Synthesis of 2α-propoxy-1α,25-dihydroxyvitamin D3 and comparison of its metabolism by human CYP24A1 and rat CYP24A1

Nozomi Saito; Yoshitomo Suhara; Daisuke Abe; Tatsuya Kusudo; Miho Ohta; Kaori Yasuda; Toshiyuki Sakaki; Shinobu Honzawa; Toshie Fujishima; Atsushi Kittaka

doi:10.1016/j.bmc.2009.05.032

Synthesis of 2α-propoxy-1α,25-dihydroxyvitamin D₃ and comparison of its metabolism by human CYP24A1 and rat CYP24A1

Nozomi Saito, Yoshitomo Suhara, Daisuke Abe, Tatsuya Kusudo, Miho Ohta, Kaori Yasuda, Toshiyuki Sakaki, Shinobu Honzawa, Toshie Fujishima, Atsushi Kittaka

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

22 Citations (Scopus)

Abstract

A new vitamin D₃ analogue, 2α-propoxy-1α,25-dihydroxyvitamin D₃ (C3O1), was synthesized starting from d-glucose as a chiral template of the A-ring with a CD-ring bromoolefin unit using the Trost coupling method. We studied the metabolism of the new analogue by human CYP24A1 and rat CYP24A1 to learn of species-based differences and found that the former has multiple metabolic pathways, but the latter has only a single pathway.

Original language	English
Pages (from-to)	4296-4301
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry
Volume	17
Issue number	13
DOIs	https://doi.org/10.1016/j.bmc.2009.05.032
Publication status	Published - 2009 Jul 1
Externally published	Yes

Keywords

Human CYP24A1
Metabolism
Rat CYP24A1
Vitamin D analogues

ASJC Scopus subject areas

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

Access to Document

10.1016/j.bmc.2009.05.032

Cite this

@article{cb9f7eb308b34a82b974b654b67b0202,

title = "Synthesis of 2α-propoxy-1α,25-dihydroxyvitamin D3 and comparison of its metabolism by human CYP24A1 and rat CYP24A1",

abstract = "A new vitamin D3 analogue, 2α-propoxy-1α,25-dihydroxyvitamin D3 (C3O1), was synthesized starting from d-glucose as a chiral template of the A-ring with a CD-ring bromoolefin unit using the Trost coupling method. We studied the metabolism of the new analogue by human CYP24A1 and rat CYP24A1 to learn of species-based differences and found that the former has multiple metabolic pathways, but the latter has only a single pathway.",

keywords = "Human CYP24A1, Metabolism, Rat CYP24A1, Vitamin D analogues",

author = "Nozomi Saito and Yoshitomo Suhara and Daisuke Abe and Tatsuya Kusudo and Miho Ohta and Kaori Yasuda and Toshiyuki Sakaki and Shinobu Honzawa and Toshie Fujishima and Atsushi Kittaka",

note = "Funding Information: We are grateful to Ms. Junko Shimode and Ms. Akiko Tonoki (Teikyo University) for the spectroscopic measurements. This work has been supported in part by Grants-in-Aid from the Ministry of Education, Culture, Sports, Science and Technology, Japan (to N.S., Y.S., T.F., and S.H.) and by Grant-in-Aid from Japan Society for the Promotion of Science (to A.K.). Copyright: Copyright 2009 Elsevier B.V., All rights reserved.",

year = "2009",

month = jul,

day = "1",

doi = "10.1016/j.bmc.2009.05.032",

language = "English",

volume = "17",

pages = "4296--4301",

journal = "Bioorganic and Medicinal Chemistry",

issn = "0968-0896",

publisher = "Elsevier Limited",

number = "13",

}

TY - JOUR

T1 - Synthesis of 2α-propoxy-1α,25-dihydroxyvitamin D3 and comparison of its metabolism by human CYP24A1 and rat CYP24A1

AU - Saito, Nozomi

AU - Suhara, Yoshitomo

AU - Abe, Daisuke

AU - Kusudo, Tatsuya

AU - Ohta, Miho

AU - Yasuda, Kaori

AU - Sakaki, Toshiyuki

AU - Honzawa, Shinobu

AU - Fujishima, Toshie

AU - Kittaka, Atsushi

N1 - Funding Information: We are grateful to Ms. Junko Shimode and Ms. Akiko Tonoki (Teikyo University) for the spectroscopic measurements. This work has been supported in part by Grants-in-Aid from the Ministry of Education, Culture, Sports, Science and Technology, Japan (to N.S., Y.S., T.F., and S.H.) and by Grant-in-Aid from Japan Society for the Promotion of Science (to A.K.). Copyright: Copyright 2009 Elsevier B.V., All rights reserved.

PY - 2009/7/1

Y1 - 2009/7/1

N2 - A new vitamin D3 analogue, 2α-propoxy-1α,25-dihydroxyvitamin D3 (C3O1), was synthesized starting from d-glucose as a chiral template of the A-ring with a CD-ring bromoolefin unit using the Trost coupling method. We studied the metabolism of the new analogue by human CYP24A1 and rat CYP24A1 to learn of species-based differences and found that the former has multiple metabolic pathways, but the latter has only a single pathway.

AB - A new vitamin D3 analogue, 2α-propoxy-1α,25-dihydroxyvitamin D3 (C3O1), was synthesized starting from d-glucose as a chiral template of the A-ring with a CD-ring bromoolefin unit using the Trost coupling method. We studied the metabolism of the new analogue by human CYP24A1 and rat CYP24A1 to learn of species-based differences and found that the former has multiple metabolic pathways, but the latter has only a single pathway.

KW - Human CYP24A1

KW - Metabolism

KW - Rat CYP24A1

KW - Vitamin D analogues

UR - http://www.scopus.com/inward/record.url?scp=66449103103&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=66449103103&partnerID=8YFLogxK

U2 - 10.1016/j.bmc.2009.05.032

DO - 10.1016/j.bmc.2009.05.032

M3 - Article

C2 - 19482479

AN - SCOPUS:66449103103

SN - 0968-0896

VL - 17

SP - 4296

EP - 4301

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 13

ER -