N-confused porphyrin possessing glucamine-appendants: Aggregation and acid/base properties in aqueous media

Yoshiya Ikawa; Hiroaki Ogawa; Hiroyuki Harada; Hiroyuki Furuta

doi:10.1016/j.bmcl.2008.10.079

N-confused porphyrin possessing glucamine-appendants: Aggregation and acid/base properties in aqueous media

Yoshiya Ikawa, Hiroaki Ogawa, Hiroyuki Harada, Hiroyuki Furuta^*

^*Corresponding author for this work

Department of Chemistry

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

25 Scopus citations

Abstract

A water-soluble derivative of N-confused porphyrin (NCP: 5,10,15,20-tetraaryl-2-aza-21-carbaporphyrin) was synthesized by introducing glucamine groups at the para-position of meso-aryl groups. The tetraglucamine-appended NCP (TG-NCP) exists as monocation in aqueous solution containing 6 mM sodium dodecyl sulfate (SDS) but exists as freebase to form aggregates in pure water. These properties are distinct from those of corresponding regular porphyrin, which exists as freebase in the micellar solution and practically insoluble in water.

Original language	English
Pages (from-to)	6394-6397
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	18
Issue number	24
DOIs	https://doi.org/10.1016/j.bmcl.2008.10.079
State	Published - 2008/12/15

Keywords

Aggregate
Gulcamine
N-confused porphyrin
Water-soluble porphyrin
pK

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmcl.2008.10.079

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title = "N-confused porphyrin possessing glucamine-appendants: Aggregation and acid/base properties in aqueous media",

abstract = "A water-soluble derivative of N-confused porphyrin (NCP: 5,10,15,20-tetraaryl-2-aza-21-carbaporphyrin) was synthesized by introducing glucamine groups at the para-position of meso-aryl groups. The tetraglucamine-appended NCP (TG-NCP) exists as monocation in aqueous solution containing 6 mM sodium dodecyl sulfate (SDS) but exists as freebase to form aggregates in pure water. These properties are distinct from those of corresponding regular porphyrin, which exists as freebase in the micellar solution and practically insoluble in water.",

keywords = "Aggregate, Gulcamine, N-confused porphyrin, Water-soluble porphyrin, pK",

author = "Yoshiya Ikawa and Hiroaki Ogawa and Hiroyuki Harada and Hiroyuki Furuta",

note = "Funding Information: This work was partly supported by Grants-in-Aid for Young Scientists (A) (No.18685020 to Y.I.), Exploratory Research (No.19657071 to Y.I.), and the Global COE program, “Science for Future Molecular Systems” (to H.F.) from the Ministry of Education, Culture, Science, Sports and Technology of Japan. ",

year = "2008",

month = dec,

day = "15",

doi = "10.1016/j.bmcl.2008.10.079",

language = "英語",

volume = "18",

pages = "6394--6397",

journal = "Bioorganic and Medicinal Chemistry Letters",

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TY - JOUR

T1 - N-confused porphyrin possessing glucamine-appendants

T2 - Aggregation and acid/base properties in aqueous media

AU - Ikawa, Yoshiya

AU - Ogawa, Hiroaki

AU - Harada, Hiroyuki

AU - Furuta, Hiroyuki

N1 - Funding Information: This work was partly supported by Grants-in-Aid for Young Scientists (A) (No.18685020 to Y.I.), Exploratory Research (No.19657071 to Y.I.), and the Global COE program, “Science for Future Molecular Systems” (to H.F.) from the Ministry of Education, Culture, Science, Sports and Technology of Japan.

PY - 2008/12/15

Y1 - 2008/12/15

N2 - A water-soluble derivative of N-confused porphyrin (NCP: 5,10,15,20-tetraaryl-2-aza-21-carbaporphyrin) was synthesized by introducing glucamine groups at the para-position of meso-aryl groups. The tetraglucamine-appended NCP (TG-NCP) exists as monocation in aqueous solution containing 6 mM sodium dodecyl sulfate (SDS) but exists as freebase to form aggregates in pure water. These properties are distinct from those of corresponding regular porphyrin, which exists as freebase in the micellar solution and practically insoluble in water.

AB - A water-soluble derivative of N-confused porphyrin (NCP: 5,10,15,20-tetraaryl-2-aza-21-carbaporphyrin) was synthesized by introducing glucamine groups at the para-position of meso-aryl groups. The tetraglucamine-appended NCP (TG-NCP) exists as monocation in aqueous solution containing 6 mM sodium dodecyl sulfate (SDS) but exists as freebase to form aggregates in pure water. These properties are distinct from those of corresponding regular porphyrin, which exists as freebase in the micellar solution and practically insoluble in water.

KW - Aggregate

KW - Gulcamine

KW - N-confused porphyrin

KW - Water-soluble porphyrin

KW - pK

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U2 - 10.1016/j.bmcl.2008.10.079

DO - 10.1016/j.bmcl.2008.10.079

M3 - 学術論文

C2 - 18993069

AN - SCOPUS:56249141087

SN - 0960-894X

VL - 18

SP - 6394

EP - 6397

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 24

ER -

N-confused porphyrin possessing glucamine-appendants: Aggregation and acid/base properties in aqueous media

Abstract

Keywords

ASJC Scopus subject areas

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