for using an intracutaneous microneedle array
patent, July 2001

Cyclodextrin polymers for carrying and releasing drugs
patent, April 2000

Iontophoretic drug delivery device having high-efficiency DC-to-DC energy conversion circuit
patent, December 2000

Tumor localization and therapy with labeled anti-CEA antibody
patent, September 1982

Carbonate diester solutions of PGE-type compounds
patent, May 1982

Low temperature interconnection of nanoparticles
patent, February 2005

Flow cytometry for high throughput screening
patent, May 2005

Method for diagnostically imaging lesions in the brain inside a blood-brain barrier
patent, October 1991

Taste-masked microcapsule compositions and methods of manufacture
patent, October 2000

Solar cells incorporating light harvesting arrays
patent, June 2002

Method and apparatus for flow cytometry
patent, July 2003

Compositions and methods for the delivery of drugs by platelets for the treatment of cardiovascular and other diseases
patent, June 1998

Localization of tumors by radiolabelled antibodies
patent, December 1975

Dermatological patch and process for producing thereof
patent, July 2001

Wire interconnects for fabricating interconnected photovoltaic cells
patent, August 2005

Micronized aerosol steroids
patent, November 1983

Alkyl ether analogs of chlorins having an N-substituted imide ring
patent, September 1999

Polyethylene glycol modified interferon therapy
patent, February 2003

Track soundproofing arrangement
patent, July 2001

Non-immunogenic polypeptides
patent, December 1979

Composition and method for delivery of biologically-active factors
patent, August 2001

Steroidal aerosol compositions and process for the preparation thereof
patent, August 1977

Transparent regenerating photoelectrochemical cell
patent, August 1995

High density non-volatile memory device
patent, December 2003

Device for local drug delivery and methods for using the same
patent, January 1998

Transdermal patch
patent, September 1999

Multistate triple-decker dyads in three distinct architectures for information storage applications
patent, April 2004

Device and method for non-occlusive localized drug delivery
patent, November 1999

Method for targeted and controlled release of drugs in the intestinal tract and more particularly in the colon
patent, May 1999

Drug mitochondrial targeting agents
patent, November 2001

Immunoglobulin half-molecules and process for producing hybrid antibodies
patent, October 1984

Transdermal patch incorporating a polymer film incorporated with an active agent
patent, January 2000