Home LiteratureArticle Details
PMID: 4117670 Published · ppublish English Journal Article

Arene oxides and the NIH shift: the metabolism, toxicity and carcinogenicity of aromatic compounds.

Experientia ·Vol. 28 ·No. 10 ·1972-10-15 ·Pages 1129-49

Daly JW, Jerina DM, Witkop B

Abstract

暂无摘要

MeSH Terms
Animals Benz(a)Anthracenes/metabolism Benzene/metabolism Carcinogens Chemical Phenomena Chemistry Deuterium Ethers, Cyclic Hydro-Lyases/metabolism Hydrocarbons/toxicity Hydrocarbons, Halogenated/metabolism Hydroxylation Iodobenzenes/metabolism Microsomes, Liver/enzymology,metabolism Mixed Function Oxygenases/metabolism Naphthalenes/metabolism Nitrobenzenes/metabolism Oxides Oxygenases/metabolism Phenanthrenes/metabolism Phenols/biosynthesis Phenytoin/metabolism Polycyclic Compounds/metabolism Rats Tritium
Chemicals
Benz(a)Anthracenes Carcinogens Ethers, Cyclic Hydrocarbons Hydrocarbons, Halogenated Iodobenzenes Naphthalenes Nitrobenzenes Oxides Phenanthrenes Phenols Polycyclic Compounds Tritium Phenytoin Deuterium Mixed Function Oxygenases Oxygenases Hydro-Lyases Benzene
Authors & Affiliations
3 authors, click to expand affiliations / ORCID
Daly J W
Jerina D M
Witkop B
References (111)
111 references, click to expand
  1. The fate of diphenyl in the rat.
    Arch Biochem Biophys. 1956 Jan;60(1):14-20 PMID: 13283582
  2. Studies in detoxication. 63. The metabolism of halogenobenzenes; (a) meta-dichlorobenzene (b) further observations on the metabolism of chlorobenzene.
    Biochem J. 1955 Mar;59(3):415-22 PMID: 14363110
  3. Carcnogenicity of epoxides, lactones, and peroxy compounds. VI. Structure and carcinogenic activity.
    J Natl Cancer Inst. 1967 Dec;39(6):1217-28 PMID: 6079867
  4. The carcinogenic activities in mice of compounds related to 3-methylcholanthrene.
    Int J Cancer. 1967 Sep 15;2(5):505-8 PMID: 6081593
  5. Enzymatic hydroxylation of benzopyrene and its relationship to cytotoxicity.
    Proc Natl Acad Sci U S A. 1969 Dec;64(4):1188-94 PMID: 4318345
  6. Studies in detoxication. 68. The metabolism of [14C]nitrobenzene in the rabbit and guinea pig.
    Biochem J. 1956 Feb;62(2):339-46 PMID: 13293194
  7. Cis-1,2-dihydroxy-1,2-dihydronaphthalene: a bacterial metabolite from naphthalene.
    Arch Biochem Biophys. 1971 Jan;142(1):394-6 PMID: 5545490
  8. The role of arene oxide-oxepin systems in the metabolism of aromatic substrates. 3. Formation of 1,2-naphthalene oxide from naphthalene by liver microsomes.
    J Am Chem Soc. 1968 Nov 6;90(23):6525-7 PMID: 5682453
  9. Enzymic and nonenzymic hydroxylation and chlorination of p-deuteroanisole.
    Arch Biochem Biophys. 1968 Mar 20;124(1):612-5 PMID: 5661630
  10. Influence of "feeder cells" and inducers and inhibition of microsomal mixed-function oxidases on hydrocarbon-induced malignant transformation of cells derived from C3H mouse prostate.
    Cancer Res. 1972 Apr;32(4):721-5 PMID: 5014783
  11. Epoxides as microsomal metabolites of polycyclic hydrocarbons.
    FEBS Lett. 1971 Oct 15;18(1):76-80 PMID: 11946087
  12. Metabolism of the acaricide chemical, fenazaflor(5,6-dichloro-1-phenoxycarbonyl-2-trifluoromethylbenzimidazole) in certain mammals, insects, and plants.
    J Agric Food Chem. 1969 Sep;17(5):956-66 PMID: 21428329
  13. 1,2-dihydro-1,2-dihydroxybenzene and several other substances in the metabolism of benzene.
    J Biochem. 1963 Jan;53:23-7 PMID: 13986736
  14. Bromobenzene-induced hepatic necrosis: species differences and protection by SKF 525-A.
    Res Commun Chem Pathol Pharmacol. 1971 Nov;2(6):877-88 PMID: 5005496
  15. Oxygen activation by the iron(II)-2-mercaptobenzoic acid complex. A model for microsomal mixed function oxygenases.
    Z Naturforsch B. 1969 Jun;24(6):699-704 PMID: 4390017
  16. Arene oxides as intermediates in the oxidative metabolism of aromatic compounds. Isomerization of methyl-substituted arene oxides.
    Biochemistry. 1972 Aug 1;11(16):3080-8 PMID: 5041913
  17. Conversion of naphthalene to trans-naphthalene dihydrodiol: evidence for the presence of a coupled aryl monooxygenase-epoxide hydrase system in hepatic microsomes.
    Biochem Biophys Res Commun. 1972 Feb 25;46(4):1713-20 PMID: 5015607
  18. Metabolism of polycyclic compounds. 21. The metabolism of phenanthrene in rabbits and rats: dihydrodihydroxy compounds and related glucosiduronic acids.
    Biochem J. 1962 Sep;84:571-82 PMID: 13872198
  19. Intramolecular migration of deuterium and tritium during enzymic hydroxylation of p-deuteroacetanilide and p-tritioacetanilide.
    Arch Biochem Biophys. 1967 May;120(2):413-9 PMID: 6033457
  20. Isotope studies on the mechanism of action of adrenal tyrosine hydroxylase.
    Arch Biochem Biophys. 1968 Aug;126(2):593-8 PMID: 5672518
  21. Biochemical studies of toxic agents. 11. The occurrence of premercapturic acids.
    Biochem J. 1958 Sep;70(1):111-9 PMID: 13584310
  22. Lack of hydroxylation-induced migration with 4-iodophenylalanine.
    Biochim Biophys Acta. 1970 Jul 21;215(1):187-8 PMID: 5494511
  23. Metabolic studies with deuterated phenobarbital.
    J Med Chem. 1967 May 1;10(3):371-4 PMID: 22185135
  24. Reactivity of the K-region epoxides of some polycyclic hydrocarbons towards the nucleic acids and proteins of BHK 21 cells.
    Biochem Pharmacol. 1971 Jun;20(6):1297-302 PMID: 5165731
  25. Hepatic epoxide hydrase. Structure-activity relationships for substrates and inhibitors.
    Biochemistry. 1971 Dec 21;10(26):4858-66 PMID: 5134533
  26. Hydroxylation of alkyl and halogen substituted anilines and acetanilides by microsomal hydroxylases.
    Biochem Pharmacol. 1968 Jan;17(1):31-6 PMID: 5638557
  27. Quantitative studies on the hydroxylation-induced migration of deuterium and tritium during phenylalanine hydroxylation.
    Arch Biochem Biophys. 1967 Oct;122(1):212-7 PMID: 6076217
  28. Studies in detoxication. 51. The determination of catechols in urine, and the formation of catechols in rabbits receiving halogenobenzenes and other compounds; dihydroxylation in vivo.
    Biochem J. 1953 Aug;55(1):146-51 PMID: 13093631
  29. Metabolism of polycyclic compounds. 5. Formation of 1:2-dihydroxy-1:2-dihydronaphthalenes.
    Biochem J. 1949;44(3):361-5 PMID: 16748527
  30. Qualitative and quantitative studies on the metabolism of a series of aromatic hydrocarbons by rat-liver preparations.
    Biochem Pharmacol. 1970 Mar;19(3):795-818 PMID: 5507686
  31. Metabolism of acetanilides and anisoles with rat liver microsomes.
    Biochem Pharmacol. 1970 Dec;19(12):2979-93 PMID: 5513035
  32. Aryl hydrocarbon hydroxylase, epoxide hydrase, and 7,12-dimethylbenz(a)anthracene-produced skin tumorigenesis in the mouse.
    Mol Pharmacol. 1972 May;8(3):374-9 PMID: 5040935
  33. The mechanism of enzymic formation of homogentisate from p-hydroxyphenylpyruvate.
    J Am Chem Soc. 1970 Dec 16;92(25):7446-9 PMID: 5487549
  34. A simple radiometric assay for microsomal aryl hydroxylase activity.
    Anal Biochem. 1970 Feb;33(2):286-96 PMID: 5439483
  35. Low carcinogenicity of the K-region epoxides of 7-methylbenz(a)-anthracene and benz(a)anthracene in the mouse and rat.
    Proc Soc Exp Biol Med. 1967 Mar;124(3):915-9 PMID: 6023434
  36. Metabolism of polycyclic compounds. 20. The metabolism of phenanthrene in rabbits and rats: mercapturic acids and related compounds.
    Biochem J. 1962 Sep;84:564-70 PMID: 13872197
  37. Dimethylbenzanthracene tumorigenesis and aryl hydrocarbon hydroxylase in mouse skin: inhibition by 7,8-benzoflavone.
    Science. 1970 Oct 9;170(3954):169-71 PMID: 5456610
  38. Metabolism of thiazole acetic acid derivatives and the NIH shift.
    Nature. 1969 Feb 8;221(5180):582 PMID: 4978060
  39. Metabolism of iodobenzene.
    J Biol Chem. 1953 Oct;204(2):547-52 PMID: 13117828
  40. Hepatotoxic activity of retrorsine, senkirkine and hydroxysenkirkine in newborn rats, and the role of epoxides in carcinogenesis by pyrrolizidine alkaloids and aflatoxins.
    Nature. 1970 Jul 25;227(5256):401-2 PMID: 5428444
  41. The conversion of phenanthrene 9,10-oxide and dibenz[a,h]anthracene 5,6-oxide into dihydrodiols by a rat-liver microsomal enzyme.
    Biochem Pharmacol. 1970 Jan;19(1):299-303 PMID: 5507644
  42. Rearrangement of (1- 2 H)- and (2- 2 H)naphthalene 1,2-oxides to 1-naphthol. Mechanism of the NIH shift.
    Biochemistry. 1972 May 9;11(10):1961-6 PMID: 5025637
  43. N-hydroxy-2-acetylaminofluorene sulfotransferase: its probable role in carcinogenesis and in protein-(methion-S-yl) binding in rat liver.
    Cancer Res. 1970 Mar;30(3):577-95 PMID: 5425283
  44. Substrate specificity of hepatic epoxide hydrase in microsomes and in a purified preparation: evidence for homologous enzymes.
    Arch Biochem Biophys. 1971 May;144(1):253-61 PMID: 5117530
  45. Studies in detoxication. 62. The metabolism of halogenobenzenes; ortho- and para-dichlorobenzenes.
    Biochem J. 1955 Mar;59(3):410-5 PMID: 14363109
  46. Effect of superoxide generation and dismutation on hydroxylation reactions catalyzed by liver microsomal cytochrome P-450.
    J Biol Chem. 1971 Dec 25;246(24):7826-9 PMID: 4400080
  47. Acetylation of the carcinogen N-hydroxy-2-acetylaminofluorene by acetyl Coenzyme A to form a reactive ester.
    Mol Pharmacol. 1971 Jul;7(4):381-8 PMID: 5113233
  48. Mixed functional oxygenations during the biosynthesis of cyclopenin and cyclopenol, benzodiazepine alkaloids of penicillium cyclopium westling. Incorporation of molecular oxygen and NIH-shift.
    FEBS Lett. 1969 Jun;3(4):292-296 PMID: 11947032
  49. Mutagenicity to mammalian cells of epoxides and other derivatives of polycyclic hydrocarbons.
    Proc Natl Acad Sci U S A. 1971 Dec;68(12):3195-9 PMID: 5289256
  50. Labeling in vivo of rat liver proteins by tritium-labeled dimethylnitrosamine. Effect of prior treatment with 3-methylcholanthrene, phenobarbitone, dimethylformamide, diethyl-formamide, aminoacetonitrile, ethionine and carbon tetrachloride.
    Biochem Pharmacol. 1971 Dec;20(12):3493-9 PMID: 5132895
  51. Studies in detoxication; the metabolism of chlorobenzene in the rabbit; isolation of dihydrodihydroxychlorobenzene, p-chlorophenylglucuronide, 4-chlorocatechol glucuronide and p-chlorophenylmercapturic acid.
    Biochem J. 1950 Sep;47(3):284-93 PMID: 14800882
  52. Migration of substituents during Hydroxylation of aromatic substrates (NIH shift). Oxidations with peroxytrifluoroacetic acid.
    Biochemistry. 1971 Feb 2;10(3):366-72 PMID: 5543961
  53. A survey of molecular aspects of chemical carcinogenesis.
    Am J Pharm Sci Support Public Health. 1966 Jan;15(1 Pt 1):217-41 PMID: 5326655
  54. Interactions of the K-region epoxides of phenanthrene and dibenz (a,h)anthracene with nucleic acids and histone.
    Biochem Pharmacol. 1970 Jul;19(7):2251-9 PMID: 5535340
  55. Metabolism of polycyclic compounds. 6. Conversion of phenanthrene into dihydroxydihydrophenanthrenes.
    Biochem J. 1950 Jun-Jul;47(1):64-9 PMID: 14791307
  56. Biochemical studies of toxic agents. VII. The metabolism of naphthalene in animals of different species.
    Biochem J. 1954 Dec;58(4):647-55 PMID: 13230015
  57. The intermediary metabolism of phenylalanine labeled with radioactive carbon.
    J Biol Chem. 1949 Sep;180(2):663-73 PMID: 18135800
  58. Metabolism of polycyclic compounds. 12. An acid-labile precursor of 1-naphthylmercapturic acid and naphthol: an N-acetyl-S-(1:2-dihydrohydroxy-naphthyl)-L-cysteine.
    Biochem J. 1958 Mar;68(3):440-7 PMID: 13522642
  59. Decarboxylation of alpha-ketoglutarate coupled to collagen proline hydroxylase.
    Proc Natl Acad Sci U S A. 1968 Aug;60(4):1473-8 PMID: 5244754
  60. The role of arene oxide-oxepin systems in the metabolism of aromatic substrates. II. Synthesis of 3,4-toluene-4-2H oxide and subsequent "NIH shift" to 4-hydroxytoluene-3-2H.
    J Am Chem Soc. 1968 Nov 6;90(23):6523-5 PMID: 5682452
  61. Mutagenicity of epoxides of polycyclic hydrocarbons correlates with carcinogenicity of parent hydrocarbons.
    Nat New Biol. 1971 Dec 8;234(49):186-7 PMID: 4109388
  62. [Microsomal oxidation of estradiol-17 beta. 2-hydroxylation and 1- respectively 4- thioether production with and without 17-hydroxy dehydrogenation].
    Hoppe Seylers Z Physiol Chem. 1971 Jun;352(6):817-36 PMID: 4397278
  63. Absence of isotope effects in the microsomal hydroxylation of acetanilide.
    Biochem Pharmacol. 1967 Nov;16(11):2230-3 PMID: 6076615
  64. Production of m-methyltyrosine and p-hydroxymethylphenylalanine from p-methylphenylalanine by phenylalanine hydroxylase.
    Arch Biochem Biophys. 1968 Apr;125(1):136-41 PMID: 5649509
  65. Ascorbic acid in aromatic hydroxylation. I. A model system for aromatic hydroxylation.
    J Biol Chem. 1954 Jun;208(2):731-9 PMID: 13174582
  66. Epoxy derivatives of aromatic polycyclic hydrocarbons. The preparation of benz( )anthracene 8,9-oxide and 10,11-dihydrobenz( )anthracene 8,9-oxide and their metabolism by rat liver preparations.
    Biochem J. 1971 Nov;125(1):159-68 PMID: 5158901
  67. Enzymatic hydration of 8,9-indan oxide, Homoallylic addition of water.
    J Am Chem Soc. 1970 Feb 11;92(3):702-3 PMID: 5411062
  68. Migration of deuterium during aryl hydroxylation. 3. Effect of ortho- and meta- substituents.
    Arch Biochem Biophys. 1969 Oct;134(1):266-8 PMID: 5345594
  69. Incorporation of radioactive- -aminolevulinic acid into microsomal cytochrome P 450 : selective breakdown of the hemoprotein by allylisopropylacetamide and carbon tetrachloride.
    Arch Biochem Biophys. 1972 Jan;148(1):262-9 PMID: 4400522
  70. Epoxides of carcinogenic polycyclic hydrocarbons are frameshift mutagens.
    Science. 1972 Apr 7;176(4030):47-9 PMID: 4551487
  71. Possible mechanism of liver necrosis caused by aromatic organic compounds.
    Proc Natl Acad Sci U S A. 1971 Jan;68(1):160-4 PMID: 4395686
  72. Malignant transformation of cells derived from mouse prostate by epoxides and other derivatives of polycyclic hydrocarbons.
    Cancer Res. 1972 Apr;32(4):716-20 PMID: 5014782
  73. A RAPID AND SIMPLE RADIOASSAY FOR TYROSINE HYDROXYLASE ACTIVITY.
    Anal Biochem. 1964 Sep;9:122-6 PMID: 14246117
  74. Rapid analysis of tryptophan hydroxylase in rat tissue using 5- 3 H-tryptophan.
    Anal Biochem. 1971 Sep;43(1):269-74 PMID: 5130402
  75. Incorporation of oxygen-18 into benzene by Pseudomonas putida.
    Biochemistry. 1970 Mar 31;9(7):1631-5 PMID: 5436152
  76. FUNGAL DETOXICATION. VII. METABOLISM OF 2,4-DICHLOROPHENOXYACETIC AND 4-CHLORO-2-METHYLPHENOXYACETIC ACIDS BY ASPERGILLUS NIGER.
    J Chem Soc. 1965 Feb;39:1187-91 PMID: 14267231
  77. Ascorbic acid in aromatic hydroxylation. II. Products formed by reaction of substrates with ascorbic acid, ferrous ion, and oxygen.
    J Biol Chem. 1954 Jun;208(2):741-50 PMID: 13174583
  78. Aerobic aromatic hydroxylation catalyzed by horseradish peroxidase: absense of NIH shift.
    Biochim Biophys Acta. 1970 May 12;208(2):340-2 PMID: 5420986
  79. [Non-enzymatic hydroxylation of phenylalanine to tyrosine using tetrahydrogenated pterines].
    Helv Chim Acta. 1966 Mar 10;49(2):884-8 PMID: 5909903
  80. Metabolism of polycyclic compounds. 24. The metabolism of benz[alpha]anthracene.
    Biochem J. 1964 Jun;91(3):493-506 PMID: 5840709
  81. Arene oxides as intermediates in the metabolism of aromatic substrates: alkyl and oxygen migrations during isomerization of alkylated arene oxides.
    Proc Natl Acad Sci U S A. 1971 Oct;68(10):2545-8 PMID: 5289888
  82. An epoxide is an intermediate in the microsomal metabolism of the chemical carcinogen, dibenz(a,h)anthracene.
    Biochem Biophys Res Commun. 1971 Jun 4;43(5):1010-6 PMID: 4398130
  83. Metabolism of polycyclic compounds: Anthrylmercapturic acid.
    Biochem J. 1936 Jul;30(7):1225-7 PMID: 16746146
  84. Tyrosine hydroxylation catalyzed by mammalian tyrosinase: an improved method of assay.
    Biochem Biophys Res Commun. 1964 Jun 1;16(2):188-94 PMID: 5871805
  85. Aromatic ring hydroxylation of estradiol in man.
    Biochemistry. 1970 Mar 31;9(7):1593-8 PMID: 5436147
  86. Migration of deuterium during hydroxylation of aromatic substrates by liver microsomes. I. Influence of ring substitutents.
    Arch Biochem Biophys. 1968 Nov;128(2):517-27 PMID: 5698035
  87. Oxotransition metal oxidants as mimics for the action of mixed-function oxygenases. "NIH shift" with chromyl reagents.
    J Am Chem Soc. 1971 May 5;93(9):2316-8 PMID: 5553075
  88. Retention of deuterium in p-tyrosine formed enzymatically from p-deuterophenylalanine.
    Biochem Biophys Res Commun. 1966 Sep 8;24(5):720-4 PMID: 5970504
  89. 7-Hydroxylation of thymine in a Neurospora strain coupled to oxidative decarboxylation of 2-ketoglutarate.
    Biochim Biophys Acta. 1970 Jul 15;212(1):50-7 PMID: 5500945
  90. Hydroxylation-induced migration and retention of tritium on conversion of (4-3H) cinnamic acid to 4-hydroxycinnamic acid by an enzyme from pea seedings.
    Biochim Biophys Acta. 1968 Nov 12;170(1):210-3 PMID: 5721918
  91. In vitro transformation of rodent cells by K-region derivatives of polycyclic hydrocarbons.
    Proc Natl Acad Sci U S A. 1971 Jun;68(6):1098-101 PMID: 4108174
  92. The mixed function oxygenation of 4-halogenoacetanilides in rat liver microsomes and model systems.
    Hoppe Seylers Z Physiol Chem. 1968 Jan;349(1):85-94 PMID: 5666913
  93. Hydroxylation-induced migration: the NIH shift. Recent experiments reveal an unexpected and general result of enzymatic hydroxylation of aromatic compounds.
    Science. 1967 Sep 29;157(3796):1524-30 PMID: 6038165
  94. Pharmacologic and metabolic studies with deuterated zoxazolamine.
    J Med Chem. 1970 Jan;13(1):30-2 PMID: 5412111
  95. Selective exchange of nuclear protons in hydroxyindoles.
    J Am Chem Soc. 1967 Feb 15;89(4):1032-3 PMID: 5298577
  96. Enzymic aromatization of 3,5-cyclohexadiene-1,2-diol.
    Biochim Biophys Acta. 1959 May;33(1):111-9 PMID: 13651190
  97. [Hydroxylation and defluorination of fluorinated derivatives of aniline].
    Arch Int Pharmacodyn Ther. 1968 Jan;171(1):240-2 PMID: 5646022
  98. Biosynthesis and metabolism of hydroxyphenylacetic acids in higher plants.
    Eur J Biochem. 1969 Jan;7(3):340-7 PMID: 5791579
  99. Significance and rearrangements of quinol models of tyrosine metabolites.
    Experientia. 1952 Oct 15;8(10 ):377-9 PMID: 13010217
  100. The metabolism of C14-ICI 54,450 (myalex) in various species--an in vivo NIH shift.
    J Pharmacol Exp Ther. 1970 Mar;172(1):115-21 PMID: 4984667
  101. A radiometric assay for hepatic epoxide hydrase activity with [7-3H] styrene oxide.
    Biochim Biophys Acta. 1971 Mar 10;227(3):685-91 PMID: 4328054
  102. A simple radioisotope assay for phenylalanine hydroxylase.
    Anal Biochem. 1967 Jun;19(3):548-55 PMID: 6069102
  103. Rapid loss of cytochrome P-450 and haem caused in the liver microsomes by the porphyrogenic agent 2-allyl-2-isopropylacetamide.
    FEBS Lett. 1970 Feb 25;6(4):343-345 PMID: 11947411
  104. Solubilization, purification, and properties of a hepatic epoxide hydrase.
    Biochim Biophys Acta. 1971 Mar 10;227(3):692-7 PMID: 4998715
  105. C-2 hydroxylation of 2-deuterioestrogen in the rat. Lack of "NIH" shift".
    Chem Pharm Bull (Tokyo). 1971 Aug;19(8):1727-30 PMID: 5122676
  106. [Conversion of (4-3H)L-phenylalanine into (4-3H)pyrocatechol and (3-3H)hydroquinone in leaves of Bergenia crassifolia].
    Hoppe Seylers Z Physiol Chem. 1969 Oct;350(10):1289-90 PMID: 5352360
  107. The production of meta-tritiotyrosine from p-tritiophenylalanine by phenylalanine hydroxylase.
    Biochem Biophys Res Commun. 1966 Oct 20;25(2):253-9 PMID: 5971770
  108. Biosynthetic studies on mescaline and related cactus alkaloids.
    Acta Pharm Suec. 1971 Jun;8(3):275-302 PMID: 5560272
  109. FURTHER STUDIES ON PHENYLPYRUVATE OXIDASE. OCCURRENCE OF SIDE CHAIN REARRANGEMENT AND COMPARISON WITH P-HYDROXYPHENYLPYRUVATE OXIDASE.
    J Biol Chem. 1964 Oct;239:3389-95 PMID: 14245392
  110. The migration of deuterium during aryl hydroxylation. II. Effect of induction of microsomal hydroxylases with phenobarbital or polycyclic aromatic hydrocarbons.
    Arch Biochem Biophys. 1969 Apr;131(1):238-44 PMID: 5781725
  111. A new metabolite of 5,5-diphenylhydantoin (Dilantin).
    Biochem Biophys Res Commun. 1970 Feb 6;38(3):444-9 PMID: 5443691
Article Info
Journal
Experientia
Abbr.
Experientia
ISSN
0014-4754
DOI
10.1007/BF01946135
Published
1972-10-15
Pages
1129-49
Language
English
Region
Switzerland
NLM ID
0376547
Subset
IM
External Links
PubMed source DOI: 10.1007/BF01946135
Analysis Services
Analysis Services

Contact

No. 2 Wenbo Road, Zhangqiu District, Jinan, Shandong

Qilu Normal University · Genelibs Bioinformatics Lab

750 Shunhua Rd, Jinan

2F, Bldg F, University Science Park

Tel: 0531-88819269

WeChat Official Account

Follow our WeChat subscription account for real-time updates and the latest in medical and biological research.


Business Email

E-mail: [email protected]

Copyright © 2026.Genelibs Jinan Honghui Biotechnology Co., Ltd. 鲁ICP备20007159号-2