Compounds > 2,3-dihydro-2-(n(7)-guanyl)-3-hydroxyaflatoxin b1
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2,3-dihydro-2-(n(7)-guanyl)-3-hydroxyaflatoxin b1

Description

2,3-dihydro-2-(N(7)-guanyl)-3-hydroxyaflatoxin B1: aflatoxin-guanine adduct in urine of aflatoxin B1 treated rats; RN given refers to (6aS-(6aalpha,8beta,9alpha,9aalpha))-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID135562701
MeSH IDM0091285

Synonyms (14)

Synonym
dhghab
63425-04-7
unii-j2ik9qtj31
8,9-dihydro-8-(n(7)-guanyl)-6-hydroxyaflatoxin b1
afb-n(7)-gua
2,3-dihydro-2-(n(7)-guanyl)-3-hydroxyaflatoxin b1
8,9-dihydro-(7'-guanyl)-9-hydroxyaflatoxin b1
cyclopenta(c)furo(3',2':4,5)furo(2,3-h)(1)benzopyran-1,11-dione, 8-(2-amino-1,6-dihydro-6-oxo-7h-purin-7-yl)-2,3,6a,8,9,9a-hexahydro-9-hydroxy-4-methoxy-, (6as-(6aalpha,8beta,9alpha,9aalpha))-
j2ik9qtj31 ,
aflatoxin b1-guanine
cyclopenta(c)furo(3',2':4,5)furo(2,3-h)(1)benzopyran-1,11-dione, 8-(2-amino-1,6-dihydro-6-oxo-7h-purin-7-yl)-2,3,6a,8,9,9a-hexahydro-9-hydroxy-4-methoxy-, (6as,8r,9r,9ar)-
(3r,4r,7s)-5-(2-amino-6-oxo-1h-purin-7-yl)-4-hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,9,11,13(17)-tetraene-16,18-dione
9-hydroxy-8-(6-hydroxy-2-imino-2,3-dihydro-7h-purin-7-yl)-4-methoxy-2,3,6a,8,9,9a-hexahydrocyclopenta[c]furo[3',2':4,5]furo[2,3-h][1]benzopyran-1,11-dione
DTXSID20979603

Dosage Studied

ExcerptReference
" Using the multiple monoclonal antibody affinity column with rat urines obtained from dosed animals, between 90 and 95% of total aflatoxin metabolites can be bound to the column and isolated."( Molecular dosimetry in rat urine of aflatoxin-N7-guanine and other aflatoxin metabolites by multiple monoclonal antibody affinity chromatography and immunoaffinity/high performance liquid chromatography.
Donahue, PR; Groopman, JD; Hasler, JA; Pikul, A; Trudel, LJ; Wogan, GN, 1992)
" Utilizing the same multiple dosing protocol, patterns of covalent modifications of DNA by AFB1 were determined."( Modulation of aflatoxin metabolism, aflatoxin-N7-guanine formation, and hepatic tumorigenesis in rats fed ethoxyquin: role of induction of glutathione S-transferases.
Davidson, NE; Egner, PA; Groopman, JD; Kensler, TW; Pikul, A; Roebuck, BD, 1986)
" Comparison of the dose-response curve for adduct excretion with that previously observed for adduct formation in rat liver DNA in vivo revealed a high degree of qualitative similarity, with the levels of adduct excreted in urine representing 30 to 40% of the levels seen initially in liver DNA."( Excretion of an aflatoxin-guanine adduct in the urine of aflatoxin B1-treated rats.
Bennett, RA; Essigmann, JM; Wogan, GN, 1981)
" The immunoaffinity column and the indirect competitive ELISA were evaluated and validated by quantitation of aflatoxin B1-N7-guanine in urine from rats dosed with aflatoxin B1 (1 mg/kg body weight)."( Quantitation of aflatoxin B1-N7-guanine adduct in urine by enzyme-linked immunosorbent assay coupled with immunoaffinity chromatography.
Bhat, RV; Rao, BS; Sujatha, N; Vidyasagar, T; Vyjayanthi, V, )
" Earlier work also showed that after ten daily doses the AFB dose-response relationship with gamma-glutamyl transpeptidase (GGT) positive preneoplastic foci measured at 3 months was sublinear, with a threshold at a dose of about 150 micrograms/kg body weight/day."( Dissimilarity in aflatoxin dose-response relationships between DNA adduct formation and development of preneoplastic foci in rat liver.
Campbell, TC; Lange, T; Root, M, 1997)
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (27)

TimeframeStudies, This Drug (%)All Drugs %
pre-19907 (25.93)18.7374
1990's11 (40.74)18.2507
2000's8 (29.63)29.6817
2010's1 (3.70)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (6.90%)5.53%
Reviews1 (3.45%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other26 (89.66%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
ethoxyquin
Ethoxyquin: Antioxidant; also a post-harvest dip to prevent scald on apples and pears.. ethoxyquin : A quinoline that is 1,2-dihydroquinoline bearing three methyl substituents at position 2, 2 and 4 as well as an ethoxy substituent at position 6.		1.9610aromatic ether;
quinolines		antifungal agrochemical;
food antioxidant;
genotoxin;
geroprotector;
herbicide;
Hsp90 inhibitor;
neuroprotective agent;
UDP-glucuronosyltransferase activator
lysine
Lysine: An essential amino acid. It is often added to animal feed.. lysine : A diamino acid that is caproic (hexanoic) acid bearing two amino substituents at positions 2 and 6.. L-lysine : An L-alpha-amino acid; the L-isomer of lysine.		2.1310aspartate family amino acid;
L-alpha-amino acid zwitterion;
L-alpha-amino acid;
lysine;
organic molecular entity;
proteinogenic amino acid		algal metabolite;
anticonvulsant;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite
thiophenes
Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.		3.4920mancude organic heteromonocyclic parent;
monocyclic heteroarene;
thiophenes;
volatile organic compound		non-polar solvent
pyrazines
Pyrazines: A heterocyclic aromatic organic compound with the chemical formula C4H4N2.. pyrazine : A diazine that is benzene in which the carbon atoms at positions 1 and 4 have been replaced by nitrogen atoms.		3.4920diazine;
pyrazines		Daphnia magna metabolite
d-alpha tocopherol
Vitamin E: A generic descriptor for all TOCOPHEROLS and TOCOTRIENOLS that exhibit ALPHA-TOCOPHEROL activity. By virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus, these compounds exhibit varying degree of antioxidant activity, depending on the site and number of methyl groups and the type of ISOPRENOIDS.. tocopherol : A collective name for a group of closely related lipids that contain a chroman-6-ol nucleus substituted at position 2 by a methyl group and by a saturated hydrocarbon chain consisting of three isoprenoid units. They are designated as alpha-, beta-, gamma-, and delta-tocopherol depending on the number and position of additional methyl substituents on the aromatic ring. Tocopherols occur in vegetable oils and vegetable oil products, almost exclusively with R,R,R configuration. Tocotrienols differ from tocopherols only in having three double bonds in the hydrocarbon chain.. vitamin E : Any member of a group of fat-soluble chromanols that exhibit biological activity against vitamin E deficiency. The vitamers in this class consists of a chroman-6-ol core which is substituted at position 2 by a methyl group and (also at position 2) either a saturated or a triply-unsaturated hydrocarbon chain consisting of three isoprenoid units. The major function of vitamin E is to act as a natural antioxidant by scavenging free radicals and molecular oxygen.. (R,R,R)-alpha-tocopherol : An alpha-tocopherol that has R,R,R configuration. The naturally occurring stereoisomer of alpha-tocopherol, it is found particularly in sunflower and olive oils.		1.9910alpha-tocopherolalgal metabolite;
antiatherogenic agent;
anticoagulant;
antioxidant;
antiviral agent;
EC 2.7.11.13 (protein kinase C) inhibitor;
immunomodulator;
micronutrient;
nutraceutical;
plant metabolite
oltipraz
oltipraz : A 1,2-dithiole that is 3H-1,2-dithiole-3-thione substituted at positions 4 and 5 by methyl and pyrazin-2-yl groups respectively.		3.49201,2-dithiole;
pyrazines		angiogenesis modulating agent;
antimutagen;
antineoplastic agent;
antioxidant;
EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor;
neurotoxin;
protective agent;
schistosomicide drug
1,2-dithiol-3-thione
1,2-dithiol-3-thione: has antioxidant activity; structure given in first source		1.98101,2-dithiole
3-chloroperbenzoic acid
3-chloroperbenzoic acid: oxidizing agent		1.9910monochlorobenzenes;
peroxy acid
cytidylyl-3',5'-adenosine
cytidylyl adenosine: CPA removed as SY because it is also used as an abbreviation for N6-cyclopentyladenosine, CYCLOPHOSPHAMIDE, and cyclopiazonic acid		1.9810nucleoside analogue;
purines
aflatoxin q1
aflatoxin Q1 : A member of the class of aflatoxins that is aflatoxin B1 in which the hydrogen at the pro-3S position is replaced by a hydroxy group.		2.0210aflatoxin;
aromatic ether;
aromatic ketone		carcinogenic agent;
human xenobiotic metabolite
aflatoxin b1
Aflatoxin B1: A potent hepatotoxic and hepatocarcinogenic mycotoxin produced by the Aspergillus flavus group of fungi. It is also mutagenic, teratogenic, and causes immunosuppression in animals. It is found as a contaminant in peanuts, cottonseed meal, corn, and other grains. The mycotoxin requires epoxidation to aflatoxin B1 2,3-oxide for activation. Microsomal monooxygenases biotransform the toxin to the less toxic metabolites aflatoxin M1 and Q1.. aflatoxin B1 : An aflatoxin having a tetrahydrocyclopenta[c]furo[3',2':4,5]furo[2,3-h]chromene skeleton with oxygen functionality at positions 1, 4 and 11.		8.59272aflatoxin;
aromatic ether;
aromatic ketone		carcinogenic agent;
human metabolite
aflatoxin b
aflatoxin B2: RN given refers to cpd without isomeric designation. aflatoxin B2 : An aflatoxin having a hexahydrocyclopenta[c]furo[3',2':4,5]furo[2,3-h]chromene skeleton with oxygen functionality at positions 1, 4 and 11.		2.3720aflatoxin
2,3-dihydro-2,3-dihydroxyaflatoxin b(1)
2,3-dihydro-2,3-dihydroxyaflatoxin B(1): acid hydrolysis product of RNA-aflatoxin B(1) adduct formed by liver microsomes; structure; RN given refers to (6aS-(6aalpha,8beta,9alpha,9aalpha))-isomer		1.9610coumarins
alpha-carotene
alpha-carotene: RN given refers to (all-E)-isomer; see also related record beta-carotene. alpha-carotene : A cyclic carotene with a beta- and an epsilon-ring at opposite ends respectively.		1.9910carotenoid beta-end derivative;
cyclic carotene		plant metabolite;
provitamin A
beta carotene
beta Carotene: A carotenoid that is a precursor of VITAMIN A. Beta carotene is administered to reduce the severity of photosensitivity reactions in patients with erythropoietic protoporphyria (PORPHYRIA, ERYTHROPOIETIC).. provitamin A : A provitamin that can be converted into vitamin A by enzymes from animal tissues.		1.9910carotenoid beta-end derivative;
cyclic carotene		antioxidant;
biological pigment;
cofactor;
ferroptosis inhibitor;
human metabolite;
mouse metabolite;
plant metabolite;
provitamin A
aflatoxin m1
Aflatoxin M1: A 4-hydroxylated metabolite of AFLATOXIN B1, one of the MYCOTOXINS from ASPERGILLUS tainted food. It is associated with LIVER damage and cancer resulting from its P450 activation to the epoxide which alkylates DNA. Toxicity depends on the balance of liver enzymes that activate it (CYTOCHROME P-450) and others that detoxify it (GLUTATHIONE S TRANSFERASE) (Pharmac Ther 50.443 1991). Primates & rat are sensitive while mouse and hamster are tolerant (Canc Res 29.236 1969).. aflatoxin M1 : A member of the class of aflatoxins that is aflatoxin B1 in which the hydrogen at position 9a is replaced by a hydroxy group.		2.4620aflatoxin;
aromatic ether;
aromatic ketone;
tertiary alcohol		Aspergillus metabolite;
human xenobiotic metabolite;
mammalian metabolite
oligonucleotides
[no description available]		210
guanine
[no description available]		8.592722-aminopurines;
oxopurine;
purine nucleobase		algal metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
aflatoxin b1-formamidopyrimidine
aflatoxin B1-formamidopyrimidine: persistent aflatoxin-deoxyribonucleic acid(DNA) adduct		2.4220
ConditionIndicatedRelationship StrengthStudiesTrials
Hepatitis B Virus Infection
[description not available]		0450
Hepatitis B
INFLAMMATION of the LIVER in humans caused by a member of the ORTHOHEPADNAVIRUS genus, HEPATITIS B VIRUS. It is primarily transmitted by parenteral exposure, such as transfusion of contaminated blood or blood products, but can also be transmitted via sexual or intimate personal contact.		0450
Genetic Predisposition
[description not available]		02.0210
Cancer of Liver
[description not available]		07.48102
Cancer of Lung
[description not available]		03.3220
Cocarcinogenesis
The combination of two or more different factors in the production of cancer.		02.0210
Liver Neoplasms
Tumors or cancer of the LIVER.		07.48102
Lung Neoplasms
Tumors or cancer of the LUNG.		03.3220
Hepatocellular Carcinoma
[description not available]		06.1162
Carcinoma, Hepatocellular
A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.		06.1162
Alcohol Drinking
Behaviors associated with the ingesting of ALCOHOLIC BEVERAGES, including social drinking.		01.9910
Chronic Illness
[description not available]		01.9910
Chronic Disease
Diseases which have one or more of the following characteristics: they are permanent, leave residual disability, are caused by nonreversible pathological alteration, require special training of the patient for rehabilitation, or may be expected to require a long period of supervision, observation, or care (Dictionary of Health Services Management, 2d ed). For epidemiological studies chronic disease often includes HEART DISEASES; STROKE; CANCER; and diabetes (DIABETES MELLITUS, TYPE 2).		01.9910
Body Weight
The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.		01.9910
Condition, Preneoplastic
[description not available]		01.9910
Precancerous Conditions
Pathological conditions that tend eventually to become malignant.		01.9910
Experimental Hepatoma
[description not available]		02.3820