Multi-gram synthesis of a porphyrazine platform for cellular translocation, conjugation to Doxorubicin, and cellular uptake

Evan R. Trivedi; Carl M. Blumenfeld; Todd Wielgos; Sharon Pokropinski; Prasad Dande; Ton T. Hai; Anthony G.M. Barrett; Brian M. Hoffman

doi:10.1016/j.tetlet.2012.07.087

Multi-gram synthesis of a porphyrazine platform for cellular translocation, conjugation to Doxorubicin, and cellular uptake

Evan R. Trivedi, Carl M. Blumenfeld, Todd Wielgos, Sharon Pokropinski, Prasad Dande, Ton T. Hai, Anthony G.M. Barrett, Brian M. Hoffman^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

19 Scopus citations

Abstract

We report the synthesis of the near infrared (NIR) fluorescent porphyrazine (Pz) 285, with pendant hydroxyl groups, as a non-toxic platform for delivery of conjugated chemotherapeutic agents to tumor cells. Conjugation of Pz 285 to Doxorubicin via an acid labile linker and initial biological studies are reported.

Original language	English (US)
Pages (from-to)	5475-5478
Number of pages	4
Journal	Tetrahedron Letters
Volume	53
Issue number	41
DOIs	https://doi.org/10.1016/j.tetlet.2012.07.087
State	Published - Oct 10 2012

Funding

This work was supported by the Baxter Healthcare Corporation through the Baxter-Northwestern Alliance. Imaging work was performed at the Northwestern University Biological Imaging Facility generously supported by the NU Office for Research.

Keywords

Chemotherapy
Porphyrinoid
Tetrapyrrole

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.tetlet.2012.07.087

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title = "Multi-gram synthesis of a porphyrazine platform for cellular translocation, conjugation to Doxorubicin, and cellular uptake",

abstract = "We report the synthesis of the near infrared (NIR) fluorescent porphyrazine (Pz) 285, with pendant hydroxyl groups, as a non-toxic platform for delivery of conjugated chemotherapeutic agents to tumor cells. Conjugation of Pz 285 to Doxorubicin via an acid labile linker and initial biological studies are reported.",

keywords = "Chemotherapy, Porphyrinoid, Tetrapyrrole",

author = "Trivedi, {Evan R.} and Blumenfeld, {Carl M.} and Todd Wielgos and Sharon Pokropinski and Prasad Dande and Hai, {Ton T.} and Barrett, {Anthony G.M.} and Hoffman, {Brian M.}",

note = "Funding Information: This work was supported by the Baxter Healthcare Corporation through the Baxter-Northwestern Alliance. Imaging work was performed at the Northwestern University Biological Imaging Facility generously supported by the NU Office for Research. ",

year = "2012",

month = oct,

day = "10",

doi = "10.1016/j.tetlet.2012.07.087",

language = "English (US)",

volume = "53",

pages = "5475--5478",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

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TY - JOUR

T1 - Multi-gram synthesis of a porphyrazine platform for cellular translocation, conjugation to Doxorubicin, and cellular uptake

AU - Trivedi, Evan R.

AU - Blumenfeld, Carl M.

AU - Wielgos, Todd

AU - Pokropinski, Sharon

AU - Dande, Prasad

AU - Hai, Ton T.

AU - Barrett, Anthony G.M.

AU - Hoffman, Brian M.

N1 - Funding Information: This work was supported by the Baxter Healthcare Corporation through the Baxter-Northwestern Alliance. Imaging work was performed at the Northwestern University Biological Imaging Facility generously supported by the NU Office for Research.

PY - 2012/10/10

Y1 - 2012/10/10

N2 - We report the synthesis of the near infrared (NIR) fluorescent porphyrazine (Pz) 285, with pendant hydroxyl groups, as a non-toxic platform for delivery of conjugated chemotherapeutic agents to tumor cells. Conjugation of Pz 285 to Doxorubicin via an acid labile linker and initial biological studies are reported.

AB - We report the synthesis of the near infrared (NIR) fluorescent porphyrazine (Pz) 285, with pendant hydroxyl groups, as a non-toxic platform for delivery of conjugated chemotherapeutic agents to tumor cells. Conjugation of Pz 285 to Doxorubicin via an acid labile linker and initial biological studies are reported.

KW - Chemotherapy

KW - Porphyrinoid

KW - Tetrapyrrole

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UR - http://www.scopus.com/inward/citedby.url?scp=84865790938&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2012.07.087

DO - 10.1016/j.tetlet.2012.07.087

M3 - Article

AN - SCOPUS:84865790938

SN - 0040-4039

VL - 53

SP - 5475

EP - 5478

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 41

ER -

Multi-gram synthesis of a porphyrazine platform for cellular translocation, conjugation to Doxorubicin, and cellular uptake

Abstract

Funding

Keywords

ASJC Scopus subject areas

UN SDGs

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