Differentiation of skeletal osteogenic progenitor cells to osteoblasts with 3,4-diarylbenzopyran based amide derivatives: Novel osteogenic agents
A series of 3,4-diarylbenzopyran based amide derivatives was synthesized and evaluated for osteogenic activity in in vitro and in vivo models of osteoporosis. Compounds 17a, 21b–c and 22a–b showed significant osteogenic activity in osteoblast differentiation assay. Among the synthesized compounds, 2...
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Published in | European journal of medicinal chemistry Vol. 121; pp. 82 - 99 |
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Main Authors | , , , , , , , , , , , |
Format | Journal Article |
Language | English |
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Elsevier Masson SAS
04.10.2016
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Abstract | A series of 3,4-diarylbenzopyran based amide derivatives was synthesized and evaluated for osteogenic activity in in vitro and in vivo models of osteoporosis. Compounds 17a, 21b–c and 22a–b showed significant osteogenic activity in osteoblast differentiation assay. Among the synthesized compounds, 22b was identified as lead molecule which showed significant osteogenic activity at 1 pM concentration in osteoblast differentiation assay and at 1 mg kg−1 body weight dose in estrogen deficient balb/c mice model. In vitro bone mineralization and expression of osteogenic marker genes viz BMP-2, RUNX-2, OCN, and collagen type 1 further confirmed the osteogenic potential of 22b. Gene expression study for estrogen receptor α and β (ER-α and ER-β) in mouse calvarial osteoblasts (MCOs) unveiled that possibly 22b exerted osteogenic efficacy via activation of Estrogen receptor-β preferentially. In vivo pharmacokinetic, estrogenicity and acute toxicity studies of 22b showed that it had good bioavailability and was devoid of uterine estrogenicity at 1 mg kg−1 and inherent toxicity up to 1000 mg kg−1 body weight dose respectively.
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•3,4-diarylbenzopyran based amide derivatives as novel osteogenic agents were identified.•22b showed osteogenic activity at 1 pM in osteoblast differentiation assay and at 1 mg kg−1 body weight dose in estrogen deficient balb/c mice model.•Bone mineralization and expression of osteogenic marker genes confirmed osteogenic potential of 22b.•22b showed good bioavailability and devoid of uterine estrogenicity at 1 mg kg−1in-vivo.•22b had no inherent toxicity up to 1000 mg kg−1 body weight dose in in-vivo model respectively. |
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AbstractList | A series of 3,4-diarylbenzopyran based amide derivatives was synthesized and evaluated for osteogenic activity in in vitro and in vivo models of osteoporosis. Compounds 17a, 21b–c and 22a–b showed significant osteogenic activity in osteoblast differentiation assay. Among the synthesized compounds, 22b was identified as lead molecule which showed significant osteogenic activity at 1 pM concentration in osteoblast differentiation assay and at 1 mg kg−1 body weight dose in estrogen deficient balb/c mice model. In vitro bone mineralization and expression of osteogenic marker genes viz BMP-2, RUNX-2, OCN, and collagen type 1 further confirmed the osteogenic potential of 22b. Gene expression study for estrogen receptor α and β (ER-α and ER-β) in mouse calvarial osteoblasts (MCOs) unveiled that possibly 22b exerted osteogenic efficacy via activation of Estrogen receptor-β preferentially. In vivo pharmacokinetic, estrogenicity and acute toxicity studies of 22b showed that it had good bioavailability and was devoid of uterine estrogenicity at 1 mg kg−1 and inherent toxicity up to 1000 mg kg−1 body weight dose respectively.
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•3,4-diarylbenzopyran based amide derivatives as novel osteogenic agents were identified.•22b showed osteogenic activity at 1 pM in osteoblast differentiation assay and at 1 mg kg−1 body weight dose in estrogen deficient balb/c mice model.•Bone mineralization and expression of osteogenic marker genes confirmed osteogenic potential of 22b.•22b showed good bioavailability and devoid of uterine estrogenicity at 1 mg kg−1in-vivo.•22b had no inherent toxicity up to 1000 mg kg−1 body weight dose in in-vivo model respectively. A series of 3,4-diarylbenzopyran based amide derivatives was synthesized and evaluated for osteogenic activity in in vitro and in vivo models of osteoporosis. Compounds 17a, 21b-c and 22a-b showed significant osteogenic activity in osteoblast differentiation assay. Among the synthesized compounds, 22b was identified as lead molecule which showed significant osteogenic activity at 1 pM concentration in osteoblast differentiation assay and at 1 mg kg(-1) body weight dose in estrogen deficient balb/c mice model. In vitro bone mineralization and expression of osteogenic marker genes viz BMP-2, RUNX-2, OCN, and collagen type 1 further confirmed the osteogenic potential of 22b. Gene expression study for estrogen receptor α and β (ER-α and ER-β) in mouse calvarial osteoblasts (MCOs) unveiled that possibly 22b exerted osteogenic efficacy via activation of Estrogen receptor-β preferentially. In vivo pharmacokinetic, estrogenicity and acute toxicity studies of 22b showed that it had good bioavailability and was devoid of uterine estrogenicity at 1 mg kg(-1) and inherent toxicity up to 1000 mg kg(-1) body weight dose respectively. A series of 3,4-diarylbenzopyran based amide derivatives was synthesized and evaluated for osteogenic activity in in vitro and in vivo models of osteoporosis. Compounds 17a, 21b-c and 22a-b showed significant osteogenic activity in osteoblast differentiation assay. Among the synthesized compounds, 22b was identified as lead molecule which showed significant osteogenic activity at 1 pM concentration in osteoblast differentiation assay and at 1 mg kg(-1) body weight dose in estrogen deficient balb/c mice model. In vitro bone mineralization and expression of osteogenic marker genes viz BMP-2, RUNX-2, OCN, and collagen type 1 further confirmed the osteogenic potential of 22b. Gene expression study for estrogen receptor a and 13 (ER-alpha and ER-beta) in mouse calvarial osteoblasts (MCOs) unveiled that possibly 22b exerted osteogenic efficacy via activation of Estrogen receptor-beta preferentially. In vivo pharmacokinetic, estrogenicity and acute toxicity studies of 22b showed that it had good bioavailability and was devoid of uterine estrogenicity at 1 mg kg(-1) and inherent toxicity up to 1000 mg kg(-1) body weight dose respectively. 2016 Elsevier Masson SAS. All rights reserved. |
Author | Kureel, Jyoti Sultan, Eram Chanda, Debabrata John, Aijaz A. Gupta, Atul Alauddin Wahajuddin Singh, Divya Verma, Amita Prabhaker, S. Agarwal, Naresh Kumar Ahmad, Imran |
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Keywords | Isoflavone Osteogenic Benzopyran Antiosteoporotic Estrogen IPRIFLAVONE MECHANISMS GENISTEIN BONE-RESORPTION BREAST-CANCER ISOFLAVONES POSTMENOPAUSAL OSTEOPOROSIS EQUOL DAIDZEIN ESTROGEN-RECEPTOR-ALPHA |
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Snippet | A series of 3,4-diarylbenzopyran based amide derivatives was synthesized and evaluated for osteogenic activity in in vitro and in vivo models of osteoporosis.... A series of 3,4-diarylbenzopyran based amide derivatives was synthesized and evaluated for osteogenic activity in in vitro and in vivo models of osteoporosis.... |
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SubjectTerms | Amides - chemistry Amides - pharmacokinetics Amides - pharmacology Animals Antiosteoporotic Benzopyran Benzopyrans - chemistry Benzopyrans - pharmacokinetics Benzopyrans - pharmacology Biological Availability Cell Differentiation - drug effects Chemistry, Medicinal Estrogen Estrogen Receptor beta - metabolism Isoflavone Life Sciences & Biomedicine Mice Mice, Inbred BALB C Osteoblasts - cytology Osteogenesis - drug effects Osteogenic Osteoporosis - chemically induced Pharmacology & Pharmacy Science & Technology Stem Cells - cytology Structure-Activity Relationship |
Title | Differentiation of skeletal osteogenic progenitor cells to osteoblasts with 3,4-diarylbenzopyran based amide derivatives: Novel osteogenic agents |
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