Literature DB >> 21417431

Remarkable regioselective position-10 bromination of bacteriopyropheophorbide-a and ring-B reduced pyropheophorbide-a.

Manivannan Ethirajan1, Penny Joshi, White H William, Kei Ohkubo, Shunichi Fukuzumi, Ravindra K Pandey.   

Abstract

Both bacteriopyropheophorbide-a and ring-B reduced pyropheophorbide-a on reacting with NBS (N-bromosuccinamide) undergo electrophilic bromination to provide 10-bromo analogs. The electronic nature of the substituents present at position-3 did not make any difference in the regioselective outcome of the brominated products. These relatively stable brominated chlorins and bacteriochlorins provide an easy way of introducing a wide variety of functionalities, which could be extremely useful in developing improved agents for biomedical applications and supramolecular chemistry.
© 2011 American Chemical Society

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Year:  2011        PMID: 21417431      PMCID: PMC3076286          DOI: 10.1021/ol200314v

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  17 in total

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Authors:  Annemarie B Wöhri; Gergely Katona; Linda C Johansson; Emelie Fritz; Erik Malmerberg; Magnus Andersson; Jonathan Vincent; Mattias Eklund; Marco Cammarata; Michael Wulff; Jan Davidsson; Gerrit Groenhof; Richard Neutze
Journal:  Science       Date:  2010-04-30       Impact factor: 47.728

2.  Intramolecular energy transfer within butadiyne-linked chlorophyll and porphyrin dimer-faced, self-assembled prisms.

Authors:  Richard F Kelley; Suk Joong Lee; Thea M Wilson; Yasuyuki Nakamura; David M Tiede; Atsuhiro Osuka; Joseph T Hupp; Michael R Wasielewski
Journal:  J Am Chem Soc       Date:  2008-03-08       Impact factor: 15.419

3.  An in vivo quantitative structure-activity relationship for a congeneric series of pyropheophorbide derivatives as photosensitizers for photodynamic therapy.

Authors:  B W Henderson; D A Bellnier; W R Greco; A Sharma; R K Pandey; L A Vaughan; K R Weishaupt; T J Dougherty
Journal:  Cancer Res       Date:  1997-09-15       Impact factor: 12.701

4.  Hexylether derivative of pyropheophorbide-a (HPPH) on conjugating with 3gadolinium(III) aminobenzyldiethylenetriaminepentaacetic acid shows potential for in vivo tumor imaging (MR, Fluorescence) and photodynamic therapy.

Authors:  Joseph A Spernyak; William H White; Manivannan Ethirajan; Nayan J Patel; Lalit Goswami; Yihui Chen; Steven Turowski; Joseph R Missert; Carrie Batt; Richard Mazurchuk; Ravindra K Pandey
Journal:  Bioconjug Chem       Date:  2010-05-19       Impact factor: 4.774

5.  Role of the chlorophyll dimer in bacterial photosynthesis.

Authors:  A Warshel
Journal:  Proc Natl Acad Sci U S A       Date:  1980-06       Impact factor: 11.205

6.  Highly selective synthesis of the ring-B reduced chlorins by ferric chloride-mediated oxidation of bacteriochlorins: effects of the fused imide vs isocyclic ring on photophysical and electrochemical properties.

Authors:  Chao Liu; Mahabeer P Dobhal; Manivannan Ethirajan; Joseph R Missert; Ravindra K Pandey; Sathyamangalam Balasubramanian; Dinesh K Sukumaran; Min Zhang; Karl M Kadish; Kei Ohkubo; Shunichi Fukuzumi
Journal:  J Am Chem Soc       Date:  2008-10-02       Impact factor: 15.419

7.  A facile synthetic method for conversion of chlorophyll-a to bacteriochlorophyll-c.

Authors:  Shin-Ichi Sasaki; Tadashi Mizoguchi; Hitoshi Tamiaki
Journal:  J Org Chem       Date:  2007-05-12       Impact factor: 4.354

8.  Comparative positron-emission tomography (PET) imaging and phototherapeutic potential of 124I- labeled methyl- 3-(1'-iodobenzyloxyethyl)pyropheophorbide-a vs the corresponding glucose and galactose conjugates.

Authors:  Suresh K Pandey; Munawwar Sajjad; Yihui Chen; Xiang Zheng; Rutao Yao; Joseph R Missert; Carrie Batt; Hani A Nabi; Allan R Oseroff; Ravindra K Pandey
Journal:  J Med Chem       Date:  2009-01-22       Impact factor: 7.446

9.  Regioselective 15-bromination and functionalization of a stable synthetic bacteriochlorin.

Authors:  Dazhong Fan; Masahiko Taniguchi; Jonathan S Lindsey
Journal:  J Org Chem       Date:  2007-06-13       Impact factor: 4.354

10.  Unexpected bromination ring-opening of tetraarylporphyrins.

Authors:  Chao Liu; Dong-Mei Shen; Qing-Yun Chen
Journal:  Chem Commun (Camb)       Date:  2006-01-11       Impact factor: 6.222

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  2 in total

1.  Synthesis, photophysical and electrochemistry of near-IR absorbing bacteriochlorins related to bacteriochlorophyll a.

Authors:  Andrei Kozyrev; Manivannan Ethirajan; Ping Chen; Kei Ohkubo; Byron C Robinson; Kathleen M Barkigia; Shunichi Fukuzumi; Karl M Kadish; Ravindra K Pandey
Journal:  J Org Chem       Date:  2012-10-31       Impact factor: 4.354

2.  Synthesis, Tumor Specificity, and Photosensitizing Efficacy of Erlotinib-Conjugated Chlorins and Bacteriochlorins: Identification of a Highly Effective Candidate for Photodynamic Therapy of Cancer.

Authors:  Ravindra R Cheruku; Joseph Cacaccio; Farukh A Durrani; Walter A Tabaczynski; Ramona Watson; Kevin Siters; Joseph R Missert; Erin C Tracy; Mykhaylo Dukh; Khurshid Guru; Richard C Koya; Pawel Kalinski; Heinz Baumann; Ravindra K Pandey
Journal:  J Med Chem       Date:  2021-01-05       Impact factor: 8.039

  2 in total

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