Synthesis and biological evaluation of hydroxamate isosteres of acidic cannabinoids

Hawraz Ibrahim M. Amin; Francisco Ruiz-Pino; Juan A. Collado; Giovanni Appendino; Manuel Tena-Sempere; Eduardo Munoz; DIEGO CAPRIOGLIO

doi:10.3389/fntpr.2023.1190053

Synthesis and biological evaluation of hydroxamate isosteres of acidic cannabinoids

Hawraz Ibrahim M. Amin, Francisco Ruiz-Pino, Juan A. Collado, Giovanni Appendino, Manuel Tena-Sempere, Eduardo Munoz, DIEGO CAPRIOGLIO

Dipartimento di Scienze del Farmaco

Risultato della ricerca: Contributo su rivista › Articolo in rivista › peer review

Lingua originale	Inglese
Rivista	FRONTIERS IN NATURAL PRODUCTS
Volume	2
DOI	https://doi.org/10.3389/fntpr.2023.1190053
Stato di pubblicazione	Pubblicato - 2023

Keywords

Despite their early discovery
the bioactivity of acidic cannabinoids was long overlooked. Issues of stability and a pharmacological focus on Δ9-THC and its biological profile combined to relegate the non-narcotic native form of phytocannabinoids to a sort of investigational limbo. Recent studies have disclosed an attractive bioactivity profile for specific acidic phytocannabinoids but concerns about their limited stability have remained substantially unaddressed. To solve this issue
we have developed the hydroxamate derivatives of Δ8-tetrahydrocannabinolic acid-A (Δ8-THCA-AH
6) and cannabidiolic acid (CBDAH
5) as novel acidic cannabinoid bioisosteres
and we report here their synthesis and bioactivity profile against specific cannabinoid targets
as well as promising in vivo activity in a murine model of polycystic ovary syndrome (PCOS) associated with obesity.

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Accesso al documento

10.3389/fntpr.2023.1190053

https://hdl.handle.net/11579/177925

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title = "Synthesis and biological evaluation of hydroxamate isosteres of acidic cannabinoids",

keywords = "Despite their early discovery, the bioactivity of acidic cannabinoids was long overlooked. Issues of stability and a pharmacological focus on Δ9-THC and its biological profile combined to relegate the non-narcotic native form of phytocannabinoids to a sort of investigational limbo. Recent studies have disclosed an attractive bioactivity profile for specific acidic phytocannabinoids but concerns about their limited stability have remained substantially unaddressed. To solve this issue, we have developed the hydroxamate derivatives of Δ8-tetrahydrocannabinolic acid-A (Δ8-THCA-AH, 6) and cannabidiolic acid (CBDAH, 5) as novel acidic cannabinoid bioisosteres, and we report here their synthesis and bioactivity profile against specific cannabinoid targets, as well as promising in vivo activity in a murine model of polycystic ovary syndrome (PCOS) associated with obesity., Despite their early discovery, the bioactivity of acidic cannabinoids was long overlooked. Issues of stability and a pharmacological focus on Δ9-THC and its biological profile combined to relegate the non-narcotic native form of phytocannabinoids to a sort of investigational limbo. Recent studies have disclosed an attractive bioactivity profile for specific acidic phytocannabinoids but concerns about their limited stability have remained substantially unaddressed. To solve this issue, we have developed the hydroxamate derivatives of Δ8-tetrahydrocannabinolic acid-A (Δ8-THCA-AH, 6) and cannabidiolic acid (CBDAH, 5) as novel acidic cannabinoid bioisosteres, and we report here their synthesis and bioactivity profile against specific cannabinoid targets, as well as promising in vivo activity in a murine model of polycystic ovary syndrome (PCOS) associated with obesity.",

author = "Amin, {Hawraz Ibrahim M.} and Francisco Ruiz-Pino and Collado, {Juan A.} and Giovanni Appendino and Manuel Tena-Sempere and Eduardo Munoz and DIEGO CAPRIOGLIO",

year = "2023",

doi = "10.3389/fntpr.2023.1190053",

language = "English",

volume = "2",

journal = "FRONTIERS IN NATURAL PRODUCTS",

issn = "2813-2602",

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T1 - Synthesis and biological evaluation of hydroxamate isosteres of acidic cannabinoids

AU - Amin, Hawraz Ibrahim M.

AU - Ruiz-Pino, Francisco

AU - Collado, Juan A.

AU - Appendino, Giovanni

AU - Tena-Sempere, Manuel

AU - Munoz, Eduardo

AU - CAPRIOGLIO, DIEGO

PY - 2023

Y1 - 2023

KW - Despite their early discovery

KW - the bioactivity of acidic cannabinoids was long overlooked. Issues of stability and a pharmacological focus on Δ9-THC and its biological profile combined to relegate the non-narcotic native form of phytocannabinoids to a sort of investigational limbo. Rec

KW - we have developed the hydroxamate derivatives of Δ8-tetrahydrocannabinolic acid-A (Δ8-THCA-AH

KW - 6) and cannabidiolic acid (CBDAH

KW - 5) as novel acidic cannabinoid bioisosteres

KW - and we report here their synthesis and bioactivity profile against specific cannabinoid targets

KW - as well as promising in vivo activity in a murine model of polycystic ovary syndrome (PCOS) associated with obesity.

KW - Despite their early discovery

KW - the bioactivity of acidic cannabinoids was long overlooked. Issues of stability and a pharmacological focus on Δ9-THC and its biological profile combined to relegate the non-narcotic native form of phytocannabinoids to a sort of investigational limbo. Rec

KW - we have developed the hydroxamate derivatives of Δ8-tetrahydrocannabinolic acid-A (Δ8-THCA-AH

KW - 6) and cannabidiolic acid (CBDAH

KW - 5) as novel acidic cannabinoid bioisosteres

KW - and we report here their synthesis and bioactivity profile against specific cannabinoid targets

KW - as well as promising in vivo activity in a murine model of polycystic ovary syndrome (PCOS) associated with obesity.

UR - https://iris.uniupo.it/handle/11579/177925

U2 - 10.3389/fntpr.2023.1190053

DO - 10.3389/fntpr.2023.1190053

M3 - Article

SN - 2813-2602

VL - 2

JO - FRONTIERS IN NATURAL PRODUCTS

JF - FRONTIERS IN NATURAL PRODUCTS

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