Details of the Drug-Related molecule(s) Interaction Atlas

General Information of Drug (ID: DM802V7)

• Drug Name: Syringic Acid Drug Info
• Synonyms: SYRINGIC ACID; 530-57-4; 4-Hydroxy-3,5-dimethoxybenzoic acid; 3,5-Dimethoxy-4-hydroxybenzoic acid; Cedar acid; Gallic acid 3,5-dimethyl ether; Benzoic acid, 4-hydroxy-3,5-dimethoxy-; 3,5-Dimethoxy-4-hydroxybenzyl acid; UNII-E390O181H5; NSC 2129; EINECS 208-486-8; 4-Hydroxy-3,5-dimethoxy-benzoic acid; BRN 2115262; CHEMBL1414; AI3-24376; CHEBI:68329; JMSVCTWVEWCHDZ-UHFFFAOYSA-N; MFCD00002552; E390O181H5; Syringic acid, 97%; Syringlicacid; Syringicacid; PubChem2673; SpecPlus_000485; AC1L1VUN; Spectrum3_001866; Spectrum5_000963

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1]

• Cross-matching ID:
  PubChem CID: 10742
  ChEBI ID: CHEMBL1414
  CAS Number: CAS 530-57-4
  TTD Drug ID: DM802V7

Molecule-Related Drug Atlas

Drug(s) Targeting Carbonic anhydrase VI (CA-VI)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Salicyclic acid	DM2F8XZ	Acne vulgaris	ED80	Approved	[5]
Sulfamylon	DMIO1K0	Bacterial infection	1A00-1C4Z	Approved	[6]
Curcumin	DMQPH29	Solid tumour/cancer	2A00-2F9Z	Phase 3	[7]
PARABEN	DMEW5Z8	N. A.	N. A.	Phase 3	[1]
Coumate	DMVKW0N	Breast cancer	2C60-2C65	Phase 2	[8]
SAR566658	DM6Q295	Solid tumour/cancer	2A00-2F9Z	Phase 2	[9]
FERULIC ACID	DMJC7NF	Discovery agent	N.A.	Patented	[1]
SPERMINE	DMD4BFY	N. A.	N. A.	Terminated	[10]
ELLAGIC ACID	DMX8BS5	Discovery agent	N.A.	Investigative	[1]
COUMARIN	DM0N8ZM	Discovery agent	N.A.	Investigative	[11]

Drug(s) Targeting Carbonic anhydrase I (CA-I)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Salicyclic acid	DM2F8XZ	Acne vulgaris	ED80	Approved	[5]
Ethoxzolamide	DMVO4ED	Glaucoma/ocular hypertension	9C61	Approved	[12]
Dichlorphenamide	DMH7IDQ	Chronic glaucoma	9C61.0Z	Approved	[12]
Methazolamide	DM7J2TA	Glaucoma/ocular hypertension	9C61	Approved	[13]
Acetazolamide	DM1AF5U	Absence epilepsy		Approved	[12]
Curcumin	DMQPH29	Solid tumour/cancer	2A00-2F9Z	Phase 3	[7]
PARABEN	DMEW5Z8	N. A.	N. A.	Phase 3	[1]
CG-100649	DMIKMA9	Arthritis	FA20	Phase 3	[14]
PHENOL	DM1QSM3	N. A.	N. A.	Phase 2/3	[7]
Coumate	DMVKW0N	Breast cancer	2C60-2C65	Phase 2	[8]

Drug(s) Targeting Carbonic anhydrase XII (CA-XII)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Salicyclic acid	DM2F8XZ	Acne vulgaris	ED80	Approved	[5]
Sulfamylon	DMIO1K0	Bacterial infection	1A00-1C4Z	Approved	[15]
Curcumin	DMQPH29	Solid tumour/cancer	2A00-2F9Z	Phase 3	[7]
PARABEN	DMEW5Z8	N. A.	N. A.	Phase 3	[1]
PHENOL	DM1QSM3	N. A.	N. A.	Phase 2/3	[7]
Coumate	DMVKW0N	Breast cancer	2C60-2C65	Phase 2	[8]
FERULIC ACID	DMJC7NF	Discovery agent	N.A.	Patented	[1]
ELLAGIC ACID	DMX8BS5	Discovery agent	N.A.	Investigative	[1]
COUMARIN	DM0N8ZM	Discovery agent	N.A.	Investigative	[11]
CATECHIN	DMY38SB	Discovery agent	N.A.	Investigative	[7]

Drug(s) Targeting Carbonic anhydrase II (CA-II)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Salicyclic acid	DM2F8XZ	Acne vulgaris	ED80	Approved	[5]
Sulfamylon	DMIO1K0	Bacterial infection	1A00-1C4Z	Approved	[15]
Dorzolamide	DMA17D0	Ocular hypertension	9C61.01	Approved	[16]
Chlorothiazide	DMLHESP	Chronic heart failure	BD1Z	Approved	[17]
Ethoxzolamide	DMVO4ED	Glaucoma/ocular hypertension	9C61	Approved	[18]
Dichlorphenamide	DMH7IDQ	Chronic glaucoma	9C61.0Z	Approved	[18]
Cyclothiazide	DMJ4AWC	Congestive heart failure	BD10	Approved	[19]
Ethinamate	DMK57GB	Insomnia	7A00-7A0Z	Approved	[20]
Benzthiazide	DMQWZ0H	High blood pressure	BA00	Approved	[21]
Curcumin	DMQPH29	Solid tumour/cancer	2A00-2F9Z	Phase 3	[7]

Drug(s) Targeting Carbonic anhydrase XIV (CA-XIV)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Sulfamylon	DMIO1K0	Bacterial infection	1A00-1C4Z	Approved	[22]
TRIENTINE	DMD2WPG	Inborn error of metabolism	5C50-5C59	Approved	[10]
Curcumin	DMQPH29	Solid tumour/cancer	2A00-2F9Z	Phase 3	[7]
PARABEN	DMEW5Z8	N. A.	N. A.	Phase 3	[1]
PHENOL	DM1QSM3	N. A.	N. A.	Phase 2/3	[7]
Coumate	DMVKW0N	Breast cancer	2C60-2C65	Phase 2	[8]
FERULIC ACID	DMJC7NF	Discovery agent	N.A.	Patented	[1]
SPERMINE	DMD4BFY	N. A.	N. A.	Terminated	[10]
ELLAGIC ACID	DMX8BS5	Discovery agent	N.A.	Investigative	[1]
COUMARIN	DM0N8ZM	Discovery agent	N.A.	Investigative	[11]

Drug(s) Targeting Carbonic anhydrase (CA)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Salicyclic acid	DM2F8XZ	Acne vulgaris	ED80	Approved	[23]
Sulfamylon	DMIO1K0	Bacterial infection	1A00-1C4Z	Approved	[6]
Quinethazone	DMWCOSR	Hypertension	BA00-BA04	Approved	[24]
Curcumin	DMQPH29	Solid tumour/cancer	2A00-2F9Z	Phase 3	[7]
PARABEN	DMEW5Z8	N. A.	N. A.	Phase 3	[1]
PHENOL	DM1QSM3	N. A.	N. A.	Phase 2/3	[7]
Coumate	DMVKW0N	Breast cancer	2C60-2C65	Phase 2	[8]
SULFAMIDE	DMMAS3K	N. A.	N. A.	Phase 1	[25]
FERULIC ACID	DMJC7NF	Discovery agent	N.A.	Patented	[1]
PMID30074415-Compound-21	DM3NPOU	N. A.	N. A.	Patented	[26]

Drug(s) Targeting Carbonic anhydrase IV (CA-IV)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Salicyclic acid	DM2F8XZ	Acne vulgaris	ED80	Approved	[5]
Sulfamylon	DMIO1K0	Bacterial infection	1A00-1C4Z	Approved	[27]
Brinzolamide	DMBAPFG	Ocular hypertension	9C61.01	Approved	[12]
Curcumin	DMQPH29	Solid tumour/cancer	2A00-2F9Z	Phase 3	[7]
PARABEN	DMEW5Z8	N. A.	N. A.	Phase 3	[1]
PHENOL	DM1QSM3	N. A.	N. A.	Phase 2/3	[7]
Coumate	DMVKW0N	Breast cancer	2C60-2C65	Phase 2	[8]
Sodium pyruvate	DMST6A3	Asthma	CA23	Phase 1/2	[28]
SULFAMIDE	DMMAS3K	N. A.	N. A.	Phase 1	[25]
FERULIC ACID	DMJC7NF	Discovery agent	N.A.	Patented	[1]

Drug(s) Targeting Carbonic anhydrase IX (CA-IX)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Curcumin	DMQPH29	Solid tumour/cancer	2A00-2F9Z	Phase 3	[7]
PARABEN	DMEW5Z8	N. A.	N. A.	Phase 3	[1]
PHENOL	DM1QSM3	N. A.	N. A.	Phase 2/3	[7]
Coumate	DMVKW0N	Breast cancer	2C60-2C65	Phase 2	[8]
INDISULAM	DM9SX6Y	Lymphoma	2A80-2A86	Phase 2	[29]
Girentuximab I-124	DMG3O2Z	Renal cell carcinoma	2C90	Phase 2	[30]
SULFAMIDE	DMMAS3K	N. A.	N. A.	Phase 1	[31]
BAY 79-4620	DM14XQN	Solid tumour/cancer	2A00-2F9Z	Phase 1	[32]
90Y-cG250	DMJR6TC	Solid tumour/cancer	2A00-2F9Z	Phase 1	[33]
FERULIC ACID	DMJC7NF	Discovery agent	N.A.	Patented	[1]

Drug(s) Affected By Mitogen-activated protein kinase 3 (MAPK3)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Cisplatin	DMRHGI9	Adenocarcinoma	2D40	Approved	[34]
Progesterone	DMUY35B	Amenorrhea	GA20.0	Approved	[35]
Cannabidiol	DM0659E	Dravet syndrome	8A61.11	Approved	[36]
Sertraline	DM0FB1J	Coronary heart disease	BA80.Z	Approved	[37]
Beta-carotene	DM0RXBT	Vitamin deficiency	5B55-5B71	Approved	[38]
Fulvestrant	DM0YZC6	Breast cancer	2C60-2C65	Approved	[39]
Secobarbital	DM14RF5	Epilepsy	8A60-8A68	Approved	[40]
Gefitinib	DM15F0X	Colon adenocarcinoma		Approved	[41]
Fexofenadine	DM17ONX	Allergic rhinitis	CA08.0	Approved	[42]
Hydrogen peroxide	DM1NG5W	Infectious disease	1A00-CA43.1	Approved	[43]

Drug(s) Affected By Mitogen-activated protein kinase 1 (MAPK1)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Ethanol	DMDRQZU	Chronic pain	MG30	Approved	[44]
Progesterone	DMUY35B	Amenorrhea	GA20.0	Approved	[35]
Carvedilol	DMHTEAO	Chronic heart failure	BD1Z	Approved	[45]
Paclitaxel	DMLB81S	Breast carcinoma		Approved	[46]
Etoposide	DMNH3PG	Acute myelogenous leukaemia	2A41	Approved	[47]
Cisplatin	DMRHGI9	Adenocarcinoma	2D40	Approved	[34]
Urokinase	DM0GOUD	Myocardial infarction	BA41-BA43	Approved	[48]
Cannabidiol	DM0659E	Dravet syndrome	8A61.11	Approved	[49]
Sertraline	DM0FB1J	Coronary heart disease	BA80.Z	Approved	[37]
Beta-carotene	DM0RXBT	Vitamin deficiency	5B55-5B71	Approved	[38]

Drug(s) Affected By Mitogen-activated protein kinase 8 (MAPK8)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Cisplatin	DMRHGI9	Adenocarcinoma	2D40	Approved	[50]
Cannabidiol	DM0659E	Dravet syndrome	8A61.11	Approved	[51]
Gefitinib	DM15F0X	Colon adenocarcinoma		Approved	[52]
Hydrogen peroxide	DM1NG5W	Infectious disease	1A00-CA43.1	Approved	[53]
Colchicine	DM2POTE	Acute gout flare	FA25.0	Approved	[54]
Quercetin	DM3NC4M	Obesity	5B81	Approved	[55]
Zidovudine	DM4KI7O	Human immunodeficiency virus infection	1C62	Approved	[56]
Glucosamine	DM4ZLFD	Osteoarthritis	FA00-FA05	Approved	[57]
Vinblastine	DM5TVS3	Advanced cancer	2A00-2F9Z	Approved	[54]
Ethacrynic acid	DM60QMR	Edema	MG29	Approved	[58]

Drug(s) Affected By Transcription factor p65 (RELA)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Cannabidiol	DM0659E	Dravet syndrome	8A61.11	Approved	[49]
Beta-carotene	DM0RXBT	Vitamin deficiency	5B55-5B71	Approved	[59]
Selenium	DM25CGV	N. A.	N. A.	Approved	[60]
Sulindac	DM2QHZU	Acute myelogenous leukaemia	2A41	Approved	[61]
Simvastatin	DM30SGU	Arteriosclerosis	BD40	Approved	[62]
Deoxycholic acid	DM3GYAL	Subcutaneous fat disorder	EF02	Approved	[63]
Quercetin	DM3NC4M	Obesity	5B81	Approved	[64]
Troglitazone	DM3VFPD	Diabetic complication	5A2Y	Approved	[65]
Tretinoin	DM49DUI	Acne vulgaris	ED80	Approved	[66]
Glucosamine	DM4ZLFD	Osteoarthritis	FA00-FA05	Approved	[67]

Drug(s) Affected By FAS-associated death domain protein (FADD)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Cannabidiol	DM0659E	Dravet syndrome	8A61.11	Approved	[68]
Selenium	DM25CGV	N. A.	N. A.	Approved	[69]
Dactinomycin	DM2YGNW	Adult kidney Wilms tumor		Approved	[70]
Quercetin	DM3NC4M	Obesity	5B81	Approved	[71]
obeticholic acid	DM3Q1SM	Primary biliary cholangitis	DB96.1	Approved	[72]
Acetic Acid, Glacial	DM4SJ5Y	infection in the ear canal	AA0Y	Approved	[73]
Arsenic trioxide	DM61TA4	Acute lymphoblastic leukaemia	2A85	Approved	[74]
Hydroquinone	DM6AVR4	Melasma	ED60.1	Approved	[75]
Marinol	DM70IK5	Anorexia nervosa cachexia	6B80	Approved	[76]
Acocantherin	DM7JT24	Atrial fibrillation	BC81.3	Approved	[77]

Drug(s) Affected By Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 (PIN1)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Quercetin	DM3NC4M	Obesity	5B81	Approved	[78]
Arsenic trioxide	DM61TA4	Acute lymphoblastic leukaemia	2A85	Approved	[79]
Ciclosporin	DMAZJFX	Graft-versus-host disease	4B24	Approved	[80]
Valproate	DMCFE9I	Epilepsy	8A60-8A68	Approved	[81]
Ivermectin	DMDBX5F	Intestinal strongyloidiasis due to nematode parasite	1F6B	Approved	[82]
Temozolomide	DMKECZD	Adenocarcinoma	2D40	Approved	[83]
Cupric Sulfate	DMP0NFQ	Fungal infection	1F29-1F2F	Approved	[84]
Acetaminophen	DMUIE76	Allergic rhinitis	CA08.0	Approved	[85]
Methotrexate	DM2TEOL	Anterior urethra cancer		Approved	[86]
LY294002	DMY1AFS	Neuroblastoma	2D11.2	Phase 1	[78]

Drug(s) Affected By Mitogen-activated protein kinase 14 (MAPK14)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Cisplatin	DMRHGI9	Adenocarcinoma	2D40	Approved	[87]
Cannabidiol	DM0659E	Dravet syndrome	8A61.11	Approved	[88]
Hydrogen peroxide	DM1NG5W	Infectious disease	1A00-CA43.1	Approved	[53]
Methotrexate	DM2TEOL	Anterior urethra cancer		Approved	[89]
Quercetin	DM3NC4M	Obesity	5B81	Approved	[90]
Tretinoin	DM49DUI	Acne vulgaris	ED80	Approved	[66]
Chlorpromazine	DMBGZI3	Acute intermittent hepatic porphyria	5C58.11	Approved	[91]
Ethacrynic acid	DM60QMR	Edema	MG29	Approved	[58]
Arsenic trioxide	DM61TA4	Acute lymphoblastic leukaemia	2A85	Approved	[92]
Aspirin	DM672AH	Acute coronary syndrome	BA41	Approved	[93]

Drug(s) Affected By Ubiquitin-like-conjugating enzyme ATG3 (ATG3)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Quercetin	DM3NC4M	Obesity	5B81	Approved	[64]
Tretinoin	DM49DUI	Acne vulgaris	ED80	Approved	[94]
Cyclophosphamide	DM4O2Z7	Advanced cancer	2A00-2F9Z	Approved	[95]
Trovafloxacin	DM6AN32	Acute gonococcal cervicitis		Approved	[96]
Ciclosporin	DMAZJFX	Graft-versus-host disease	4B24	Approved	[80]
Cantharidin	DMBP5N3	Molluscum contagiosum infection	1E76	Approved	[97]
Valproate	DMCFE9I	Epilepsy	8A60-8A68	Approved	[81]
Ivermectin	DMDBX5F	Intestinal strongyloidiasis due to nematode parasite	1F6B	Approved	[82]
Gentamicin	DMKINJO	Bacteremia	1A73	Approved	[95]
Artesunate	DMR27C8	Infection of P. falciparum	1F40	Approved	[98]

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Carbonic anhydrase (CA)	TTUNARX	NOUNIPROTAC	Inhibitor	[1]
Carbonic anhydrase I (CA-I)	TTHQPL7	CAH1_HUMAN	Inhibitor	[1]
Carbonic anhydrase II (CA-II)	TTANPDJ	CAH2_HUMAN	Inhibitor	[1]
Carbonic anhydrase IV (CA-IV)	TTZHA0O	CAH4_HUMAN	Inhibitor	[1]
Carbonic anhydrase IX (CA-IX)	TT2LVK8	CAH9_HUMAN	Inhibitor	[1]
Carbonic anhydrase VI (CA-VI)	TTCFSPE	CAH6_HUMAN	Inhibitor	[1]
Carbonic anhydrase XII (CA-XII)	TTSYM0R	CAH12_HUMAN	Inhibitor	[1]
Carbonic anhydrase XIV (CA-XIV)	TTEYTKG	CAH14_HUMAN	Inhibitor	[1]

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
FAS-associated death domain protein (FADD)	OTV7GFHH	FADD_HUMAN	Protein Interaction/Cellular Processes	[2]
Mitogen-activated protein kinase 1 (MAPK1)	OTH85PI5	MK01_HUMAN	Gene/Protein Processing	[3]
Mitogen-activated protein kinase 14 (MAPK14)	OT5TCO3O	MK14_HUMAN	Gene/Protein Processing	[4]
Mitogen-activated protein kinase 3 (MAPK3)	OTCYKGKO	MK03_HUMAN	Gene/Protein Processing	[3]
Mitogen-activated protein kinase 8 (MAPK8)	OTEREYS5	MK08_HUMAN	Gene/Protein Processing	[4]
Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 (PIN1)	OTDS5WAU	PIN1_HUMAN	Gene/Protein Processing	[4]
Transcription factor p65 (RELA)	OTUJP9CN	TF65_HUMAN	Gene/Protein Processing	[4]
Ubiquitin-like-conjugating enzyme ATG3 (ATG3)	OT28VBVK	ATG3_HUMAN	Gene/Protein Processing	[3]

References

• [1] Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids. Bioorg Med Chem. 2010 Mar 15;18(6):2159-2164.
• [2] Octyl syringate is preferentially cytotoxic to cancer cells via lysosomal membrane permeabilization and autophagic flux inhibition. Cell Biol Toxicol. 2023 Feb;39(1):183-199. doi: 10.1007/s10565-021-09653-6. Epub 2021 Sep 15.
• [3] In vitro and in vivo anticancer effects of syringic acid on colorectal cancer: Possible mechanistic view. Chem Biol Interact. 2021 Mar 1;337:109337. doi: 10.1016/j.cbi.2020.109337. Epub 2021 Feb 4.
• [4] Syringic acid regulates suppression of the STAT3/JNK/AKT pathway via inhibition of human ovarian teratoma cancer cell?(PA-1) growth-in vitro study. J Biochem Mol Toxicol. 2021 Jun;35(6):1-9. doi: 10.1002/jbt.22776. Epub 2021 Mar 23.
• [5] Carbonic anhydrase inhibitors: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem. 2008 Aug 1;16(15):7424-8.
• [6] Cloning, expression, post-translational modifications and inhibition studies on the latest mammalian carbonic anhydrase isoform, CA XV. J Med Chem. 2009 Feb 12;52(3):646-54.
• [7] Carbonic anhydrase inhibitors. Antioxidant polyphenols effectively inhibit mammalian isoforms I-XV. Bioorg Med Chem Lett. 2010 Sep 1;20(17):5050-3.
• [8] Carbonic anhydrase inhibitors. Interaction of the antitumor sulfamate EMD 486019 with twelve mammalian carbonic anhydrase isoforms: Kinetic and X-r... Bioorg Med Chem Lett. 2008 Aug 1;18(15):4282-6.
• [9] An Antibody-Drug Conjugate Targeting MUC1-Associated Carbohydrate CA6 Shows Promising Antitumor Activities. Mol Cancer Ther. 2020 Aug;19(8):1660-1669.
• [10] Polyamines inhibit carbonic anhydrases by anchoring to the zinc-coordinated water molecule. J Med Chem. 2010 Aug 12;53(15):5511-22.
• [11] Deciphering the mechanism of carbonic anhydrase inhibition with coumarins and thiocoumarins. J Med Chem. 2010 Jan 14;53(1):335-44.
• [12] Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
• [13] URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 2597).
• [14] Understanding the Dual Inhibition of COX-2 and Carbonic Anhydrase-II by Celecoxib and CG100649 Using Density Functional Theory Calculations and other Molecular Modelling Approaches. Protein Pept Lett. 2015;22(10):903-12.
• [15] Sulfonamide linked neoglycoconjugates--a new class of inhibitors for cancer-associated carbonic anhydrases. J Med Chem. 2010 Apr 8;53(7):2913-26.
• [16] Carbonic anhydrase inhibitors. Inhibition studies of a coral secretory isoform by sulfonamides. Bioorg Med Chem. 2009 Jul 15;17(14):5054-8.
• [17] Localization of diuretic effects along the loop of Henle: an in vivo microperfusion study in rats. Clin Sci (Lond). 2000 Apr;98(4):481-8.
• [18] The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42.
• [19] Selective effect of thiazides on the human osteoblast-like cell line MG-63. Kidney Int. 1996 Nov;50(5):1476-82.
• [20] Inhibition of carbonic anhydrases I and II by N-unsubstituted carbamate esters. J Biol Chem. 1992 Dec 15;267(35):25044-50.
• [21] Nature of the inhibition of carbonic anhydrase by acetazolamide and benzthiazide. J Pharmacol Exp Ther. 1961 Mar;131:271-4.
• [22] Carbonic anhydrase inhibitors: inhibition of the transmembrane isozyme XIV with sulfonamides. Bioorg Med Chem Lett. 2005 Sep 1;15(17):3828-33.
• [23] Carbonic anhydrase inhibitors: Inhibition of the new membrane-associated isoform XV with phenols. Bioorg Med Chem Lett. 2008 Jun 15;18(12):3593-6.
• [24] Carbonic anhydrase inhibitors. Interaction of indapamide and related diuretics with 12 mammalian isozymes and X-ray crystallographic studies for th... Bioorg Med Chem Lett. 2008 Apr 15;18(8):2567-73.
• [25] Carbonic anhydrase inhibitors: crystallographic and solution binding studies for the interaction of a boron-containing aromatic sulfamide with mamm... Bioorg Med Chem Lett. 2010 Jun 15;20(12):3601-5.
• [26] Carbonic anhydrase inhibitors as antitumor/antimetastatic agents: a patent review (2008-2018).Expert Opin Ther Pat. 2018 Oct;28(10):729-740.
• [27] Carbonic anhydrase inhibitors. Inhibition of the membrane-bound human and bovine isozymes IV with sulfonamides. Bioorg Med Chem Lett. 2005 Feb 15;15(4):1149-54.
• [28] Carbonic anhydrase inhibitors. Interaction of isozymes I, II, IV, V, and IX with carboxylates. Bioorg Med Chem Lett. 2005 Feb 1;15(3):573-8.
• [29] Carbonic anhydrase inhibitors: E7070, a sulfonamide anticancer agent, potently inhibits cytosolic isozymes I and II, and transmembrane, tumor-assoc... Bioorg Med Chem Lett. 2004 Jan 5;14(1):217-23.
• [30] Potential role of (124)I-girentuximab in the presurgical diagnosis of clear-cell renal cell cancer. Biologics. 2012;6:395-407.
• [31] Carbonic anhydrase inhibitors. Inhibition of isozymes I, II, IV, V, and IX with anions isosteric and isoelectronic with sulfate, nitrate, and carbo... Bioorg Med Chem Lett. 2005 Feb 1;15(3):567-71.
• [32] Therapeutic mechanism and efficacy of the antibody-drug conjugate BAY 79-4620 targeting human carbonic anhydrase 9. Mol Cancer Ther. 2012 Feb;11(2):340-9.
• [33] Application of monoclonal antibody G250 recognizing carbonic anhydrase IX in renal cell carcinoma. Int J Mol Sci. 2013 May 29;14(6):11402-23.
• [34] Treatment with anticancer agents induces dysregulation of specific Wnt signaling pathways in human ovarian luteinized granulosa cells in vitro. Toxicol Sci. 2013 Nov;136(1):183-92. doi: 10.1093/toxsci/kft175. Epub 2013 Aug 16.
• [35] Progesterone increases csk homologous kinase in HMC-1560 human mast cells and reduces cell proliferation. J Cell Biochem. 2007 Dec 1;102(5):1271-80. doi: 10.1002/jcb.21357.
• [36] Cannabidiol upregulates melanogenesis through CB1 dependent pathway by activating p38 MAPK and p42/44 MAPK. Chem Biol Interact. 2017 Aug 1;273:107-114. doi: 10.1016/j.cbi.2017.06.005. Epub 2017 Jun 7.
• [37] Sertraline, an antidepressant, induces apoptosis in hepatic cells through the mitogen-activated protein kinase pathway. Toxicol Sci. 2014 Feb;137(2):404-15. doi: 10.1093/toxsci/kft254. Epub 2013 Nov 5.
• [38] Growth stimulation of human pulmonary adenocarcinoma cells and small airway epithelial cells by beta-carotene via activation of cAMP, PKA, CREB and ERK1/2. Int J Cancer. 2006 Mar 15;118(6):1370-80. doi: 10.1002/ijc.21537.
• [39] Estrogen and pure antiestrogen fulvestrant (ICI 182 780) augment cell-matrigel adhesion of MCF-7 breast cancer cells through a novel G protein coupled estrogen receptor (GPR30)-to-calpain signaling axis. Toxicol Appl Pharmacol. 2014 Mar 1;275(2):176-81. doi: 10.1016/j.taap.2014.01.005. Epub 2014 Jan 17.
• [40] Inhibition of activator protein 1 by barbiturates is mediated by differential effects on mitogen-activated protein kinases and the small G proteins ras and rac-1. J Pharmacol Exp Ther. 2004 Dec;311(3):1232-40. doi: 10.1124/jpet.104.071332. Epub 2004 Jul 19.
• [41] Growth of hormone-dependent MCF-7 breast cancer cells is promoted by constitutive caveolin-1 whose expression is lost in an EGF-R-mediated manner during development of tamoxifen resistance. Breast Cancer Res Treat. 2010 Feb;119(3):575-91. doi: 10.1007/s10549-009-0355-8. Epub 2009 Mar 15.
• [42] Effect of histamine H1 receptor antagonists on TARC/CCL17 and MDC/CCL22 production from CD14+ cells induced by antigenic stimulation in vitro. Int Arch Allergy Immunol. 2011;155(1):38-51. doi: 10.1159/000318720. Epub 2010 Nov 25.
• [43] SIRT3 Mediates the Antioxidant Effect of Hydrogen Sulfide in Endothelial Cells. Antioxid Redox Signal. 2016 Feb 20;24(6):329-43. doi: 10.1089/ars.2015.6331. Epub 2015 Nov 10.
• [44] Downregulation of mitogen-activated protein kinases (MAPKs) in chronic ethanol-induced fatty liver. Toxicol Mech Methods. 2020 Jul;30(6):407-416. doi: 10.1080/15376516.2020.1747126. Epub 2020 Apr 1.
• [45] A unique mechanism of beta-blocker action: carvedilol stimulates beta-arrestin signaling. Proc Natl Acad Sci U S A. 2007 Oct 16;104(42):16657-62. doi: 10.1073/pnas.0707936104. Epub 2007 Oct 9.
• [46] The stent-eluting drugs sirolimus and paclitaxel suppress healing of the endothelium by induction of autophagy. Am J Pathol. 2009 Nov;175(5):2226-34.
• [47] Modulation of apoptosis in HaCaT keratinocytes via differential regulation of ERK signaling pathway by flavonoids. J Biol Chem. 2005 Sep 9;280(36):31498-507. doi: 10.1074/jbc.M505537200. Epub 2005 Jul 13.
• [48] ADReCS-Target: target profiles for aiding drug safety research and application. Nucleic Acids Res. 2018 Jan 4;46(D1):D911-D917. doi: 10.1093/nar/gkx899.
• [49] Cannabidiol Modulates the Immunophenotype and Inhibits the Activation of the Inflammasome in Human Gingival Mesenchymal Stem Cells. Front Physiol. 2016 Nov 24;7:559. doi: 10.3389/fphys.2016.00559. eCollection 2016.
• [50] Cisplatin induces autophagy to enhance hepatitis B virus replication via activation of ROS/JNK and inhibition of the Akt/mTOR pathway. Free Radic Biol Med. 2019 Feb 1;131:225-236. doi: 10.1016/j.freeradbiomed.2018.12.008. Epub 2018 Dec 11.
• [51] Inhibition of autophagic flux differently modulates cannabidiol-induced death in 2D and 3D glioblastoma cell cultures. Sci Rep. 2020 Feb 14;10(1):2687. doi: 10.1038/s41598-020-59468-4.
• [52] Frankincense myrrh attenuates hepatocellular carcinoma by regulating tumor blood vessel development through multiple epidermal growth factor receptor-mediated signaling pathways. World J Gastrointest Oncol. 2022 Feb 15;14(2):450-477. doi: 10.4251/wjgo.v14.i2.450.
• [53] Neuroprotective effects of glucomoringin-isothiocyanate against H(2)O(2)-Induced cytotoxicity in neuroblastoma (SH-SY5Y) cells. Neurotoxicology. 2019 Dec;75:89-104. doi: 10.1016/j.neuro.2019.09.008. Epub 2019 Sep 12.
• [54] Nocodazole-induced p53-dependent c-Jun N-terminal kinase activation reduces apoptosis in human colon carcinoma HCT116 cells. J Biol Chem. 2002 Nov 15;277(46):43648-58. doi: 10.1074/jbc.M203214200. Epub 2002 Sep 6.
• [55] Quercetin potentiates apoptosis by inhibiting nuclear factor-kappaB signaling in H460 lung cancer cells. Biol Pharm Bull. 2013;36(6):944-51. doi: 10.1248/bpb.b12-01004.
• [56] Lon protease and eiF2 are involved in acute, but not prolonged, antiretroviral induced stress response in HepG2 cells. Chem Biol Interact. 2016 May 25;252:82-6. doi: 10.1016/j.cbi.2016.03.021. Epub 2016 Apr 1.
• [57] Disease-modifying effects of glucosamine HCl involving regulation of metalloproteinases and chemokines activated by interleukin-1beta in human primary synovial fibroblasts. J Cell Biochem. 2008 May 1;104(1):38-50. doi: 10.1002/jcb.21597.
• [58] Characterization of cell death induced by ethacrynic acid in a human colon cancer cell line DLD-1 and suppression by N-acetyl-L-cysteine. Cancer Sci. 2003 Oct;94(10):886-93.
• [59] -Carotene Induces Apoptosis in Human Esophageal Squamous Cell Carcinoma Cell Lines via the Cav-1/AKT/NF-B Signaling Pathway. J Biochem Mol Toxicol. 2016 Mar;30(3):148-57. doi: 10.1002/jbt.21773. Epub 2016 Jan 6.
• [60] Selenium and vitamin E: cell type- and intervention-specific tissue effects in prostate cancer. J Natl Cancer Inst. 2009 Mar 4;101(5):306-20.
• [61] Differential gene expression of sulindac-treated human breast epithelial cells. Int J Oncol. 2005 Dec;27(6):1727-36.
• [62] Suppression of RAGE as a basis of simvastatin-dependent plaque stabilization in type 2 diabetes. Arterioscler Thromb Vasc Biol. 2006 Dec;26(12):2716-23.
• [63] Prevention of deoxycholate-induced gastric apoptosis by aspirin: roles of NF-kappaB and PKC signaling. J Surg Res. 2008 Mar;145(1):66-73. doi: 10.1016/j.jss.2007.04.039. Epub 2007 Jul 20.
• [64] Comparison of phenotypic and transcriptomic effects of false-positive genotoxins, true genotoxins and non-genotoxins using HepG2 cells. Mutagenesis. 2011 Sep;26(5):593-604.
• [65] Peroxisome proliferator-activated receptor-gamma agonists inhibit respiratory syncytial virus-induced expression of intercellular adhesion molecule-1 in human lung epithelial cells. Immunology. 2007 May;121(1):71-81. doi: 10.1111/j.1365-2567.2006.02539.x.
• [66] Differential modulation of PI3-kinase/Akt pathway during all-trans retinoic acid- and Am80-induced HL-60 cell differentiation revealed by DNA microarray analysis. Biochem Pharmacol. 2004 Dec 1;68(11):2177-86.
• [67] Glucosamine regulation of LPS-mediated inflammation in human bronchial epithelial cells. Eur J Pharmacol. 2010 Jun 10;635(1-3):219-26. doi: 10.1016/j.ejphar.2010.02.044. Epub 2010 Mar 20.
• [68] Cannabidiol enhances cytotoxicity of anti-cancer drugs in human head and neck squamous cell carcinoma. Sci Rep. 2020 Nov 26;10(1):20622. doi: 10.1038/s41598-020-77674-y.
• [69] Doxorubicin and selenium cooperatively induce fas signaling in the absence of Fas/Fas ligand interaction. Anticancer Res. 2007 Sep-Oct;27(5A):3075-82.
• [70] Response rate of fibrosarcoma cells to cytotoxic drugs on the expression level correlates to the therapeutic response rate of fibrosarcomas and is mediated by regulation of apoptotic pathways. BMC Cancer. 2005 Jul 7;5:74. doi: 10.1186/1471-2407-5-74.
• [71] The effects of quercetin in cultured human RPE cells under oxidative stress and in Ccl2/Cx3cr1 double deficient mice. Exp Eye Res. 2010 Jul;91(1):15-25.
• [72] Pharmacotoxicology of clinically-relevant concentrations of obeticholic acid in an organotypic human hepatocyte system. Toxicol In Vitro. 2017 Mar;39:93-103.
• [73] Motexafin gadolinium and zinc induce oxidative stress responses and apoptosis in B-cell lymphoma lines. Cancer Res. 2005 Dec 15;65(24):11676-88.
• [74] The role of Fas-FasL-FADD signaling pathway in arsenic-mediated neuronal apoptosis in vivo and in vitro. Toxicol Lett. 2022 Mar 1;356:143-150. doi: 10.1016/j.toxlet.2021.11.012. Epub 2021 Dec 22.
• [75] Survival of retinal pigment epithelium after exposure to prolonged oxidative injury: a detailed gene expression and cellular analysis. Invest Ophthalmol Vis Sci. 2004 Oct;45(10):3767-77.
• [76] THC exposure of human iPSC neurons impacts genes associated with neuropsychiatric disorders. Transl Psychiatry. 2018 Apr 25;8(1):89. doi: 10.1038/s41398-018-0137-3.
• [77] Ouabain induces apoptotic cell death in human prostate DU 145 cancer cells through DNA damage and TRAIL pathways. Environ Toxicol. 2019 Dec;34(12):1329-1339. doi: 10.1002/tox.22834. Epub 2019 Aug 21.
• [78] Inhibition of angiogenesis by quercetin in tamoxifen-resistant breast cancer cells. Food Chem Toxicol. 2010 Nov;48(11):3227-34. doi: 10.1016/j.fct.2010.08.028. Epub 2010 Sep 4.
• [79] Arsenic targets Pin1 and cooperates with retinoic acid to inhibit cancer-driving pathways and tumor-initiating cells. Nat Commun. 2018 Aug 9;9(1):3069. doi: 10.1038/s41467-018-05402-2.
• [80] Comparison of HepG2 and HepaRG by whole-genome gene expression analysis for the purpose of chemical hazard identification. Toxicol Sci. 2010 May;115(1):66-79.
• [81] Human embryonic stem cell-derived test systems for developmental neurotoxicity: a transcriptomics approach. Arch Toxicol. 2013 Jan;87(1):123-43.
• [82] Quantitative proteomics reveals a broad-spectrum antiviral property of ivermectin, benefiting for COVID-19 treatment. J Cell Physiol. 2021 Apr;236(4):2959-2975. doi: 10.1002/jcp.30055. Epub 2020 Sep 22.
• [83] Temozolomide induces activation of Wnt/-catenin signaling in glioma cells via PI3K/Akt pathway: implications in glioma therapy. Cell Biol Toxicol. 2020 Jun;36(3):273-278. doi: 10.1007/s10565-019-09502-7. Epub 2019 Nov 22.
• [84] Physiological and toxicological transcriptome changes in HepG2 cells exposed to copper. Physiol Genomics. 2009 Aug 7;38(3):386-401.
• [85] Predictive toxicology using systemic biology and liver microfluidic "on chip" approaches: application to acetaminophen injury. Toxicol Appl Pharmacol. 2012 Mar 15;259(3):270-80.
• [86] Gene expression profiling of 30 cancer cell lines predicts resistance towards 11 anticancer drugs at clinically achieved concentrations. Int J Cancer. 2006 Apr 1;118(7):1699-712. doi: 10.1002/ijc.21570.
• [87] Madecassoside ameliorates cisplatin-induced nephrotoxicity by inhibiting activation of the mitogen activated protein kinase pathway. Environ Toxicol. 2023 Jul;38(7):1473-1483. doi: 10.1002/tox.23777. Epub 2023 Apr 23.
• [88] Gingival Stromal Cells as an In Vitro Model: Cannabidiol Modulates Genes Linked With Amyotrophic Lateral Sclerosis. J Cell Biochem. 2017 Apr;118(4):819-828. doi: 10.1002/jcb.25757. Epub 2016 Nov 28.
• [89] Inflammation in methotrexate-induced pulmonary toxicity occurs via the p38 MAPK pathway. Toxicology. 2009 Feb 27;256(3):183-90. doi: 10.1016/j.tox.2008.11.016. Epub 2008 Nov 28.
• [90] Quercetin modulates Nrf2 and glutathione-related defenses in HepG2 cells: Involvement of p38. Chem Biol Interact. 2012 Jan 25;195(2):154-64.
• [91] Effects of chlorpromazine with and without UV irradiation on gene expression of HepG2 cells. Mutat Res. 2005 Aug 4;575(1-2):47-60. doi: 10.1016/j.mrfmmm.2005.03.002. Epub 2005 Apr 26.
• [92] Arsenic trioxide promotes ERK1/2-mediated phosphorylation and degradation of BIM(EL) to attenuate apoptosis in BEAS-2B cells. Chem Biol Interact. 2023 Jan 5;369:110304. doi: 10.1016/j.cbi.2022.110304. Epub 2022 Dec 10.
• [93] Aspirin-mediated COX-2 transcript stabilization via sustained p38 activation in human intestinal myofibroblasts. Mol Pharmacol. 2004 Feb;65(2):470-8.
• [94] Low Autophagy (ATG) Gene Expression Is Associated with an Immature AML Blast Cell Phenotype and Can Be Restored during AML Differentiation Therapy. Oxid Med Cell Longev. 2018 Mar 18;2018:1482795. doi: 10.1155/2018/1482795. eCollection 2018.
• [95] Effect of nephrotoxicants and hepatotoxicants on gene expression profile in human peripheral blood mononuclear cells. Biochem Biophys Res Commun. 2010 Oct 15;401(2):245-50. doi: 10.1016/j.bbrc.2010.09.039. Epub 2010 Sep 16.
• [96] TNF enhances trovafloxacin-induced in vitro hepatotoxicity by inhibiting protective autophagy. Toxicol Lett. 2021 May 15;342:73-84. doi: 10.1016/j.toxlet.2021.02.009. Epub 2021 Feb 17.
• [97] Endoplasmic reticulum stress contributes to autophagy and apoptosis in cantharidin-induced nephrotoxicity. Food Chem Toxicol. 2022 May;163:112986. doi: 10.1016/j.fct.2022.112986. Epub 2022 Apr 6.
• [98] Artesunate alleviates liver fibrosis by regulating ferroptosis signaling pathway. Biomed Pharmacother. 2019 Jan;109:2043-2053. doi: 10.1016/j.biopha.2018.11.030. Epub 2018 Nov 26.