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DNA Cleavage, Antiviral And Cytotoxic Reactions Photosensitized By Simple Enediyne Compounds.

J. Kagan, X. Wang, X. Chen, K. Lau, I. V. Batac, R. W. Tuveson, J. Hudson
Published 1993 · Biology, Medicine

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Very potent antibiotic antitumor natural products contain a enediyne moiety which, upon thermal activation, is capable of abstracting hydrogens from DNA. 1,6-Diphenyl-3-hexene-1,5-diyne was selected as a candidate for inducing DNA strand breaks photochemically. Easily interconverted with light, both geometric isomers 1 and 2 were expected to be phototoxic. As anticipated, they photosensitized the production of strand breaks in double-stranded supercoiled pBR322, and in single-stranded M13 DNA. The DNA cleavage reactions were favored by the presence of oxygen and were inhibited by ethanol. Preliminary experiments with the (Z)-isomer indicated moderate light-dependent antiviral activity against human immunodeficiency virus (HIV), Sindbis virus, and mouse cytomegalovirus. The enediynes were cytotoxic to Escherichia coli, a gram-negative organism, to Streptococcus faecalis, a gram-positive organism, to Daphnia magna and to fish (Pimephales promelas), but only in the presence of light. The production of o-terphenyl, the expected product of Bergman cyclization of 1, could not be confirmed. However, both 1 and 2 photosensitized the formation of singlet oxygen and of superoxide anion radical, and photodynamic reactions could have been responsible for some of the phototoxic reactions observed.
This paper references
10.1111/j.1751-1097.1992.tb04210.x
PHOTOSENSITIZATION BY 2‐CHLORO‐3, 11‐TRIDECADIENE‐5, 7, 9‐TRIYN‐1‐OL: DAMAGE TO ERYTHROCYTE MEMBRANES, Escherichia coli, AND DNA
J. Kagan (1992)
10.1098/rspa.1956.0102
A new sensitive chemical actinometer - II. Potassium ferrioxalate as a standard chemical actinometer
C. G. Hatchard (1956)
10.1021/BI00494A006
Visible light induced DNA cleavage by the hybrid antitumor antibiotic dynemicin A.
T. Shiraki (1990)
10.1021/JA00222A077
Cyclic conjugated enediynes related to calicheamicins and esperamicins: calculations, synthesis, and properties
K. Nicolaou (1988)
10.1021/AR00023A003
Molecular design, chemical synthesis, and biological action of enediynes
K. C. Nicolaou (1992)
10.1016/0045-6535(86)90578-3
Alpha-terthienyl, a powerful fish poison with light-dependent activity
J. Kagan (1986)
10.1002/CHIN.198846120
Palladium‐Mediated Reactions Between 1‐Alkynylzinc Chlorides and (E)/(Z)‐1,2‐Dibromoethylene or (E)‐1,2‐Dibromo‐1,2‐diphenylethylene.
B. Andreini (1988)
Ultraviolet-mediated antibiotic activity of synthetic thiophenes and their acetylenic derivatives
J. Hudson (1989)
10.1111/j.1751-1097.1978.tb06972.x
A NEW METHOD FOR THE DETECTION OF SINGLET OXYGEN IN AQUEOUS SOLUTIONS
I. Kraljić (1978)
10.1021/JA00404A018
KINETIC EVIDENCE FOR THE FORMATION OF DISCRETE 1,4-DEHYDROBENZENE INTERMEDIATES. TRAPPING BY INTER- AND INTRAMOLECULAR HYDROGEN ATOM TRANSFER AND OBSERVATION OF HIGH-TEMPERATURE CIDNP
T. Lockhart (1981)
10.1016/0045-6535(89)90080-5
PHOTOACTIVE ANTIVIRAL AND CYTOTOXIC ACTIVITIES OF SYNTHETIC THIOPHENES AND THEIR ACETYLENIC DERIVATIVES
J. Hudson (1989)
10.1016/0045-6535(91)90046-G
Variables affecting the phototoxicity of α-terthienyl toward fish in the laboratory
J. Kagan (1991)
10.1016/S0040-4039(00)89115-7
Stereospecific syntheses fo cis- and trans-1,6-bistrimethylsilyl-hex-3-ene-1,5-diyne
K. Peter (1985)
10.1111/j.1751-1097.1992.tb02146.x
PSORALENS CLEAVE pBR322 DNA UNDER ULTRAVIOLET RADIATION
J. Kagan (1992)
10.1002/ANIE.199113873
Chemistry and Biology of the Enediyne Anticancer Antibiotics
K. C. Nicolaou (1991)
10.1016/1011-1344(89)80059-4
Photosensitization with α-terthienyl: the formation of superoxide ion in aqueous media
J. Kagan (1989)
10.1021/JA00046A071
Kedarcidin, a new chromoprotein antitumor antibiotic : structure elucidation of kedarcidin chromophore
J. Leet (1992)
10.1021/AR00008A003
Calicheamicins: discovery, structure, chemistry, and interaction with DNA
M. D. Lee (1991)
10.1111/j.1751-1097.1990.tb08663.x
EFFICIENCY OF THE PHOTOPROCESSES LEADING TO SINGLET OXYGEN ( 1 δg) GENERATION BY α‐TERTHIENYL: OPTICAL ABSORPTION, OPTOACOUSTIC CALORIMETRY AND INFRARED LUMINESCENCE STUDIES*
J. Scaiano (1990)
10.1016/0166-3542(93)90057-P
The anti-HIV activity of the phytochemical α-terthienyl
J. Hudson (1993)
10.1021/JA00757A071
p-Benzyne. Generation as an intermediate in a thermal isomerization reaction and trapping evidence for the 1,4-benzenediyl structure
R. M. Jones (1972)
10.1002/ANIE.199110321
Enediyne compounds equipped with acid-, base- and photo-sensitive triggering devices. Chemical simulation of the dynemicin A reaction cascade
K. C. Nicolaou (1991)
10.1021/JA00045A005
Design, synthesis, and study of simple monocyclic conjugated enediynes. The 10-membered ring enediyne moiety of the enediyne anticancer antibiotics
K. Nicolaou (1992)
10.1016/0006-291X(89)91544-1
Light-induced DNA cleavage by esperamicin and neocarzinostatin.
Y. Uesawa (1989)
10.1126/SCIENCE.3240341
Calicheamicin gamma 1I: an antitumor antibiotic that cleaves double-stranded DNA site specifically.
N. Zein (1988)



This paper is referenced by
10.1021/acs.jpca.7b10576
An ab Initio Exploration of the Bergman Cyclization.
Adam Luxon (2018)
10.1201/9781420027587.CH19
From Natural to Rationally Designed Artificial Enediynes: Towards New Anticancer Antibiotics Activable at Will
A. Basso (2005)
10.1111/cbdd.12252
Biological Activity of Sporolides A and B from Salinispora tropica: in silico Target Prediction Using Ligand‐Based Pharmacophore Mapping and in vitro activity Validation on HIV‐1 Reverse Transcriptase
K. Dineshkumar (2014)
10.1002/anie.201208380
Tandem cyclizations of 1,6-enynes with arylsulfonyl chlorides by using visible-light photoredox catalysis.
G. Deng (2013)
10.1021/ja8077076
Photochemical generation and reversible cycloaromatization of a nine-membered ring cyclic enediyne.
D. R. Pandithavidana (2009)
10.1021/OL0001158
Synthesis and Thermal Reaction of 1,3-Bis(alkylseleno)allenes.
Shimizu (2000)
10.1039/B417012A
Lysine-enediyne conjugates as photochemically triggered DNA double-strand cleavage agents.
S. V. Kovalenko (2005)
10.1021/ACS.ORGANOMET.7B00589
Photoactivated Transition-Metal Triggers for Ambient Temperature Enediyne and Dienyne Cyclization: Ruthenium-η6-Naphthalene Complexes
Pengjin Qin (2017)
10.1039/B414951C
Photoswitchable enediynes: use of cyclopropenone as photocleavable masking group for the enediyne triple bond.
Andrei A. Poloukhtine (2005)
10.1016/0040-4039(94)88250-9
Photochemical analogue of the bergman cycloaromatization reaction
N. Turro (1994)
10.1201/B12252-24
Photochemical Bergman Cyclization and Related Photoreactions of Enediynes
I. Alabugin (2012)
10.1021/ja902140m
C-lysine conjugates: pH-controlled light-activated reagents for efficient double-stranded DNA cleavage with implications for cancer therapy.
Wang-Yong Yang (2009)
10.1039/c2ob00052k
Hybrids of amino acids and acetylenic DNA-photocleavers: optimising efficiency and selectivity for cancer phototherapy.
Boris Breiner (2012)
10.1002/POLA.25013
A convergence of photo‐bergman cyclization and intramolecular chain collapse towards polymeric nanoparticles
Benchuan Zhu (2011)
10.3762/bjoc.7.93
Fine-tuning alkyne cycloadditions: Insights into photochemistry responsible for the double-strand DNA cleavage via structural perturbations in diaryl alkyne conjugates
Wang-Yong Yang (2011)
10.1039/b911871c
Dual reactivity of a photochemically-generated cyclic enyne-allene.
A. Kuzmin (2009)
10.1002/ANGE.200504479
Protected 32P‐Labels in Deoxyribonucleotides: Investigation of Sequence Selectivity of DNA Photocleavage by Enediyne–, Fulvene–, and Acetylene–Lysine Conjugates
Boris Breiner (2006)
10.1002/9781118754887.CH30
Photochemical Bergman Cyclization and Related Reactions
Rana K Mohamed (2015)
10.1158/0008-5472.CAN-05-0015
The antitumor enediyne C-1027 alters cell cycle progression and induces chromosomal aberrations and telomere dysfunction.
M. McHugh (2005)
10.1002/CHEM.200305001
Theoretical investigation of the photochemical C2-C6 cyclisation of enyne-heteroallenes.
C. Spöler (2003)
10.1002/jcc.22889
The bergman cyclizations of the enediyne and its N‐substituted analogs using multiconfigurational second‐order perturbation theory
H. Dong (2012)
10.1071/CH10185
Photochemical Triggering of the Bergman and Myers–Saito Cyclizations
Andrei Polukhtine (2010)
10.1021/jm2010282
Engineering pH-gated transitions for selective and efficient double-strand DNA photocleavage in hypoxic tumors.
Wang-Yong Yang (2011)
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