Design and synthesis of dalbergin analogues and evaluation of anti-osteoporotic activity

Padam Kumar; Priyanka Kushwaha; Naseer Ahmad; Saransh Wales Maurya; Kapil Dev; Vikram Khedgikar; Ibadur Rahman Siddiqui; Ritu Trivedi; Rakesh Maurya

doi:10.1016/j.bmcl.2017.02.062

Design and synthesis of dalbergin analogues and evaluation of anti-osteoporotic activity

Padam Kumar
, Priyanka Kushwaha
, Naseer Ahmad
, Saransh Wales Maurya
, Kapil Dev
, Vikram Khedgikar
, Ibadur Rahman Siddiqui
, Ritu Trivedi
, Rakesh Maurya

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

7 Scopus citations

Abstract

The chemical modifications of the hydroxyl group of dalbergin have been described via the introduction of cyclic amine, ester and amide groups. Among the twenty-three prepared novel analogues of dalbergin, compound 4d (EC₅₀ 2.3 μM) showed significantly increased proliferation as assessed by alkaline phosphatase activity and mineralization in calvarial osteoblast cells in vitro. Compound 4d, at a dose of 1.0 mg/kg body weight exhibited the significant osteoprotective effect. It showed a significant increase in osteogenic gene expression RunX2 (∼4fold), ALP (∼5fold), OCN (∼4fold) and COL1 (∼4fold) as compared to control group at the same dose in vivo assay.

Original language	English
Pages (from-to)	1765-1775
Number of pages	11
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	27
Issue number	8
DOIs	https://doi.org/10.1016/j.bmcl.2017.02.062
State	Published - 2017
Externally published	Yes

Keywords

Aminodalbergin
Dalbergin
Micro-CT
Post-menopausal osteoporosis
Ritter reaction

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10.1016/j.bmcl.2017.02.062

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title = "Design and synthesis of dalbergin analogues and evaluation of anti-osteoporotic activity",

abstract = "The chemical modifications of the hydroxyl group of dalbergin have been described via the introduction of cyclic amine, ester and amide groups. Among the twenty-three prepared novel analogues of dalbergin, compound 4d (EC50 2.3 μM) showed significantly increased proliferation as assessed by alkaline phosphatase activity and mineralization in calvarial osteoblast cells in vitro. Compound 4d, at a dose of 1.0 mg/kg body weight exhibited the significant osteoprotective effect. It showed a significant increase in osteogenic gene expression RunX2 (∼4fold), ALP (∼5fold), OCN (∼4fold) and COL1 (∼4fold) as compared to control group at the same dose in vivo assay.",

keywords = "Aminodalbergin, Dalbergin, Micro-CT, Post-menopausal osteoporosis, Ritter reaction",

author = "Padam Kumar and Priyanka Kushwaha and Naseer Ahmad and Maurya, \{Saransh Wales\} and Kapil Dev and Vikram Khedgikar and Siddiqui, \{Ibadur Rahman\} and Ritu Trivedi and Rakesh Maurya",

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year = "2017",

doi = "10.1016/j.bmcl.2017.02.062",

language = "English",

volume = "27",

pages = "1765--1775",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

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}

TY - JOUR

T1 - Design and synthesis of dalbergin analogues and evaluation of anti-osteoporotic activity

AU - Kumar, Padam

AU - Kushwaha, Priyanka

AU - Ahmad, Naseer

AU - Maurya, Saransh Wales

AU - Dev, Kapil

AU - Khedgikar, Vikram

AU - Siddiqui, Ibadur Rahman

AU - Trivedi, Ritu

AU - Maurya, Rakesh

PY - 2017

Y1 - 2017

N2 - The chemical modifications of the hydroxyl group of dalbergin have been described via the introduction of cyclic amine, ester and amide groups. Among the twenty-three prepared novel analogues of dalbergin, compound 4d (EC50 2.3 μM) showed significantly increased proliferation as assessed by alkaline phosphatase activity and mineralization in calvarial osteoblast cells in vitro. Compound 4d, at a dose of 1.0 mg/kg body weight exhibited the significant osteoprotective effect. It showed a significant increase in osteogenic gene expression RunX2 (∼4fold), ALP (∼5fold), OCN (∼4fold) and COL1 (∼4fold) as compared to control group at the same dose in vivo assay.

AB - The chemical modifications of the hydroxyl group of dalbergin have been described via the introduction of cyclic amine, ester and amide groups. Among the twenty-three prepared novel analogues of dalbergin, compound 4d (EC50 2.3 μM) showed significantly increased proliferation as assessed by alkaline phosphatase activity and mineralization in calvarial osteoblast cells in vitro. Compound 4d, at a dose of 1.0 mg/kg body weight exhibited the significant osteoprotective effect. It showed a significant increase in osteogenic gene expression RunX2 (∼4fold), ALP (∼5fold), OCN (∼4fold) and COL1 (∼4fold) as compared to control group at the same dose in vivo assay.

KW - Aminodalbergin

KW - Dalbergin

KW - Micro-CT

KW - Post-menopausal osteoporosis

KW - Ritter reaction

UR - https://www.scopus.com/pages/publications/85014348584

U2 - 10.1016/j.bmcl.2017.02.062

DO - 10.1016/j.bmcl.2017.02.062

M3 - Article

C2 - 28274632

AN - SCOPUS:85014348584

SN - 0960-894X

VL - 27

SP - 1765

EP - 1775

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 8

ER -

Design and synthesis of dalbergin analogues and evaluation of anti-osteoporotic activity

Abstract

Keywords

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