Exploration of Indole Alkaloids from Marine Fungus Pseudallescheria boydii F44-1 Using an Amino Acid-Directed Strategy

 

Mei-Xiang Yuan 1, Yi Qiu 1, Yan-Qin Ran 2, Gong-Kan Feng 3, Rong Deng 3, Xiao-Feng Zhu 3, Wen-Jian Lan 4,* and Hou-Jin Li 1,*O
1School of Chemistry, Sun Yat-sen University, Guangzhou 510275, China; [email protected] (M.-X.Y.); [email protected] (Y.Q.)
2School of Traditional Chinese Medicine, Guangdong Pharmaceutical University, Guangzhou 510006, China; [email protected]
3State Key Laboratory of Oncology in South China, Collaborative Innovation Center for Cancer Medicine, Cancer Center, Sun Yat-sen University, Guangzhou 510060, China; [email protected] (G.-K.F.); [email protected] (R.D.); [email protected] (X.-F.Z.)
4School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China
* Correspondence: [email protected] (W.-J.L.); [email protected] (H.-J.L.); Tel.: +86-20-39943042 (W.-J.L.); +86-20-84113698 (H.-J.L.)

 

 

1.Introduction
Marine indole alkaloids are an increasingly growing class of secondary metabolites. From 2003 to 2015, about 800 new marine indole alkaloids were obtained [1]. Indole alkaloids一including mono-, bisand trisindole alkaloids一are biosynthetically derived from one-, two- and three-indole building blocks, respectively, and have high structural diversity. Some of them were found to possess diverse biological activity, such as cytotoxic, antiviral, antiplasmodial, antifungal, antibacterial and anti-inflammatory activity, and are therefore promising leads for new drug development [2—5]. The natural occurrence of indole alkaloids is the result of biosynthesis via the coupling of the inessential amino acid tryptophan with other amino acids and structural fragments. Based on this consideration, our research group established an amino acid-directed strategy to explore the potential of marine fungi to produce diverse alkaloids. To date, more than forty novel and/or bioactive indole alkaloids have been obtained from marine fungi. For example, when cultured in glucose-peptone-yeast (GPY) extract medium supplemented with L-tryptophan, L-phenylalanine, L-threonine, and D,L-methionine, the marine fungus Scedosporium apiospermum F41-1 produced 12 new indole alkaloids. Among them, scedapin C and scequinadoline D displayed significant antiviral activity against hepatitis C [6]. A total of 18 indole alkaloids were isolated from the marine fungus Dichotomomyces cejpii F31-1 by feeding it with L-tryptophan and L-phenylalanine [7]. Scequinadoline A possesses the potential for further development as a dengue virus inhibitor [8].

 

Pseudallescheria species are filamentous fungi widely distributed in nature. The literature on the secondary metabolites of this fungal genus is still limited. In our previous research on marine fungi, three fungal strains were collected from marine organisms, and their metabolites showed chemodiversity and biodiversity. Two isobenzofuranone derivatives, pseudaboydins A and B [9], two new chlorinated benzofuran derivatives, 6-chloro-2-(2-hydroxypropan-2-yl)-2,3-dihydro-5-hydroxybenzofuran and 7-chloro-2-(2-hydroxypropan-2-yl)-2,3-dihydro-5-hydroxybenzofuran [10], were isolated from Pseudallescheria boydii, associated with the starfish Acanthaster planci. Pseudaboydin A showed moderate cytotoxic activity [9]. Two aromadendrane-type sesquiterpene diastereomers pseuboydones A and B, two diketopiperazines pseuboydones C and D, and a cyclopiazonic acid analogue pseuboydone E were isolated from the culture broth of the marine fungus Pseudallescheria boydii F19-1, which is associated with the soft coral Lobophytum crassum. Pseuboydone C displayed significant cytotoxicity against Sf9 cells from the fall armyworm Spodoptera frugiperda [11]. The pseudellones A—D [12] and (5S,6S)-dihydroxylasiodiplodin [13] were isolated from the marine fungus Pseudallescheria ellipsoidea F42-3, associated with the soft coral Lobophytum crissum.

 

Recently, another marine fungus Pseudallescheria boydii (collection no. F44-1) was isolated from the soft coral Sarcophyton sp. collected in the Hainan Sanya National Coral Reef Reserve, China. This fungal strain was cultured in GPY medium and GPY medium supplied with amino acids, including L-tryptophan, L-phenylalanine, L-methionine, and L-threonine. The culture extracts were analyzed with HPLC detected at UV 254 nm. HPLC traces indicated that Pseudallescheria boydii F44-1 cultured in the GPY medium containing additional amino acids could produce more metabolites with strong UV absorption (Figure 1 and Supplementary Figure S1). This meant that amino acids could regulate the production of metabolites containing aromatic rings. By tracking the characteristic 1H NMR signals in the aromatic region 6.5—8.5 ppm, two new bisindole alkaloids pseudboindoles A and B (1 and 2), together with 11 known indole alkaloids (Figure 2), were obtained efficiently. Here, we reported the isolation, structure elucidation and cytotoxic activity of these compounds.

2.Results and Discussion
2.1.Structural Elucidation
Pseudboindole A (1) was obtained as a brown amorphous powder. The molecular formula was determined to be C19H18N2O by HR-(+)ESI-MS at m/z 291.14789 [M + H]+ (calculated for C19H19N2O, 291.14919) (Supplementary Figure S2), which has 12 degrees of unsaturation. The IR spectrum indicated the presence of the hydroxy group (3409 cm-1) and benzene ring (1618 and 1456 cm-1). UV maxima at 222 and 282 nm also displayed the conjugated system containing a benzene ring. The 13C NMR and DEPT showed one methylene, six methines and three quaternary carbons (Table 1 and Supplementary Figures S4-S6). The 1H NMR spectrum showed a set of adjacent aromatic protons at 8h 7.61 (brd, 8.0, H-4), 7.34 (brd, 8.0, H-7), 7.21 (ddd, 8.0, 8.0, 0.8, H-6) and 7.12 (ddd, 8.0, 8.0, 0.8, H-5) (Supplementary Figure S3), indicating the existence of an ortho-disubstituted aromatic ring. Besides, the 1H NMR spectrum also displayed one methylene group (8H 3.09, dd, 14.4, 4.8; 2.95, dd, 14.4, 8.0), one methine group (8H 4.30, dddd, 8.0, 8.0, 4.8,4.8, H-9), one hydroxyl group (8H 2.08, brs), and a broad singlet (8H 8.10, brs, NH) (Supplementary Figure S7). The 1H-1H COSY cross-peaks of H-1/H-2, H-4/H-5/H-6/H-7 (Figure 3 and Supplementary Figure S8) and the HMBC correlations from H-4 to C-7a (8c 136.3), H-7 to C-4a (8c 127.6), H-2 to C-3 (8c 112.4) (Supplementary Figure S9) were indicative of the presence of a 3-substitued indole alkaloid skeleton. In addition, the 1H-1H COSY correlations of H-8/H-9 demonstrated the presence of a —CH2CH- moiety. C-3 was connected to C-8 based on the HMBC correlations of H-8 with C-2/C-3/C-4a, and the NOESY correlation of H-4/H-8 (Supplementary Figure S10). The remaining hydrogen deficiency index further determined that two identical structural moieties were connected to C-9 (8c 71.5). Consequently, the chemical structure of pseudboindole A (1) was illustrated as 1,3-di(1H-indol-3-yl)propan-2-ol (Figure 1).

 

The molecular formula of pseudboindole B (2) was revealed to be C20H20N2OS by HR-(-)ESI-MS at m/z 335.12247 [M-H]- (Supplementary Figure S11) requiring 13 degrees of unsaturation. IR absorption at 1659 and 1419 cm-1 and UV maxima at 222 and 282 nm also indicated the existence of the benzene ring conjugated system. The 13C NMR and DEPT spectra (Supplementary Figures S13-S15) displayed one methyl, two methylenes, six methines and three quaternary carbons (Table 1). In the 1H NMR spectrum (Supplementary Figure S12), the integral ratios of aryl proton, methylene, and methyl were 1:1:1.5 and indicated that the molecular structure was symmetrical. The 1H NMR spectrum displayed aromatic protons at 8H 7.55 (dd, 7.6, 7.6, H-5), 7.34 (d, 8.0, H-7), 7.16 (dd, 8.0, 7.6, H-6) and 7.04 (d, 7.6, H-4) and 1H-1H COSY correlations of H-4/H-5/H-6/H-7 (Figure 3) revealed the existence of an ortho-disubstituted aromatic ring. Additionally, the 1H-1H COSY correlations of H-1/H-2 (Supplementary Figure S17) and the key HMBC correlations of H-4 (H-6)/C-7a (8C 136.60 or 136.56), H-5 (H-7)/C-4a (8C 126.80 or 126.71), and H-2/C-4a/C-7a/C-3 (8C 118.67 or 118.40) (Supplementary Figures S16 and S18) indicated a 3-substitued indole skeleton. The 1H-1H COSY cross peaks of H-8/H-9/H-10 revealed the fragment of -CHCH2CH2-. The remaining methyl singlet signal at 8H 2.47 (H3-12) was connected to a sulfoxide group, which can enable the  further analysis of the HMBC correlation of H3-I2 to C-10 (8c 53.0). Consequently, the chain partial structure of —CHCH2CH2SOCH3 was established. The HMBC correlations of H-8/C-3 indicated that two 3-substitued indole parts were connected to C-8 (8c 33.2), which was confirmed by the NOESY correlation of H-4/H-8 (Supplementary Figure S19).

 

Therefore, the chemical structure of pseudboindole B (2) was unambiguously established, as shown in Figure 2.
Compound 3 was a brown amorphous powder. It had the molecular formula C22H22N2, which was established on the basis of the HR-(—)ESI-MS ion at m/z 313.17120 [M—H]— (calcd. for C22H21N2,313.17102) (Supplementary Figure S20) and indicated 13 degrees of unsaturation. The 1D and 2D NMR data recorded in CDCI3 and acetone-d6 were slightly different (Table 2 and Supplementary Figures S21-S33). The 13C NMR and DEPT spectra displayed three methylenes, five methines and four quaternary carbons. Compared with the NMR data of pseudboindoles A and B, the fragment of 3-substitued indole also existed. The 1H-1H COSY cross peaks of H-9/H-10/H-11 (Figure 3) revealed the remaining three methylene forming the fragment of — CH2CH2CH2 —. However, the integrals of H-9, H-10, H-11 and aromatic proton were 2:2:1:1. Based on the above analysis, compound 3 was inferred containing a symmetric framework and belonged to the bisindole class. The analysis of the HMBC correlations ofH-2 (8h 7.10, d, 1.8)/C-8 (8c 39.5),H-9 (8h 2.55, t, 6.0)/C-8, H-10 (8h 1.66, m)/C-8, the two 3-substitued indole parts and the chain part of —CH2CH2CH2CH2CH2 — were connected to C-8. The chemical structure of compound 3 was illustrated as 3,3z-cyclohexylidenebis(1H-indole), as seen in Figure 2. The 3,3'-cyclohexylidenebis(1H-indole) (3) can be synthesized by the reaction of an indole with cyclohexanone, and showed rather potent enhancing activity (140%) on Am80-induced HL-60 cell differentiation [14,15]. This is the first report of compound 3 as a natural product and its 1H and 13C NMR data assignment were elaborated unambiguously.

Compounds 4-13 were identified as 3,3-bis(3-indolyl)butan-2-one (4) [16], 2-[2,2-di(1H-indol-3-yl) ethyl] aniline ⑸[17], 3,3'-diindolyl(phenyl)methane (6) [18], 1,1-(3,3z-diindolyl)-2-phenylethane (7) [18], perlolyrin (8) [19], pityriacitrin (9) [20], 1-acetyl-p-carboline (10) [21], 3-hydroxy-p-carboline (11) [22], 1-(9H-pyrido[3,4-b]indol-1-yl)ethan-1-ol (12) [23], and Nb-acetyltryptamine (13) [24], respectively, by comparing their spectroscopic data (Supplementary Figures S34-S74) with the literature values.

 

2.2.Biological Activity
Eight cancer cell lines, including human lung cancer cell lines A549 and GLC82, human nasopharyngeal carcinoma cell lines CNE1, CNE2, HONE1 and SUNE1, human hepatoma carcinoma cell lines BEL7402 and SMMC7721, were used to evaluate the cytotoxic activities of 1—13 in vitro. As a result, compound 3 showed significant cytotoxicity against these cancer cell lines A549, GLC82, CNE1, CNE2, HONE1, SUNE1, BEL7402, and SMMC7721 with the IC50 values of 22.84, 22.04,18.69, 20.84, 26.62,20.54,27.52 and 22.50 卩M, respectively. In contrast, 1, 2 and 4-13 were apparently inactive in this assay (IC50 > 200 卩M). 

3.Materials and Methods
3.1.General Procedures
The column chromatography made use of silica gel (SiO?, 200-300 mesh, Qingdao Marine Chemical Inc., Qingdao, China). Preparative HPLC was performed using a Shimadzu LC-20AT HPLC pump (Shimadzu Corporation, Nakagyo-ku, Kyoto, Japan) and installed with an SPD-20A dual 入 absorbance detector (Shimadzu Corporation, Nakagyo—ku, Kyoto, Japan) and a Capcell—Pak C18 UG80 HPLC column (250 mmx20 mm, Shiseido Co., Ltd., Minato-ku, Tokyo, Japan) and a Spolar HPLC packed column (250 mm x 4.6 mm, Shiseido Co., Ltd., Minato-ku, Tokyo, Japan). The melting point used the melting point apparatus WRS-3 (Shenguang, Shanghai, China) to record. UV data were obtained on a Shimadzu UV-Vis-NIR spectrophotometer (Shimadzu Corporation, Nakagyo-ku, Kyoto, Japan). IR spectra were recorded on a PerkinElmer Frontier FT-IR spectrophotometer (PerkinElmer Inc., Waltham, MA, USA). The 1D and 2D NMR experiments were measured with Bruker Avance 400 spectrometer and Bruker Avance 600 spectrometer (Bruker Bio Spin AG, Industriestrasse 26, Fallanden, Switzerland). The chemical shifts were relative to the residual solvent signals (CDO3： 6h 7.260 and 77.000; acetone-d6： 8h 2.050 and 29.840; and methanol-d. 6h 3.310 and 6c 49.000). HR-ESI-MS data were collected on a Thermo Fisher LTQ Orbitrap Elite high-resolution mass spectrometer (Thermo Fisher Scientific Inc., Waltham, MA, USA).

 

3.2.Fungal Strain and Culture Method
The marine fugus Pseudallescheria boydii (collection no. F44-1) was isolated from the inner tissue of the soft coral Sarcophyton sp. collected from Hainan Sanya National Coral Reef Reserve, China. This fungal strain was conserved in 15% (v/v) glycerol aqueous solution at —80 °C. A voucher specimen was deposited in the School of Chemistry, Sun Yat-sen University, Guangzhou, China. Analysis of the ITS rDNA by BLAST database screening provided 99.9% match to Pseudallescheria boydii.
The fermentation medium was glucose 15 g, peptone 10 g, yeast extract 2 g, L-tryptophan 2 g, L-phenylalanine 2 g, L-methionine 2 g, L-threonine 2 g, sea salt 25 g, and H2O 1L at pH 7.5. Fungal mycelia were cut and transferred aseptically to 1000 mL conical flasks each containing 400 mL sterilized liquid medium. The flasks were incubated at 28 °C for 20 days.

 

3.3.Extraction and Isolation
A total of 60 liters of liquid culture were filtered through cheesecloth. The culture broth was successively extracted five times with EtOAc (60 L). Finally, the extract was concentrated by low-temperature rotary evaporation to obtain a crude extract (39.8 g).

 

The extract was chromatographed on a silica gel column (diameter: 8 cm, length: 70 cm, silica gel, 450 g) with a gradient of petroleum ether-EtOAc (100：0-0：100, v/v) followed by EtOAc-MeOH (100:0—0:100, v/v) to yield thirty fractions (Fr.1—Fr.30). Fr. 15—Fr.19 were merged for having the similar fractions as monitored by 1H NMR prescreening, and then, the constituents was purified by silica gel column using a step gradient elution with petroleum ether—EtOAc (10:0—0:10, v/v) to obtain 8 subfractions (Fr.15-19-1—Fr.15-19-8). Compound 1 (18.3 mg) was obtained from Fr. 15-19-6 by repeated preparative HPLC using CH3CN—H2O (60:40, v/v, RT = 37.5 min) as eluent. HPLC purification of Fr. 9 with a solvent system CH3OH—H2O (75:25, v/v, RT = 23.5 min) gave compound 2 (16.5 mg). Fr.5 was purified by preparative HPLC with a mobile phase of MeOH-H?。 (75:25, v/v, RT = 54 min) to obtain compound 3 (15.3 mg). Fr.12 was purified with preparative HPLC (CH3CN—H2O, 80:20, v/v, RT = 27 min) to obtain compound 4 (5.3 mg). Fr.10-Fr.11 was merged after
NMR prescreening, and then were purified with preparative HPLC using CH3CN—H2O (85:15, v/v) as eluent to obtain compounds 5 (RT = 28 min, 6.1 mg), 6 (RT = 34 min, 1.5 mg), 7 (RT = 35 min, 1.0 mg), and 9 (RT = 52 min, 5.6 mg). Similarly, Fr.21 was purified with preparative HPLC and eluted with CH3CN—H2O (70:30, v/v) to obtain compound 8 (RT = 27 min, 20.0 mg). Compound 10 (12.3 mg) was purified from Fr.7 with preparative HPLC (CH3OH—H2O, 75:25, v/v, RT = 47.5 min). Fr.23-Fr.24 was further purified using CH3OH—H2O (75:25, v/v)as eluent and got compounds 11 (RT = 39 min, 5.5 mg), 12 (RT = 43 min, 5.2 mg) and 13 (RT =31 min, 5.4 mg).

Pseudboindole A (1). Brown amorphous powder. mp 116.2 — 116.8 0C. UV (MeOH)入max (log e): 282 (3.73), 222 (4.45). IR Umax 3409,2924, 1678, 1618, 1456,1340, 1227, 1094, 1050, 738 cm-1. 1H and 13C NMR data, see Table 1; HR-(+) ESI-MS m/z 291.14789 [M + H]+ (calcd. for C19H19N2O, 291.14919).
Pseudboindole B (2). Brown amorphous powder. mp 113.9 — 114.8 OC. UV (MeOH)入max (log e): 282 (3.82), 222 (4.51). IR Umax 3420, 2980,2926,1659,1419,1332,1197,1094,1050, 937, 881, 741 cm-1. 1H and 13C NMR data, see Table 1; HR-(—)ESI-MS m/z 335.12247 [M—H]— (calcd. for C20H19N2OS, 335.12236).

 

3,3'-cyclohexylidenebis(1H-indole) (3). Brown amorphous powder. mp 114.7—115.9 OC. UV (MeOH)入max (log e): 283 (3.88), 224 (4.63). IR Umax 3405, 2935, 1686, 1618, 1456, 1415, 1097, 1336,1242,1103, 1046, 1012, 817, 738 cm-1. 1H and 13C NMR data, see Table 2; HR-(—) ESI-MS m/z 313.17120 [M—H]— (calcd. for C22H21N2,313.17102).

 

3.4.Cytotoxicity Assay
The in vitro cytotoxic activity of 1— 13 was determined by means of the colorimetric MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide) assay. The tested human cancer cell lines were seeded in 96-well plates at a density of 3 x 107 cells/L, and the compounds were added at various concentrations (7.864—30.00 ^M). After 72 h, MTT was added to the culture medium at a final concentration of 0.5 mg/mL, and the plates were incubated for 4 h at 37 OC. The supernatant was removed. The formazan crystals were dissolved in DMSO (150 ^L) with gentle shaking at room temperature. The absorbance at 570 nm was recorded with a microplate reader (Bio-Rad, Hercules, CA, USA), and the data were analyzed with the SPSS (version 13.0) [25].

 

4.Conclusions
By tracking characteristic 1H NMR signals in the aromatic region of 6.50—8.50 ppm, two new bisindole compounds, pseudboindoles A and B (1 and 2), together with 11 known indole alkaloids (3—12) were efficiently isolated from the marine fungus Pseudallescheria boydii F44-1. The 3,3'-cyclohexylidenebis(1H-indole) (3) showed significant cytotoxic activity against various cancer cell lines. The result proves again that an amino acid-directed strategy is effective for inducing the marine fungi to produce diverse alkaloids. However, the specific quantitative relationship between amino acids and alkaloids and their biosynthesis pathways still need further study. After revealing these relationships, the application of this strategy will be more efficient.

 

Supplementary Materials: HPLC analysis of the fungal metabolites in different culture media (Supplementary Figure S1), the HR-ESI-MS and NMR spectra of compounds 1-13 (Supplementary Figures S2-S74) are available online at http://www.mdpi.com/1660-3397/17/2/77/s1.

 

Author Contributions: M.-X.Y. performed the fungus culture, extraction, isolation, structural identification and wrote the draft. Y.Q. and Y.-Q.R. identified the fungal species. G.-K.F., R.D. and X.-F.Z. tested the cytotoxicity of the compounds. W.-J.L. and H.-J.L. conceived and designed the experiments, and revised the paper.

 

Funding: This research was funded by the National Natural Science Foundation of China (No. 81872795), Guangdong Provincial Science and Technology Research Program (No. 2016A020222004), Natural Science Foundation of Guangdong Province (No. 2018A030313157), and the National Science and Technology Major Project for New Drug Innovation and Development (No. 2017ZX09305010).
Conflicts of Interest: The authors declare no conflict of interest.

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4-ThiazoleMethanol,5-broMo-2-Methyl Catalog No.:AA0095KY CAS No.:1092506-38-1 MDL No.:MFCD28156576 MF:C5H6BrNOS MW:208.0762	Farnesyl Thiosalicylic Acid Amide Catalog No.:AA007TB9 CAS No.:1092521-74-8 MDL No.:MFCD11976913 MF:C22H31NOS MW:357.5526
(4-Amino-phenyl)-methyl-carbamic acid tert-butyl ester Catalog No.:AA00927N CAS No.:1092522-02-5 MDL No.:MFCD10693199 MF:C12H18N2O2 MW:222.2835	[12]Cycloparaphenylene Catalog No.:AA008WUO CAS No.:1092522-75-2 MDL No.:MFCD20265583 MF:C72H48 MW:913.1515
6-Bromo-1-methyl-1,2,3,4-tetrahydroquinolin-2-one Catalog No.:AA0099AI CAS No.:1092523-03-9 MDL No.:MFCD18266837 MF:C10H10BrNO MW:240.0965	2-AMino-7-chloro-1-ethyl-N-Methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxaMide Catalog No.:AA008WNP CAS No.:1092523-24-4 MDL No.:MFCD22571280 MF:C12H13ClN4O2 MW:280.7102
3-Bromo-4-fluorophenylboronic acid Catalog No.:AA008YZ6 CAS No.:1092533-91-9 MDL No.:MFCD13195642 MF:C6H5BBrFO2 MW:218.8161	4-Benzyloxy-3,3-dimethylbut-1-yne Catalog No.:AA008TB8 CAS No.:1092536-54-3 MDL No.:MFCD23106327 MF:C13H16O MW:188.2655
SAR131675 Catalog No.:AA008WBB CAS No.:1092538-80-1 MDL No.: MF:C18H22N4O4 MW:358.3917	Atazanavir D6 Catalog No.:AA0094AR CAS No.:1092540-50-5 MDL No.:MFCD21363445 MF:C38H46D6N6O7 MW:710.8925
Deuterated Atazanivir-D3-2 Catalog No.:AA008VZ1 CAS No.:1092540-51-6 MDL No.:MFCD22427959 MF:C38H43D9N6O7 MW:713.9109	Bis-propargyl-peg9 Catalog No.:AA00HBBL CAS No.:1092554-87-4 MDL No.:MFCD27635156 MF:C22H38O9 MW:446.5317
4-(Chloromethyl)-2-nitrothiophene Catalog No.:AA0094G9 CAS No.:1092561-29-9 MDL No.:MFCD12197117 MF:C5H4ClNO2S MW:177.6088	4-{[2-Fluoro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbonyl}morpholine Catalog No.:AA00HBBM CAS No.:1092563-24-0 MDL No.:MFCD27936080 MF:C17H23BFNO4 MW:335.1782
4-{[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}thiomorpholine-1,1-dione Catalog No.:AA00HBBN CAS No.:1092563-25-1 MDL No.:MFCD22056473 MF:C17H26BNO4S MW:351.2686	[2-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-pyrrolidin-1-yl-methanone Catalog No.:AA01FTBZ CAS No.:1092563-41-1 MDL No.:MFCD26399448 MF:C18H26BNO3 MW:315.2149
1-(1-Boc-4-piperidyl)-3-methylpyrazole-4-boronic acid pinacol ester Catalog No.:AA003CPI CAS No.:1092563-68-2 MDL No.:MFCD22570866 MF:C20H34BN3O4 MW:391.3127	tert-Butyl 4-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-pyrazol-1-yl)methyl)piperidine-1-carboxylate Catalog No.:AA003ADW CAS No.:1092563-72-8 MDL No.:MFCD18383260 MF:C20H34BN3O4 MW:391.3127
Morpholin-4-yl-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2-trifluoromethyl-phenyl]-methanone Catalog No.:AA01FSF3 CAS No.:1092564-34-5 MDL No.:MFCD28718144 MF:C18H23BF3NO4 MW:385.1857	4-{[2-Methoxy-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbonyl}morpholine Catalog No.:AA00HBBU CAS No.:1092564-35-6 MDL No.:MFCD27936083 MF:C18H26BNO5 MW:347.2137
Methyl 3-(5-methyl-1,2,4-oxadiazol-3-yl)benzoate Catalog No.:AA0099AK CAS No.:1092566-65-8 MDL No.:MFCD12198875 MF:C11H10N2O3 MW:218.2087	5-Bromooxazolo[4,5-b]pyridin-2(3h)-one Catalog No.:AA00IM7E CAS No.:1092569-10-2 MDL No.:MFCD22561766 MF:C6H3BrN2O2 MW:215.0042
3-cyclopentyl-1Н-indole Catalog No.:AA01DUW0 CAS No.:1092574-87-2 MDL No.:MFCD11042552 MF:C13H15N MW:185.2649	(3R,4S)-Tofacitinib Catalog No.:AA008T6I CAS No.:1092578-46-5 MDL No.:MFCD23160057 MF:C16H20N6O MW:312.3696
(3S,4S)-Tofacitinib Catalog No.:AA008T6M CAS No.:1092578-47-6 MDL No.:MFCD11035920 MF:C16H20N6O MW:312.3696	5-Bromo-4-chloro-3-iodo-1h-pyrrolo[2,3-b]pyridine Catalog No.:AA008YYH CAS No.:1092579-75-3 MDL No.:MFCD13193525 MF:C7H3BrClIN2 MW:357.3736
5-Bromo-4-chloro-3-iodo-1h-pyrazolo[3,4-b]pyridine Catalog No.:AA0094I9 CAS No.:1092579-78-6 MDL No.:MFCD21604023 MF:C6H2BrClIN3 MW:358.3617	methyl 5-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)-4-oxopentanoate Catalog No.:AA00VUMB CAS No.:109258-71-1 MDL No.:MFCD00591807 MF:C14H13NO5 MW:275.2567
3-(10H-Phenothiazin-10-yl)propan-1-amine hydrochloride Catalog No.:AA019MFR CAS No.:109262-13-7 MDL No.:MFCD10686887 MF:C15H17ClN2S MW:292.8269	WAY100635 Catalog No.:AA008YU3 CAS No.:1092679-51-0 MDL No.:MFCD01321056 MF:C29H38N4O6 MW:538.6352
4-Bromo-1H-pyrazole-5-carboxylic acid Catalog No.:AA008VCL CAS No.:1092683-57-2 MDL No.:MFCD00463984 MF:C4H3BrN2O2 MW:190.9828	rac-(1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-ylacetic acid Catalog No.:AA00J10S CAS No.:1092689-34-3 MDL No.:MFCD25977713 MF:C9H12O2 MW:152.1904
tert-Butyl 2,2-difluoro-3-(methacryloyloxy)pentanoate Catalog No.:AA0093UT CAS No.:1092693-73-6 MDL No.:MFCD26743594 MF:C13H20F2O4 MW:278.2923	2-(Chloromethyl)-6-nitro-1h-benzimidazole, HCl Catalog No.:AA00HBC4 CAS No.:1092698-81-1 MDL No.:MFCD08445314 MF:C8H7Cl2N3O2 MW:248.0661
4-{[3-(2-aminoethyl)-2,4-dioxo-1,3-thiazolidin-5-ylidene]methyl}-2-methoxyphenyl 2,5-dimethylbenzene-1-sulfonate hydrochloride Catalog No.:AA019HZ7 CAS No.:1092706-04-1 MDL No.:MFCD26143578 MF:C21H23ClN2O6S2 MW:499.0001	2,2,2-Trifluoro-1-(2,4,6-trifluoro-phenyl)-ethanone Catalog No.:AA01F8L8 CAS No.:1092712-19-0 MDL No.:MFCD12547805 MF:C8H2F6O MW:228.0913
1-(2,5-Difluoro-phenyl)-2,2,2-trifluoro-ethanone Catalog No.:AA01EQNK CAS No.:1092712-24-7 MDL No.:MFCD07380754 MF:C8H3F5O MW:210.1008	1-(2,6-Difluorophenyl)-2,2,2-trifluoroethanone Catalog No.:AA00HBC5 CAS No.:1092712-26-9 MDL No.:MFCD08447307 MF:C8H3F5O MW:210.1008
Dehydro Lovastatin Catalog No.:AA008VV1 CAS No.:109273-98-5 MDL No.:MFCD18382246 MF:C24H34O4 MW:386.5244	4-(azepan-1-yl)aniline hydrochloride Catalog No.:AA019O5W CAS No.:1092733-37-3 MDL No.:MFCD06683755 MF:C12H19ClN2 MW:226.7457
Ethyl 3-hydroxyfuro[2,3-b]pyridine-2-carboxylate Catalog No.:AA009TJZ CAS No.:109274-83-1 MDL No.:MFCD13659444 MF:C10H9NO4 MW:207.1828	Furo[2,3-b]pyridine-2-carbaldehyde Catalog No.:AA007AYV CAS No.:109274-92-2 MDL No.:MFCD18384579 MF:C8H5NO2 MW:147.1308
Biotinamidocaproyl hydrazide Catalog No.:AA007AYT CAS No.:109276-34-8 MDL No.:MFCD00077659 MF:C16H29N5O3S MW:371.4982	[Ir{dFCF3ppy}2(bpy)]PF6 Catalog No.:AA01FFGN CAS No.:1092775-61-5 MDL No.:MFCD28987331 MF:C34H36F16IrN4P MW:1027.8417
[Ir{dFCF3ppy}2(bpy)]PF6 Catalog No.:AA01FOVY CAS No.:1092775-62-6 MDL No.:MFCD28987331 MF:C34H18F16IrN4P MW:1009.6987	CarbaMiMidothioic acid, N,N'-dicyclohexyl-, (5,6-dihydro-6,6-diMethyliMidazo[2,1-b]thiazol-3-yl)Methyl ester, hydrochloride (1 Catalog No.:AA0095UY CAS No.:1092776-63-0 MDL No.:MFCD22683853 MF:C21H36Cl2N4S2 MW:479.5733
PP121 Catalog No.:AA007TAX CAS No.:1092788-83-4 MDL No.:MFCD12912434 MF:C17H17N7 MW:319.3638	2-Methylquinoline-6-boronic acid Catalog No.:AA00J1V3 CAS No.:1092790-20-9 MDL No.:MFCD08062388 MF:C10H10BNO2 MW:187.0029
Isoquinoline-7-boronic acid Catalog No.:AA008U7O CAS No.:1092790-21-0 MDL No.:MFCD08234617 MF:C9H8BNO2 MW:172.9763	Methyl 4,5-dibromo-1H-pyrazole-3-carboxylate Catalog No.:AA00945X CAS No.:1092791-47-3 MDL No.:MFCD23135916 MF:C5H4Br2N2O2 MW:283.9055
Methyl 1-(2-cyanophenyl)cyclopropanecarboxylate Catalog No.:AA0093J4 CAS No.:1092794-06-3 MDL No.:MFCD20040025 MF:C12H11NO2 MW:201.2212	1-(2,3-Dihydro-1,4-benzodioxin-6-yl)ethanamine hydrochloride Catalog No.:AA0082M0 CAS No.:1092797-55-1 MDL No.:MFCD06800568 MF:C10H14ClNO2 MW:215.6767
1-(2,3-Dihydro-1,4-benzodioxin-6-yl)propan-1-amine hydrochloride Catalog No.:AA00LU53 CAS No.:1092797-59-5 MDL No.:MFCD09698670 MF:C11H15NO2 MW:193.2423	1-(4-Fluorophenyl)propan-1-amine hydrochloride Catalog No.:AA00968C CAS No.:1092797-76-6 MDL No.:MFCD09698672 MF:C9H13ClFN MW:189.6576
N-(2,6-dimethylphenyl)-4-[2-hydroxy-3-(2-methoxyphenoxy)propyl-1,1,2,3,3-d5]-1-piperazineacetamide Catalog No.:AA01EQ7G CAS No.:1092804-87-9 MDL No.: MF:C24H28D5N3O4 MW:432.5673	Lisinopril (8R,S)-Diketopiperazine (Mixture of Diastereomers) Catalog No.:AA008WMO CAS No.:1092813-99-4 MDL No.:MFCD18385050 MF:C21H29N3O4 MW:387.4727
4-(3,4-Difluorophenoxy)benzonitrile Catalog No.:AA01ABMB CAS No.:1092841-52-5 MDL No.:MFCD12075535 MF:C13H7F2NO MW:231.1976	2-Bromo-6-butoxypyridine Catalog No.:AA003GNR CAS No.:1092848-28-6 MDL No.:MFCD12026048 MF:C9H12BrNO MW:230.1017
4-(Azepan-1-ylsulfonyl)aniline Catalog No.:AA007AYO CAS No.:109286-01-3 MDL No.:MFCD01613158 MF:C12H18N2O2S MW:254.3485	H-Arg-gly-asp-cys-oh Catalog No.:AA008RPN CAS No.:109292-46-8 MDL No.:MFCD00076451 MF:C15H27N7O7S MW:449.4826
1,3-Benzenedicarbonitrile, 2,5-dichloro- Catalog No.:AA01CBM4 CAS No.:109292-89-9 MDL No.: MF:C8H2Cl2N2 MW:197.0209	n-HexadecyltriMethyl-d3-aMMoniuM BroMide Catalog No.:AA008VXP CAS No.:1092921-73-7 MDL No.:MFCD03428205 MF:C19H39BrD3N MW:367.4660
4-(2-fluorophenyl)butan-2-amine Catalog No.:AA01DX7Q CAS No.:1092924-49-6 MDL No.:MFCD11655369 MF:C10H14FN MW:167.2233	4-(3-fluorophenyl)butan-2-amine Catalog No.:AA01AIR3 CAS No.:1092924-64-5 MDL No.:MFCD11655346 MF:C10H14FN MW:167.2233
2-[N-[(3,5-Difluorophenyl)Carbamoylamino]-C-Methylcarbonimidoyl]Pyridine-3-Carboxylic Acid Catalog No.:AA01EH1B CAS No.:109293-97-2 MDL No.:MFCD03095702 MF:C15H12F2N4O3 MW:334.2776	DIFLUFENZOPYR SODIUM SALT Catalog No.:AA008S35 CAS No.:109293-98-3 MDL No.:MFCD04974587 MF:C15H11F2N4NaO3 MW:356.2594
(R)-Binsa dipotassium salt Catalog No.:AA009439 CAS No.:1092934-19-4 MDL No.:MFCD28386102 MF:C20H14KO6S2 MW:453.5499	2-(4-Ethylcyclohex-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Catalog No.:AA008WDP CAS No.:1092938-90-3 MDL No.:MFCD18383326 MF:C14H25BO2 MW:236.1581
2-(4-Methoxycyclohex-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Catalog No.:AA003LKX CAS No.:1092938-92-5 MDL No.:MFCD18383325 MF:C13H23BO3 MW:238.1309	(R)-3-(4-(7H-Pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl)-3-cyclopentylpropanenitrile phosphate Catalog No.:AA008R3K CAS No.:1092939-17-7 MDL No.:MFCD18452860 MF:C17H21N6O4P MW:404.3602
2-Bromo-N-methyl-1,3-thiazole-4-carboxamide Catalog No.:AA007AYM CAS No.:1092942-42-1 MDL No.:MFCD20265433 MF:C5H5BrN2OS MW:221.0750	Imatinib-d8 Catalog No.:AA008SN2 CAS No.:1092942-82-9 MDL No.:MFCD09955542 MF:C29H23D8N7O MW:501.6520
Gleevec-d8Mesylate(Imatinib-d8Mesylate) Catalog No.:AA01DZHO CAS No.:1092942-83-0 MDL No.: MF:C30H27D8N7O4S MW:597.7577	2,2-Dimethyl-1-phenylcyclopropan-1-amine Catalog No.:AA01B76G CAS No.:109296-40-4 MDL No.:MFCD20694520 MF:C11H15N MW:161.2435
1H-Pyrrolo[3,2-b]pyridin-3-amine Catalog No.:AA008UN2 CAS No.:1092960-98-9 MDL No.:MFCD11052612 MF:C7H7N3 MW:133.1506	7-(Bromomethyl)-1-methyl-1h-indazole Catalog No.:AA008UNI CAS No.:1092961-00-6 MDL No.:MFCD11052615 MF:C9H9BrN2 MW:225.0852
6-(Bromomethyl)-1-methyl-1h-indazole Catalog No.:AA00397L CAS No.:1092961-01-7 MDL No.:MFCD11052616 MF:C9H9BrN2 MW:225.0852	5-(Bromomethyl)-1-methyl-1h-indazole Catalog No.:AA008TQL CAS No.:1092961-02-8 MDL No.:MFCD11052617 MF:C9H9BrN2 MW:225.0852
4-(Bromomethyl)-1-methyl-1H-indazole Catalog No.:AA008U66 CAS No.:1092961-03-9 MDL No.:MFCD11052619 MF:C9H9BrN2 MW:225.0852	3,5-Dimethylpyridine-4-carbothioamide Catalog No.:AA008TVN CAS No.:1092961-05-1 MDL No.:MFCD11052632 MF:C8H10N2S MW:166.2434
4-Fluoro-1-methyl-1H-indazole Catalog No.:AA008U7R CAS No.:1092961-07-3 MDL No.:MFCD11052635 MF:C8H7FN2 MW:150.1530	(1H-Indazol-7-yl)methanol Catalog No.:AA008TZI CAS No.:1092961-09-5 MDL No.:MFCD11052637 MF:C8H8N2O MW:148.1619
(1-Methyl-1h-indazol-6-yl)methanol Catalog No.:AA008U62 CAS No.:1092961-10-8 MDL No.:MFCD06800918 MF:C9H10N2O MW:162.1885	(1-Methyl-1H-indazol-5-yl)methanol Catalog No.:AA008TNR CAS No.:1092961-11-9 MDL No.:MFCD11052640 MF:C9H10N2O MW:162.1885
(1-Methyl-1H-indazol-4-yl)methanol Catalog No.:AA008TUV CAS No.:1092961-12-0 MDL No.:MFCD11052641 MF:C9H10N2O MW:162.1885	Morphothiadin Catalog No.:AA01EOPR CAS No.:1092970-12-1 MDL No.:MFCD30738320 MF:C21H22BrFN4O3S MW:509.3918
tert-butyl N-[2-(3-butoxyphenyl)ethyl]carbamate Catalog No.:AA01DTOQ CAS No.:1092977-07-5 MDL No.:MFCD24470810 MF:C17H27NO3 MW:293.4012	Pyrimidine-5-boronic acid Catalog No.:AA00348D CAS No.:109299-78-7 MDL No.:MFCD03002366 MF:C4H5BN2O2 MW:123.9057
2,4-Di(tert-butoxy)pyrimidine-5-boronic acid Catalog No.:AA003BI9 CAS No.:109299-79-8 MDL No.:MFCD01318980 MF:C12H21BN2O4 MW:268.1171	N-[[5-(Dimethylamino)-1-naphthalenyl]sulfonyl]-N-methylglycine Catalog No.:AA003AOR CAS No.:1093-96-5 MDL No.:MFCD00069542 MF:C15H18N2O4S MW:322.3794
GalNAc1-b-3Gal-α-OMe Catalog No.:AA0082HJ CAS No.:109303-71-1 MDL No.:MFCD04039592 MF:C15H27NO11 MW:397.3750	2-Bromo-4,5-dimethoxybenzonitrile Catalog No.:AA007AYI CAS No.:109305-98-8 MDL No.:MFCD02256761 MF:C9H8BrNO2 MW:242.0693
((4R,5R)-2-Methyl-2-phenyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol) Catalog No.:AA003B9F CAS No.:109306-21-0 MDL No.:MFCD00191611 MF:C36H32O4 MW:528.6369	2-(2-Bromophenyl)pyridine Catalog No.:AA008RAG CAS No.:109306-86-7 MDL No.:MFCD15529755 MF:C11H8BrN MW:234.0919
6-Methyl-3-(p-tolyl)-1,2,4-triazin-5(2H)-one Catalog No.:AA00IRPS CAS No.:109306-98-1 MDL No.:MFCD29044822 MF:C11H11N3O MW:201.2245	3-ethyl-1-methyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-2,5-dione Catalog No.:AA01C5DD CAS No.:1093060-45-7 MDL No.:MFCD11058146 MF:C12H14N2O2 MW:218.2518
3-(4-Chlorophenyl)-4-methyl-1H-pyrazol-5-amine Catalog No.:AA01F93A CAS No.:1093060-49-1 MDL No.:MFCD10478954 MF:C10H10ClN3 MW:207.6595	5,8-Difluoro-1,2,3,4-Tetrahydroisoquinoline Hydrochloride Catalog No.:AA0099AP CAS No.:1093064-83-5 MDL No.:MFCD05861554 MF:C9H10ClF2N MW:205.6322
3-bromo-4-ethoxybenzene-1-sulfonyl chloride Catalog No.:AA019ZPU CAS No.:1093065-10-1 MDL No.:MFCD11104760 MF:C8H8BrClO3S MW:299.5693	PLpro inhibitor Catalog No.:AA008TGA CAS No.:1093070-14-4 MDL No.:MFCD12547684 MF:C22H22N2O2 MW:346.4223
Desfluoro Citalopram Oxalate Catalog No.:AA008VYL CAS No.:1093072-86-6 MDL No.:MFCD21363471 MF:C22H24N2O5 MW:396.4364	5-methylfuran-2-carbothioamide Catalog No.:AA01AIH8 CAS No.:1093076-67-5 MDL No.:MFCD11179440 MF:C6H7NOS MW:141.1909
Methyl 3-amino-5-fluoro-4-methylbenzoate Catalog No.:AA008XNR CAS No.:1093087-06-9 MDL No.:MFCD14694719 MF:C9H10FNO2 MW:183.1796	1-bromo-2,3-dichloro-4-fluorobenzene Catalog No.:AA00HBCF CAS No.:1093092-14-8 MDL No.:MFCD11845895 MF:C6H2BrCl2F MW:243.8885
6-Bromo-[1,2,4]triazolo[4,3-a]pyridine-3-thiol Catalog No.:AA008TX0 CAS No.:1093092-64-8 MDL No.:MFCD11504977 MF:C6H4BrN3S MW:230.0851	2-[N'-(4-methylphenyl)hydrazinecarbonyl]benzoic acid Catalog No.:AA00INM5 CAS No.:109310-97-6 MDL No.:MFCD00793723 MF:C15H14N2O3 MW:270.2833
B-Raf inhibitor 1 Catalog No.:AA008TBV CAS No.:1093100-40-3 MDL No.:MFCD22571725 MF:C26H19ClN8 MW:478.9357	6-(2-Fluoropyridin-3-yl)-9-(tetrahydro-2H-pyran-2-yl)-9H-purine Catalog No.:AA0039Y2 CAS No.:1093101-52-0 MDL No.:MFCD28402162 MF:C15H14FN5O MW:299.3030