Page last updated: 2024-12-08

neocryptolepine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

neocryptolepine: isolated from the roots of the African plant Cryptolepis sanguinolenta; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
CryptolepisgenusA plant genus of the family ASCLEPIADACEAE. Members contain the alkaloids quindoline, CSA-3, cryptolepine, and neocryptolepine.[MeSH]ApocynaceaeThe dogbane family of the order Gentianales. Members of the family have milky, often poisonous juice, smooth-margined leaves, and flowers in clusters.[MeSH]

Cross-References

ID SourceID
PubMed CID390526
CHEMBL ID115585
CHEMBL ID465591
SCHEMBL ID1833360
MeSH IDM0371894

Synonyms (17)

Synonym
NCI60_031752
NCI60_031751
nsc687967
nsc-687967
CHEMBL115585
neocryptolepine
5-methylindolo[2,3-b]quinoline
CHEMBL465591 ,
114414-78-7
5-methyl-5h-quinindoline
5h-quinindoline, 5-methyl-
5h-quinodoline, 5-methyl-
bdbm50412204
SCHEMBL1833360
DTXSID90150720
5-methyl-5h-indolo[2,3-b]quinoline
EX-A5436

Research Excerpts

Overview

Neocryptolepine is a tetracyclic nitrogen heterocycle isolated from the African climber Cryptolepis sanguinolenta. It is widely used in traditional African medicine.

ExcerptReferenceRelevance
"Neocryptolepine is a tetracyclic nitrogen heterocycle isolated from the African climber Cryptolepis sanguinolenta, which is widely used in traditional African medicine in many countries of Central and West Africa."( Neocryptolepine: A Promising Indoloisoquinoline Alkaloid with Interesting Biological Activity. Evaluation of the Drug and its Most Relevant Analogs.
Arroyo Aguilar, AA; Bracca, AB; Heredia, DA; Kaufman, TS; Larghi, EL; Pergomet, JL; Simonetti, SO, 2015
)
2.58

Toxicity

ExcerptReferenceRelevance
" With both P388 and HL-60 cells, cryptolepine proved about four times more toxic than its isomer."( Cytotoxicity and cell cycle effects of the plant alkaloids cryptolepine and neocryptolepine: relation to drug-induced apoptosis.
Bailly, C; Dassonneville, L; Lansiaux, A; Mahieu, C; Pieters, L; Van Miert, S; Wattelet, A; Wattez, N, 2000
)
0.54

Bioavailability

ExcerptReferenceRelevance
" Optimization of the natural product as a cytotoxic agent implied improvements in its bioavailability and activity, while the need of non-cytotoxic compounds guided the design and optimization of antimalarial agents."( Neocryptolepine: A Promising Indoloisoquinoline Alkaloid with Interesting Biological Activity. Evaluation of the Drug and its Most Relevant Analogs.
Arroyo Aguilar, AA; Bracca, AB; Heredia, DA; Kaufman, TS; Larghi, EL; Pergomet, JL; Simonetti, SO, 2015
)
1.86
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (58)

Assay IDTitleYearJournalArticle
AID453261Displacement of methyl green dye from DNA2009Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20
Structure-activity relationship of antiparasitic and cytotoxic indoloquinoline alkaloids, and their tricyclic and bicyclic analogues.
AID1858985Cytotoxicity against human MRC5 cells assessed as cell growth inhibition2022European journal of medicinal chemistry, Jan-05, Volume: 227Role of basic aminoalkyl chains in the lead optimization of Indoloquinoline alkaloids.
AID402125Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum W2 infected human erythrocytes by [3H]hypoxanthine uptake1997Journal of natural products, Jul, Volume: 60, Issue:7
In vitro and in vivo antiplasmodial activity of cryptolepine and related alkaloids from Cryptolepis sanguinolenta.
AID753997Selectivity index, ratio of IC50 for rat L6 cells to IC50 for chloroquine-sensitive erythrocytic stage of Plasmodium falciparum NF542013European journal of medicinal chemistry, Jun, Volume: 64Synthesis and antimalarial testing of neocryptolepine analogues: addition of ester function in SAR study of 2,11-disubstituted indolo[2,3-b]quinolines.
AID349756Inhibition of beta-hematin formation after 18 hrs by microtiter plate assay2009Journal of medicinal chemistry, May-14, Volume: 52, Issue:9
Synthesis and antiplasmodial activity of aminoalkylamino-substituted neocryptolepine derivatives.
AID206160Tested for antimicrobial activity against Staphylococcus aureus PCM 458 at concentration of 0.01-5 uM/mL1994Journal of medicinal chemistry, Oct-14, Volume: 37, Issue:21
Synthesis and structure-activity relationship of methyl-substituted indolo[2,3-b]quinolines: novel cytotoxic, DNA topoisomerase II inhibitors.
AID727322Selectivity index, ratio of IC50 for chloroquine-resistant Plasmodium falciparum K1 to IC50 for chloroquine-sensitive Plasmodium falciparum NF542013Journal of medicinal chemistry, Feb-28, Volume: 56, Issue:4
Synthesis and in vitro antimalarial testing of neocryptolepines: SAR study for improved activity by introduction and modifications of side chains at C2 and C11 on indolo[2,3-b]quinolines.
AID1859001Selectivity index, ratio of IC50 for human MRC5 to IC50 for Plasmodium falciparum Ghana2022European journal of medicinal chemistry, Jan-05, Volume: 227Role of basic aminoalkyl chains in the lead optimization of Indoloquinoline alkaloids.
AID1858974Antiproliferative activity against human MRC5 cells assessed as cell growth inhibition incubated for 7 days by MTT assay2022European journal of medicinal chemistry, Jan-05, Volume: 227Role of basic aminoalkyl chains in the lead optimization of Indoloquinoline alkaloids.
AID54999Increase of calf thymus DNA denaturation temperature (delta Tm)1994Journal of medicinal chemistry, Oct-14, Volume: 37, Issue:21
Synthesis and structure-activity relationship of methyl-substituted indolo[2,3-b]quinolines: novel cytotoxic, DNA topoisomerase II inhibitors.
AID402126Antiplasmodial activity against Plasmodium falciparum K1 infected human erythrocytes by [3H]hypoxanthine uptake1997Journal of natural products, Jul, Volume: 60, Issue:7
In vitro and in vivo antiplasmodial activity of cryptolepine and related alkaloids from Cryptolepis sanguinolenta.
AID727323Selectivity index, ratio of IC50 for rat L6 cells to IC50 for chloroquine-resistant Plasmodium falciparum K12013Journal of medicinal chemistry, Feb-28, Volume: 56, Issue:4
Synthesis and in vitro antimalarial testing of neocryptolepines: SAR study for improved activity by introduction and modifications of side chains at C2 and C11 on indolo[2,3-b]quinolines.
AID727324Antimalarial activity against chloroquine-resistant Plasmodium falciparum K1 after 72 hrs by [3H]hypoxanthine incorporation assay2013Journal of medicinal chemistry, Feb-28, Volume: 56, Issue:4
Synthesis and in vitro antimalarial testing of neocryptolepines: SAR study for improved activity by introduction and modifications of side chains at C2 and C11 on indolo[2,3-b]quinolines.
AID55326Inhibition of DNA interaction using DNA Methyl Green Assay.2002Journal of medicinal chemistry, Aug-01, Volume: 45, Issue:16
Synthesis, cytotoxicity, and antiplasmodial and antitrypanosomal activity of new neocryptolepine derivatives.
AID1858987Inhibition of beta-hematin formation2022European journal of medicinal chemistry, Jan-05, Volume: 227Role of basic aminoalkyl chains in the lead optimization of Indoloquinoline alkaloids.
AID214283Tested for antimicrobial activity against Trichophyton mentagrophytes (clinical isolate) at concentration of 0.01-5 uM/mL1994Journal of medicinal chemistry, Oct-14, Volume: 37, Issue:21
Synthesis and structure-activity relationship of methyl-substituted indolo[2,3-b]quinolines: novel cytotoxic, DNA topoisomerase II inhibitors.
AID1466364Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum W2 after 24 hrs by liquid scintillation counting analysis2017European journal of medicinal chemistry, Jul-07, Volume: 134Indoles as therapeutics of interest in medicinal chemistry: Bird's eye view.
AID727326Antimalarial activity against chloroquine-sensitive Plasmodium falciparum NF54 after 72 hrs by [3H]hypoxanthine incorporation assay2013Journal of medicinal chemistry, Feb-28, Volume: 56, Issue:4
Synthesis and in vitro antimalarial testing of neocryptolepines: SAR study for improved activity by introduction and modifications of side chains at C2 and C11 on indolo[2,3-b]quinolines.
AID105992Cytotoxicity against human diploid embryonic lung cell line MRC-5 using MTT assay2002Journal of medicinal chemistry, Aug-01, Volume: 45, Issue:16
Synthesis, cytotoxicity, and antiplasmodial and antitrypanosomal activity of new neocryptolepine derivatives.
AID1858975Binding affinity to DNA (unknown origin) assessed as DNA intercalation by measuring amount of methyl green by spectrophotometry2022European journal of medicinal chemistry, Jan-05, Volume: 227Role of basic aminoalkyl chains in the lead optimization of Indoloquinoline alkaloids.
AID1858993Cytotoxicity against mouse Ehrlich cells assessed as cell growth inhibition incubated for 3 hrs by trypan blue exclusion assay2022European journal of medicinal chemistry, Jan-05, Volume: 227Role of basic aminoalkyl chains in the lead optimization of Indoloquinoline alkaloids.
AID349755Binding affinity to DNA assessed as intercalation after 24 hrs by DNA-methyl green assay2009Journal of medicinal chemistry, May-14, Volume: 52, Issue:9
Synthesis and antiplasmodial activity of aminoalkylamino-substituted neocryptolepine derivatives.
AID213655Antitrypanosomal activity against Trypanosoma cruzi2002Journal of medicinal chemistry, Aug-01, Volume: 45, Issue:16
Synthesis, cytotoxicity, and antiplasmodial and antitrypanosomal activity of new neocryptolepine derivatives.
AID1858981Selectivity index, ratio of IC50 for rat L6 cells to IC50 for Plasmodium falciparum K12022European journal of medicinal chemistry, Jan-05, Volume: 227Role of basic aminoalkyl chains in the lead optimization of Indoloquinoline alkaloids.
AID349753Cytotoxicity against human MRC5 SV2 cells after 72 hrs by resazurin-based fluorometric assay2009Journal of medicinal chemistry, May-14, Volume: 52, Issue:9
Synthesis and antiplasmodial activity of aminoalkylamino-substituted neocryptolepine derivatives.
AID453260Inhibition of beta-hematin formation by BHIA assay2009Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20
Structure-activity relationship of antiparasitic and cytotoxic indoloquinoline alkaloids, and their tricyclic and bicyclic analogues.
AID1858983Antileishmanial activity against Leishmania donovani assessed as parasite growth inhibition2022European journal of medicinal chemistry, Jan-05, Volume: 227Role of basic aminoalkyl chains in the lead optimization of Indoloquinoline alkaloids.
AID1872635Antibacterial activity against Mycobacterium fortuitum ATCC 6841 measured after 24 hrs2022European journal of medicinal chemistry, Mar-15, Volume: 232Quinoline heterocyclic containing plant and marine candidates against drug-resistant Mycobacterium tuberculosis: A systematic drug-ability investigation.
AID1466363Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum K1 after 24 hrs by liquid scintillation counting analysis2017European journal of medicinal chemistry, Jul-07, Volume: 134Indoles as therapeutics of interest in medicinal chemistry: Bird's eye view.
AID1858964Antimalarial activity against Plasmodium falciparum K1 assessed as parasite growth inhibition2022European journal of medicinal chemistry, Jan-05, Volume: 227Role of basic aminoalkyl chains in the lead optimization of Indoloquinoline alkaloids.
AID349754Selectivity index, ratio of IC50 for human MRC5 SV2 cells to IC50 for chloroquine-sensitive Plasmodium falciparum Ghana2009Journal of medicinal chemistry, May-14, Volume: 52, Issue:9
Synthesis and antiplasmodial activity of aminoalkylamino-substituted neocryptolepine derivatives.
AID1858994Antioxidant activity assessed as DPPH radical scavenging activity2022European journal of medicinal chemistry, Jan-05, Volume: 227Role of basic aminoalkyl chains in the lead optimization of Indoloquinoline alkaloids.
AID157844Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum Ghana2002Journal of medicinal chemistry, Aug-01, Volume: 45, Issue:16
Synthesis, cytotoxicity, and antiplasmodial and antitrypanosomal activity of new neocryptolepine derivatives.
AID123071Tested for antimicrobial activity against Micrococcus luteus PCM 525 at concentration of 0.01-5 uM/mL1994Journal of medicinal chemistry, Oct-14, Volume: 37, Issue:21
Synthesis and structure-activity relationship of methyl-substituted indolo[2,3-b]quinolines: novel cytotoxic, DNA topoisomerase II inhibitors.
AID1858982Antitrypanosomal activity against Trypanosoma brucei assessed as parasite growth inhibition2022European journal of medicinal chemistry, Jan-05, Volume: 227Role of basic aminoalkyl chains in the lead optimization of Indoloquinoline alkaloids.
AID157843Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum W22002Journal of medicinal chemistry, Aug-01, Volume: 45, Issue:16
Synthesis, cytotoxicity, and antiplasmodial and antitrypanosomal activity of new neocryptolepine derivatives.
AID496820Antimicrobial activity against Trypanosoma brucei2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.
AID402128Antimalarial activity as reduced parasitaemia against Plasmodium berghei infected Swiss albino mice (Mus musculus) at 50 mg/kg/day peroral dose for 4 days1997Journal of natural products, Jul, Volume: 60, Issue:7
In vitro and in vivo antiplasmodial activity of cryptolepine and related alkaloids from Cryptolepis sanguinolenta.
AID496819Antimicrobial activity against Plasmodium falciparum2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.
AID349752Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum Ghana in human erythrocytes after 72 hrs by Malstat assay2009Journal of medicinal chemistry, May-14, Volume: 52, Issue:9
Synthesis and antiplasmodial activity of aminoalkylamino-substituted neocryptolepine derivatives.
AID727325Selectivity index, ratio of IC50 for rat L6 cells to IC50 for chloroquine-sensitive Plasmodium falciparum NF542013Journal of medicinal chemistry, Feb-28, Volume: 56, Issue:4
Synthesis and in vitro antimalarial testing of neocryptolepines: SAR study for improved activity by introduction and modifications of side chains at C2 and C11 on indolo[2,3-b]quinolines.
AID213484Antitrypanosomal activity against Trypanosoma brucei.2002Journal of medicinal chemistry, Aug-01, Volume: 45, Issue:16
Synthesis, cytotoxicity, and antiplasmodial and antitrypanosomal activity of new neocryptolepine derivatives.
AID88263Inhibition of beta-hematin formation; active2002Journal of medicinal chemistry, Aug-01, Volume: 45, Issue:16
Synthesis, cytotoxicity, and antiplasmodial and antitrypanosomal activity of new neocryptolepine derivatives.
AID1858973Antimalarial activity against chloroquine sensitive Plasmodium falciparum Ghana assessed as parasite growth inhibition by measuring APADH formation incubated for 48 hrs by LDH assay2022European journal of medicinal chemistry, Jan-05, Volume: 227Role of basic aminoalkyl chains in the lead optimization of Indoloquinoline alkaloids.
AID753998Cytotoxicity against rat L6 cells assessed as growth inhibition after 70 hrs by Alamar blue staining-based inverted microscopic analysis2013European journal of medicinal chemistry, Jun, Volume: 64Synthesis and antimalarial testing of neocryptolepine analogues: addition of ester function in SAR study of 2,11-disubstituted indolo[2,3-b]quinolines.
AID753999Antimalarial activity against chloroquine-sensitive erythrocytic stage of Plasmodium falciparum NF54 infected in human red blood cells assessed as growth inhibition after 48 hrs by [3H]-hypoxanthine incorporation assay2013European journal of medicinal chemistry, Jun, Volume: 64Synthesis and antimalarial testing of neocryptolepine analogues: addition of ester function in SAR study of 2,11-disubstituted indolo[2,3-b]quinolines.
AID402127Antimalarial activity as reduced parasitaemia against Plasmodium berghei yoelii infected Swiss albino mice (Mus musculus) at 50 mg/kg/day peroral dose for 4 days1997Journal of natural products, Jul, Volume: 60, Issue:7
In vitro and in vivo antiplasmodial activity of cryptolepine and related alkaloids from Cryptolepis sanguinolenta.
AID753996Antimalarial activity against chloroquine-resistant erythrocytic stage of Plasmodium falciparum K1 infected in human red blood cells assessed as growth inhibition after 48 hrs by [3H]-hypoxanthine incorporation assay2013European journal of medicinal chemistry, Jun, Volume: 64Synthesis and antimalarial testing of neocryptolepine analogues: addition of ester function in SAR study of 2,11-disubstituted indolo[2,3-b]quinolines.
AID1858980Selectivity index, ratio of IC50 for rat L6 cells to IC50 for Plasmodium falciparum NF542022European journal of medicinal chemistry, Jan-05, Volume: 227Role of basic aminoalkyl chains in the lead optimization of Indoloquinoline alkaloids.
AID753994Resistance index, ratio of IC50 for chloroquine-resistant erythrocytic stage of Plasmodium falciparum K1 to IC50 for chloroquine-sensitive erythrocytic stage of Plasmodium falciparum NF542013European journal of medicinal chemistry, Jun, Volume: 64Synthesis and antimalarial testing of neocryptolepine analogues: addition of ester function in SAR study of 2,11-disubstituted indolo[2,3-b]quinolines.
AID96015Cytotoxicity in vitro against KB cell line1994Journal of medicinal chemistry, Oct-14, Volume: 37, Issue:21
Synthesis and structure-activity relationship of methyl-substituted indolo[2,3-b]quinolines: novel cytotoxic, DNA topoisomerase II inhibitors.
AID1858979Antimalarial activity against Plasmodium falciparum NF54 assessed as parasite growth inhibition2022European journal of medicinal chemistry, Jan-05, Volume: 227Role of basic aminoalkyl chains in the lead optimization of Indoloquinoline alkaloids.
AID402124Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum D6 infected human erythrocytes by [3H]hypoxanthine uptake1997Journal of natural products, Jul, Volume: 60, Issue:7
In vitro and in vivo antiplasmodial activity of cryptolepine and related alkaloids from Cryptolepis sanguinolenta.
AID1858986Cytotoxicity against rat L6 cells assessed as cell growth inhibition2022European journal of medicinal chemistry, Jan-05, Volume: 227Role of basic aminoalkyl chains in the lead optimization of Indoloquinoline alkaloids.
AID753995Selectivity index, ratio of IC50 for rat L6 cells to IC50 for chloroquine-resistant erythrocytic stage of Plasmodium falciparum K12013European journal of medicinal chemistry, Jun, Volume: 64Synthesis and antimalarial testing of neocryptolepine analogues: addition of ester function in SAR study of 2,11-disubstituted indolo[2,3-b]quinolines.
AID25321Acid ionization constant is determined1994Journal of medicinal chemistry, Oct-14, Volume: 37, Issue:21
Synthesis and structure-activity relationship of methyl-substituted indolo[2,3-b]quinolines: novel cytotoxic, DNA topoisomerase II inhibitors.
AID48928Tested for antimicrobial activity against Candida albicans (clinical isolate) at concentration of 0.01-5 uM/mL1994Journal of medicinal chemistry, Oct-14, Volume: 37, Issue:21
Synthesis and structure-activity relationship of methyl-substituted indolo[2,3-b]quinolines: novel cytotoxic, DNA topoisomerase II inhibitors.
AID727327Toxicity against rat L6 cells after 72 hrs by Alamar blue assay2013Journal of medicinal chemistry, Feb-28, Volume: 56, Issue:4
Synthesis and in vitro antimalarial testing of neocryptolepines: SAR study for improved activity by introduction and modifications of side chains at C2 and C11 on indolo[2,3-b]quinolines.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (38)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (5.26)18.2507
2000's10 (26.32)29.6817
2010's19 (50.00)24.3611
2020's7 (18.42)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 20.57

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index20.57 (24.57)
Research Supply Index3.69 (2.92)
Research Growth Index4.96 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (20.57)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews4 (10.26%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other35 (89.74%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]