Novel ether derivatives of 11-azaartemisinins with high order antimalarial activity against multidrug-resistant Plasmodium yoelii in Swiss mice
[Display omitted] This study investigates cutting-edge synthetic chemistry approaches for designing and producing innovative antimalarial drugs with improved efficacy and fewer adverse effects. Novel amino (–NH2) and hydroxy (–OH) functionalized 11-azaartemisinins 9, 12, and 14 were synthesized alon...
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| Published in | Bioorganic & medicinal chemistry letters Vol. 103; p. 129700 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
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01.05.2024
Elsevier |
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| Abstract | [Display omitted]
This study investigates cutting-edge synthetic chemistry approaches for designing and producing innovative antimalarial drugs with improved efficacy and fewer adverse effects. Novel amino (–NH2) and hydroxy (–OH) functionalized 11-azaartemisinins 9, 12, and 14 were synthesized along with their derivatives 11a, 13a-e, and 15a-b through ART and were tested for their AMA (antimalarial activity) against Plasmodium yoelii via intramuscular (i.m.) and oral routes in Swiss mice. Ether derivative 13c was the most active compound by i.m. route, it has shown 100 % protection at the dose of 12 mg/kg × 4 days and showed 100 % clearance of parasitaemia on day 4 at dose of 6 mg/kg. Amine 11a, ether derivatives 13d, 13e and ether 15a also showed promising antimalarial activity. β-Arteether gave 100 % protection at the dose of 48 mg/kg × 4 days and 20 % protection at 24 mg/kg × 4 days dose by oral route, while it showed 100 % protection at 6 mg/kg × 4 days and no protection at 3 mg/kg × 4 days by i.m. route. |
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| AbstractList | This study investigates cutting-edge synthetic chemistry approaches for designing and producing innovative antimalarial drugs with improved efficacy and fewer adverse effects. Novel amino (-NH2) and hydroxy (-OH) functionalized 11-azaartemisinins 9, 12, and 14 were synthesized along with their derivatives 11a, 13a-e, and 15a-b through ART and were tested for their AMA (antimalarial activity) against Plasmodium yoelii via intramuscular (i.m.) and oral routes in Swiss mice. Ether derivative 13c was the most active compound by i.m. route, it has shown 100 % protection at the dose of 12 mg/kg × 4 days and showed 100 % clearance of parasitaemia on day 4 at dose of 6 mg/kg. Amine 11a, ether derivatives 13d, 13e and ether 15a also showed promising antimalarial activity. β-Arteether gave 100 % protection at the dose of 48 mg/kg × 4 days and 20 % protection at 24 mg/kg × 4 days dose by oral route, while it showed 100 % protection at 6 mg/kg × 4 days and no protection at 3 mg/kg × 4 days by i.m. route. This study investigates cutting-edge synthetic chemistry approaches for designing and producing innovative antimalarial drugs with improved efficacy and fewer adverse effects. Novel amino (-NH ) and hydroxy (-OH) functionalized 11-azaartemisinins 9, 12, and 14 were synthesized along with their derivatives 11a, 13a-e, and 15a-b through ART and were tested for their AMA (antimalarial activity) against Plasmodium yoelii via intramuscular (i.m.) and oral routes in Swiss mice. Ether derivative 13c was the most active compound by i.m. route, it has shown 100 % protection at the dose of 12 mg/kg × 4 days and showed 100 % clearance of parasitaemia on day 4 at dose of 6 mg/kg. Amine 11a, ether derivatives 13d, 13e and ether 15a also showed promising antimalarial activity. β-Arteether gave 100 % protection at the dose of 48 mg/kg × 4 days and 20 % protection at 24 mg/kg × 4 days dose by oral route, while it showed 100 % protection at 6 mg/kg × 4 days and no protection at 3 mg/kg × 4 days by i.m. route. [Display omitted] This study investigates cutting-edge synthetic chemistry approaches for designing and producing innovative antimalarial drugs with improved efficacy and fewer adverse effects. Novel amino (–NH2) and hydroxy (–OH) functionalized 11-azaartemisinins 9, 12, and 14 were synthesized along with their derivatives 11a, 13a-e, and 15a-b through ART and were tested for their AMA (antimalarial activity) against Plasmodium yoelii via intramuscular (i.m.) and oral routes in Swiss mice. Ether derivative 13c was the most active compound by i.m. route, it has shown 100 % protection at the dose of 12 mg/kg × 4 days and showed 100 % clearance of parasitaemia on day 4 at dose of 6 mg/kg. Amine 11a, ether derivatives 13d, 13e and ether 15a also showed promising antimalarial activity. β-Arteether gave 100 % protection at the dose of 48 mg/kg × 4 days and 20 % protection at 24 mg/kg × 4 days dose by oral route, while it showed 100 % protection at 6 mg/kg × 4 days and no protection at 3 mg/kg × 4 days by i.m. route. This study investigates cutting-edge synthetic chemistry approaches for designing and producing innovative antimalarial drugs with improved efficacy and fewer adverse effects. Novel amino (-NH2) and hydroxy (-OH) functionalized 11-azaartemisinins 9, 12, and 14 were synthesized along with their derivatives 11a, 13a-e, and 15a-b through ART and were tested for their AMA (antimalarial activity) against Plasmodium yoelii via intramuscular (i.m.) and oral routes in Swiss mice. Ether derivative 13c was the most active compound by i.m. route, it has shown 100 % protection at the dose of 12 mg/kg x 4 days and showed 100 % clearance of parasitaemia on day 4 at dose of 6 mg/kg. Amine 11a, ether derivatives 13d, 13e and ether 15a also showed promising antimalarial activity. beta-Arteether gave 100 % protection at the dose of 48 mg/kg x 4 days and 20 % protection at 24 mg/kg x 4 days dose by oral route, while it showed 100 % protection at 6 mg/kg x 4 days and no protection at 3 mg/kg x 4 days by i.m. route. |
| ArticleNumber | 129700 |
| Author | Rathi, Komal Hassam, Mohammad Singh, Chandan Jat, Jawahar L. Puri, Sunil K. Prakash Verma, Ved |
| Author_xml | – sequence: 1 givenname: Komal surname: Rathi fullname: Rathi, Komal organization: Department of Chemistry, Banasthali University, Banasthali Newai 304022, Rajasthan, India – sequence: 2 givenname: Mohammad surname: Hassam fullname: Hassam, Mohammad organization: Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, Sector 10, Jankipuram Extension, Sitapur Road, Lucknow 226031, India – sequence: 3 givenname: Chandan surname: Singh fullname: Singh, Chandan organization: Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, Sector 10, Jankipuram Extension, Sitapur Road, Lucknow 226031, India – sequence: 4 givenname: Sunil K. surname: Puri fullname: Puri, Sunil K. organization: Parasitology Division, CSIR-Central Drug Research Institute, Sector 10, Jankipuram Extension, Sitapur Road, Lucknow 226031, India – sequence: 5 givenname: Jawahar L. surname: Jat fullname: Jat, Jawahar L. organization: Department of Chemistry, Babasaheb Bhimrao Ambedkar University (A Central University) Vidya Vihar, Raebareli Road, Lucknow 226025, Uttar Pradesh, India – sequence: 6 givenname: Ved surname: Prakash Verma fullname: Prakash Verma, Ved email: vedprakash079@gmail.com organization: Department of Chemistry, Banasthali University, Banasthali Newai 304022, Rajasthan, India |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/38479483$$D View this record in MEDLINE/PubMed |
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| Keywords | Multidrug-resistant Antimalarial activity rt ART AMA Artemisinin AZA i.m 11-Azaartemisnin HYDROXY-FUNCTIONALIZED 11-AZAARTEMISININS ANTICANCER PEROXIDES STABILITY |
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| References | Zyad, Tilaoui, Jaafari, Oukerrou, Mouse (b0090) 2018; 32 Kumari, Karnatak, Singh (b0050) 2019; 163 WHO World Malaria Report 2023. https://www.who.int/news-room/fact-sheets/detail/malaria (accessed March 29, 2023). Klayman (b0015) 1985; 228 O’Neill, Posner (b0035) 2004; 47 Hindley, Ward, Storr (b0070) 2002; 45 (a) 100% suppression of parasitaemia means no parasites were detected in 50 oil immersion microscopic fields, parasites if at all presents were below the detection limit. The parasites present below the detection limit could multiply and eventually could be detected during observation on subsequent days. In such cases though the drug was providing near 100% suppression of the parasitaemia on day 4 but would not provide full protection to the treated mice in the 28 days survival assay. Multidrug-resistant Puri, Singh (b0155) 2000; 94 White (b0030) 2019; 18 Sharifi-Rad, Herrera-Bravo, Semwal (b0100) 2022; 2022 Torok, Ziffer, Meshnick, Pan, Ager (b0110) 1995; 38 Lee, Weyers, Haynes, van der Kooy (b0055) 2023; 153 Singh, Verma, Hassam, Singh, Naikade, Puri (b0135) 2014; 57 used in this study is resistant to chloroquine, mefloquine and halofantrine. (b) 100% protection means all the treated mice survived till day 28. Similarly, 60% protection means three out of five treated mice survived till day 28. were prepared in groundnut oil so as to contain the required amount of the drug (0.3 mg for a dose of 24 mg/kg, 0.15 mg for a dose of 12 mg/kg and 0.075 mg for a dose of 6 mg/kg) in 0.1 ml and administered via oral and intramuscular routes for each dose. Parasitaemia level were recorded from thin blood smears on day 4 and subsequently twice a week till day 28. The treated mice surviving beyond day 28 were recorded as Swiss mice protected by the drug. Torok, Ziffer (b0105) 1995; 36 and Jambou, Legrand, Khim (b0060) 2005; 366 Singh, Verma, Hassam, Krishna, Puri, Singh (b0130) 2008; 10 Posner, Paik, Sur (b0080) 2003; 46 Academic Press: London Meshnick, Taylor, Kamchonwongpaisan (b0065) 1996; 60 Karnatak, Hassam, Singh (b0140) 2022; 58 Grellepois, Chorki, Ourevitch (b0085) 2004; 47 Rosenthal, Chen, Liu (b0095) 2009; 52 The Swiss albino mice used for the present experiments were duly noted and approved by the Institutional Animal Ethics Committee of Central drug research institute (CDRI), Lucknow, UP, India and the Committee for the Purpose of Control and Supervision of Experiments on Animals (CPCSEA), Government of India. Mice were procured from animal breeding facilities at CDRI Lucknow. (a) Peters, W. Techniques for the study of drug response in experimental malaria. In Muraleedharan, Avery (b0045) 2009; 14 Meshnick, Taylor, Kamchonwongpaisan (b0020) 1996; 60 Akash, Abdelkrim, Bayil (b0005) 2023; 27 parasitized RBC on day zero and treatment was administered to a group of five mice at each dose, from day 0 to 3, in two divided doses daily. The drug dilution of compounds Avery, Alvim-Gaston, Vroman (b0075) 2002; 45 Meng, Ma, Lyu (b0025) 2021; 41 Haynes, Wong, Lee (b0115) 2007; 2 , All compounds screened for their biological activity, the purity level of all compounds were above 99%. pp 64-136. (b) In vivo test procedure: The colony bred Swiss albino mice (25 ± 1g) were inoculated with 1X10 Yaremenko, Belyakova, Radulov (b0120) 2021; 143 Jana, Iram, Joice, Liekens, Dehaen (b0125) 2017; 25 Mice treated with β-arteether served as positive control. Tang, Dong, Vennerstrom (b0040) 2004; 24 Avery, MA (WOS:000177913500023) 2002; 45 White, NJ (WOS:000495679000002) 2019; 18 Singh, AS (WOS:000261294300036) 2008; 10 Rosenthal, AS (WOS:000263530200029) 2009; 52 Singh, C (WOS:000333578400023) 2014; 57 TOROK, DS (WOS:A1995QF82700010) 1995; 36 Grellepois, F (WOS:000220038700014) 2004; 47 Jambou, R (WOS:000233777900024) 2005; 366 Meng, YQ (WOS:000663614900001) 2021; 41 (001208474800001.2) 2023 Yaremenko, IA (WOS:000648704100040) 2021; 143 Zyad, A (WOS:000424287300003) 2018; 32 Hindley, S (WOS:000173985400008) 2002; 45 Torok, DS (WOS:A1995TM54500012) 1995; 38 Kumari, A (WOS:000458597300059) 2019; 163 Posner, GH (WOS:000181399100019) 2003; 46 The Swiss albino mice used for the present experiments were duly noted and approved by the Institutional Animal Ethics Committee of Central drug research institute (CDRI), Lucknow, UP, India and the Committee for the Purpose of Control and Supervision of Experiments on Animals (CPCSEA), Government of India. 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This study investigates cutting-edge synthetic chemistry approaches for designing and producing innovative antimalarial drugs with improved... This study investigates cutting-edge synthetic chemistry approaches for designing and producing innovative antimalarial drugs with improved efficacy and fewer... |
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| SubjectTerms | 11-Azaartemisnin Antimalarial activity Artemisinin Chemistry Chemistry, Medicinal Chemistry, Organic Life Sciences & Biomedicine Multidrug-resistant Pharmacology & Pharmacy Physical Sciences Science & Technology |
| Title | Novel ether derivatives of 11-azaartemisinins with high order antimalarial activity against multidrug-resistant Plasmodium yoelii in Swiss mice |
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